What to Expect When You Start Having 1 on 1s

Ben Horowitz advocates for 1 on 1s. So does Marc Benioff, the team at Bufferapp, and many, many others. Yet, in many ways they’re still shrouded in mystery.

Some people see them as a waste of time. Others are unsure how to make the most of them. Ask 10 managers and you very well could get 10 different answers.

If you’re convinced to get started with 1 on 1s, and never done them before, you’re in for a few surprises. Here’s a few tips for what your should expect:

1) They are different than any other meeting

As a manager and leader, you’re in a lot of meetings. Probably more than you should. And in most of them you’re being asked to give your opinion, make decisions, and answer questions that all focus on driving the business forward. One on ones are nothing like that.

As Ben Horowitz suggests after he took some heat for his firm stance on the importance of having 1 on 1s,

“The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting. This is the free-form meeting for all the pressing issues, brilliant ideas and chronic frustrations that do not fit neatly into status reports, email and other less personal and intimate mechanisms.”

It bears repeating: One on ones are all about the team member, not you nor the company. You need to flip your mindset to thinking about what’s important to them and how you can help. This context switch can be difficult, but the payoff is huge. Set the standard that you recognize that these meetings are different from other meetings and you’ll be on your way.

2) You will learn important things you won’t hear any other way

You may think you know your team really well. You may think you know everything they’re thinking about for work and have addressed all their concerns they’ve aired publicly. If you’ve put in some effort to listen to your team in a group setting, that’s a great start, but there is always more they’ll bring up privately in 1 on 1s.

As URX CEO John Milinovich recently said in his interview with First Round Capital,

“There will always be things that people won’t bring up in a community forum that are still so important to address, especially before they become bigger issues.”

Build a trusting environment in your one on ones and follow through on what you hear and you’ll be amazed at what you’ll learn people are thinking about or have concerns with. The more you act on what they confide in you, the more they’ll share that will improve the company, your team, your management, and them as an employee. For the introverts on your team, who are less likely to bring up any issues publicly, this will be especially important.

3) They should bring things to talk about, and so should you.

It’s easy to put the obligation on your team member to drive the 1 on 1. It’s definitely important to let them talk about things that are important to them. However, especially early on, you need to bring some questions as well.  There’s a ton of different 1 on 1 questions you can rotate through and you can also use 1 on 1s as great coaching opportunities.

As Jason Lemkin (CEO EchoSign, VC @ Storm Ventures) writes,

“You may think you know if you have drinks together, or go see movies together, or whatever…But you don’t.  Even if people complain in that context, it will be general complaints.  You won’t learn what your top people need to find their growth path at your company.  Where they feel stalled out and frustrated.  You have to ask.

By mixing up the questions you ask, you will ensure you’re not missing anything they may be afraid to bring up.  You’ll also avoid 1 on 1s getting into a rut where certain topics become safe and easy, at the expense of never discussing any elephants in the room. You get out what you put into your 1 on 1s, so prepare, listen carefully, and follow through.

4) They may be a little awkward at first

Your first one on one won’t be easy. It can be especially awkward if you recently got promoted and now you’re having a one on one with a former peer. Fight through the ‘fight or flight’ urge to not ask the questions a manager should ask in a one on one. Those early questions will break the ice and give you your first opportunities to build deeper trust and rapport with them. Over time, you’ll get in a rhythm and build trust. Then you’ll probably even look forward to them.

Stick with them. The benefits are huge as Michael Wolfe (PipeDrive, Vontu, Kana) wrote,

“Over time you can build up a very good relationship with most people simply through this time investment. Even though you may need to discuss tough issues, try to build up enough trust and openness between you that you can enjoy solving problems and working to make the company better.”

It’s a relief when a problem at work is solved. If you form a real partnership with your team member to address the issues they bring up, they’ll trust and respect you more even if you don’t always give them the answer they want to hear.

5) You will quickly learn why this is a manager’s best tool.

The conversations in one on ones are the keys to understanding your people and motivating them.  Everyone has different drivers and idiosyncrasies; the better you understand them, the more effective you’ll be able to work with them.

As Ben Horowitz notoriously recalls when he almost fired two people over a manager not having one on ones,

“Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong…and things always go wrong.”

Unfortunately, if you don’t do one on ones, Ben continued,

“…there is no possible way for him to even be informed as to whether or not his organization is good or bad.”

You can fix so many problems and improve the morale of everyone on your team with these meetings. You’ll find out about issues before they blow up. You’ll be able to help people when they’re struggling, and give them good and bad feedback regularly.  You can talk about career goals and growth opportunities regularly. Bit by bit you’ll see improvements across your company and you’ll wonder why you didn’t do them sooner.

black_alphaWant help getting started with one on ones? Want to build a better relationship with your team members?

Lighthouse keeps you organized and prepared for everything that matters to your team members including goals and 1 on 1s. Learn more at GetLighthouse.com

10 Common Ways to Lose Good Employees

I’m leaving. My last day is next Friday.”

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 times before 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.

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?

Get LighthouseWant 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.

Learn more and sign up at GetLighthouse.com

10 Critical Mistakes You Could Be Making in Your 1 on 1s

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?

Get LighthouseWant 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.

Learn more and sign up at GetLighthouse.com

101 Questions to Ask in One on Ones

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.

Questions to talk about Manager Improvement

The saying goes, “People don’t leave jobs, they leave managers.” That means receiving and getting feedback from your team members is a crucial part of your job.

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?

Wow. That was *a lot*!

Shout outs to Popforms, Manager Tools, and this Quora thread for help inspiring this list.


Want to make these part of Your One on Ones?

Get LighthouseYou 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

21 Reasons You Should Start Having One on Ones with Your Team

“I don’t have time.”

“My team is fine.”

“I have too many reports.”

“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.

Convinced to start or try again? Learn how to start having effective 1 on 1s here.


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.