3 Keys to Starting to do 1 on 1s with Your Team

“…if Tim doesn’t meet with each one of his employees in the next 24 hours, I will have no choice but to fire him and to fire you. Are we clear?”

– Ben Horowitz, The Hard Things About Hard Things, pg. 102

Ben Horowitz, VC and founder of Opsware (sold to HP for $1.6 Billion), said this to one of his reports when he discovered that a manager had not held 1 on 1s with his team members in over 6 months. Horowitz cared so much about a great work environment for his employees that he considered a lack of 1 on 1s a fireable offense for the manager and the manager’s manager.

Crazy? Over the top? Maybe not. Former Intel CEO and legendary author on leadership and management Andy Grove is an advocate for 1 on 1s as well. Many well known companies today including HubSpot, Moz, and Atlassian, use them, too.

And why do they all make 1 on 1s a key part of their management?

1 on 1s are an open line of communication to understand what is on the mind of each of your team members. It helps you get in front of problems before they blow up and it gives your team a recurring way to have their voices heard. It can also save you from having an employee leave the company without warning.

Even if you’ve bought into the importance of 1 on 1s, there’s still the question of how to get started from scratch. It can be intimidating and a little awkward at first, but with the right plan, you will learn invaluable things in the meeting and have much happier employees.

Ready to start your 1 on 1s? Here are some tips I’ve learned along the way from my own mistakes and the advice of more experienced leaders.

3 Keys to Starting 1 on 1s on Your Team

1) Scheduling 1 on 1s

At least 30 minutes, no more than 60 minutes.

– Context switching can be hard for you and your report. Meetings are usually about work issues, so switching to talking about themselves often doesn’t click right away. For this reason 15 minute 1 on 1s are ill-advised, because you’ll just be getting warmed up when it’s over. Shorter 1 on 1s also run the risk of a late start leaving no time for actual discussion. You can always end a meeting early if everything is good, but you want the flexibility to run a little longer if you’re digging into something important.

Always the same time and day.

– You want to get into a rhythm with these meetings. This ensures you have a regular discussion that your team member can count on. It also helps you avoid having to cancel and move them around constantly. Ideally, you’ll pick a time you know you’re more likely to be around and available on a regular basis.

Choose a frequency you can handle.

– Weekly is best, but if you have too many reports for that or know your team very well, every 2 weeks is fine. If you push to a full month between 1 on 1s you may be going too long between discussions. You will know you need to have 1 on 1s more frequently if every 1 on 1 seems to run long or you struggle to dig into issues that are really important to them.

2) Having a Good 1 on 1

This is their time.

– This meeting is not a status report on projects they’re working on. The other 39 hours (or likely really 59 or more for many of you) are all about what you and the company need. 1 on 1s are a time to listen to them and hear them out. The goal is to help them be more happy and productive at work. Set that standard from the very first meeting and you’ll have much more productive 1 on 1s.

Try to get out of the office.

– You want to hear about issues they’re having and talk about their goals and interests. This context switch from getting work done to talking about them can be hard. It can also be uncomfortable to talk about a problem you’re having with a coworker in a conference room near that person. Getting into a different environment, like going for a hike, to a coffee shop, or to grab a beer at a pub, can all help aide that context switch. Bonus points if you can pick a location they particularly like to further reinforce that this is their time.

Have a few questions ready.

– When you first start 1 on 1s, people can be a bit nervous and reserved.  Some more introverted employees will always be that way, so start from the first meeting having a few questions ready to ask them to spark conversation.  Some good examples of questions include:

  • How do you feel [current project they’re on] is going? Is anything frustrating you? What are you enjoying about it?
  • Is anything exciting you at work right now?
  • What are your long term goals? Do you feel you’re making progress on them? (This is a question that often changes and needs revisited as you build trust.)
  • How could we make the team you’re on better?
  • You’ll find 101 questions for your one-on-ones here.

Be open and listen. It’s a friendly conversation, not an interrogation. The more they feel heard, the more they’re likely to open up. You won’t get everything in the very first meeting, but over time, you’ll see them trust you more and more as long as you avoid the pitfalls that can ruin 1 on 1s.

3) Avoiding Major Pitfalls

Never Cancel a 1 on 1.

– It may not seem like a big deal to you, but it really hurts your team member when you cancel a 1 on 1 with them. In their view, you’re saying, “this meeting isn’t important to me,” which then says to them they aren’t important to you. This is why scheduling the meetings at a recurring time you can stick to is so important. If you absolutely can’t make a 1 on 1, realize that rescheduling is much better than flat out canceling.

Always follow through.

– If you talk about problems they have, but never do anything about them, you’ll only further frustrate your team members. They’ll then shut you out and won’t give you feedback any more. The benefits of 1 on 1s will be lost. Instead, make sure you follow through and follow up with them on the issues they raise. That feeling of progress is what will build trust to discuss more things openly with you. It will also act as a pressure release valve on issues that may otherwise lead to major problems or them getting upset enough to look for other jobs.

Stick with it.

– The first 1 on 1 is often kind of awkward, like a first date. You may have never had a candid conversation about their needs, frustrations, and desires before, which means there is often some guardedness.  Stick with it, because over time, that awkwardness will fade. You’ll build a much stronger relationship with your team, which will have major impacts in the quality of all their work, their happiness on the job, and likelihood of staying with the company long term.


Get LighthouseWant to have better one on ones? Need help staying on top of what matters most to your team?

Then sign up for Lighthouse, the app to help you be a better manager.

How to make your team love you for less than $10

During my time running product at KISSmetrics, I got to work with some awesome people. One of my favorite engineers was a guy named Nate. Nate lives in Ohio with his wife and two kids. He’s a good family man and a solid engineer. He’s always down to go the extra mile to make a feature awesome for customers. He also happens to be a HUGE Mark Price fan.

Nate had been doing some particularly awesome work with me lately and I wanted to thank him in a memorable way.  I had heard others in engineering talk repeatedly about how Nate was obsessed with retired Cleveland Cavalier Mark Price, even wearing his jersey during engineering standups. Having noted that weeks ago, I knew that was the key to a great gift.

Finding the Gift:

Living in San Francisco, there isn’t a lot of Mark Price memorabilia available, so I went to Ebay to see what they had.  Within minutes of searching, I stumbled upon Mark Price Figures and knew I had just the thing.

Mark Price Figurine

#Winning. I could make Nate’s day for less than $10!

The Results:

Using the Buy It Now feature, I quickly received the figure. I then added a personal note and shipped it off to Nate. When he received it, he reacted like a kid on Christmas:

Screen Shot 2014-05-05 at 1.49.40 PM

Screen Shot 2014-05-05 at 11.20.02 AM

Nate also texted me the day he got it.

Even better, Mark Price sits on Nate’s desk to this day.

Nate's desk

Nate’s desk with Mark Price mug and *figure*

You can do this too.

With just a few minutes of my time and less than $10 spent, I made Nate’s day. More importantly, I strengthened our work relationship. There is no amount of cash or gift card that would have meant nearly as much or had as deep an impact. And with it sitting on his desk, he is reminded every day of it.

How to give a great gift to a team member

What you’re saving financially is being made up for in thoughtfulness. Everyone wants to be recognized and appreciated as a unique individual and that’s why these gifts are so much better than money. There are a few keys to remember if you’re going to do this for a team member and want to have the same results.

1) Meaning

The most important thing is to give a gift that uniquely resonates with that person. A Mark Price figure to any of my other coworkers would have been meaningless, but to Nate, it was perfect.

These aren’t just things they Like on Facebook. Pay attention to what your team talks about.  What do they *love*? What are they passionate about beyond what most people are? Those are the things that matter. It could be books, board games, a fashion designer, their car, a certain sports team or player, or a restaurant they’re completely in love with. Just realize that the stronger the emotion, the more meaningful it will be when you present the gift.

2) Timing

Don’t just give the gift to them at a random time. Use it as a reward for great work or a behavior you want to reinforce in your culture. Nate had been going above and beyond on a number of projects and been really helpful in explaining technical challenges to me, a non-coding Product Manager.  It was the perfect time to thank him.

The best gifts are also unexpected. It’s great to use these on birthdays, work anniversaries and the like, but it’s even more powerful when they don’t expect it at all.

3) Reinforcing

If you’ve chosen a gift a team member will uniquely love and will present it to them at a time they’ve been doing great work, congratulations, you’re 90% there. The last thing to do is to reinforce the behavior you’re rewarding.

When I sent the figure to Nate, I included a personal note thanking him specifically for the the things I enjoyed working with him on and the help he gave in explaining technical challenges. This ensured that the gift that got such a positive emotional reaction was now tied to the behaviors I wanted to see more of.

But what about….

I know what you’re thinking. Your team is too big, too remote, too private, too busy, or too <excuse> to do this kind of thing.

If you want to really retain and motivate your best team members, these kinds of things pay massive dividends. You should make time for it. This took me about 30 minutes in total between ordering, writing the note, and shipping it. You cannot put a price on what a heavily motivated employee will do for your company, especially compared to one that feels unrecognized and unappreciated.

The Power of 1 on 1s

The best time to find out these kinds of things is in 1 on 1s. This is especially true if your reports are remote so you don’t get general office interactions. 1 on 1s are the one time a week an employee gets to talk about themselves instead of just what the company needs. Pay attention and you’ll learn what their motivations and passions are. Aligning work with those motives and recognizing their passions will pay massive dividends in team morale.

Nate wasn’t my direct report, but every 2 weeks we had a Google Hangout to talk about what was going on in the company, and catch up personally.  I did this while I was the only PM at a 35 person company often juggling 4 different projects. I also never met Nate in person while I worked at KISSmetrics. What’s your excuse?

Remember the little things

I have the memory of a goldfish (or at least the urban legend version of one). Even meaningful things like this can slip my mind if I don’t record them. That’s why years ago I started keeping track of the passions, interests and motivations of people I work with. The system, when combined with good 1 on 1s and goal setting has helped me be a much better manager and is why I’m starting a company to help others do the same.

If you’re interested in getting early access to my app that will help you be a great, thoughtful manager, you can sign up below:


Get LighthouseWant to remember what matters most to your team? Check out Lighthouse, the app to help you remember key personal details (like Nate’s love for Mark Price), as well as have great one on ones, and grow your team.

Learn more and sign up at GetLighthouse.com

The most important word for motivating your team

Progress. It’s a word that has driven man for generations to grow, develop, learn, and reach for the stars (sometimes even literally). It often feels stale and disheartening when progress isn’t being made.  There’s a reason that Elon Musk, Jeff Bezos, and Richard Branson have all invested in space travel; NASA stopped making progress and they were all inspired to push to advance mankind to space.

For us mere mortals, progress may not be measured on a societal scale, but we all still have goals. These goals are what drive us and motivate us to get up in the morning. As a manager, you are not only accountable to your own goals, but that of everyone on your team.

Do each of your team members make regular progress on their goals? Do projects drag on for months, or do they see results of the fruit of their labors on a regular basis? Whether you’re in sales, marketing, engineering, design or support, progress is hugely important to the mental well being of every team member.

The stakes for progress on your team couldn’t be higher. Engineers that don’t ship product for months have a high propensity for burn out.  Employees in any department will become frustrated and seek challenges at new companies if they feel like they’re no longer growing, learning, and working on things they’re excited about.

As a manager, you need to help your team make progress: Ship. Close deals. Get wins. See results.

But how do you reliably do this? How do you get out in front of potential disaster?

How to ensure your team members are making regular progress

1) Remove Blockers

Few things are as frustrating as feeling like you can’t get your work done because of someone else. Waiting for decisions or dealing with someone who is a bottleneck in a work flow can quickly stall out even the most talented person’s ability to make progress.

As a manager, you can often be the cause of those blockers. Diffuse that source of frustration for your team as much as you can. A great lesson I learned from Jonathan Kay, CEO of Apptopia, is to regularly ask everyone on your team, “Am I blocking you?” and then follow through on anything they ask for you to help them with right away.

When you meet with your team, always ask them if they’re being blocked in any way. The more you can help remove the blockers (even when you’re not directly responsible), the more your team will be able to get done and feel productive.

2) Empower Your Team

Are you a dictator that rules with an iron fist, making every little decision for your team? Or do you delegate effectively to your team, trusting them to make decisions on their own in their areas of expertise?

As a manager, there are too many decisions to make to micromanage everyone. You become much more scalable (and less likely to block them), when you let your team make the little decisions in their jobs. You also are then empowering them to have ownership over their work and focused on accountability to you on the results.

Work with your team to set the goals and expectations, but trust them to do the work you hired them in the best way they see fit. If you can’t trust them to do so, you need to hire people you can trust.

3) Align goals

Every person has different motivations and interests. If you understand what their goals are, you can help them get on the right projects with the right responsibilities. When someone’s work is aligned with their personal and professional goals, you will see them operate at their highest possible performance level.

As a manager, you need to regularly talk about each team member’s goals and interests. Not only will they differ person to person, but they will also change over time. Yee Lee, VP of Engineering at TaskRabbit, reminds himself to check with every member of the engineering team at least every 3 months to see if their long term goals have changed (they often do for many reasons). This ensures that everyone is making progress on their goals and the company keeps everyone aligned with what their asked to do on the job.

4) Watch for warning signs

Every big problem started out as a small one. The more you can identify problems when they’re small, the more likely you are to avoid having to constantly triage major issues that will take up all the time you don’t have.

When projects are making less progress or dragging on, you can often tell based on a shift in morale. Look for signs that people are not as engaged in a project or seem to be growing in frustration. What seems small to you on the outside may be a big issue brewing for those on the inside on a project.

The best early warning is your one on ones. When you ask them how something is going one on one, they’re more likely to be candid than in a group and you can also dig a little deeper by asking revealing questions such as, “What’s the most frustrating part of our project you’re working on now?” Whatever you hear, act on it appropriately and you will not only diffuse the situation, but build trust in your team that they can bring important issues to you no matter the size.

5) Take no one for granted

It’s easy to think that someone who crushes it at their job will want to keep doing it forever. Unfortunately, times and motivations change for everyone and, if you’re not careful, you will lose people when those motivations shift.

You need a strong communication channel to keep your best people. If they trust you, they will tell you.  Joe Stump, co-founder of Sprintly, had a great engineer who told Joe that he wanted to try something new (in his case, marketing). As much as Joe hated losing an engineer, he hated losing a talented team member even more, so Joe worked with the engineer to shift to a growth hacking role they were excited to do and the company needed.

As a manager, it’s easy to spend all your time on weaker team members or people that need the most mentorship. Don’t forget to check in on even your best talents or you may find out when it’s too late. This is why you should do one on ones with *everyone* on your team.

Your people are motivated by one word: Progress.  Are you helping them get there?


Get LighthouseGreat managers help their team make progress on their work, their career goals, and fix problems while they’re small.

If you’re looking for help making *progress* on these things, then give Lighthouse a try. It keeps you organized and helps you follow the best practices of great leaders. Learn more at GetLighthouse.com

Founders: You don’t own your employees

[Ed. note: This is in response to a post by David Hauser entitled, “The Startup Side Project Bubble” which you can read here: http://buff.ly/10Lw9ek]

So many founders forget something simple: You do not own your employees.

They are human beings with their own passions, interests and lives. You have a vision of a reality you want to create. After much labor and hard work to get it off the ground, either funding or your own revenue allows you to hire help. Those people are choosing to devote a significant portion of their lives to your cause to help make it possible. Take a moment to appreciate that. 

In David’s post he argues that employees having side projects is bad for them and his business. This is so backwards.

First, telling someone what they should and shouldn’t do in their free time is a tremendous insult to them and their personal judgment.  It’s also incredibly short-sighted.

You want employees with side projects.

Especially for the creators at a startup (ie- the people that design and build your product), there is tremendous benefit to them having side projects. A few of those benefits are:

  • Experimentation. An outlet to experiment with new technologies before suggesting the company use them; no amount of research compares to having used a new framework and being able to provide first person accounts of the tradeoffs.
  • Independence. A place where they can make all the decisions (for better and worse) versus the negotiations that often happen in a company. You can also call this their creative release.
  • Mastery. The ability to further hone skills in a self-directed fashion, getting them to the 10,000 hours to mastery faster than standard work hours alone would provide.
  • Relief. Providing some variety in their life’s work can help avoid the burnout that comes from only working on one thing for too long.
  • Focus. Motivating them to get their work done efficiently because they don’t have every hour of the day to work on it. The saying goes, “If you want something done, ask a busy person” for a reason.
  • Contribute. The ability to help the greater tech community through contributions to open source projects, which wouldn’t exist without many people having side projects.
  • Network. They’ll often work with people outside their day job on these side projects, which will grow their learning and network. It might even provide the next recruit when you need more help at your startup.

And I’m sure there are others.

Great employees are a package deal.

In the early days of a startup, you want athletes, which are often entrepreneurs themselves.  Later, you want specialists who have deep expertise in their skills. By their nature the same skills you value each day in either group’s work for you also lends itself to having these side projects: In early employees that means a breadth of knowledge, while later, the depth of knowledge that comes from side projects is what makes many great later stage startup employees.

I would not be running product at KISSmetrics if I had only put my head down and worked on my past jobs (I wouldn’t even be in tech now most likely…I have a degree in Electrical Engineering). The skills that are core to my job came from side projects like Greenhorn Connect, taking the time to learn new skills in my free time and reading voraciously. Every founder wants to hire people with passion for their craft and a wide range or depth of skills.  This is a package deal.

“Why don’t you quit your job already?”

Taking a step back and looking at David’s argument, it seems centered around the idea that if an employee has a side project, they should quit their job immediately and start a company. While they should definitely quit their job if they’re ready to make a run at it as a business, they may not do that right away because of a few reasons:

  • Funding. They lack the personal funds and see the foolishness in fundraising when they don’t even know whether an idea has legs whatsoever.  Not all side projects have clear paths to revenue/bootstrapping either.
  • Motivation. Many side projects are for fun and passion. Sometimes those become businesses worthy of full time attention, but usually they are just an enjoyable thing to do with only part of their time.
  • Stability. Depending on what else is happening in their life, it may not be the time to start a company. If they’re getting married, just moved to a new city or a close family member is on their deathbed, they may not want the upheaval of launching a startup on top of that.

None of these reasons prevent a person from being a valuable contributor to your startup. In fact, someone may work for your company and add tremendous value you’d otherwise never receive.

This is a seller’s market.

If you have hard to find skills like design, product management or engineering, it’s a great time to be a startup employee. Companies must compete for you. With salaries skyrocketing, it takes more than money to attract talent. Having a good culture, treating people well and supporting them as individuals become important factors as well.

David’s views may work for him, but I caution other founders from adopting his cynical attitude towards those with side projects. The potential gains far outweigh any losses in hours David seems so concerned with and run the risk of turning off potential great team members.

Building a network is about playing the long game

When I moved to San Francisco, in many ways I was totally starting over. After 8 years in Boston including 3 in its tech scene, I had built many great friendships and connections. I still keep in touch with many of them today, but being across the country is definitely not the same as having beers, dinners and coffees regularly.

I find nothing more fascinating than the challenges and struggles in building a company and how some succeed where so many others fail. I greatly value the insights into how companies are run and the tough decisions leaders face, so it was really disappointing to suddenly miss out on all those conversations I was often privy to in Boston. As I’ve worked to rebuild what I had in Boston, I’ve come to realize an important lesson:

Building a network is about playing the long game.

A number of my friends in Boston are now successful founders and C level leaders. Many are raising B and C rounds right now and two even sold to Twitter for a substantial sum. I’ve learned an immense amount in conversations with them and found their first hand accounts inspiring.

As much as I would love to know the same caliber of successful founders in the Valley right away, it’s unlikely to happen. Instead, what I can do is the same thing I unintentionally did in Boston: get to know people before their startup success. Some of the aforementioned founders I knew when they had just raised an angel round, others before they even started working on their ideas and were instead employees at other startups.

You don’t know Jack.

I hear many people try to get to know the big names in town or even pretend they already do because they talked to Ev or Jack or Zuck once at an event. When you think about the odds of them remembering you or answering your email (if you even have their contact info) it’s pretty slim.

…but you could know the next Jack.

Instead, focus on getting to know the talented people around you that will be successful. Find ways to be helpful for them (much more likely than you being able to help Zuck) and keep it all in perspective; over time you will grow and develop and so will your friends. Like a fine wine you’ll find your network gets better with age. Those same people will happily return your emails and provide assistance no matter how successful they become. They may even work with you on your next venture.