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?
When a friend left his job, his coworker made the surprise comment that he was about to leave the company as well. What seemed like a few minor problems on the team soon snowballed into a costly mass exodus.
Employee retention is one of the most overlooked aspects of managing your team…right until you start losing good employees. It costs much more than you might expect to replace them. I was curious myself just how much it could cost and the surprising results are below.
Note: All salaries are assumed to be $100,000, which is $40/hr assuming you work 50 hours a week for 50 weeks a year. Adjust the numbers accordingly if anyone costs more or less for you.
The Costs of Sourcing a Hire:
Unless you’re a really hot company, it’s unlikely that great people are beating down your door to fill open roles. And even if you are well known, the best people probably aren’t refreshing your jobs page for an opening. You have to go find them.
You can source candidates a ton of different ways, but they all cost money either in the form of payment to another company or in time invested by one of your employees.
With just a few attempts at sourcing some good hires, between third party costs and labor in your company, sourcing costs can easily reach over $26,000. The scariest thing is, you haven’t even interviewed any of these candidates yet!
The Costs of Interviewing a Hire:
Now that you have a full funnel of candidates kickstarted, you start the dreaded interview process. You’ve got to filter through all the LinkedIn profiles, social accounts, resumes, and cover letters to find those gems who will then navigate your hiring process.
Here the costs are a bit more hidden. It’s all about lost time for various team members. What other great work could your team be doing instead of working on candidate hiring? Every minute spent hiring is a lost dollar invested in your business.
Assuming you have a clear funnel where you only have to look at 120 resumes, only have a third of them make a phone screen, a quarter of those make it to in person interviews, and you prep 3 offers, interviewing costs you over $5,000. For some specialized roles it could be significantly higher if you have many more interviews and phone screens.
The Cost of Onboarding a New Hire:
Congratulations! You found the candidate you’ve been looking for. Now you need to onboard them so they become a productive, integrated member of your team. Again, you have hidden costs. Now, you have losses both in how productive a new hire is versus a veteran on your team, and your team training them (an important investment, but also a significant time sink for your team).
When you hire an employee, there’s often some kind of bonus you need to give them. It might be a salary bump, moving costs, or something else to sweeten the offer. It’s part of the cost of doing business. When you combine that with your costs as they start on your team and get up to speed, onboarding can cost you over $10,000.
Of course, we’re assuming your hire works out, which unfortunately, it won’t always. You can go ahead and double these costs and many of the ones in earlier sections if you have to go back to the drawing board on another candidate.
The Cost of Lost Productivity:
While your team member has departed, the show must go on. The rest of your team has to cover for them, whether that means writing their code, calling their leads, or finishing their reports. As much as you’d like to think the rest of the team can just make up for them, if the hire really was good, that’s impossible. When someone leaves, team members are distracted. Those that were close to them in particular will be less focused and productive. They’ll probably grab beers with their friend before they leave, when they otherwise may have worked late.
Meanwhile, if you push your team to cover for them, the stress and extra hours can affect their physical and mental health, which will lead to vacation and sick days. If hiring drags on, you’ll probably hire a consultant or freelancer to cover which could easily exceed $100 an hour for their work.
All of this combines to lead to a Productivity loss cost of over $24,000.
So let’s add this up…
Ouch! Replacing even a single team member is expensive! Wouldn’t it be a lot cheaper to retain all your good people?
What can you do?
Next time a good employee asks for a raise, investment in equipment to help them on their job, or a morale boosting opportunity is presented, consider the cost of losing them before saying, “we have no budget for this.”
If your manager is blocking you from helping your team, remind them what you’re asking for is a lot less than the $65,000 cost to replace a lost member of your team (let alone the cost of multiple losses!).
While free lunches, ping pong tables, extra vacation days, and other perks are a nice bonus, they aren’t what keep people at a company. Even raises only satisfy people for a short period of time.
What really retains teams is managing people well.
This comes by having discussions with them about their personal growth & goals, company and self-improvement, and recognizing the things that are important to them personally.
I know that’s easier said then done. You have a million things on your plate as a leader and what little time you can spare has to be maximized. And it probably isn’t right now.
You have notes on people all over the place. One on ones are sporadically effective, because you may not always be prepared for the next one. Goals are a great idea in theory, but they’re buried in your HR app you can’t stand. There must be a better way.
That’s why I started Lighthouse. It helps you stay on top of what matters quickly and efficiently for each of your people. It’s designed with managers like you in mind, because I’m a manager myself.
If you want to be the manager people love to work for & save the costs of replacing people, sign up at GetLighthouse.com.
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.
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.
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.)
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.
Want to have better one on ones? Need help staying on top of what matters most to 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?
Great 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
There is nothing harder than starting out or starting over. When you are new, it can be difficult to get your foot in the door and make a good impression. It can be hard to tell the difference between incompetence and a simple lack of experience.
Therefore, if you’re just starting out, there are two skills that are essential and will carry you farther than any others:
If you only have 2 skills when you're young, let them be a fierce attention to detail & a hunger to learn. The rest will take care of itself
Any manager with a new hire has in the back of their mind the questions of, “Can they handle this?” and “How much do I need to keep an eye on their work?” If your manager knows you have an excellent eye for the details, they will be much more trusting in your abilities, knowing that you’ve taken good notes of their instructions, will triple check your work for careless mistakes and won’t do anything to make them look bad. Building this trust can be the difference between a fast accelerating career with new responsibilities and languishing as an entry-level hire for years.
The longer I’ve been a manager and worked on product teams, the more I appreciate this trait. Over and over again we see the evidence of how the little details are what people notice and love (A great example is how Crashlytics built for Tweets which led to their viral growth). This is at the heart of great craftsmanship.
2) A Hunger to Learn.
Unfortunately, minding the details is not enough to succeed. You must also be eager to learn new skills. The faster you level up, the more likely you are to advance in your career whether always at the same company or at new ones. You need to learn from others and seek out sources of information on your own, which are skills in and of themselves to develop.
Many people in other careers have asked me how to get into product management, which isn’t always easy. However, one of the easiest ways to change your role is to work at a growing company and show how fast you can learn and grow. This gives a company the confidence to give you more and new responsibilities.
The Combination is the Key.
When you combine an attention to detail with a hunger to learn, you will be unstoppable. Watching for the little details will make you more inquisitive and help you find the hidden gems and little secrets others gloss over. The little details are where life’s curiosities and greatest lessons lie.
As you grow the confidence of others and use curiosity to drive your learning, you will open new doors and build great relationships with others in your field. You are likely to attract great mentors who enjoy watching your development and love sharing stories and lessons to further your learning. They will also become your strongest advocates, either as great references, or the kinds of people that hire you again and again.
What do you think are the most important skills for those starting out?
Want help developing great young talent? Managing new people for the first time and want to feed their hunger to learn and keep your own attention to detail?
Looking for a system to track your team’s long term goals and break them down into the near term goals you need? 
