The rules of work have changed. Gone are the days where you spend your whole career at one company that gives you a great pension and a retirement party. And yet, we still act like that’s the case when we hire people, and in how we approach managing them.
We live in the world of “at will” employment. Layoffs and “it’s just not working out” discussions are always just around the corner. Meanwhile, many employees job hop from company to company always searching for greener grass.
When talking to candidates, we interview them expecting to hear how committed they are to anything the company wants, even though both sides know a lifetime commitment is pure fantasy.
Why are we lying to ourselves?
Rather than be in denial, we should accept the new rules and take full advantage of them. That’s what Reid Hoffman, Ben Casnocha and Chris Yeh advocate for in their new book, The Alliance I just read.
The current system is bad for everyone.
It creates major problems for both the company replacing team members regularly and the former employees who see their tenures cut short.
The worst parts about replacing team members are:
They leave when you don’t expect it.
You have no plan for what to do without them.
Work is left incomplete even if they give some notice.
Their knowledge and experience is lost from the company.
And for the employee, the worst parts are:
Unfinished work and incomplete milestones that now can’t be put on their resume.
Less development in their career as companies fear to invest in them.
Damaged relationships due to resentment over the first 2 items.
Distrust in every employer they have going forward.
Hoffman, Casnocha, and Yeh advocate for a new system that considers employment as an Alliance: a mutually beneficial relationship, without the empty promises of long term employment.
Why You Should Think of Your Employees as Allies in the Future of Work
In an alliance, both sides work together for mutual benefit. This means shifting your thinking on employees. It’s a lot more than, “do this work and I pay you.” Instead, the relationship is, “I help you grow, learn, and tackle these challenges, and the company benefits from that work.”
The authors call this a Tour of Duty. You select a length of time (a year or two up through 5+ years) and a set of goals for them to achieve with core responsibilities. The agreement is that you will help them have a Tour that is of interest and value to them, and they will do good work for your company.
By agreeing on the time frame and what the Tour entails, you eliminate many of the biggest problems for both sides:
Employees now have a clear set of goals and milestones and a plan to get there.
Employers have more certainty how long they can count on having an employee.
Employees have a clear point where they can cleanly transition out if they want.
Employers can plan ahead as a tour is about to complete, avoiding any surprises.
Both sideshave more certainty and a clear commitment to one another.
Now the end of a Tour is not the end of someone’s employment. What Reid Hoffman found with Linkedin, was that people were often hungry for new Tours. It provided opportunities to quickly progress people onto tracks for major leadership roles (they call them Foundational Tours), or give them a new, interesting, challenging job different than what they just completed.
Either way, you can keep renewing the Tours as long as there’s a good fit between company needs and employee interests. And if there’s not a clear fit at the end of a tour, you can have a very smooth transition for both sides, allowing the employee to find work elsewhere without hurting the company or vice versa.
Your people want tours. You just don’t know it.
As I’ve been working on my app for managers, I’ve spoken to a lot of employees in addition to managers. What I keep hearing over and over again is how frustrated people get over a lack of progress in their work.
Employees want to grow and learn new things. They want to be challenged. They want to be recognized for their good work, and feel like they’re working towards something greater than just a list of tasks for the day. When they don’t feel that progress, they feel stifled and quickly lose motivation. Not long after, they’re looking for the door.
Tours address all of these issues. A Tour:
Creates a clear set of goals to achieve in a role.
Creates a set end point where new opportunities can be explored.
Ensures a discussion about an employee’s goals and how they fit into the company.
Necessitates regular check ins to be sure progress is made on a Tour and will be completed on schedule.
Planning Tours take effort and have big payoffs.
Planning Tours for your team members doesn’t happen by accident. It’s why they wrote the book and are building a site around the idea (www.theAllianceFramework.com).
You have to have healthy discussions with each team member and plan out a path for them. What can they achieve in a few years? How does that align with their long term goals? What are the measures of success for a Tour for them? Do those goals interest them? If those are questions that are foreign to you, you need to start discussing them.
The best time to have these discussions is during your 1 on 1s.
With so much work to do, so many short term priorities to address, who has time for this? But if you want to keep your best people motivated and engaged and level up your team as a whole, you need to make time for these discussions. That leaves 1 on 1s as your best chance to have the time (You are having 1 on 1s, right?).
You’re already hopefully having candid conversations in 1 on 1s, so it’s time to shift part of each 1 on 1 to work on aligning their long term goals with their current roles and responsibilities. It won’t happen all in one meeting, but you can slowly put together a plan over a series of meetings.
You’ll see the benefits quickly.
Once you start this process, pay attention. Watch closely. The more you align someone’s work with their goals the more motivated they will be. Show them how the work you’re asking them to do gets them closer to what they want and they’ll work harder to help you with what you need.
It’s no mistake. It’s the Alliance at work. As Hoffman, Casnocha, and Yeh, write,
“Every employee relationship should be bidirectional in nature; it should be clear how the employee benefits and how the employer benefits.”
That’s because it creates the best situation for productive, happy work. And the Tour takes that to its greatest outcome by sustaining that over a multi-year period.
Are you creating aligned work for your team? Are you engaging your team towards mutual benefit? If not, learn more in The Alliance and start doing Tours at your company.
Looking for a system to track your team’s long term goals and break them down into the near term goals you need?
Want to have more effective 1 on 1s that build towards alignment like what’s described in the Alliance?
I still remember the surprise when one of my old coworkers announced that to the company. He was one of the longest tenured members of the team and seemed content on the job. Little did I know he had a number of motivations for wanting to make a change that may have been avoidable.
The competition for talent is always high, and especially now you can’t afford to lose a good employee. Even the most loyal members of your team have breaking points that will make them want to look for a new job. And worst of all, when employees leave, it often happens in waves, meaning that you lose more than just one person at a time.
People leave bad managers, not jobs, which means as a manager, you have the power to prevent many of these losses to your team. Avoiding these pitfalls will put you well on your way to retaining your team.
Commons Ways to Lose Good Employees
1) Don’t Follow Through
I’ve written about this a number of timesbefore and it bears repeating: not following through with commitments to your team will quickly build resentment. That resentment will lead to complaining amongst team members behind your back and a lot of frustration and distrust that can hamstring your team’s productivity.
What to do instead: Use a to do list or other system to track your commitments to your team to make sure nothing slips. If there’s something that prevents you from following through that’s beyond your control, be transparent with your team and help them understand why you couldn’t do it.
2) Don’t have 1 on 1s with them
If you’re not having 1 on 1s with your team, you don’t know what they’re really thinking. 1 on 1s are a huge opportunity to have a private line of communication with each of your reports. You can learn tons of different things based on the questions you ask in a 1 on 1, and fix a lot of problems before they blow up. There’s a reason Ben Horowitz was willing to fire a manager for not having 1 on 1s.
What to do instead: You may think you don’t have time to have 1 on 1s, but what you really don’t have time for is to lose your best people and have to go through the hiring process and covering for lost staff again. Get started having 1 on 1s at least once a month (ideally more) and use an app like Lighthouse to help you stay on top of them.
3) Ignore Their Ideas
Are your employees trying to tell you something? Do they see a problem you don’t? Do they have ideas to improve the way they work or a system around them? This is a gold mine of ways to make your company better and make your team happier. Yet, many ignore this and see people instead get frustrated by a lack of change in areas they think are important.
What to do instead: Use part of your 1 on 1 time to ask questions about ideas they have to improve the company, the team, and their own work environment. Take action when you can on those suggestions and explain why some things may not be possible right now.
4) Don’t Treat Them Like Adults
Do you trust your team? If you can’t trust them you may not have the right team. Good people, especially those with long tenures, expect some transparency into what is going on outside of the team. They also want to be trusted with their work instead of being micromanaged.
What to do instead: Trust, but verify. Give people the independence to do their job, but hold them accountable to the results you agreed upon. Trust them with information they want to know and make sure they’re keeping anything private you asked them to.
5) Under Compensate Them
Are you paying anyone well below market rate? Have some of your team grown in their roles and are now significantly outperforming their compensation? Have you moved a team member to a more expensive city without properly increasing their salary for cost of living? Any of these, as well as disparities in equity can lead to a lot of resentment. It can also tempt people to see what they’re worth elsewhere and by the time they have an offer, it’s too late.
What to do instead: Plan ahead for managing people’s compensation, especially for people taking on more responsibility. Your budget may be tight, but if you make incremental improvements you won’t wake up a few years down the line searching for a massive amount of money to adjust someone’s salary who has one foot out the door.
6) Don’t Praise, Recognize or Reward Good Work
Do you reinforce the good work done by your team? Do you tell them specifically why the work was great? If you don’t recognize good work, your team will not be as motivated to repeat those efforts again. Mary Kay Ash, of the founder of Mary Kay cosmetics, put it best when she said:
“There are 2 things people want more than sex and money: recognition & praise.” – Mary Kay Ash
What to do instead: Take time to recognize people for great work. If it’s really awesome, recognize it in front of their peers. Also give them specific reinforcement over email and in 1 on 1s. As long as you are specific why you’re giving them praise, it will be well received.
7) Keep Bad Employees
Nothing frustrates good employees like working with bad ones. Bad team members make it harder for everyone else to get their work done, slow down progress, and lower the bar for the quality of work a team outputs. Bad team members can quickly turn a strong work environment into a toxic one either by their own work or due to how the team reacts negatively to them.
What to do instead: If you can, fire them. Your team will breathe a sigh of relief and you’ll find your team is more productive without them. If you can’t fire them, try to minimize how they impact others by putting them on work that they don’t affect as many people on the team.
8) Don’t Align Their Work with Their Goals
Do you know what the goals of your team members are? Does their work put them in line to accomplish those goals? Are they growing? If an employee isn’t achieving their goals, they will feel stifled and likely grow bored with their job. When a person’s job doesn’t help them achieve their goals, they’ll be motivated to look elsewhere to reach them.
What to do instead: Have conversations about goals in your 1 on 1s. Work to align parts of their job with these goals and make them feel like there’s a plan to help them achieve them over time. Apps like Lighthouse can help you manage and remember these.
9) Embarrass Them in Front of Their Peers
This may seem like an obvious one you would never do nor allow in your company, but it might have happened without you realizing. Ever casually call someone out across the office over a mistake or to make a joke?
I had a boss who wanted to prove that everyone (except me) cheated in school and proceeded to try to ask everyone around the office if they cheated. I think it was meant to be funny, but I remember how uncomfortable I felt then. Whatever it is, it can seem innocent, but even things you think are light-hearted can hurt people no matter what face they put on publicly.
What to do instead: Don’t be the one to do these sorts of things and shut down anyone you see doing it as well. If you’re treating your team like adults, then embarrassing peers is a childish behavior you should not tolerate. If it does happen, apologize and make sure it doesn’t happen again.
10) Don’t Help Them Make Progress Regularly
The feeling of progress is crucial to people’s satisfaction. They need to feel like they’re progressing on their work and that their work matters to the company’s bigger picture. When people aren’t making progress, they start to burn out. Nothing is more devastating to a great employee than burn out. It saps them of their abilities to be a productive, skilled team member.
What to do instead: Make sure team members have projects that are broken into small enough chunks that they can regularly make progress on them. Check in with them on their goals to make sure they’re making progress on them. Read more about progress on teams here.
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These are all hard lessons to learn, but the good news is that usually people leave for more than one reason. That means an occasional slip up will be forgiven, while breaking many of these will have your team looking elsewhere for work.
What are the behaviors you’ve seen cause good people to leave?
Want help keeping your team motivated and turning down recruiting emails from friends and recruiters? Lighthouse was designed from the ground up with a workflow to help you follow the best practices of great managers.
One on ones are a crucial part of good management practices, but just because you have regular one on ones with your team doesn’t mean you’re making the most of them. You could even be doing serious damage to your relationship with your team if you don’t do them correctly.
As a manager, your job is to amplify your team to allow them all to perform more efficiently and effectively. Your 1 on 1s with them are your best weapon to raise performance and address issues. However, making these crucial mistakes below can damage your relationship with your employee and prevent you from discovering the kinds of things that will fix problems, raise morale, and motivate team members. Hopefully you aren’t doing many of them, but if you are, there’s no time like the present to turn it all around.
Critical Mistakes You Could Be Making in 1 on 1s
1) Not following through
If you’re talking about ideas, problems, or things important to your report in your one on one, but then nothing is ever done about what you talk about, you’re making a lethal mistake. The effectiveness of one on ones is based on trust, and that comes from following up and following through on what you discuss.
When you lose the trust of your report, they will shut you out and won’t share feedback, ideas, or problems with you. They will feel there is no reason to waste effort talking about things that will never happen and they’ll resent you for it. This is the path straight to losing a team member.
What to do about it: End your one on ones by specifically setting what you and your report’s tasks are because of what you have discussed in the meeting. When you take action on something important they brought up, let them know and thank them for bringing it up.
2) Canceling one on ones
One on ones are the one meeting your report has that’s all about them. The rest are all about what the company wants and needs. When you cancel their one on one, you may think it’s ok, and they’ll probably even say it’s ok if you ask, but it’s not. They will resent you for not treating the conversation about them as important.
It will also break your rhythm of these meetings regularly covering important topics and addressing them; if you go a month without having a one on one, so much may build up that you’ll miss covering something important.
What to do about it: Book your one on ones on your calendar for a consistent time you know you can stick to. If you absolutely can’t make a one on one, then reschedule it for as soon as you can after the cancellation rather than not having it at all.
3) Turning them into status updates
One of the most common things I’ve heard as I talk to people about management is how often a significant portion of the meeting is spent giving a status update of their projects. Nobody wants to have more meetings than necessary, but by putting a status update into a one on one, you’re squeezing time spent on the most important subject of one on ones: your team member.
What to do about it: Have a separate meeting to do status updates or consider using an app like idonethis to stay up to date on what people are accomplishing without having to talk about it in one on ones.
4) Not preparing
Yes, one on ones are all about your report. And yes, they should be bringing things to talk about in the meeting. However, assuming you don’t need to prepare at all for the discussion is a big mistake. Context switching to the meeting can be difficult if you’ve been working on other things and like it or not, your report can tell when you’re really ready for the meeting. Not preparing also makes you miss out on great coaching and feedback opportunities.
What to do about it: Save a few notes and to do items from each meeting. Review them before your next meeting and bring a couple questions for the one on one with you.
5) Not talking about their goals
It’s easy to spend all your time focused on short term issues in your one on ones, but what will make people happiest is when they’re making progress on their long term goals while working at your company. You are unlikely to find out what those goals are unless you talk about them and there is no other time as ideal as the privacy of a one on one to explore their big life goals.
What to do about it: Every month or two, revisit questions about their goals and what you can do to help them make progress on them. Keep these goals written somewhere you can easily reference, like Lighthouse, so you can take action on them when opportunities arise.
6) Not asking tough questions
It’s easy to get into a rut with one on ones and thus only cover a fraction of the topics that you could. Your one on one time is an amazing opportunity to get insights on many things including: improving the company, feedback on being a better manager for them, feedback and coaching them, improving morale in the company, managing goals and uncovering team issues. Don’t waste it only talking about a fraction of those things.
What to do about it: Rotate through the topics on this list of questions for one on ones and always follow through so your report knows they can really talk to you about anything.
7) Not having them at the right frequency
When someone is brand new to your team, it’s important to have one on ones often so you can build rapport and trust quickly. Also, if every one on one is running long, you may want to have your one on ones more often with them.
On the other hand, if you’re doing them weekly and finding often the meetings aren’t yielding much to talk about even as you cover all the tough questions, then backing off to biweekly or monthly may make sense. This will happen especially with colleagues you’ve worked with or known for a long time.
What to do about it: Challenge yourself to look hard at what’s happening in the one on ones. Are you covering everything you should? Do you know them well enough to detect a problem early without a 1 on 1? If so, you may be able to have them less often. If not, you may want them more often.
8) Not holding them accountable
You’re not having one on ones to play psychologist. You are having them to address issues, understand your team members, and hear what they want. Both of you should have takeaways from each one to make sure you’re both making progress in the areas you agree are important. Letting them slip by with not being actionable in your discussions or not taking care of the action items you discuss, is wasting the time of both of you.
What to do about it: End every one on one by asking them what you can hold them accountable to before your next one on one. Circle back in the next meeting to make sure things are getting done. You should notice an increase in satisfaction that comes with a sense of progress from completing agreed upon takeaways.
9) Not being present in meetings
Have you ever caught yourself zoning out, checking your phone, or looking at email when you’re supposed to be listening to them? Just like canceling a meeting hurts them, not giving them your undivided attention will as well. You may be able to get away with it in a big meeting (though that’s not good either), but this is a one on one, so you are the center of the other person’s attention. You aren’t as sneaky or as good at multi-tasking as you think.
What to do about it: If your computer in the meeting is too tempting, leave it at your desk. Do the same for your phone if you have to. Many managers use Moleskin notebooks for these meetings since all you can do is jot notes, not the million other distractions we have today. They then transfer them to their note taking app later.
10) Thinking you don’t need a 1 on 1, too
I know. You’re busy, and your manager is even busier. And that’s all the more reason for you to touch base in a 1 on 1 for yourself, too. Some of those subjects you’re covering with your team in their one on ones will need to bubble up to your manager, who can also help you in many of the same ways you have been helping your team.
Just because you’ve gotten a promotion to manager doesn’t mean your career is set. Continuing to learn where you can improve and talking about your goals is all the more important when you are trying to lead a team of others.
What to do about it: Share with your manager the positive results you’re getting from the one on ones you’re having with your team and tell him you want to do the same. Results will grab their attention and convince them of the value.
What mistakes have you made in 1 on 1s? How have you improved them?
Want to have great 1 on 1s with your team? Lighthouse helps you have great 1 on 1s by helping you follow best practices, always be prepared, and follow through on what you discuss. Your team will love you for it.
Ever been handed a 10 page product spec that no one wants to read? Ever write one yourself? Tired of struggling to communicate what needs built next to your designers and engineers so they really understand the who, what, when, where, why of the next feature you need?
I’ve been using customer development, analytics, and information from my team to learn to build the right thing for years, but I always struggled communicating all the information locked in my head to the rest of the team. They needed to know why we were building it and all the necessary information to build the right thing without endless meetings or a massive spec they won’t read.
Fortunately, when I joined KISSmetrics, Hiten and I got to learn a better way from Josh Elman, who worked on product teams at Twitter, Facebook, and Linkedin. Josh taught me about the Thesis, which is a lightweight way to communicate all the essential details your product team needs.
Now that I’ve used the Thesis on dozens of projects and tweaked it based on what I found worked best, I’m going to teach you how to write your own thesis for the next feature or product you build.
The Product Spec Alternative: How to Write a Product Thesis
> Know when to write a Product Thesis
The biggest crime product managers can commit against their team and their profession is to make up answers to critical decisions. Don’t be that guy/gal.
If you don’t know the answer to one of the sections in the Thesis, go find out. Dive into your analytics, talk to customers, run a survey, talk to your sales/account management/support teams that interact with customers regularly. You will gain the full respect of your designers and engineers if they know you always have a customer story and/or data to back up everything they may ask you about in the Thesis.
The following are all sections of the Thesis. I literally use these as headings to break up the parts and try to keep each section to 5-10 bullet points or a few concise paragraphs.
1) Why are we working on this next?
Every company, and especially startups, are resource constrained. What you choose to build affects your company’s bottom line, their standing in the market, and what your team thinks of your judgment. Use this area to concisely present your case for why this is the most important thing to work on right now.
I try to have a mix of qualitative and quantitative data here. If a mandate came from the leadership team to focus on this area, or sales needed it for a big customer, I make sure to include that. The more your designers and engineers can understand why this matters, the more interested they will be in working on it. In the end, you’re a team and everyone on the product team wants to be sure they’re building the right thing.
2) What are the use cases for this?
Most products end up having a variety of different users and ways that people use the product. To help your team better design a specific feature for the right part of your customer base, you need to detail who this new feature is for.
Be specific! A use case section that is just something like, “As a marketer, I want a mobile app so I can access my data away from a computer” is total weaksauce. Instead, provide the kind of context and detail that paints a picture of the situation:
On their way to work on the subway, content marketers like to check how their blog traffic is doing for items they published that morning or the day before. It helps them get into work and know how they’re doing before they sit down. If a number is low, they may try promoting it extra to try to raise the number. If the number is high, they may share the win with others on the team.
Could you picture that situation in your mind? Can you see Jenn the marketer opening an app on her iPhone while sitting on a subway car? I bet you could. Your team can too and they can also then start thinking about what the perfect (not just good) solution would be for them.
Write out as many use cases as you feel are needed. I often have as many as 4 or 5 detailed cases for a big feature.
3) What Problems do we need to solve?
Features are really solutions to your customer’s problems. It doesn’t do any good to build a feature that doesn’t actually solve the problem, so it’s important to detail what problems you need to ensure the solution your team creates addresses them.
Problems should either be existing problems your product has (especially if you’re iterating on an existing feature) or the problems related to the use cases you just described above. Some example problems may be:
Performance Problem: Customers are experiencing frequent crashes. This feature is critical for customers and they are constantly having to refresh and start over, losing their work in the process.
Design Problem: Customers are having issues with the current UI. They can’t find key features that exist that they asked me for (Include a markup of the interface to show these.)
New Problem:Customers spend hours manually copying numbers to a spreadsheet and making their own visuals for their VP. If we automatically make those reports, we’ll save them time and can then have the VP see our branded reports frequently.
I usually write out 5-7 problems that a feature addresses in bullet form. If it only applies to some of the use cases I described, I’ll specify that as well.
I also try to rank the problems, so that the most important issues get the most attention. Top problems may be because it affects the most people or functionality issues like the feature crashing constantly. When it’s time for tradeoffs when building the feature, having these detailed, ranked problems will help you make sure the right things avoid being descoped.
4) What are Future Considerations that must be accounted for?
Products are always evolving. Startups can be unpredictable, but you still know generally the direction you may be heading, especially if you’re driving hard towards product-market fit. Help your team anticipate what’s coming next whenever you can.
Depending on the feature, this could be very short or long section. If there are things you know are not going to make the first version of this feature but expect will be needed to be added later, be sure you tell your team! This section is all about avoiding hearing from engineering, “I wish you had told me that before we built [X]!”
Balancing the present and the future is a constant struggle for a product. The best thing you can do for your team is give them the key information you know so they can do their best to balance their work against the present and future as well.
5) What is our KPI for this Thesis?
You should ask yourself, “What would make this new feature a success?” A KPI (Key Performance Indicator) is the most common way to determine that success since ideally you will tie the success of the feature to one or more of your company’s key metrics.
It’s okay to have more than one KPI, but keep it simple or there will be too many things to measure. When I’ve had multiple KPIs for a feature they’ve been things like:
Support requests will drop by 90% for this feature after relaunch.
Usage of the app will grow by at least 50% after relaunch.
Because this feature affects the sign up flow, we expect a 5% lift in conversion after this relaunch.
You will fail sometimes, but by forcing yourself to quantify what you expect to happen, you will keep you and your team honest. By setting a number that you must hit you can also know when you should go back and iterate.
6) Further Reading:
Your main document shouldn’t be longer than 2-3 pages, so Further Reading can act as an Appendix for you. In this section, I include links, screenshots, early mockups of ideas, markup of existing features for UX issues, and anything else that I believe would provide additional, helpful information and inspiration related to the project.
Remember: You want all the detail you can without the fluff and verbosity that makes engineers and designers skip reading it. Further reading is a great place for specific information that didn’t fit in the above sections and may be relevant to specific team members.
How does your team document what features need built next?
So you’re having one on ones with your team. Awesome. It’s an essential element to being a good manager. But are you making the most of them?
Do you come in prepared and ready to make the most of each one or do some go better than others as you wing it half the time? Are you too dependent on them bringing the agenda? Do you ask the same 3-5 questions every time?
This list will help you make the most of each meeting and have a quick reference when you feel your questions may be getting stale or you have a few minutes left in a one on one.
101 Questions to ask in one on ones
One on ones are all about your people and building a strong, trusting relationship with them. Asking questions like the ones below and following through on what you talk about will build a strong, lasting relationship for each member of your team.
Asking 1 or 2 of these questions each one on one will keep things fresh, while ensuring you’re covering important subjects regularly. It also gives you ample time to dive into each question as they often will open up into greater detail as long as you follow up with questions like “Why?” and “Tell me more…”
I’ve organized these questions by the high level categories you’ll commonly touch on in one on ones so you can quickly skim through it for a question in a topic you want to cover that meeting.
Questions to talk about Short Term Goals
Short term goals are things to be done in the current quarter or month. They’re high level projects assigned to that person.
1) How is [project] going? What could we do to make it better?
2) Is there anything blocking you from getting your work done?
3) Are there any projects you’d really like to work on if you were given the opportunity?
4) What parts of your job would you like to deepen your skills in or get additional training in?
5) Is any part of your project unclear or confusing?
These are all about getting feedback so you can improve their day to day and relieve frustrations on their projects. You already spend a lot of time on their day to day job in standups, status reports, etc so this is intentionally a short set of questions relative to other areas you spend a lot less time talking about usually.
Questions to talk about Long Term Goals
Long term goals are all about who they want to become. Everyone is growing in different ways and people are happiest when they feel like they’re making progress on their big life goals. These questions will help you learn what those goals are and see if they feel they’re making progress on them.
6) What do you want to be doing in 5 years? 10 years? 3 years?
7) What are your long term goals? Have you thought about them?
8) Do you feel like you’re making progress on your big goals here? Why or why not?
9) What’s one thing we could do today to help you with your long term goals?
10) Do you feel we’re helping you advance your career at a pace you would like?
11) Who do you really admire? Why? (People often admire those they want to become) 12) If you had millions of dollars, what would you do every day?
13) What are your super powers? What powers would you like to develop?
14) What are your big dreams in life? Are you making progress on them?
15) Could you see yourself making progress on more of your goals here? What would need to change to do so?
16) What work are you doing here that you feel is most in line with your long term goals?
17) As a kid, what did you want to be when you grew up?
These questions will help you make sure your people are progressing in the areas that matter most to them. Realize they will change over time, and it takes time for people to really open up about their dreams, so it helps to revisit them regularly.
Questions to talk about Company Improvement
Company suggestion boxes have a pretty bad reputation for being unread and never acted on. It’s also hard to convey the nuances of a problem or opportunity for a company on a tiny note card or feedback form.
Asking questions about improving the company during one on one time can help uncover what people in the trenches are seeing and get great ideas to improve the company. All of this while having the chance to easily ask follow up questions to better understand them.
18) What is the company not doing today that we should do to better compete in the market?
19) What’s one thing we’d be *crazy* not to do in the next quarter to improve our product?
20) How could we change our team meetings to be more effective?
21) If you were CEO, what’s the first thing you’d change?
22) Do you think our company is loyal to its employees? Why or why not?
23) Are there any aspects of our culture you wish you could change?
24) What are your favorite parts about our culture?
25) Do you feel over-worked, under-worked, or just the right workload?
26) Why do you think [employee who recently quit] left? What did they tell you?
27) What would convince you to leave for a job somewhere else?
28) Which company values do you like the most? Which the least? Why?
29) What is the #1 Problem at our company? Why?
30) Do you feel like you’re on the same page with your team? How often do you think you need meetings to ensure you stay that way?
31) What do you think are the long term prospects of the company?
32) How many hours a day do you feel you’re productive? How could we help you be more productive?
33) How could we be more creative or innovative as a company?
You may not always like the answers you hear when you dig in for feedback like this, but that’s the point. If you take action on the things you can change and help your reports understand why some others are the way they are, you can help relieve a lot of frustration while making people feel heard.
Questions to talk about Self Improvement
Creating a culture of learning and self improvement starts with discussions like one on ones to help people understand what they should do differently. By discussing them in private, you avoid embarrassing them in a more public setting and can coach them through the changes needed.
34) Do you feel challenged at work? Are you learning new things?
35) What area of the company would you like to learn more about?
36) What skills would you like to develop right now?
37) Who in the company would you like to learn from? What do you want to learn?
38) How do you prefer to receive feedback?
39) Do you feel you’re getting enough feedback?
40) What’s a recent situation you wish you handled differently? What would you change?
41) What additional training or education would you like?
42) Are there any roles in the company you’d like to learn more about?
43) What do you think are the key skills for your role? How would you rate yourself for each of them?
44) Is there an aspect of your job you would like more help or coaching?
These questions will all reveal ways you can help people grow and improve them in their job. The key is to realize that the follow up questions need to include action items and advice for helping them make progress on what you just discussed. Doing always trumps just talking about it.
Asking your team directly for feedback will help you not only improve, but also build the trust that you’re as open to feedback as you want them to be. Set a good example with questions like these below.
45) What could I do as a manager to make your work easier?
46) What do you like about my management style? What do you dislike?
47) Would you like more or less direction from me on your work?
48) What could I do to make you enjoy your work more?
49) How can I better support you?
50) What would you like to know about me?
51) Is there a situation you’d like my help with?
52) What is something I could do better? What is a criticism you have for me?
When your reports have the courage to give you candid feedback, make sure you fully understand it and thank them. It can be scary to say something negative to their manager. If you don’t follow through on the feedback, you will lose their trust and they may start to resent you.
Questions to talk about Happiness
Whether it’s a work related issue or a personal one, a person’s happiness will have a major impact on their productivity and morale at work. A one on one is the best time to dig into any issues that may be affecting them and do things to help them with it.
53) Are you happy?
54) Are you happy working here?
55) Are you happy with your recent work? Why or why not?
56) What would make you leave this job for another?
57) What’s one thing we do to help you enjoy your job more?
58) Is your job what you expected when you accepted it?
59) What worries you?
60) What’s on your mind?
61) What’s not fun about working here? What do you enjoy most about working here?
62) Who are you friends with at work? (Shown to be a key to enjoying your job)
63) When was the time you enjoyed working here the most?
64) What do you feel is your greatest accomplishment here?
65) What’s something you feel is undervalued that you contribute to the team?
66) What part of your job do you wish you didn’t have to do?
These can be some of the hardest questions to ask. If someone is unhappy, they can be particularly cagey, so do your best to give them space and listen carefully. Helping them based on these answers can save an employee you were on the brink of losing.
Questions to talk about Personal Life
Your employees are one complete person. No matter how much you’d like them to, problems in their personal life will affect them at work. You don’t need to be there therapist, but a little empathy can go a long way with these kinds of questions.
67) How are you? How is life outside of work?
68) How do you feel your work/life balance is right now?
69) How do you feel about your current compensation (salary and benefits)?
70) What’s one thing we could change about work for you that would improve your personal life?
71) If around a holiday: What did you do for [Holiday]? How was it?
72) How are your parents/grandparents? Where do they live?
73) If they have children: How is [name of child] doing? (Ask something related to their age like starting school, playing sports, or other interests.)
74) What do you like to do in your free time? What are your hobbies?
75) What did you do for fun in the past that you haven’t had as much time for lately?
76) What drives you? What motivates you to come to work each day?
These questions can help you much better understand people’s motivations and interests. Empathizing with situations like a divorce, sick parent or grandparent, a death in the family, or positive moments like children, a successful side project, or fun activity can all go a long way towards building great rapport for your team. It can also inspire inexpensive ways to thank a team member.
Questions to talk about Team Relations
Your team spends 8+ hours a day working together. One of the biggest opportunities for improvement in productivity comes from improving the interpersonal relationships among team members. Questions like these help uncover problems and opportunities to help every person become a better team member.
77) Who on the team do you have the most difficulty working with? Why?
78) How would you describe the work environment on the team? Is it more competitive or collaborative?
79) How could we improve the ways our team works together?
80) Who is kicking ass on the team? What have they done?
81) Who do you admire on the team? Why?
82) Do you feel your ideas are heard by the team and I?
83) Who would you like to work more often with? Why?
84) Is everyone pulling their weight on the team?
85) Do you help other members on the team? Do others help you when you need it?
86) What’s one thing we should change about how our team works together?
87) What characteristics make someone a good fit for our team? How would you look for those characteristics in an interview?
88) What’s the biggest thing you’d like to change about our team?
89) What do you like most about working on our team?
90) Has anyone on the team ever made you feel uncomfortable? What happened?
One on ones are a great time to coach people on issues they’re having with coworkers. You can also use it as an opportunity to uncover problems on the team before they blow up into a big deal.
Questions to talk about Work Habits
The more you can learn and understand how each team member operates, the more productive they can become. These questions can help you work with them to learn what their work habits are.
91) What part of the day do you have the most energy and focus? When do you have the least? What changes could we make to your work schedule to accommodate this?
92) What are 3 things would you buy to improve your productivity if money was no object?
93) What is an ideal, productive day at work for you? Walk me through the day…
94) What’s an inexpensive thing we could do to improve our office environment?
95) What are the biggest time wasters for you each week?
96) What makes you excited and motivated to work on a project?
97) When you get stuck on something, what is your process for getting unstuck? Who do you turn to for help?
98) What part of your work routine do you find is working best? What area do you want to improve?
99) Are there any meetings or discussions you feel you should be a part of that you’re not? Are you included in any you don’t want to be a part of?
100) What do you do when you feel low energy or unmotivated?
101) How can I help…? (be more productive/happier at work/enjoy work more/etc)
The best ideas come from people in the trenches. While you may be in meetings, buzzing around the office or traveling, they likely see things in the office that affect their productivity a lot (for better and worse). Making changes can have a huge impact on your team’s output.
…and the 2 questions to ask in *every* one on one:
None of the things you talk about in one on ones matter if you don’t follow through and take action on them. These two questions will ensure you always follow through with the important things you discuss in your one on ones:
1) What can I hold you accountable for next time we talk? 2) What can I be accountable to you for the next time we talk?
You can get a pair of these questions, as well as a reminder of what you talked about last time, as part of a prep email from Lighthouse, the app to help you be a better manager.
It also helps you manage the actionable questions you should ask at the end of *every* one on one. Learn more and sign up at GetLighthouse.com
“I don’t want to mix personal and professional discussions.”
“We’re all adults here that can handle their own problems.”
“The meetings don’t scale and we only do scalable things here.”
There are a lot of excuses why you might not be doing 1 on 1s with your team. And while they may seem like good reasons, there are a lot more reasons why you should be doing them. If you’re a hold out or skeptic of 1 on 1s, or trying to convince someone to do 1 on 1s, here’s a set of reasons they’re a key weapon in a great manager’s arsenal.
21 Reasons You Should Have 1 on 1s with Your Team
1) Follow veteran leaders who swear by them.
Ben Horowitz, VC at A16Z and former CEO of Opsware (acquired by HP for $1.6Bn), considered it a fireable offense for any manager that did not hold regular 1 on 1s. Andy Grove, founder & CEO of Intel and legendary leadership author also advocates for them.
2) Give timely feedback and constructive criticism.
Are you doing annual reviews? Even if you’ve accelerated them to quarterly, it’s still not timely enough to discuss performance improvement. Think you can do it ad hoc? When was the last time you really made time to give that feedback? Chances are you thought of it, then got distracted by 37 other things and didn’t want to schedule a meeting just for that. The great thing about 1 on 1s is that this can be just a small part of the meeting that’s all about the team member.
3) Get private feedback.
It’s often hard to get feedback as a manager even though you know there are places you could improve. Not everyone wants to write out feedback on forms. In 1 on 1s where you’ve built rapport and trust, you have the perfect channel for the candid feedback that will help you improve, too.
4) Float your ideas before they’re fully baked.
Thinking about a new initiative and want unfiltered feedback before you invest a lot of time in it? A 1 on 1 is the perfect place for your semi-baked ideas you think may have an impact. Using 1 on 1s for this can be a great way to build trust that this is a place they can be vulnerable as well and not feel like you need a 50 slide powerpoint ready before getting feedback from your team on an idea.
5) Make time to talk about their career consistently.
Everyone has career aspirations. They will want to grow and try new things. If you don’t have the conversations with your people about this growth, they’ll look for growth opportunities outside your company. Without one on ones, these conversations often get lost in the shuffle and only surface during annual reviews which are quickly forgotten and never acted on.
6) Fix problems when they’re small.
Are you constantly fighting fires and dealing with issues once they’ve exploded? Then you need 1 on 1s. These meetings will help you catch these issues early on, whether between two coworkers or a problem discovered in a process in the company. You still have to follow through on what you hear, but knowing about the problem when it’s small makes it much easier to address than when you have to triage later.
7) Show you care.
You’re making a major statement to your team when you set aside time for them regularly to talk about them. Do not underestimate the impact that showing you care and that they’re important will have on morale, commitment, and trust in you as a leader.
8) Coach & develop your people.
In the middle of a busy meeting is no time to coach one person about something they need to learn, but a one on one is a perfect time for that. As the saying goes:
CFO asks CEO: “What happens if we invest in developing our people & then they leave us?”
CEO: “What happens if we don’t, and they stay?”
You can’t afford to not grow your people and one on ones are a key place to discuss and plan your team member’s development.
9) Learn empathy for them.
Everyone on your team is different. They come from different backgrounds and experiences. If they’re struggling with something outside work, it rarely can avoid impacting their work. You can give them tough love and they’ll resent you, or you can help and show empathy and they’ll appreciate you.
10) Get forgiven for your mistakes.
We all make mistakes. When a friend or trusted colleague makes a mistake, we are much more likely to forgive them. As a manager, you’re going to make mistakes and the more trust and rapport you have with your team, the more likely they will understand and forgive you. You build that trust and rapport by having your own empathy for them, which comes from one on ones.
11) Make them feel heard.
Every employee has a unique perspective of how the company operates. Valuing everyone’s insights as to what they’re seeing not only helps you with getting more signal on important issues, but makes them feel like a valued part of the company. Especially as a company or department grows, people can feel marginalized and lost. One one ones are an opportunity to make sure you don’t miss out on what they have to say.
12) Avoid surprise departures.
If someone is thinking about leaving the company, the warning signs will come up in 1 on 1s. If you don’t have 1 on 1s, it will be much easier to feel like you’re not missing anything. Most lost employees can be saved if you address what’s bothering them, which is generally a discussion for 1 on 1s; most people won’t come to you with a series of complaints out of the blue.
13) Learn what drives your team.
Not everyone is motivated by the same things. Outside of sales teams, money is rarely the largest long term driver for people. The more you get to know your people in 1 on 1s, the more you’ll know how to motivate each person uniquely.
14) Create a safe space for their ideas.
Just like you can float ideas to your people, 1 on 1s can be a great place for your reports to share with you loosely formed ideas they have. Often a brief discussion in a 1 on 1 can help encourage them to prepare it to present to the team or understand why it’s not a good idea right now. Either way, they need a safe place to spare them making 50 slides on an idea to feel like they can share it.
15) Give them control of a meeting for once.
If you’re in a very hierarchical organization, lower level employees can feel powerless. One on ones give them that one time per week that they feel in control. It gives them the freedom to talk about whatever is most important to them without having to try to fight for time on your busy calendar ad hoc.
16) Relieve boredom or stagnation on your team.
Many employees, especially in Generation Y, are constantly looking for new ways to grow and learn. If they spend too much time with the same role and responsibilities, they can become bored and feel like they’ve plateaued. You can either milk them for their experience until they leave for a new company, or have a regular conversation about it in 1 on 1s and possibly help them get into a new role in the company.
17) Break up your day.
One on ones are a change of pace from other meetings. These meetings aren’t about deadlines and decision making; they’re about your employee and what’s important to them. That can be a breath of fresh air in a hectic day of meetings, powerpoint decks, and fighting for Inbox Zero.
18) Have an excuse to get outside the office.
It’s often helpful to get outside the conference room for these meetings, as it helps further establish the context switch from being all about what the company needs to what your report needs. If the weather permits, going for a walk can be refreshing. Aaron Sorkin, Mark Zuckerberg, and Arianna Huffington are well known for walking meetings, so why not give them a try?
19) Have the conversations you never get around to.
How many times does a thought cross your mind that you should talk to someone about? Maybe it’s something you know you should do in person, so you don’t send an email. Then a week goes by and you realize you never took the time to have that conversation and now the problem has gotten worse. One on ones are a great time to talk about those topics and by having them regularly, these topics will never build up too much.
20) Be more consistent with your team.
Are you treating your team equally? Do you fairly divide your attention or does the squeaky wheel get the grease? No matter how hard you try, there’s a good chance you’re investing more time in some people than others. By giving everyone a set amount of your time to focus on them in a 1 on 1, you can ensure no one is getting completely lost in the shuffle.
21) Have a happy, motivated team.
In the end, all of these reasons are just small pieces of what it’s really all about: getting the most out of your team and developing your people. One on ones are a big part of making sure you do all the little things that add up to creating a happy, motivated team.
(Bonus) Do it right the second time.
Maybe you tried 1 on 1s before and they didn’t work for you. Were you consistent in holding them? Did you follow through on issues they brought up? Did you give them a real chance? You have to follow through on what you hear and give a few months to really build trust to tackle big issues in 1 on 1s. They’re too important not to give them another chance.
Can you really fit all of this in a one on one?!?!?
No, you can’t cover all of this in a single one on one. And without one on ones, it’s highly doubtful you can ever hope to cover all of those important things. However, over time, you can cover all of these areas in regular one on ones.
It’s never too late to start. As the old Chinese proverb says:
“The best time to plant a tree is 20 years ago. The second best time is today.”
There are many competing demands of your attention as a manager, many of which pay off faster than the long term investment in your people. One on ones are a tremendous tool and an essential part of being an effective manager.
Being a manager is hard. It’s an entirely different set of skills than what you learned as an individual contributor and good resources are few and far between. Most companies, especially if they’re startups, have no leadership training, so you’re often on your own. Making matters worse, you often have more bad examples of management around you than good ones.
So what’s an aspiring great manager to do? It starts with understanding the harsh truths of the role and then getting the right help.
The Harsh Truths of Being a Manager
1) Leadership is service to your team.
When you become a manager, it’s no longer about you. You are judged based on how your team performs, not how you produce. The most important thing you can do is motivate your team and focus them on their most important tasks.
This is a hard mentality to set when you are used to only having to worry about yourself. However, if you shift your mindset to that of serving your team, you’ll find it a lot easier.
Service to your team means . . .
. . . removing blockers for your team so they can get things done.
. . . listening to problems and helping address them quickly.
. . . shielding your team from distractions.
. . . accepting responsibility if something goes wrong.
. . . showering credit and praise on your team when something goes right.
There’s a special kind of satisfaction that you get when you see your team excited after conquering a major challenge that you rallied them to complete.
2) Your best people are easiest to take for granted and most devastating if they leave.
You don’t have to work for long to recognize A players. They’re hard working, always learning and produce great results in their field. As a manager it’s easy to take these stars for granted while you’re fire fighting and dealing with struggling team members. Unfortunately, taking them for granted means that you may not realize they’re unhappy until they have another job offer and it’s too late.
To retain your team, you should never take anyone for granted or go too long without talking with them. One on ones are the most powerful tool in a manager’s arsenal to avoid this grave misstep, so start them today if you haven’t already. You can also use the Management by Walking Around approach to also accomplish some of this, although the privacy of a one on one will give deeper insights.
You need to challenge your best people regularly, create opportunities for them to grow, praise them, and give them work that excites them. These things will change over time, which is why you need to regularly talk with them and not wait for them to come to you. You also need to listen carefully as they are often your front line for detecting problems early; fixing problems while they’re small helps you avoid constantly triaging major problems that consume all your time.
3) Your team members are more than just cogs in your machine.
Even at a big company, 9-to-5 job your team members are still giving you one third of their current life by working for you. If you’re part of a startup, it’s often significantly more time. Appreciate this as well as the fact that there are things that happen outside their work hours that are important to them.
Members of your team are complete human beings. They have a family, hopes, dreams, hobbies and passions. When you show you care about them as a complete person, it makes them more engaged with their work and more trusting in you. It will vary from person to person, but there is usually something personal that can lead to work “resentment” as Marissa Mayer calls it. And on the positive side, giving a small thoughtful gift based on their interests will be remembered long after an Amazon gift card or cash bonus.
When someone is extra excited, they often want to share it. When they’re upset, they may need someone to confide in or understand what they’re dealing with. We’re all human and sometimes things outside work (cancer, death in the family, bad breakups, etc) affect us no matter how hard we try. Being there for your team members and recognizing when they need some help (time off, extension on a project or just someone to listen) will pay massive dividends in retaining and motivating your team.
4) Your example sets the tone for your team.
One of the most fascinating things I have observed in my career is how a company takes on the personality of their founders and leaders. For better and worse, you’ll see nuances in how people communicate, deal with good and bad news, and react to customers, clients and team members based on the example set by leaders.
Are you excited about your mission? Are you motivated each day? Do you show patience or are you quick to judge? Are you the first one in the office each day or the first to leave? When you are a manager or leader, the spotlight is on you and everyone is watching. If you watch carefully, you will notice people picking up on your behaviors and often mirroring many of them. You will also see how even something as simple as a sigh or negative body language by you can take the wind out of the sails of an excited team member.
Self-awareness is one of the hardest, but most important, skills you can develop as a manager. Recognize your strengths and weaknesses and pay attention to how your actions impact those around you. The more your team is picking up good behaviors from you, the higher they will perform.
5) A lack of consistency and follow through kills your credibility.
When a leader says one thing and does another or is perceived as playing favorites, they lose credibility quickly. Without credibility, a team will not be inspired to follow them nor perform at a high level.
So on top of all the above challenges, you have the need to be consistent in everything you do so as not to be perceived as a hypocrite. Of course, the challenge is that with all you have going on as a manager, it’s very easy to not be consistent. You may not mean to, but when things get busy and stressful, it’s easy to be forgetful.
This is the harsh truth I struggle with the most. Even knowing so well the above lessons, reading regularly and seeking the advice of mentors, it is still very hard not to slip up and fail to follow through or be consistent. Even the best leaders I’ve spoken to have to constantly work on this one.
How are you supposed to avoid all these harsh truths without any help?
There are apps to help you ship code, track projects, analyze your customers and manage your sales process. And yet, there’s nothing to specifically help managers like you motivate, engage and support your team.
Bloated HR tools like Success Factors are not the answer and were not built with a manager in mind.
I’ve developed a system that has helped me motivate and retain team members for my startup, Greenhorn Connect, and as product manager at KISSmetrics. I’ve learned these techniques from talking to great leaders at startups and publicly traded companies, as well as reading many books on the subject. If you’d like to learn more, sign up for Lighthouse:
Being a manager is tough. If you want help staying on top of what matters to your team and to follow best practices of great leaders of past and present, sign up for Lighthouse.
When I was fresh out of college with a internship at E Ink (maker’s of the display screen for the Amazon Kindle) I emailed the founder and then CEO, Russ Wilcox, to see if he would meet with me to give me some advice on entrepreneurship. Lucky for me, he was willing to schedule a meeting before my internship ended. You can read the full story here, but one of the best pieces of advice he gave me during our meeting was simple, yet powerful: Read 100 Books.
At the time it almost didn’t make sense and led to more questions than answers. What books? Why that many? How fast? By when?
I remember frantically writing down a bunch of book titles he started mentioning and then he stopped me and said the important thing was that they were on a diverse set of topics with different viewpoints instead of any specific books. He suggested trying to read 5-10 on categories like sales, marketing, leadership, negotiation, etc.
Mission Accomplished.
5 Years and 4 months after that conversation, I’ve finally hit the number and now looking back, I realize it’s one of the most important pieces of advice I ever received. I would not be where I am today if I hadn’t read as much as I have. Reading 100 books has done all the following for me:
Helped me better understand the responsibilities of coworkers (especially important as a product manager and startup founder).
Being comfortable in a conversation on just about any subject due to what I’ve read.
Rapidly improved my skills in key work responsibilities helping me accelerate my career and avoid costly mistakes.
If you’re reading this, I encourage you to also read 100 books. But realize it’s not about the number, but a routine of reading regularly that will serve you well throughout life.
Here’s my quick advice on how to make it happen and make the most of it:
1) Read what you can apply immediately.
I’ve managed to read a wide variety of books that have helped in my career and I’ve always chosen books based on what my current challenges and interests are. This has helped me apply concepts I pick up as I read a book, usually over the span of 2-4 weeks, depending on the length.
When I was moving to SF to run product at KISSmetrics, I started out with a great book on Product Management, then dove into a few books on design, before finding myself diving into sales, marketing, leadership and strategy books depending on what was happening at work and my personal life. Every time, I found great ways to build on what I read in my life around me which has helped tremendously with retention and understanding.
I read on public transportation. First it was riding the T in Boston and now MUNI around SF. I love this for so many reasons:
It gives you something to look forward to even when a bus commute might be lengthy.
A book won’t get stolen like your cell phone might be when you have it out as you play Angry Birds/check Facebook, etc.
It gives you bite size chunks of reading as most rides are 10-30 minutes…just enough for a chapter or two.
A book is a great way to get just a little bit more personal space on a crowded bus.
It’s a great warm up and cool down to your work day if you read during your commute.
If that’s not an option for you, build a routine around it in some other way. Maybe it’s 20 minutes before you go to bed, while you eat breakfast or perhaps audio books while you drive to work. It is the routine of always reading something that will carry you through that many books over the years.
4) Carry your book around with you.
Nothing sparks a conversation like someone noticing what you’re reading. Often those that notice read a lot too, which is a great way to make friends and you can get more recommendations for books from them. This also means that if a friend is running late, you always have a productive way to fill the time. I brought Dale Carnegie’s “How to Win Friends and Influence People” with me to Bootstrap Live and ended up talking with Andrew Warner and the guy next to me about how much we all loved it.
5) Write all over your books.
Despite working in technology, I still prefer physical books in my hand. I underline, I highlight and dog ear all my books. Something about it helps me with retention of what I read. Even if you prefer to read on a tablet or Kindle, be sure to take notes and challenge yourself to think about how to apply what you’re reading. It helps a lot to review books you’ve read before when you have that subject come up. It’s amazing to me how often past events line up as examples (or counter-examples) of something I’m reading. I’m always sure to take a moment to consider it and write it down in the book.
6) Always make progress.
Life doesn’t always go as hoped or planned. There are times of frustration and stagnancy both personally and professionally in all our lives. I’ve found one of the best things for me is knowing that no matter what is happening in my life I’m always learning because of what I’m reading. I can always look back and see progress there.
It has also helped that when I’ve had down times, if I read something related to it like a book on happiness or successfully navigating your 20s, I’m actually being proactive about the problem and getting advice from someone great who took the time to research and write a book about the subject. —
Remember, this is not a race. The point of reading all these books is to absorb all the ideas and skills shared in the books, not race to the end.
I’ve heard some people like to skim books and think that doing things like reading the opening and closing paragraphs of a chapter and reading headlines in the chapter is enough. They’re either reading the wrong books or missing out on some deep lessons.
As a wise man once said, “Anything worth doing is worth doing well.” It is the journey to 100 books that I both enjoyed and grew tremendously from…not the milestone of specifically 100 that matters to me; I haven’t stopped reading and won’t anytime soon.My Amazon Wishlist is longer than ever (please suggest the best books you’ve read in the comments!) and I can’t wait to learn through more great books for the rest of my life.
In January 1975, Popular Science magazine ran an article on the first consumer computer: the Altair. Ed Roberts, the founder of the company making the Altair, ran ads in the magazine for pre-orders of his device for a then-shocking $400. He needed to sell 200 to break even, but ended up selling over 2,000 instead. There were many challenges in actually delivering the device and plenty of upset customers due to delays and limited functionality, but it marked a key moment at the start of the PC revolution. A small company named Microsoft would work closely with them to run BASIC software on it and many other hobbyist computers would emerge in coming years.
Today, the chosen pre-order crowd-funding source is Kickstarter and once again early adopter backing is funding a new revolution: consumer 3D Printing.
A quick search shows there have been over 75 projects posted on Kickstarter related to 3D printing. Of those, 5 are currently active and 35 have been funded (a 50% fund rate on completed campaigns). Since the start of 2013, 38 of these projects have launched, with 17 funded and 16 failed (the other 5 are still active). Some projects have even raised millions of dollars like the Buccaneer ($1.43mn, 3,520 backers), RigidBot ($1.09mn, 1,952 backers) and the 3Doodler ($2.34mn, 26,457 backers). All 3 of those projects launched in the last 6 months.
So with all this funding, how is it affecting those that post? To find out, I spoke to a variety of companies currently crowd-funding, planning to crowd-fund and already completed both successful and failed campaigns.
Preparation matters
The first thing that stood out for all the companies that I spoke with was how important preparation was for their projects. No matter how much time they spent to understand the work ahead, there were always surprises and new challenges. Those that hadn’t figured out the finer details of their project before launching the Kickstarter were significantly more likely to fail in funding.
The preparation also extends to marketing. Designer Todd Blatt, creator of the funded Google Glass project, GlassKap, observed, “[Many projects] think you just make a Kickstarter and people come. You can’t count on that.” I asked companies what the ratio was for backers that came organically from Kickstarter versus their own efforts and it was usually 60% their efforts. Getting ahead in their marketing meant thinking about press and forums to post to at launch and building lists in advance. DeltaPrintr, a delta-style RepRap design launching in the fall, is smartly already collecting signups on their detailed website which explains their product’s benefits and differentiators.
The value extends beyond funds
Like a good angel investor, many of the backers on Kickstarter add more value than just their money. File2Part, a 2012 campaign for better 3D printing software, found that about 15% of their backers were tremendously helpful in debugging their beta release of their software as the backers were also software engineers. Meanwhile, DGlass3D, a current campaign to create a better dual extruder for 3D printers, has already gotten great feedback from hobbyists and hackers backing the project.
With so much traffic and attention given to many of the Kickstarter projects, it can also be a signal to those in the market that your company is someone they should work with. Volumental, a current campaign for browser-based 3D scanning and printing, has received numerous business opportunities because of the attention around their Kickstarter. They’ve also turned the campaign into press that extends beyond the project and helped raise the visibility of their company.
Even more impressive is how a failed campaign by 3Dagogo actually inspired them to start their business. Their May 2013 campaign to sell 250 useful 3d printing designs did not fund, but many members of the 3D community reached out to them saying they were working on an important problem. That was all the encouragement they needed and they’re now working towards a site launch.
Critics can be harsh
While Kickstarter tries to manage backer expectations on projects, there are still times when users can be difficult or even angry. In the case of DGlass3D, some potential backers were upset with the way they planned to handle their IP for their design (a hot button subject in the 3d community). After some passionate discussion, it led to DGlass3D changing their IP plans and updating their description of it on their Kickstarter page.
Meanwhile, File2Part has had a number of delays on their project enraging some backers. Co-founder Eugene Giller told me that when they launched the campaign, they had a prototype of the software working with the printer they owned. Unfortunately, there are many variations on the firmware for other printers and some companies not only change them, but sometimes make them closed to 3rd parties (most notably, MakerBot). It has put them in a endless loop playing catch up, which unfortunately not all backers empathized with:
Stories like File2Part’s is why when I spoke with DeltaPrintr, they told me they are trying to have everything in line, even suppliers and manufacturing, before they launch their campaign. They hope that Kickstarter can simply then be the platform to connect with their first customers and add the funding needed to fulfill orders with their manufacturer, without delays and drama.
Funded projects do not guarantee success
It would be great to say that every campaign that funds on Kickstarter has a fairy tale ending of delivering on time and launching to ongoing success. Unfortunately, we know that’s far from true.
Going beyond the disappointment of the end user who may receive their orders late, below their expectations or sadly, not at all, companies can face struggles as well. After the costs of making his video, marketing and adding the cost of printing the objects, 3D designer Todd Blatt found he didn’t make any money on his funded GlassKap project. He did tell me, he will likely do another project in the future based on his learnings from this one.
File2Part, who had the aforementioned firmware challenges, actually hired a consultant to help them with those issues. Unfortunately, the cost of that consultant exhausted all their funds raised which led them to take a loss overall on the project.
Understand your audience
The stories of success on Kickstarter have spread far and wide, which is why all of the people I spoke with turned to the platform for their company. However, it’s important to realize that like any website, there’s a specific audience that is generally found on Kickstarter. They are often consumers, with a bit of an early adopter and hacker edge to them. Some will back many projects, showing more allegiance to Kickstarter than any of the individual companies they back.
This proved a solid audience for GlassKap, as Todd was able to fund his project even though there are only 10,000 Google Glasses in the public now. Similarly, the consumer-friendliness of Volumental’s browser-based scanning also funded well with the Kickstarter audience.
Meanwhile, 3Dagogo’s 250 3D print designs failed to fund, as many Kickstarter backers are still waiting for their Kickstarter-backed printers and many of the hackers and hobbyists with printers already have proven to be less interested in the pre-made designs. And while File2Part did fully fund, they found many of their backers were not who they were hoping for; their goal is to build an industrial-grade 3D printer to sell and were not expecting to have so many consumer printers to support.
Kickstarter is an amazing platform for discovery and funding of great projects. Like the pre-orders of the Altair, it doesn’t always go as planned, but great things can come of it. Two 20-somethings from Harvard moved to New Mexico to write the software for the Altair. We may not have had Microsoft today if early adopters of the Altair hadn’t sent those checks to get their first consumer computers.
What new industry titans will come from crowdfunding like Kickstarter and the ecosystems they help create?
You can have the best idea in the world, but until you find someone besides yourself that wants it, it’s not really a business. To find those people, as Paul Graham wrote in a recent essay, you have to “Do Things That Don’t Scale.” The problem is, it is often unclear what those “Things” are.
Before we get into the massive list of tactics below, I want to be clear on what to do with this list and what to expect when you find a few tactics you want to follow:
Understand you’re going to have a low success rate.
There is no silver bullet for finding users for your startup, just tactics like the ones below that work to varying degrees depending on your idea and market. Even for good channels, a 10-20% response rate is normal, so don’t get discouraged.
Don’t worry about scaling! None of the ideas below are really scalable when taken literally. However, like Paul Graham said in his essay: don’t worry about scaling right now. Just do whatever it takes to find people and the scalable methods will emerge later. If you have a cofounder worried about scaling early, have them read the Paul Graham essay.
Remember your manners and personalize. You’re likely asking people to talk to you when you have nothing but an idea and maybe a prototype of some sort. Be respectful in communicating with them. Also realize that no one likes a form note, so the more you personalize it and make it feel like they’re special, the better chance you have of a response. Elizabeth Yin of Launchbit has an awesome slideshare with advice on reaching out to customers effectively.
Don’t get banned.
If you abuse any of the tactics below, many of the sites and groups will ban or block you. Pay attention to restrictions to how often you can do certain things (like Meetup.com allows you to message 12 users per day). Realize the more times you break a terms of service, the more likely you are to get noticed and banned. On the flip side, it is easier to ask for forgiveness than permission. Just don’t be egregious.
A special thanks to these people that helped edit & provide ideas for this post:
You can sign up for updates and early access to chapters that will help you build product customers will love by signing up here.
95 Ways to Find Your First Customers for Customer Development and Sales
Linkedin:
1) Use Linkedin Answers: Look for people asking questions around your problem and market or ask your own.
2) JoinLinkedin Groups: Join Linkedin Groups for your target market. Engage in discussions there, reach out to people that post relevant ideas or questions, or post looking for help.
3) UseSearch + InMail: If you know the kind of person you want to talk to, try searching for them (like VP Marketing at companies between 25-200 employees) and using InMail to message them.
4) Check your existing connections: People change careers a lot more than you may expect. You may have also lost touch with an old classmate that is now in just the right market. Either way, your existing connects are very likely to respond and you’ll have access to their email address, which is better than their LinkedIn inbox.
5) Ask your connections for intros: It’s quite possible the perfect people to talk to aren’t already a connection, but they may be one degree away. Don’t be afraid to ask connections you have a good relationship with for an intro.
6) Post to the Linkedin Social Network: Linkedin now has status updates you can post. It’s a lot less active than other networks, but it can’t hurt to see if anyone notices.
7) Run Linkedin Ads: Linkedin is the network for professionals and their careers. If your startup idea has them as the target customer (say marketers or executives), then an alternative to the high maintenance of Linkedin Groups can be to run ads. Linkedin also has a partner network for a lot of business content sites which can further the reach. There’s a great guide on KISSmetrics for Linkedin Ads here.
Facebook:
8) Look up your friends: For most people, their closest people in their life now and in the past are on Facebook. If you haven’t already exhausted your existing network on Linkedin, definitely look to see if any of your friends are in the market and worth talking to.
9) Ask your friends: There’s also a lot of random people you met in college and other times. You never know who knows who so you have to ask. I just got introduced to another person in tech through someone I was in a beirut league with in college.
10) Look for Fan Pages: There’s fan pages for just about anything you can think of. People that run those pages in your market are great people to talk to both as potential customers and to see if they’ll post something on your behalf on their page. Friends who have leveraged this have found it cheaper than Facebook ads, even when they pay the Fan Page owner. Just click the “message” button on the fan page.
11) RunTargeted Facebook Ads: If you think you really know your audience demographics, then running a small set of Facebook ads to a landing page, can be a great way to garner interest.
12) Try the new Graph Search: I haven’t had a lot of success using it, but it’s worth searching for things related to your market to see if anything else turns up, especially now that you can message people you aren’t friends with. In particular, Facebook has a great geographic filtering ability you won’t find on Twitter or otherwise.
Twitter: (My personal favorite)
13) Ask your followers: If you have any kind of follower base at all, you should definitely tweet about who you want to talk to. If you don’t have a big follower base, ask the people with bigger followings you’re friends with to ReTweet you. As you develop your idea, you may want to tweet different requests, which may be seen by different people since no one sees every tweet of their followers.
14) Ask your followers for referrals: It’s not just about who you know. The bigger benefit is who your network knows so be sure to not just ask people you follow or follow you if they’re a fit, but ask others for referrals.
15) Run Twitter Ads: Twitter ads can be a cheap way to reach people you’d never know otherwise. We got thousands of sign ups for MyAnalytics App at KISSmetrics using them. Like any channel, the more mature it gets, the more expensive it will become, so by 2015, this may not be nearly as economical (like many Adwords today).
16) Ask Twitter Accounts to tweet on your behalf: Just like you can ask Fan Pages on Facebook to talk about you, you can reach out to Twitter accounts in your target market to see if they’ll tweet something for you or ReTweet you. If it makes sense for your business, you can also ask some celebrities via tools like BuySellAds and Sponsored Tweets.
17) Search for relevant Hashtags: Hashtags are a big part of Twitter for many markets. For example, in the analytics market, there’s #Measure. Find accounts using the hashtag and reach out to them and join the conversations happening. Find relevant hashtags by asking others or checking out sites like Hashtags.org
18) Join a Twitter Chat: Many groups have regular chats that can be found based on the group’s hashtag they use. A great example is the Community Manager chat, #cmgrchat. This is a great way to ask questions and engage your target audience if they’re holding Twitter chats.
19) Search Twitter for People Talking about your Problem: Remember that time you were really annoyed at a company? What did you probably do? You tweeted about it. Try searching different ways for people talking about frustrations and you’re bound to find people happy to talk because they’re excited someone is going to make things better. I’ve successfully used this to talk to people about, of all things, email migration.
Email:
20) Email relevant friends/contacts: There’s a right way and wrong way to do this. Yes, you can spam all your contacts in one big dump asking for help. What will yield a better result is if you invest the time to be more targeted in who you reach out to. Close friends and family won’t mind and those actually related to your target industry.
21) Start a personal newsletter: I’ve known some people to start a personal newsletter to have their contacts *opt into* that then regularly updates them on your startup journey and can ask for specific help then repeatedly in the newsletter. This works great for getting mentors and early supporters engage in a small ask (just opt in) and later help more as you have different needs.
22) Use Rapportive to find emails & cold email: Somehow you may have stumbled upon someone you’d *love* to talk to, but you don’t know them. You can use tools like Rapportive to guess the email address and send them a personal note asking to speak with them about what you’re working on. You can find more advice on this tactic here and here.
23) Make your GChat status a call for help/intros: This may seem simple and passive, but you’d be surprised who reads your GChat statuses. Adding a note of what you’re looking for and leave it up for a few days and you might just get a few people to help you out. This works for other chat tools as well, of course.
24) Make your signature a call for help/intros: Just like your GChat status is a long tail way to get people’s attention, you can use your email signature the same way. Below your name in your signature is the perfect place to let people know. Don’t forget to update your mobile app’s signature as well as your computer’s.
Meetup.com:
25) Join & Attend Meetups in your category: Meetup has become an amazing hub of groups around just about any topic you can think of. Whether you’re making an app for LARPers or a hardware startup, there’s a meetup group likely in your area you should join to meet and talk with group members in your target market.
26) Ask organizers to message the group: Organizers have unique privileges to send messages to their groups. You don’t get what you don’t ask for, so don’t be afraid to reach out to group organizers to talk to them (they may be a great target user) and see if they’ll message the group. They often make no money in running their groups, so you can think of them like the Facebook Fan Page owners previously mentioned.
27) Ask the organizer to allow you to address the audience at a Meetup: Potentially even better than getting into everyone’s cluttered inbox is the opportunity to address the whole group at one of their events. This allows people most interested to immediately approach you. This can be a great consolation ask if they don’t want to message their whole group since this requires no work on their part.
28) Mention in your Meetup profile what you’re looking for: Like the GChat status, this is a passive move that alone won’t get you everyone to talk to, but you’d be surprised how often people read the profiles of other new members in a group. Be sure to include your desired contact method if you want Meetup members to reach out to you.
29) Message users on Meetup.com: Not every member of a Meetup group attends every event and if there’s no upcoming meetups or it’s a group outside your area, you can still reach users by sending them individual messages. Per a great write up by Melissa Tsang, Meetup has a limit of 12 messages per day, which is still enough to get some quality responses as she writes in detail about.
30) Create a Meetup group: Just because a group doesn’t exist, does not mean there would not be interest. Countless people have launched successful businesses based on the idea of organizing a high value group. Just remember that if you do this, not only will you build trust and relationships with all the attendees, you’ll be the organizer who can send all those messages, decide who addresses the audience, etc.
Your Blog:
31) Write a blog post about the problem you’re solving: If you feel you know some of the key problems that users are facing in your target market, write about it! If it resonates with them, they will share, upvote, tweet, etc it and some will even sign up as long as you remember to have a call to action to sign up at the end. You can see an example here, where 1,000 reads turned into 10 sign ups and a look at some famous companies that started with a blog here.
32) Post your blog to discussion sites in appropriate categories: Sites like Reddit and HackerNews are awesome to access established audiences for your market. Before posting, do your homework so you actually post it somewhere it’s welcome; a baker would not be well served to post their baking innovation on HackerNews, but a marketing startup would do very well posting to Inbound.org. By posting it to these sites you’ll significantly increase the reach of #31 and might also get some interesting commenters there you can reach out to like this example from Vero.
33) Update your About Page for what you’re looking for: Just like #23 and #28, it is always beneficial to list what your looking for on your About page. The most engaged people on your blog are likely to click to your about page to see who you are and if they see this, they can help even if they don’t read your specific blog post about your idea.
34) Make a page on your blog just about your market: Depending on your blogging platform, this could be easy or hard, but it can never hurt to organize your information in a way that people can easily navigate it. If you’re writing a whole series of items or have already created a lot of related content, this can be a great way to assert your expertise and act as a honeypot to draw in interested potential customers.
35) Start a blog just to talk about your industry: Don’t already have a blog or don’t want to talk about your startup on your existing blog? Then start a new one. It helps to have more content than just one post, so if you go this route, try to have a few posts you can post over a few weeks. If you know your startup’s domain, you can make this the start of your company’s blog. Especially for blogs like this, try to get users to either sign up for an email list or to explicitly sign up for customer interviews.
Other Blogs:
36) Reach out to other bloggers for interviews: Chances are, there are other people writing about the market and potentially even the problem you’re interested in solving. These people are generally very knowledgable on the market and so they make great customer interview candidates and can also shed a light on more places to look for people in your market.
37) Ask other bloggers to run an ad for you: Many bloggers, like those fan page owners, don’t make a lot of money, so they may be willing to run an ad for you for very cheap or mention you in a relevant post just because they’re nice or like you.
38) Ask other bloggers to write about you: Going beyond an ad (which may be seen on multiple posts) you can see if a blogger is willing to write a whole post about you. If you’ve already interviewed them and they’re excited about your idea, this may be an easier ask than you think (and thus do it for free).
39) Ask to write a guest blog post: If your own blog has no audience, the best thing you can do is get a post you’d write on your market/problem on a blog that does have your desired audience. Bloggers love having more content to share, so if it’s a good post, they’re very likely to be willing to publish it. Look for guidelines and advice on guest blogging on sites you want to write for like on KISSmetrics’s blog.
40) Use Blog lists to find the right blogs: Not sure who to reach out to? Sites like Technorati, Blog Catalog and AllTop are great for finding out top blogs for things like Top Fashion Blogs or just about any other category. You can also look for other influencers on sites like Klout and PeerIndex.
41) Reach out to commenters: If you see passionate comments on someone else’s blog, follow the link and the profile/name from the comment to find out who they are and reach out to them. People usually will include a link back to their own blog, About.me profile or Twitter account from such a comment. This will give you a more direct, personal way to reach them, and avoid writing a bunch of comments, which the blog owner may then mark as spam and never be seen.
42) Reach out to people that ask relevant questions: If you can see who asked a good question related to the problem you’re solving, reach out to them using any methods the site allows to see if they’ll do an interview.
43) Answer questions about your problem/market: If you’re already knowledgable on your market, don’t be afraid to jump in and answer open questions. The people that ask can become great people to talk to and are more likely to be responsive if you already helped them with your answer. Don’t be afraid to drop a mention of what you’re working on right in the answers. Thomas Schranz at Blossom.io has done a great job of doing this in a helpful, non-spammy way.
44) Reach out to great answers: If you see someone who has given some great answers, they are likely very knowledgeable in your market and the problem you’re solving. Reach out to them to do an interview. Obviously, you’ll want to be careful it’s not a competitor. ;)
45) Ask questions to see who answers: There’s no reason not to join the conversation by asking questions as well. Reach out to the authors of any answers you find satisfactory or interesting. The best part of asking your own questions is that virtually every Q&A site will send you alerts when your question gets answered so you can easily keep track of them even if you ask a few.
46) Put Calls to Action in your Profile and Answer Subheadings: Sites like Quora allow you to put whatever subheading you want below an answer, so don’t be afraid to mention something about your startup there. Also, like the other sections, always put in your profile what you’re up to so anyone that checks you out (even for answers you may have written in other areas) can find you and potentially reach out.
47) Approach people in native environments: Would your target customer be found in a coffee shop, grocery store or mall? Then go there and try talking to people. Like anything this is a skill. This can come off as harassing or creepy (and the store may ask you to leave) or it can work great. The founders of Sincerely have been know to walk over to a nearby mall and offer strangers money and app credits so they can see how a user uses their app.
48) Look for people unhappy with a service: Are you trying to make a real world activity (like finding a locksmith or a good mechanic) better? Then looking for disappointed people near that service may be just the unhappy customers you could delight with your service. After taking a bad cab ride, you’d be the perfect person to explain all the reasons you’d likely prefer to take an Uber next time.
49) Go to conferences for your target audience: Just about every industry has a few conferences related to it. Established businesses get booths, thought leaders speak and many deals get done. You should be there too as you’ll never find such a concentration of people in your industry. Take advantage of attendee lists to figure out who you want to meet with. Offer to volunteer or just ask for a discount ticket because you’re a startup and you’ll be surprised what you may get.
50) Go to trade organization events: Depending on the business you’re in there may be regularly “Chamber of Commerce” style events where your target customers may be. This would work especially well if you’re targeting people who own brick and mortar stores or provide contract services.
51) Go to places you know they’ll congregate: Have an idea for people that own boats? Then going to your local marina is a *great* place to find boaters to talk to. Golfers might just be at the golf course or driving range, frequent fliers at an airport and teachers at a school. Timing is obviously everything, so be cognizant of when someone looks like they’re approachable and have time to kill versus trying to hurry somewhere else.
52) Ask people on long train rides or airplanes: I’m always amazed by the kinds of people I meet when riding Amtrak or flying. Sometimes serendipity can work in crazy ways, so don’t be afraid to tell random people you meet what you’re working on. They might just be helpful or someone nearby will overhear and jump in.
Your existing user base (even if small)
53) Offer a user Referral Program: You need a great product before you should be trying to aggressively hack your growth, but that shouldn’t stop you from offering an incentive to your existing users to help you get more users. They likely know where to find more of them (their social graph, emailing friends, etc) so a little incentive will get them to help you out. There’s a great Quora thread on the subject here.
54) Ask your users via email: Especially in the early days, you should regularly talk to your users and be updating your whole user base regularly. As part of those updates for new features, major bug fixes and outreach, don’t be afraid to ask them for referrals to more users or people to talk to.
55) Always ask your users when you talk: Whether you’re doing a customer development interview, usability testing or just talking to a user about a support case, remember that you don’t get what you don’t ask for. Ask them both if they know anyone specific who might also be interested in your startup as well as places they generally find other people. The latter may turn out to be a meetup, a Twitter chat or something else that is very target rich for you, but you would never have known.
Craigslist
56) Look for relevant postings: Does your startup idea do anything that is relevant to one of the many Craigslist categories? Quite a few companies have had great success building a massive business off just 1 category (see below). Try reaching out to posters to talk to them and later you can potentially scale this. AirBnb is the most famous recent example, which Andrew Chen highlights well here.
57) Make your own post: Just like you can respond to posters, you can also make your own posting in the appropriate category and filter the ensuing responses to find the right people to talk to. A friend working on a startup recently used this to success by making a basic post and then sending all respondents a qualifying survey to make sure they were a match. A small cash incentive in the posting will generally drive a solid response rate.
Forums, Micro Networks & Communities on the web
58) Join in the conversations on the sites: Just about any community exists on the web today. Many of them are in places you would have no idea exists until you dig in. If you can’t find them initially, ask some of the early users you meet using some of the other tactics listed in this post. Once there, look around for people already talking about your problem you’re solving and join that conversation to learn more. You can also post new discussions specifically on your target subject to see who is interested.
59) Message individual users of interest: If you see someone talking a lot about the problems or opportunities you’re working on, see if you can send a private message to them on the forum or at worst just reply to one of their comments asking to speak with them. Anyone sufficiently passionate will be excited to share their thoughts.
60) Reach out to moderators: If this is truly a community site (and not another company’s forums) then the moderators are often the most passionate people of all. Reach out to them as great people to talk to and learn from. As a moderator, they’ll be spending as much time as anyone following all the conversations there so they could provide valuable insight beyond their own experiences. If it is a company’s forum, then tread a bit more carefully depending on if your idea is competitive or complimentary.
61) Ask Moderators to post on your behalf or run an ad: Many forums on the web are run with very little revenue and more as a passion project. Therefore, much like some of the previously mentioned Fan Pages, etc, they may be open to posting on your behalf or running an ad for a very small fee. They’ll know the ins and outs of the site, which will give you a better chance of reaching the maximum audience.
Google Adwords & other ad networks
62) Run Adwords with a landing page: An efficient (though at times costly) way to build an early user list is to run a quick, targeted Adwords campaign linking to a sign up landing page. You can learn how to set that up here. There’s also good advice on evaluating the success or failure of such a campaign here and here. Realize that paying to get a bunch of people on a list doesn’t validate much on its own. It’s then using that list to reach out to users and talk to them and ask them to pay for something that does.
63) Run ads on lesser known networks: Google may have the largest audience, but not the cheapest or best targeted. Consider your market and think about if other ad networks would work better. There’s everything to consider from Yahoo and Bing to mobile ad networks or blogger ad networks. You can find a list of alternatives here.
64) Have your SEO basics in order: What’s better than the perfect Adwords campaign? Showing up organically for searches on your problem. Great SEO takes time, but you can make sure to have the basics right from day 1 so that you can at least get a trickle of interested users to your blog or site. There are a lot of great tips on the KISSmetrics blog including this great SEO Guide for Beginners.
Newsletters
65) Talk to newsletter owners: Just like passionate people often run forums simply for the love of it, others will run newsletters. If you already subscribe to them, don’t be afraid to just reply to the newsletter and ask for a few minutes to talk to them. Most people are excited to hear from people who read their work!
66) Buy Ads using a newsletter ad tool: There’s a great newsletter ad network called Launchbit. It can be a great help in both finding out what newsletters exist in a category and allowing you to quickly set up an ad campaign across multiple such newsletters.
67) Ask for mentions in a newsletter: In addition to talking to newsletter owners as potential early adopters, you can also ask them for exposure. Many newsletters have no formal advertising system like Launchbit, so often you can just go direct to them to ask for a mention for little or no cost. The more excited they are for what you’re doing, the less likely it will cost you anything.
68) Start your own industry newsletter: If you don’t find any newsletters in your category or are think there’s room for another one, then don’t be afraid to start your own! It will take time to build up an audience, but it’s a great way to put to work all those signups you’ve been driving to your landing page. Often times, it’s easier to first get people on a newsletter and then later convert them to a paying customer.
Complimentary Startups
69) Reach out to complimentary startups: No matter your industry or idea, there will be others in the market you compliment. At KISSmetrics, there were many other SaaS tools we were happy to integrate with and swap customer/mailing lists. In most cases, our analytics was something their users needed and many of our customers could use a support tool, call tracking metrics or track a MailChimp email campaign. The best case for success with this method is to target companies of similar size (ie- mailing lists and user bases are of similar size) as that assures an equally mutually beneficial relationship.
70) Ask to guest post on their blog: Just like there are industry blogs run by volunteers and people just generally passionate about the space, there are also companies with prominent blogs. One of the biggest challenges they often have is having enough content. Reach out to someone on the marketing team or any contact info you see on the blog and propose topics that allow you to naturally link to what you’re doing.
71) Find their users and reach out to them directly: If you think your idea would be helpful to that company’s audience, look for people actively engaging and discussing the company on all the platforms I’ve been writing about throughout this post. While it’s better to ask for forgiveness than permission, remember again to use tact so as to not be spammy or offend the company.
Your Competition
72) Watch what they do: As the saying goes, “When in Rome, do as the Romans do.” Chances are your competition has figured out at least a couple of spots where your customers exist and you can enter the conversation there as well. In more modern terms, if something they do works, then consider Jobs’s favorite quote, “Great artists steal.” Like their Facebook page, and follow the company and key employees on Twitter for some inspiration based on what they link to.
73) Look for social mentions: Especially if you’re trying to disrupt a large incumbent, there’s likely many people talking about your competition. Look for especially people complaining about the product or experience. These are perfect people to reach out to learn from and hopefully convert to giving you a try. This also works for other startups you’re competing with.
74) Use research tools: Tools like MixRank, which shows the ads a site has been running, and Spyfu, which shows you the expected ad spend and keywords purchased for competition. If you’re looking for inspiration on the kinds of ads to try, those tools will help you get there.
Data Research Tools
75) Use Datanyze: This tool will tell you what apps any of the top 1,000,000+ websites are using as well as what they’ve recently quit. It’s transformed more than one sales team I know and provides priceless information on the state of just about any web SaaS market. Their free demo can help you understand market share, while the pricey version has alerts for specific tools and lets you see what any site is currently using.
76) Leverage tools that tell you contact info for key roles: If you know the persona of your target customer, then a list like Hoover’s or Jigsaw can help you find some of those types of users at especially bigger companies. Note that this lists they have aren’t 100% accurate, nor are they cheap. Try to hustle access via a friend or advisor.
Your College, University or School
77) Ask your professors: Many professors live vicariously through their students, and are happy to help out current students as well as alumni. If you had a professor that you had a particularly strong relationship with that is relevant to your startup, definitely reconnect with them. Also realize that many professors will talk to alumni who they never taught. Most professors have industry contacts they can help you with introductions as well as be a great channel to their students as potential customers or hires whether via emailing them or letting you address the class.
78) Leverage your alumni network: Whether it’s old clubs you belonged to, a fraternity or sorority or simply the alumni group for the city you’re in, you’d be amazed what people may be doing after school regardless of major or study habits. Don’t be afraid to both reach out to old classmates and club members as well as reach out to the clubs themselves for help from current members. Every student group I was in loved to hear from alumni.
79) Use your alumni directory: Many schools have searchable alumni directories that can allow you to track down contacts at some of the most powerful positions in the world. The shared experience of going to the same school is often all you need to mention to get someone who normally would be unreachable to suddenly be accessible to you for a meeting, mentorship or the right introduction.
80) Reach out to student groups: Even if you weren’t a member of the group, student groups are usually excited to hear from alumni. If any student group fits as a target customer for your startup, you should reach out to them. Playing the alumni card often gets you a great response and can often lead to offers to help you in many ways. They can email their list, let you address the group at a meeting or assist in recruiting help.
Leveraging the Physical World
81) Post an offer in public places: Bulletin boards still physically exist in many places and people still put up physical signs for all kinds of things. The stereotype are things like meetings and guitar lessons, but that doesn’t mean you can’t get attention being creative. If you know there are places your target audience will go to or pass by, consider posting something to get their attention. If you’re doing a Concierge MVP for your idea, this is a great way to start.
82) Use handouts, fliers or mailers: If hanging something up and hoping people will read it and respond doesn’t work for you, consider a more 1 to 1 communication through handouts you can give out or mail. One person I met that had a parking ticket app would carry fliers with him and put their flier under the wiper of a car that already had a parking ticket on it as well. It had a massive conversion rate. Get creative!
83) Buy someone’s service: So you want to start a business serving artists, or maybe housecleaners or some other service? Try buying their service and take a few minutes before or after their service to talk to them. If they care about customer service, they’ll be happy to discuss their problems with you. A friend of mine started his mobile invoicing startup based on the problems his cleaning lady had tracking payments.
Kickstarter & other funding sites
84) Look for products getting funded in your industry: Funding sites are booming which means all kinds of companies and ideas are getting funded. Others in your industry can be incredible sources of knowledge not just on how to run a campaign, but what they’ve learned from interacting with their new customers.
85) Ask complimentary funded projects for help: A fellow crowd-funded project that has finished their funding will be very busy trying to deliver their product to their supporters, but they might just be willing to send a message, tweet or post on your behalf. If their funding is still open, you may be able to swap promotion to your audience and theirs. Remember: You don’t get what you don’t ask for!
86) Reach out to users that backed the project: Every Kickstarter has a tab for Backers which includes their profiles, which you can click to see what else they’ve backed. While they have no messaging system (Indiegogo does), with their full names on Kickstarter, you can likely Google or search Twitter or Linkedin for them and message them there.
87) Put your idea on a funding site: If you feel you’ve validated your idea enough, then running your own crowd-funding campaign is a great way to validate interest for your idea. There is tons of information on the web about making the most of a campaign, just search on Google or Quora.
Youtube
88) Talk to Youtube Channel owners: Youtube is filled with creators making content on all kinds of markets. If you go to Youtube’s channel search, you can search for your category and see who has channels and how many subscribers they reach. Just like you can talk to bloggers as experts in a market, you can learn a lot by interviewing channel owners.
89) Ask channel owners for promotion: If your idea resonates with the channel owner, there’s a good chance you can get them to talk about you on one of their episodes or maybe even have you as a guest. They may charge you a fee, but if it’s your exact target audience, it might just be worth it.
90) Start your own channel: If you think video is a great medium to communicate with your audience then creating a channel to connect with them may be a great option. Just like starting your own Meetup group, it can initially be hard, but once you’ve built an audience it will have a great, long-term payoff.
91) Run ads on Youtube: Youtube leverages Google’s ad powers to run targeted ads. You only pay for the ads people fully watch (not skip) so if video seems a powerful way to communicate with your audience, it’s worth experimenting. Remember, Dropbox started with nothing but a video and got over 75,000 signups (although they did not run it as a video ad).
Your own Product:
92) Put your name on it: If any part of your product can be seen by a non-customer, make sure your name is on it. This is easy, free marketing that your customers can provide for you simply in using your product. KISSinsights (now Qualaroo) had incredible growth without doing any paid advertising because of a simple link in each of their pop up surveys.
93) Make sharing an option for more access: If your product has metered usage, then you will always have customers who are uncomfortable moving up to a new, costlier tier. MixPanel has a free 50,000 events plan that can become a free 175,000 plan if you put their logo on your homepage.I’ve seen countless startups with that logo in their footer for just this reason, so don’t think your users won’t do it until you try.
95) Run ads in your side project apps: A number of my friends have built apps as side projects that end up having a few thousand users that never really monetized or amounted to anything. As a free user base you can always insert your own ads into your app. I met one of the founders at QBix that built the Groups App for the iPhone (helping you organize your contacts) and they used this tactic to drive people to their other apps. You can also send them to mobile landing pages to avoid building anything.
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Woah…that was a lot. Thank you for making it to the end.
I hope a few of these have inspired you and point you in the right direction to find those difficult first few users. While some of them are paid options, I hope you see how many alternatives there are to paid acquisition on Day 1.
Looking for a system to track your team’s long term goals and break them down into the near term goals you need? 
