Managers: You’re not prepared for your one-on-one meetings. Here’s what to do.

Four steps to take when you’ve got a one-on-one meeting coming up.

You’re not prepared.

Or at least that’s what employees think when it comes to one-on-one meetings. In a recent survey we conducted of 125 managers and 45 employees, we found 35% of employees believe their manager is only “somewhat prepared” — and 15% of employees think their manager is “not prepared” or “not prepared at all.”

That’s almost half of employees thinking that their managers aren’t as prepared for one-on-one meetings as they could be.

Managers seem to agree. Sixteen percent of managers we surveyed said their biggest frustration with one-on-one meetings is they’re never sure how to prepare or what to ask.

Fortunately, preparing for a one-on-one meeting is neither hard nor time-consuming. Before your next one-on-one, here are the four things you can do (and each takes ten minutes or less):

#1: Get up-to-speed.

You waste time when you’re not up-to-speed. When you walk into a one-on-one meeting not knowing what the person has been working on for the past month, you squander 10 -15 minutes to get caught up on old information. That’s 10 -15 minutes that could’ve been spent discovering and discussing new information. Instead, spend a few minutes getting up to speed before the meeting rather than during it. Specifically:

  • Review status updates ahead of time. You’ll save time by not rehashing “What’s the latest on X?” And you’ll better orient yourself on what the focus of the one-on-one meeting should be.
  • Revisit notes from the last one-on-one meeting. You’ll realize there’s an important topic you need to circle back on, or an action item you need to complete. These notes can also help inform the questions you want to ask for this upcoming meeting.

#2: Ask your direct report to create an agenda.

Ask the employee to create an agenda ahead of time with what might be on her mind. You can say or write something like: “Mind kicking-off the first draft of the agenda for our one-on-one meeting? I want to focus on what you want to talk about, first. And then I’m happy to take a pass and add anything else to it.”

By letting her take the lead and initiate the agenda, you demonstrate to her that it’s her priorities that you want to address first. She’s in the driver’s seat, not you.

Then, of course, you’ll want to review the agenda before the meeting, and offer any additions for what you want to talk about.

#3: Clearly define for yourself: What do you want to know?

Yes, you’re asking the employee to write the agenda — but you also want to think for yourself what you want to know. Is there a concern you have about this person’s ability to work well with others? Are you wondering if they feel challenged enough by the work itself? If nothing specific comes to mind, consider these four areas of focus for a one-on-one meeting:

  • Concerns and issues. What potential problems might be bubbling up that you don’t know about, but should?
  • Feedback about work performance. What does your direct report need to be doing differently? How can you improve your own management style?
  • Career direction. How can you help support this person progress toward their career goals? Are you both on the same page for what progress looks like?
  • Personal connection. What outside of work in their life is going on that you want to know more about?

Reflect on these four areas to generate ideas for questions you should be asking, or topics you think should be covered during the one-on-one meeting.

I’d recommend picking one or two of these focus areas, and then brainstorming at least 3 -7 questions for each area. You may not ask all the questions (or any!), but they are helpful to have in your back pocket should the conversation lag or veer off-topic.

To help you get started, here are some examples for one-on-one meeting questions in each focus area:

Questions that uncover concerns / issues…

  • “When have you felt most motivated about the work you’ve been doing?”
  • “When have you felt bored in the past quarter?”
  • “Is anything holding you back from doing the best work you can do right now?”
  • “Is there any red tape you’d like to cut at the company?”

Questions that elicit feedback about work performance…

  • “Would you like more or less feedback on your work? Why/why not?”
  • “Would you like more or less direction from me? Why/why not?”
  • “What aspect of your job you would like more help or coaching?”
  • “What’s a recent situation you wish you handled differently? What would you change?”

Questions that help provide career direction…

  • “What have you been wanting to learn more of, get better at, and improve on?”
  • “What’s one thing we could do today to help you with your long term goals?”
  • “Is there an area outside your current role where you feel you could be contributing?”
  • “If you could design your ideal role in a company, what would it look like?”

Questions that foster a sense of personal connection…

  • “How’s life?”
  • “What have you been reading lately?”
  • “Been anywhere recently for the first time?”
  • “What have you been excited about lately?”

I always try to ask at least one question focused on personal connection, and use that question to open up the meeting. This helps break the ice at the beginning of your meeting, and builds rapport with your employee. Without this sense of rapport, your employee won’t feel comfortable divulging anything meaningful — nor will she find the conversation much fun.

For more ideas for questions to ask during a one-on-one meeting, you can visit here.

#4: Calibrate your mindset.

Take a minute to remind yourself: This meeting is not like other meetings. You aren’t running it. Your primary job is to absorb the information being shared with you, poke holes to figure out how an employee is actually feeling, let things marinate, and then figure out when you need to do. You shouldn’t be talking. You should be listening and scanning for the truth.

These four steps takes 15 minutes, maybe 30 minutes at most, to complete in total. That’s 15 minutes — 30 minutes of preparation that ensures your hour-long one-on-one meeting is not an hour wasted. Invest in preparing for your one-on-one to get the most out of this time together.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

How to run your first meeting as a new manager

Whether you’re a first-time manager or are taking over a new team, here’s how to approach that first meeting with your team.

It happened: You’re a new manager now.

Perhaps, it’s the first time you’re leading a team. Or you’re taking over a new team as a manager. Either way, that first meeting as a new manager is a daunting event. What should the agenda for that first meeting with the new team be? How should you set expectations as a new manager? Should you make prepare some sort of “new manager introduction speech”?

First impressions are often lasting ones. And there’s no better time and place to solidify that impression than the first meeting with your entire team.

Whether you’re taking over a brand new team, or you’re a first-time manager, here’s how to approach that first meeting. I’ll walk through what you should be thinking about, some things you can say, and some questions you can ask…

Build trust, don’t chart a vision (yet).

The goal of this initial meeting with your new team is NOT to map out the vision for the next nine months or declare your mandate for change. You’ll have the space (and greater knowledge) to do both in the coming weeks. This first meeting is to establish trust and set the tone for the kind of team environment you wish to foster.

Specifically, as a new leader, you’ll want to internalize these goals for your first meeting:

  • Show you’re worthy of your team’s trust.
  • Show that you’re humble and ready to learn.
  • Show that you’re intention is that you want to help.

This may feel like a passive approach to your new leadership role at first. But keep in mind this one truth: You’re new. And your team will be skeptical of you (rightfully so). So, as tempting as it might be to come into a new team situation and project confidence, certainty, and a sense of direction — know that it will only be seen positively by your team if they trust you. Without trust, your confidence will seem arrogant, your certainty will seem oblivious, and your sense of direction will seem misguided. Nothing moves forward without trust.

How can you build trust within this first meeting? Read on…

Get to know your team members — and take notes.

This may be one of the most over-looked aspects for new managers: Getting to know their team members, personally. Icebreakers can feel forced and trite — but I encourage you to spend some time in your first meeting asking at least a few get-to-know-you-questions to the group. (Here are the 25 best icebreaker questions we’ve found to work well, based on four years of data.) Take notes. Think about how you can incorporate their answers in future interactions, events, etc. For example, someone’s favorite food is ice cream? Consider bringing in ice cream to celebrate their birthday or work anniversary.

Share who you are, more than surface-level stuff.

This isn’t about touting your accomplishments and expertise (though, of course, you can share those things in this first meeting if it feels right). Rather, when introducing yourself to the team, it’s a chance to expose who you really are — what motivates you, inspires you, and brings you fulfillment. The more your team knows of the real you, the more likely they are to trust you.

How to do this? Share your leadership philosophy: What do you see as the purpose of a manager? What do you value? Who do you look up to? What drew you to the organization? Share your intentions: That you are here to help, to help them do the best work of their careers, to get out of their way and support them to accomplish something greater. Share your personal interests: What do you like doing in your free time? What social causes or nonprofits do you support? Be mindful to make sure you don’t spend more than 25% of the meeting, tops, talking about yourself. In building trust, the last thing you want to do is come across as self-absorbed.

Make it clear that you’re in “learning mode.”

If you want to build trust as a leader, you have to be vulnerable. You should let your team know that you don’t have all the answers and you have much to learn. This is one of the hardest parts of being a leader. As leaders, it feels like we’re supposed to have all the answers. Admitting that we don’t can feel like a blow to our sense of self. Yet exposing this vulnerability helps build trust in a team — it shows you’re humble, fallible, and human like the rest of us.

To do this, try saying something like this: “I am the new person here, and so all of you in this room know more than me. You carry with you insights and experiences that I don’t have. I am sponge, and I am to learn from all of you.” No need to beat yourself up and say that you’re ignorant, by any means. Essentially, you are saying that you’re “in learning mode” as a new leader. A learning mindset is one of the greatest ways to show vulnerability, and build trust with your team.

Ask 2–4 probing, thoughtful questions.

The majority of your first meeting as a new manager should be spent asking a few key questions to your team as a group. I’d also strongly recommend setting up separate one-on-one time with each individual employee before or after the first team meeting to further learn what’s on their mind (whichever is most appropriate).

Here are some ideas for questions you can ask…

  • What do you want to change in this team?
  • What do you not want to change in this team?
  • What’s typically been taboo to talk about in the past? What have you been nervous to bring up?
  • What looming concerns or apprehension might you have?
  • What’s been the most frustrating thing to have encountered with the team lately?
  • Where do you see the biggest opportunity for improvement with the team?
  • How do you prefer to receive feedback? (Verbal, written, in-person)? How do you prefer to give feedback? (Verbal, written, in-person)?
  • What’s been the most motivating project you’ve worked on all year? With whom? And why?
  • What excites and energizes you about the company?
  • What are you most grateful for in being a part of this company?
  • What do you think has been a big obstacle to progress?
  • What do you wish was communicated to you more often?
  • When have you felt micromanaged? When have you felt like you’ve needed more support?
  • Who’s the best boss you’ve ever had and why? The worst boss you’ve ever had and why?
  • What was the best team experience for you? The worst team experience?
  • How do you like to be shown gratitude?
  • How often would you like to set up a standing one-on-one or check- in meeting? Every week? Biweekly? Once a month? Once a quarter?

If this list of questions overwhelms you, remember, you only need to pick two to four of these questions for the all-team meeting. Save the rest for your one-on-one followup conversations.

As you listen to the answers, there are a few things to pay particularly close attention to:

  • Listen for the things you can fix, solve, and knock out quickly. Is there a project that is deadweight? Is there a useless policy that’s slowing people down? The best way to build trust with your new team and show that you’re here to help is to actually help.
  • Listen for what people view as “success” and progress, and consider how you’re going to define and measure that. As a leader, one of your primary jobs will be to say what “success” is, and how well the team is doing to get there.
  • Listen for what people’s communication needs are. What do they feel “in the dark” about? How might people prefer you sharing what’s going on? How regularly will you need to set up touch points with team members?

Be proactive in your next steps

As you wrap up your meeting, one of the worst things you can say as a new manager is this: “Feel free to stop by my office if you need anything.” Don’t say that. Why? You’re implying that if they have questions or concerns, they have to come to you. The burden is on them, not you. Instead, try saying: “In the next __ days, I’ll be setting up a time to meet with each of you. From there, based on your preferences, we can set a standing one-on-one time. In the meantime, if you want to meet anytime sooner, grab me in the hall, send me an email — I’d love to sit down sooner.” There’s a huge difference between the two statements. One is reactive and sounds lazy (the former), while the other sounds proactive and that you want to help (the latter). A strong way to end your first meeting is to show that you’re willing to come to them — that you won’t be waiting for them to bring up issues. You want to show as much proactiveness as possible.

Be prepared for tough questions

Note that you may get asked questions during your meeting such as, “What do you think you’ll change?” and “What do you see as the vision for the team?” Some might be tough to answer, especially with you being new. Be prepared to answer them honestly — and with a good dose of humility. There is much for your to learn. This is only Day 1, and the more you can level with your team that you’re here to learn from them about what the direction or what those changes should be, the better. You’re here to listen and to serve.

This is by no means comprehensive. Every team is different — from who managed the team before you, to the interpersonal dynamics at play, to the challenges that they’re facing with their work. You’ll likely need to tweak some of the question suggestions I offered, or some of the phrases I recommended. Regardless, I hope at the very least these tips give you a framework to start planning your first meeting as a new manager, and kick things off on the right foot.

Best of luck to you!


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

Meetings are Toxic


Meetings are one of the worst kinds of workplace interruptions. They’re held too frequently, run too long, and involve more people than necessary. You may have gathered that we really dislike meetings at Basecamp. And many of you do too! This episode of Rework features:

  • A group of philosophy professors in a meeting they Kant seem to end. You might say it had…No Exit. One attendee, at least, found enough Hume-r in it to tell us about it.
  • A meeting about a meeting.
  • A dramatic reading about conference calls from hell.
  • Basecamp programmer Dan Kim talking about his post on recurring meetings and what you—yes, you!—can do to start changing the ingrained culture of meetings at your company.
  • A brief, pedantic aside to note the difference between garters and garter belts.
  • A cringeworthy meeting with an unwanted participant—and an unexpected outcome.

https://art19.com/shows/rework/episodes/74204975-faa7-425a-a3b7-02c384cdfcc6

We had more listener-submitted meeting stories than we could feature in the episode, so here are a couple bonus ones!

No Work Done

I had an intense 12-hour meeting over two consecutive days. We were writing, correcting and estimating stories for a three-month project. Devs were in the room with managers, scrum master and biz owners.

So at the end of the second day, we finished the last story and we were supposed to groom and task it out next day (a third meeting day, yay). But our manager talked with us the next day and told us that some biz owners were mad about some unclear criteria in the stories, so he said that the (managers and biz) will regroup and this time “correctly rewrite all stories” and that we will have another 12-hour meeting next week.

That’s the story of how I had 24 hours of meetings in two weeks and NO WORK DONE (we couldn’t start working in the project until we had the second 12-hour meeting).

Quelle Horreur

I recently worked as a product manager for an Austrian company that was owned by a big French group. We were an IT service provider for two products, and in this meeting we were supposed to discuss payment providers for our new e-commerce offer.

The office and project language was English. My boss spoke English, French and German. I spoke English and German. Our French colleagues spoke French and English (with difficulties).

The meeting was a jour fixe (recurring) video conference scheduled for one hour, done over a big screen in HD. On our side, it was my boss and me. On their side, it was three project and product managers joined by a “payment expert” and an “SEO expert.” So that was seven people. Five minutes before the meeting, our CFO informed us that he would be joining shortly just to clarify “some budget things” with the department lead. So in total, we had nine people in the meeting: six on their side and three on ours. After the introduction round in English, the CFO and the department lead started to discuss budget details in French and that lasted for 40 minutes. Nine people in the meeting, two people talking to each other, and one of the nine (me) doesn’t understand a word that was said. Once they were done, they both left the meeting, so the rest of us had 20 minutes to discuss what we wanted to discuss.

I’ve read Rework and already had formed my opinion about Jour Fixes and working in meetings. I also complained often and openly about meetings I was invited to but had nothing to say and could have just read the minutes afterward. But this one was a special kind of meeting. It was almost like it was directed by Monty Python. I no longer work there 🙂


We publish Rework on alternate Tuesday mornings. To get new episodes on your phone as soon as they’re released, subscribe via Apple Podcasts, Google Play Music, or RadioPublic, or search for REWORK in your favorite podcast app.

Opening the Rework Mailbag, Part 1

It’s our first mailbag episode! Jason Fried and DHH answer listener questions on topics like the role of luck and timing in starting Basecamp; how they approach pricing (spoiler: It’s something called “ass pricing”); hiring in the early stages of a business; and more.

We’ll have Part 2 with even more questions next week, so be sure to subscribe to Rework via Apple Podcasts, Google Play Music, or your favorite podcatcher so you don’t miss it.

If you have a question for Jason or David to tackle on a future mailbag episode, leave us a message at 708–628–7850. We’re also collecting stories about meetings for a future episode. I heard from someone whose CEO held monthly 8-hour Skype meetings. Yes, they were eight hours long (with only two breaks under 20 minutes each) and consisted of him reading aloud some Google Docs. Do you have a similar story? Or—shudder—one that tops a recurring 8-hour Skype call? Call us or send an email to hello@rework.fm.

It’s time for recurring meetings to end

Why are we still doing this to each other?

It’s thankfully been a really long time since I’ve been invited to a recurring meeting. But I heard a couple mentions of them last week, and it brought back terrible pre-Basecamp memories.

It reminded me that not everyone is so lucky — many people still have to attend those soul-sucking, brain-draining, pointless recurring meetings. You know the ones — they’re usually filed under euphemisms like “stand-ups”, “status”, and “check ins” and happen on a daily or weekly basis.

They’re terrible. Let’s discuss why and see if we can help each other get rid of them.


They force people to meet even when there’s nothing to discuss

Ever gone to a recurring meeting only to find a bunch of blank expressions and everyone just kinda looking at each other? Welcome to the recurring meeting.

For some reason the default corporate mindset is that there will always be something to discuss, so having a regularly scheduled meeting is good because it “gives folks a chance to catch up.”

But if you really think about it, is there always something to discuss? Aren’t there just some days or weeks where things have gone smoothly or people are just doing their work and there’s nothing to chat about?

How often are these recurring meetings actually needed? 10% of the time? 50%? I have no idea, I can’t see into the future — so why do meeting organizers think they can?

A common retort you’ll hear from organizers is that you should keep recurring meetings around because “you can always cancel them”. And sure, in a perfect world, that helps a little — it gives me back some of my day. But this also assumes that every meeting organizer is super vigilant in managing their meetings. And let’s be honest, they’re not.

Beyond that, canceling an instance of a recurring meeting doesn’t fix all the other problems they cause in aggregate. Keep reading.

They create a vicious cycle of meetings and overwork

Here’s what meeting organizers do: they look at everyone’s calendar and try to find the best time for everyone.

But because there are so many recurring meetings, blocks of time are hard to come by. So organizers start scheduling new meetings at inconvenient times because those are the only times available: early in the morning, late in the evening, over lunch. All times you should be relaxing, not working.

If a majority of recurring meetings were simply off the books and scheduled as needed, everyone would have more available time and fewer meetings overall. Imagine the possibilities!

This also shows why “just canceling” a recurrence doesn’t fix everything — a recurrence is already eating a block of time that other organizers can’t schedule against, so it has a cascading effect of breeding meetings at even worse times.

They hurt your team’s work and workflow

If you know you have a meeting in an hour, do you start your deepest, most complex problem solving work? I’d venture to guess most people don’t. I certainly don’t.

It makes sense — if you know you’re about to be interrupted in an hour, why start the really deep-thinking work you need to do. You’re probably more likely to tackle a few small, easy things. It’s a subtle effect, but imagine that happening multiple times a week. How much good, deep-thinking work is lost because of looming meetings?

If those recurring meetings weren’t there, people might choose an entirely different set of work. They’d have longer stretches of uninterrupted time, which are crucial for deep thinking and problem solving — things designers and programmers need every day to do their best work.

Oh and to address the magic bullet of “just cancel the meeting” again — getting a cancellation 30 minutes before the meeting gives me the meeting time back, but it’s already screwed at least a couple hours of my day’s work.

They become a dumping ground

The recurring meeting is the dumping ground of everything you don’t want to deal with now (probably because you’re stuck in another meeting).

How often have you seen this happen — you start talking with someone, can’t make a call, and then they say “let’s talk about it at the status meeting”?

Recurring meetings are a crutch — they let you defer decisions you probably should (and could easily) just make now. Remember, decisions are temporary!

“If circumstances change, your decisions can change. Decisions are temporary.”
Jason Fried, Rework

This is yet another reason why “just cancel it” may sound good on paper, but doesn’t work in practice. People tend to find ways to fill scheduled meeting times.

They drown out the important stuff

Recurring meetings can cause serious calendar overload for many people — they can be double or even triple booked at times. There’s considerable mental overhead to look at a busy calendar and try to decipher what’s important and what’s not. Ever missed an important meeting because you got things crossed up on your excessively noisy calendar?

And from a human perspective, meetings also make people think twice about scheduling important personal appointments. Yes, of course most of the time it’s OK to miss a recurring meeting. But have you ever thought twice about scheduling a personal appointment because there’s a meeting on your calendar? Of course you have, and so have I. It may be a small thing, but even the most unimportant meeting might make someone think “I should really go to this” instead of taking care of something far more important to them.

“Yes, awesome, another recurring meeting!”

I’m half joking, but honestly, have you ever heard anyone say this? Or is it more often a deep sigh followed by “Ugh, another meeting”.

Or how about this — remember the last time one of your meetings got canceled and how overjoyed you were that you didn’t have to go?

Doesn’t that tell you something?


Alright, so we’ve established I’m not a fan of recurring meetings. Maybe I’ve convinced you they’re terrible, or maybe I haven’t.

Either way, would you perhaps, pretty please consider trying a few things either as a meeting organizer or attendee? You might be pleasantly surprised by the results.

Organizers: Try reversing your default mindset

If you’re a meeting organizer, try this for one project—reverse your thinking and assume you don’t need one of the recurring meetings you usually schedule. Instead see how things go without it, and if a discussion needs to happen, schedule a standalone meeting with the fewest people necessary to make the call.

Things might be a little uncomfortable or harder at first, but in the end I bet everything will be fine (and your team a lot happier for it).

Attendees: Ask the meeting organizer if you can skip

This might be tough because a lot of times meeting organizers are in positions of power (managers, directors, your boss, etc.) But if you’re one of the people getting killed by recurring meetings, try asking the organizer if you can skip them unless there is something specific you’re needed for. Most of the time any reasonable person will be OK with that.

This still makes you a willing participant and available, but by default you get to do your real work unless they specifically call on you to attend.

Attendees (Bonus Points): Thank the never-calls-a-recurring-meeting organizer

They’re a rare breed, but if you ever notice someone who breaks from the mold and rarely calls a recurring meeting, thank them. No, seriously. They might chuckle, but they’ll appreciate that you noticed and it’ll validate how they run things. It will give them the confidence to keep doing things their way — recurring meeting free!


So hey, it’s nearly 2018 and it’s a great time to turn a new leaf. What do you say — can we cancel any and all recurring meetings and start the year fresh?

If you enjoyed this post, please do hit the 👏 button below. Thanks!

Do you have a story of a meeting gone terribly awry? Or a time when you put your foot down on recurring meetings? We’re collecting your funniest, most memorable, and most cringeworthy meeting stories for an upcoming episode of our podcast, Rework. (If you found a way to make meetings less terrible at your business, we want to hear about that too!) Drop us a line at hello@rework.fm or leave us a voicemail at (708) 628–7850. We look forward to hearing from you!

How to prepare for a one-on-one meeting as an employee

Many managers say flat-out that their biggest frustration is when employees are not prepared for a one-on-one meeting.

Yikes, really?

Over the past four years, I’ve heard countless of managers, CEOs, and business owners say a version of this to me:

“During a one-on-one, I’ll ask a question and there’s silence on the other end. Or they’ll use it as a complaining session and it’s clear they haven’t been thoughtful about what feedback they’re offering. The lack of preparation just kills me.”

As an employee, this may be somewhat surprising to hear. We often underestimate how vexing it can be for a manager when we don’t come fully prepared to a one-on-one meeting.

I know I didn’t prepare for any of my one-on-ones, six years ago, when I was an employee. Out of fear, anxiety, and a bit of dread for what the conversation was going to be like, I pushed my impending one-on-one meeting out of mind. I didn’t think about what I wanted to say in the weeks (and days) leading up to it. “Was it really worth putting in the energy to do so? Nah…” I thought to myself. So I decided against it. As a result, when my boss asked me, “What do you think could be better in the company?” my answer was vague and not meaningful.

In the moment, it felt like the safe and comfortable thing to do. But truth is, I only hurt myself. I bungled my opportunity to influence real change. And, I only further frustrated my boss, who was perplexed that I seemed dissatisfied but never vocalized my concerns outright.

Eventually, I left the company. But I dearly wished I’d approached those one-on-one meetings differently — with less passivity and more positivity. I wish I would’ve seen those one-on-one meetings as an opportunity instead of an obstacle. I wish I would’ve seized those one-on-ones as a moment to engage and dig deeper with my manager, instead of using them to create distance and fester in apathy.

In the six years since being an employee, now as a CEO myself, I’ve since learned the power of preparing for a one-on-one. It’s not just managers who should be preparing for them, but employees too.

Knowing what I know now, here’s what I wish I would’ve considered when preparing for a one-on-one meeting with my then boss…

Share what’s been most motivating to you.

Managers crave to know what they should be doing to help you do your best work. After all, a manager’s ultimate job is to create an environment that enables you to tap into your own intrinsic motivation. During your one-on-one, make sure you share what tangibly has been most motivating to you while at the company: What’s been your favorite project? Who was someone you really enjoyed working it? Why was what you were working on so invigorating to you?

Reveal what’s been draining and demotivating to you.

As an employee, it’s always tough to bring up a critique of the company— especially if it’s about your own manager’s habits and actions. You’re worried it’ll be misinterpreted as “complain-y,” that your manager will take it personally, and that it could affect your career progression. Or perhaps worst, you’ll put in all the effort of sharing your feedback and nothing will happen. While all of those scenarios might be possible outcomes, what we must remember is that if we don’t talk about it, our managers will never know about it. The little things — whether it’s your manager interrupting you during meetings or always asking you to stay late — add up. They gnaw away at your ability to feel energized about your work. If you don’t say something, then who will? When you do speak up and vocalize tough feedback, look to approach the conversation with care, observation, fallibility, and curiosity. It’s a hard, delicate path to travel. But it’s a worthwhile path if you want your work environment to become better.

Explain how you want to stretch and grow.

Your one-on-one with your manager is your chance to let her know how you’d like to be further pushed and challenged in your role (or outside your role). Take time to reflect on what you’d like to improve or work on professionally. Perhaps it’s something more broad, like learning to be more patient and strategic in your thinking. Or maybe it’s much more about gaining a specific skill, such as becoming a better writer. Suggest potential projects for how you’d like to grow in those areas, and see if your manager has any ideas around it. Ask your manager for advice on what books, classes, or people you should be talking to help you pursue the greater learning you’re looking for.

Highlight what you’re grateful for about the company, work environment, or how your manager has treated you.

Giving feedback during a one-on-one isn’t just about zooming in on the bad. It’s the perfect time to point out the good, especially the good things your manager has done or said. Think about what your managers does that your previous manager at another company never did. What are the things you want to make sure she knows you don’t take for granted? Be specific, and say thank you. Not only will it help boost the morale of your manager (who needs the positive support, as being a manager can be a thankless job in some ways), but it helps guide your manager to double down on the things that you appreciate.

Consider what’s been confusing or concerning to you in the company.

Are you concerned that the company is growing too fast, and losing some of its original culture? Are you confused why the company decided to change its vision midyear, when things have been going so well? Consider leveling with your manager about what uncertainty is weighing on your mind during the one-on-one. It’s much more challenging to try to bring it up those questions outside of a one-on-one meeting — so take advantage of the fact you have dedicated time to discuss bigger questions about the state of the company with your manager.

Suggest one thing you see as your greatest shortcoming, and what you want to do to actively compensate for it or improve on it.

During your one-on-one, your manager is bound to share some constructive feedback in an area you could get better. While intimidating at times, it’s a good and helpful thing — and something to prepare for. To help make the conversation easier for you both and to show that you’re actively looking to improve, offer some thoughts yourself about moments you wish you would’ve handled differently. This could come in the form of goals, such as, “I want to find ways to ask more questions when interacting with customers,” or observations of areas you want to strengthening, such as, “I have a tendency to rush some of my projects, and I want to find ways to focus more on quality instead of speed.”

Prepare 3 to 4 questions to ask, to help you better understand how to focus your efforts going forward.

In case your manager doesn’t ask questions that cover everything you’d like to cover, you’ll want to have a few questions prepared. Here are some examples of questions you can ask that’ll help you better understand how you can improve as an individual contributor, and help your manager understand what she can be doing better as well:

  • Do you see any untapped potential in the work I’m doing? An area you think I could be pressing a bit harder in or exploring deeper?
  • What’s been frustrating or confusing about working with me? Where do you see the greatest opportunity for me to improve?
  • What’s the biggest challenge you feel you face as a manager? In what ways can I be helpful in overcoming or facing that challenge?
  • What worries you most about the team?
  • What are you most proud of the team having accomplished?
  • In what ways have I saved you time or made your job easier? What can I be doing to do more of those things?
  • Where do you see the team or company a year from now, and what I can do to help make sure we achieve that vision?
  • What are the biggest challenges you foresee the team or company facing in the upcoming year?

This may feel like a lot. I might recommend taking 30 minutes or so to reflect on some of these items, and even writing out some questions, yourself.

But keep in mind that the more you put into a one-on-one, the more you can get out. While a thirty-minute or one hour meeting doesn’t seem like much, it’s an opportunity to create a better relationship with your manager, to improve the work environment around you, and be plain happier in your job.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

How to have an honest one-on-one with an employee

Here are six ways to get employees talking about what they really feel (and not what they think you want to hear)…

“I can handle the truth. I’m pretty tough, Claire.”

My CEO at the time told me this during our one-on-one about five or so years ago. The year was ending, and he wanted to know what the company could do to improve, how he could improve as a leader — and he wanted to know the truth of what I actually thought.

Yet despite him saying he could “handle the truth,” I couldn’t bring myself to tell it to him.

Truth was, I wasn’t confident in the company’s overall direction. And I was troubled when I learned a few employees felt they were treated unfairly in the company… But it felt futile to mention these things. I couldn’t imagine that our CEO would take my feedback to heart and change anything in the company. If anything, I could more easily imagine that I’d provoke a negative reaction from him. Telling him the truth just didn’t seem worth it.

I’ll never forget that feeling of holding something back — choosing not to vocalize what I was thinking because I felt nothing in the company would change. To be clear: I’m not proud of my silence. Now knowing what I know about giving feedback to a manager, I wish I’d spoken up. Today as a CEO myself, I can only imagine how utterly frustrating it was for him to have that one-on-one with me… and then a few months later learn that I was leaving the company.

Having experienced this, I’ve thought deeply about the one-on-ones I do with my own team here at Know Your Team. I never want a teammate of mine to feel how I once did on the other side of the table. And I don’t want to be like my former boss, blindsided by how an employee is actually feeling.

To encourage honest responses during a one-on-one with an employee, here’s what I keep in mind…

Make empathy your mission.

Every time I have a one-on-one, I have a single mission: to understand how the other person is feeling. Everything else comes second. I don’t use the time to focus on critiquing an employee’s performance, nor do I use the time to get a status update on a project (those are separate, secondary conversations). A one-on-one is invaluable, sacred time to uncover the truth of how an employee is actually feeling.

When you make empathy your mission, the entire landscape of the conversation changes. You start listening more. You start asking more thoughtful questions. You start to level with employees, admitting you don’t have all the answers. Employees notice when an effort is being made to empathize with them, rather than pass judgement or get your own message across. The one-on-one becomes less intimidating to an employee. And when an employee is less intimidated, they’ll be more honest with you.

I’ll oftentimes make my mission of empathy clear upfront during a one-on-one to further diffuse any sentiment of intimidation. For example, I’ll say: “Today is for me to listen and truly understand where you’re feeling on things – that’s it. This isn’t a performance review or status report. This conversation is for me to understand what I can be doing to make this the best place you’ve ever worked.” When you explicitly let your employees know that empathy is your mission, you give them consent to tell you something that they might not have told you otherwise.

Ask questions to uncover two things: tension and energy.

To get to the bottom of how someone is feeling — particularly the negative stuff — I’ll ask questions around specific moments of tension, and specific moments of energy. Specific moments of tension are situations when someone felt angry, frustrated, bored in, etc. Specific moments of energy are situations when someone felt uplifted, excited, and motivated. You want to uncover what these situations have been so you understand how to create more positive situations for an employee that give them energy, and how to avoid and resolve the negative ones that create tension for them.

When you ask someone about specific moments when they felt disappointed, confused, proud, etc. at work, they can reference their emotions to something real that happened, not something ephemeral or imagined. For example, ask the question, “How’s it going?” and nine times out of ten your employee is going to say, “Things are fine” or some other vague, over-generalized response. You’re never going to hear the real stuff. Versus, if you were to ask: “When have you felt frustrated in the past year?” you’re asking an employee about a specific moment, situation, and emotion. You’re forcing them to think in more literal, concrete terms, and giving them permission to talk about how they feel about working at your company (something that doesn’t always happen all too often in the workplace).

Here are some examples of questions you can ask an employee around specific moments of tension so you know what to avoid:

  • When have you been frustrated in the past year? What can I do to help make things less frustrating for you, or get out of your way?
  • When have you felt dejected or demoralized this past year? What can I do to better support you, and make sure that’s not the case going forward?
  • When have you been disappointed with a decision or the direction that the company has gone in the past year? Was there an opportunity you think we squandered? Something you think we mishandled? How would have you preferred we proceeded?
  • When have you been annoyed, peeved, or bothered by me and something I’ve done as a CEO? Why? What would be helpful for you for me to change my behavior going forward?
  • When have you felt bored in the past year? How can I create situations going forward so you don’t feel that way?
  • When have you felt stressed or overworked in the past year? What can I do to create a better work environment going forward so you don’t feel that way?

Notice that when I ask about a specific moment of tension, I follow up with a question about what I or the company can do going forward. This way, your one-on-one doesn’t devolve into a complaining rant, but becomes a productive conversation about how to resolve, avoid, or fix a tension point in some way. This doesn’t mean you need to solve the issue right then and there (very rarely will you come up with a resolution on-the-spot). But a follow-up question about what future action can be taken will get your mind and theirs thinking in a constructive direction.

Here are some example questions you can ask around specific moments of energy — the positive stuff — so you know what to create and do more of:

  • When have you felt excited about what you’ve been working on in the past year? What can I do to provide you with more opportunities so you feel that way?
  • When have you felt most proud about being a part of the company this past year? What can I do to make sure that we do things that continue that feeling?
  • When have you felt most motivated about the work you’ve been doing? What can we do to create an environment so you feel like that more often?
  • When have you felt most “in flow” or “in control”of what you’re doing during the past week or so? What can we do to give you more space and time to feel that way?
  • What have you been wanting to learn more of, get better at, and improve on? How can we here at the company support you in doing that?
  • When have you felt that this company was one of the best places you’ve ever worked? How can I make this place the best place you’ve ever worked?

If this feels “touchy-feely” and not really your style because you’re talking too much about emotions – I understand. Try peppering just one or two questions about a specific moment of tension or energy into your next one-on-one. I guarantee those one or two questions alone will shed more light on an employee’s level of morale, more than anything else.

And, keep in mind that touchy-feely isn’t a bad thing. The way employees feel about their work affect how well they do their work.

Admit what you think you suck at.

When you’re asking employees about specific moments of tension or energy, sometimes the specificity of the question alone isn’t enough to encourage someone to respond honestly. Employees are especially wary of divulging or pointing out something negative, and may need an extra nudge. Why? Because there’s an inherent power dynamic between employees and a business owner. You need to figure out a way to disarm it.

The best way to overcome this power dynamic is to admit what you think you suck at. As you’re asking questions, reveal your fallibility. For example, if you pose the question: “What do you think we can improve on as a company?” and you’re getting a bit of radio silence on the other end, share what you’re struggling with or feel unsure about. You can suggest to them, “I think ___ could’ve gone better… what do you think?” or “I think I could probably be better at __ . Would you agree or disagree?” By showing vulnerability, it gives confidence for an employee to share something that might be perceived as negative.

Explain why you need their input.

One of the keys to making it safe for your employees to be more honest with you is explain why their input is valuable. I often forget to do this myself. But I find that when I do, it shows an employee that I’m not asking questions out of vanity or to “check a box.” Rather, I’m explaining how their feedback impacts the success of the company, and their own career development. Professor Amy Edmondson who coined the term “psychological safety” in workplaces recommends to “make explicit that there is enormous uncertainty ahead and enormous interdependence.” In other words, because the future is so uncertain and there’s much to still figure out, everyone’s opinion and input matters. For instance, you could say something like this to your employee: “Hearing your thoughts really matters to me because we haven’t figured ___ out. There’s so much unknown, and we need your input in order to get to where we want to go.”

Don’t get defensive.

When someone does respond frankly to your question, you’ll want to make sure you do not get defensive. Defensiveness is a killer of an open culture. The minute you get defensive you’re sending the message to your employee: “I actually didn’t really want to hear that.” And the next time you have a one-on-one, that employee isn’t going to speak up honestly. So when someone brings up a tough topic, watch yourself. Do you get testy and a bit defensive? Or do you calmly listen and ask insightful follow-up questions? Your reaction will be their benchmark of whether they’ll feel comfortable bringing up these hard conversations in the future.

Talk less.

Do not try to rebut every comment that is made. Do not give excuses on how swamped you’ve been. Ask your question succinctly. Listen. Take notes. Thank your employee for bringing something up, and say you’ll think on what they said and get back to her or him about it. If you catch yourself replying to an employee’s reply, reel yourself in. Remind yourself that you’ve made empathy your mission. That means you need to talk less. When you talk less, you create the space an employee needs to tell you the truth of how she or he is feeling.


This isn’t easy. Every time I do a one-on-one, I still feel a little nervous when I ask about a specific moment of tension… And I always take a deep breath to keep myself from reacting defensively when they share their answer. Navigating a one-on-one well requires discipline and a dose of courage.

Most of all, it requires a real desire for the truth. What fuels me to seek out honesty in a one-on-one is because I know that seeing the current reality for what it is — how our business is doing, what our employees think of the company — is the only way I’ll build a better company and become a better leader. Without knowing the truth, I’m squandering a chance to move the company forward, or even perpetuating a valuable employee to leave the company.

Holding an honest one-on-one with an employee is one of the few yet most effective ways to get that truth. Let’s double down on doing it well.


Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

Don’t overlook the quiet voices and contributions

A few years ago I worked at a mega corporation. I had just finished up a brutal week of all-day meetings with 20 people. My boss and I sat down to catch up. Eventually, she warned:

“Dan, you need to speak up more. You need to participate and contribute during these meetings.”

I was livid.


She felt that others had “contributed” far more than me.

It didn’t matter that people were talking just for the sake of it — repeating things that were already said and adding no value. It didn’t matter that very little was accomplished from all that talking. It didn’t matter that the week was a huge waste of time. It only mattered that people were speaking loudly and frequently.

All of my quiet contributions — selectively speaking, listening, thinking, writing, leading small group discussions — were being completely ignored.

Suffice to say, I didn’t last very long at that company.

But the sad part is that given the right environment, I could have. I had plenty of energy, ideas, and good work in me. But because I wasn’t always a loud voice, all of it was being overlooked.


If you’re a leader in a company, it’s important to keep your eyes and ears open for all types of contributions. The quiet members of your team have a wealth of insights everyone can benefit from.

While it’s easy to hear the loud voices, they might be drowning out the quiet ones. To tap into the potential of those quiet voices, here are a few tips to keep in mind:

  • Encourage writing as the preferred medium to share ideas. Writing has a wonderful way of leveling the playing field. No single voice can physically drown out or interrupt another. Not to mention it’s far more efficient than huge meetings.
  • Don’t correlate being quiet in meetings with a lack of participation. It’s likely that people are thinking about conversation at hand before responding. This is a good thing. Instant reactions aren’t what you want anyway.
  • Give people time and space to think. Don’t fret if written responses come in slower than you’re used to. Reviewing ideas, thinking, and building thorough contributions takes time and focus. These responses will be far better in quality than the speedy ones.
  • Judge contributions by quality, not quantity. Not everyone needs to chime in on everything — there’s already too much noise and commentary. Look for depth and breadth of contributions, not volume.
  • Don’t assume you’re privy to every bit of collaboration that’s happening. People share and discuss all over the place — in small groups, individually, in public, in private. Just because you don’t see collaboration, that doesn’t mean it’s not happening.
  • Ask for opinions individually. Sometimes the quiet voices just need a tiny bit of encouragement. Find the medium they prefer (IM, Hangout, face to face) and talk to them individually about a particular topic they’re interested in. You might strike gold and it will help them find their voice in the long run.
  • Avoid large group-think sessions. They’re insanely ineffective. Short bursts of collaboration in small groups is great. Huge ideas spread across hours and hours? Not so much.

I really believe in quiet voices. They’ve taught me the most and positively influenced my career — far more than the big talkers.

I hope you’ll give them a chance.


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Status meetings are the scourge

Status meetings are the worst kinds of meetings. Eliminate them and you’ll actually know more, save a pile of money, and regain dozens of hours a month.

A status meeting — sometimes called a stand-up — is a meeting where a bunch of people get together in a room (or virtually via video chat) and speak one at a time. Someone gets the floor, they fill the group in on something that’s going on, then they cede the floor to someone else who does the same thing. One after another, around they go.

It’s hard to come up with a bigger waste of money, time, or attention than status meetings.

Keep reading “Status meetings are the scourge”

Watch out for “everyone” or “no one”

Years ago I was in a meeting when this one person broke into the conversation and declared “Don’t say everyone or no one. It doesn’t mean anything.” It’s obviously a great point — one that’s easy to forget.

We all do this. We try to justify our position by saying “No one knows…” or “Everyone knows…” or some derivative thereof. When you throw around these extremes you weaken your point. There is no such thing as everyone or no one. Don’t justify your position by putting an unjustifiable abstraction at the core.

Even “Most people” is a bad one. “Many people” isn’t as bad, but it’s still loaded. I find myself saying it all the time. “Some people” is better. A clear “these people” is best.

So when you’re making a point or taking a position, watch out everyone or no one — they aren’t really there.