Stop being so nice all the time.

“Being nice” can be a crutch to avoid hard choices and uncomfortable conversations. Don’t fall into this trap.

Leaders, stop being so nice all the time.

I don’t mean to sound like an asshole. But when it comes to leadership, it’s true: Prioritizing “being nice” keeps us from being good leaders.

Now I’m not advocating for us to be mean. Disrespectful or dismissive leaders help no one. Rather, I’m calling for us as leaders to loosen our grip on “being nice.” To stop wanting our team to like us all the time. To let go of the expectation that every single interaction with our team should feel good.

Truth is, our team isn’t going to like us all the time. Our team isn’t going to feel good all the time. And trying to be nice to everyone all the time isn’t going to change that. Nor is it actually helpful for your team.

When we’re preoccupied with seeming popular instead of fair, when we optimize for pleasant conversations instead of honest ones — we hurt our teams.

I was reminded of this most recently while I was reading The Watercooler, our online community with almost 1,000 leaders. One manager revealed he was facing this exact dilemma. He was seen as “The Nice Guy” in his company, always complementary, never critical. As a result, he was struggling how to start giving his team difficult feedback — and his team was floundering.

He’s not the only one.

Have you ever found yourself in one of these situations?

  • You avoided giving tough feedback to a coworker… and now the person has made even bigger mistakes than you previously imagined.
  • You didn’t tell someone that you disagreed with them… and now you have to figure out how to course-correct without blindsiding the person.
  • You postponed firing someone… and now have to do damage control for the low morale they infused throughout the team.
  • You said something was “great!” even though it actually wasn’t… and now you have to fix the level of quality for what was produced.

Many of us focus on “being nice” as a leader more than we should. And we pay a price for it.

Hiten Shah, founder of Kissmetrics and Crazy Egg, emphasized this point to me, in a recent interview. He warned that when you’re concerned with being nice all the time, “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team.”

Prioritizing “nice” as a leader is an easy trap to fall into. Being nice fits into our desire for belonging and companionship as humans. We’re social creatures. We want to be liked. Inherently, there is nothing wrong with that.

But “being nice” becomes problematic when it becomes your rudder as a leader. It leads you astray. You lose sight of your purpose as a leader: To help your team accomplish a specific mission. Your barometer for success as a leader morphs from “Are we accomplishing our mission?” into “What does the team thinks of me?

Over time, “being nice” becomes your crutch. It’s a convenient rationalization to avoid hard decisions, uncomfortable conversations, and controversial actions. It’s easier to “be nice” than it is to have tell someone to their face that they’re rubbing a client or colleague the wrong way.

Ultimately, being nice as a leader is selfish. It doesn’t serve the team. It serves your ego. The team is looking to you to help them achieve a goal. And instead, you’re looking to have your decisions, actions, and yourself perceived as positive by them.

A leader is the only person’s whose sole job is help a team achieve the outcome they want to achieve. When you care about “being nice,” you’re essentially saying, “The needs of my team as a whole don’t matter as much as their perception of me as an individual.”

Instead of seeking to be nice, we should seek to be honest, rigorous, and consistent.

Or even better, we can seek to be nice and honest, nice and rigorous, nice and consistent. One of my favorite books, Crucial Conversations, discusses how being nice and being honest are not mutually exclusive. You can be both. The best leaders embrace this duality.

Let’s just stop being so damn focused on being only nice.


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.

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.

The 4 questions you should stop asking during your one-on-one meetings

You’re probably already asking at least one of them – but it’s never too late to stop.

Looking at the clock. Staring into the distance. Short, nondescript answers.

A CEO recently told me how he’d frequently see this body language from an employee during their one-on-one meetings. Flat. Disinterested. Preoccupied. It felt lousy to witness, but it’d always been this way. He’d silently concluded that he was wasting both of their time.

“I want to know what’s on his mind and how I can help, but these one-on-one meetings just aren’t working,” this CEO admitted to me. “I’m not really sure what to do except to stop having them.”

To see if I could help, I asked him what questions he was asking. He shared them with me… and then it clicked.

The once hazy picture zoomed into focus: This CEO was asking the wrong questions. All of his questions were common questions, no doubt. But therein lay the problem. Stock questions might be effective once or twice. But ask them during every one-on-one, every week, and over time, and the effectiveness of the question erodes. The person grows sick of answering the question. Or she doesn’t think you really care to know the answer anymore. Before too long, she starts looking at the clock, staring into the distance, and giving you those short, nondescript answers.

To avoid this, you’ll want to avoid the routine questions you lean on. Below are the four most common questions I’ve found used during one-on-one meetings that elicit dead-end, unhelpful responses. Take a look and see which ones you might be asking:

#1: “How’s it going?”

Ah, the perennial one-on-one meeting opener. It seems like a solid way to break the ice and initiate the one-on-one meeting. Yet it’s unusual that you ever get an answer other than “Fine” or “Good” in response. While someone might truly be fine and good in reality (which is great!)… the conversation usually stops there. Anything personal you wanted to learn, any sense of rapport you wanted to create dies with the question, “How’s it going?” This is because, as a society, the question “How’s it going?” has become our automatic greeting to each other, so our answer to it has become just as automatic.

What should you ask instead?

If you’re looking for a casual, open-ended way to kick off a one-on-one, ask “How’s life?” instead. It may not seem like a big difference, but it makes a big difference. “How’s life?” gives permission for someone to talk more personally about life — about what they did that weekend, how their family is doing, how their personal side project is coming along, how they’re managing their workload. “How’s life?” invites the other person to elaborate. Though, quite frankly, almost any other opening question than “How’s it going?” to going to help you learn more about how someone is doing in their life.

#2: “What’s the latest on __?”

It can be tempting to use your one-on-one session as time to get caught up on what’s going on. However, keep in mind that this completely squanders the purpose of your one-on-one meeting, to begin with. A one-on-one meeting isn’t a reporting session. It’s not an accountability tool. A one-on-one meeting is your radar. It’s your metal detector. It’s one of the only ways you have to unearth what’s actually going on in your team, and what an employee is thinking and feeling. You can get a list of deliverables in Slack any ol’ time. Client problems, unforeseen issues with the product, messy team dynamics, unspoken personal frustration — this is only time you’ll get to hear that stuff.

Some of you may be thinking, “Well, Claire, asking this question has helped me get good insights into the team’s problems.” Yes, I’m with you. This question “What’s the latest on X?” can be great if you’re using it to segue into asking deeper questions. For example, perhaps you follow it up with, “What’s most frustrating about how X has been going so far?” Or, “Where do you feel you need more support in working on X?” Merely asking “What’s the latest on X?” falls flat if you use it singularly.

What should you ask instead?

Ask something specific about the project, instead of asking for a general project update. Possibly my favorite question to ask to instead of “What’s the latest on X?” is “Can you tell me about what’s been most surprising about working on X so far?” If an employee has found something surprising, good chances that you’ll find it surprising too. A surprising insight is always useful for you to form an accurate picture of potential issues bubbling up within your team.

#3: “How can I help you?”

The intention behind this question is fantastic. You want to help, you want to get out of their way, you want to figure what you can be doing better. However, this question is the worst way to signal that. Why? It’s lazy. It makes the person receiving the question do all the hard work of having to come up with the answer. It’s also a very hard question to answer, especially on-the-spot and given that you’re a person in a position of power. You’re asking a person to critique you, “The Boss,” across all spectrums and come up with something actionable for you to do. If you do ask this question, answers tend to be, “Nothing I can think of right now,” something vague, or an answer that involves something that you’re already doing. Rarely do you get a precise, thoughtful to-do that you’ll then go implement the next day.

What should you ask instead?

Suggest something you think you can be doing to help. Then ask, “What do you think?” For example: “I was thinking I’m being too hands-on on this project. Should I back off and check-in with you only bi-weekly? What do you think?” By being targeted in what you suggest — and suggesting it yourself — you make it easier for that person to share the exact ways in which you can support them. You help your employees by suggesting what you think you can do to help, first.

#4: “How can we improve?”

This is the vaguest of questions. The problem with vague questions is they invite vague answers. You prompt the person to offer broad suppositions and knee-jerk assumptions, instead of exact details and practical examples. Ask an employee “How can we improve?” and they think, “Hmm, from a business development perspective? Marketing perspective? Leadership perspective? Where to even begin?” Now, some employees you work with will be able to craft a distinct, rich answer from this question. But it’s infrequent. And it’s probable they spent a good chunk of time thinking about the answer ahead of time. For most employees who you ask this question to without any warning, you’ll receive a variant of “I think things are pretty good right now” about 90% of the time.

What should you ask instead?

Focus your efforts on asking specific questions, instead of defaulting to general ones. For instance: “What do you think is the most overlooked area of the business?” or “Where do you think we’re behind in, that other companies are excelling at?” Notice how specific each of these questions are. The more specific the question, the more effective they are.


You may have cringed while reading this list. Many of you (including myself!) have found yourself asking all four questions, at one time or another.

No need to panic or be hard on yourself. You haven’t inflicted irreparable harm to your team. Your sins are not unforgivable. Rather, I hope sharing the unintended consequences of these four questions nudge you to evaluate the questions you ask during your one-on-one meetings a little more closely.

The questions do the heavy lifting. The questions determine the path to which your one-on-one meetings will take. Ask thoughtful, sincere questions, and there’s a higher likelihood your answers returned back to you will be thoughtful and sincere too.


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.

What’s the best use of a leader’s time?

I asked this to 1,000 managers, founders and executives from all over the world. Here’s what they said.

Time is the one constant we are all given. No one gets more or less of it than anyone else.

As leaders, it’s how we spend our time — what we choose to prioritize, and what we choose not to do at all — that reveals what’s important to us, and determines our team’s outcomes. If we want to figure out how to be an effective leader in the workplace, we must start with examining how we spend our time.

As a CEO myself, I’ve personally wrestled with this. I’ve had weeks where I’ve had fires to put out, meetings to show up to, business development calls to make, interviews to hold… Before I know it, the week is over, and I’m looking back at it thinking, “What the hell just happened? Where did my week go? Is that really where I wanted to spend my time?”

As a result, I decided to pose this question, “What’s the best use of a leader’s time?” to our online leadership community in Know Your Team, The Watercooler, with 1,000 leaders from all over the world. The answers were remarkably consistent.

Based on Watercooler members’ responses, there seemed to be three areas that leaders should focus their time on…

Recruiting + Hiring

Your team’s success hinges on the people you choose to hire. Surely, this is an obvious statement — and yet we forget about our role as a leader to drive these efforts. As a leader, you should be thinking strategically about who you want to contribute to your culture and help get your company to where you want it to be. What kinds of non-negotiable values must they have? What diversity of ideas and backgrounds should they have? Then, you should actively work to attract and recruit those folks to your organization. How are you showing that you run a company worth working for (e.g., your company’s marketing, you speaking at conferences, etc.)? How often do you meet new people outside your network, to connect and passively recruit folks who may be great to work with in the future?

As a leader, you also set the standard for what matters when hiring: the skillset, the values, the experience. You say when it’s time to hire — and when it’s not. Naturally, depending on the size of your company, you may have a hiring team helping you out with this. But regardless, your voice in this process as the leader is essential. It’s too important for you not to be spending your time on it.

Considering your team’s long-term strategy, vision, and culture

Admittedly, focusing on the long-term view of the company is hard to do. Especially, when there seems to be so many immediate needs for the company to take care of…and, when we’re not so sure about the long-term view of things, ourselves! But thinking about the long-term strategy, vision, and culture of the company is critical because, well, no one else is doing it. Literally, it is no one else’s job in the company to be thinking about the long-term, be it six months, a year or two out, or ten years down the road — other than you, as the leader. In particular, considering the long-term vision is paramount, because a company’s vision is where the most fundamental source of motivation for your team is derived. If you’re not spending time designing and adjusting a long-term vision — a picture of a better place — people won’t be motivated to do work to help get the company there.

Communicating the direction to everybody all the time

Communication is the easiest thing for leaders not to do. After all, it’s quite a repeated, draining slog to keep saying the same thing over and over again. Despite this, many members of the Watercooler emphasized that you cannot communicate enough as a leader. Why? You can’t expect your team to know anything unless you communicate it. And, depending on the size of the organization, it usually takes some time for a message to sink in or a for a decision to be thoroughly explained. Knowing what’s going on and where a company is headed is how people do their best work. People can’t perform well without the context and information to do so. If you’re not constantly communicating what people should know, the context isn’t there and people can’t do their job.


These three areas are what our Watercooler members said are the best use of a leader’s time. But how about for you? Do you find yourself spending time in these areas as a leader… or not?

Sharing these three areas prompted even one member of the Watecrooler to reflect and write about how she plans her week. I encourage you to do the same.

Our capacity to improve as leaders expands when we evaluate how we spend our time.


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.

The Little Trade-Offs

What seems small to you, as a leader, is not small to your team.

I was running a leadership training a few months ago, when a CEO said this to me…

“I think I know why it’s so easy to become a bad manager, even when we don’t mean to be: It’s because of the little trade-offs.”

I nodded and smiled. I knew exactly what he meant by “the little trade-offs.” I’d made so many myself as a leader, across my own career.

The little trade-offs are the moments when we succumb to what feels most pressing in front of us, at the expense of what our company needs down the road to be successful. We swap “The Thing That Will Help The Team in the Long-Run” for “The Thing That Needs To Be Done Right Now.”

As a leader, we make a dozen of these little trade-offs every week (if not every day!) We negotiate in our heads: “I need to finish this critical project, so I’ll postpone my one-on-one meeting with this employee. We can talk next quarter.” Or, “I need to be heads down on selling to this new client, so I don’t have time to explain the recent company changes. We can announce them later.

“Next quarter.” “Later.”

In the moment, the little trade-off seems like the right one make. Executing on “The Thing That Needs To Be Done Right Now” feels like the top priority. It’s what will pay the most dividends. And when it’s such a little trade-off, how much does it really matter?

Well, here’s the rub: Little trade-offs are not so little. You might make just one or two, in the beginning. But when you’re stressed, busy, and operating on tight timelines, the frequency of those little trade-offs inevitably increases. The little trade-offs you make as a leader become big trade-offs over time.

Consider these seemingly “little” trade-offs:

  • You choose to respond to an investor’s message within 24 hours — but don’t respond to a team members’ email or message for days (or weeks) on end.
  • You choose to be out on the road marketing the company’s new vision to potential customers — but don’t take the time to communicate the vision to the rest of the company.
  • You choose to actively ask a client for feedback and how your product can improve — but are always late to deliver an employee surveys or hold one-on-ones to solicit feedback on how the company can improve.

These little trade-offs say: “I value investors over my team. I value my potential customers over my team. I value my current customers over my team.” These are not little trade-offs. They’re big.

Over time, the little trade-offs reveal your true preferences as a leader and the basic underlying assumptions you hold. It becomes clear who and what really has a hold on you, and where your interest lies. For your team, the little trade-offs you make speaks volumes to them, more than any stirring inspirational speech or pay increase you give. It’s the little trade-offs that they’ll most remember.

No wonder it’s so easy to become a bad manager. Our little trade-offs pile up. Rather than being the exception, they become the rule.

How many more little trade-offs are you willing to make?


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.

Someone’s underperforming. Now what?

14 questions to ask an employee who’s struggling during your next one-on-one meeting so you can figure out how to best help.

Someone’s slipping. You see it. You feel it. You’re not on the same page. You desperately want to pull the person up, but you’re not sure exactly how. Do you encourage them? Switch them off the project? Change how you’re leading them?

You’re now facing one of the toughest tasks as a leader: How do you manage underperformance at work? And more specifically, how do you sit down and talk about their underperformance with them, during a one-on-one meeting with her or him?

It’s tempting to look outward first. To blame the person herself or extenuating circumstances. “They don’t pay attention to detail.” Or, “The client is being unreasonable with them.”

While those may very well be the case, you should also turn inward. As leaders, when an employee is underperforming, we must self-reflect. What are you doing that is stopping this person from doing their best work?

The hard part about managing an underperforming employee is choosing to look both inward and outward for the sources of underperformance at work: What are you doing to hold an underperforming employee back? And what is the underperforming employee doing to hold herself back?

Oftentimes, we think we know the answer to those questions. We have hunches about what’s causing the underperformance: “It’s their perfectionist tendency getting in the way, obviously…” or “It’s my lack of context I shared about the project, clearly…”

So, we just create a performance improvement plan based on those hunches, and move forward.

That path is instinctual — but that path is flawed. Assuming what’s wrong doesn’t help you get any closer to finding out what actually is wrong. While your hunches may end up being spot-on, in my experience, I discover the truth of what’s really holding an employee back when I ask, not when I assume. Coaching a struggling employee to success begins with asking the right questions, not simply arriving with the supposed answers.

Given this, when you sit down in a one-on-one with an underperforming employee, what should you ask? What questions will help you look both inward and outward to get to the underlying source of underperformance?

Here are 14 questions to try. They are by no means the only questions you ask during a one-on-one (here are other ones to consider). But, they provide a good starting place to delve into how to better manage an underperforming employee.

Ask these questions to look inward.

You’re trying to figure out: “How have I been letting this person down? How have I been getting in the way?”

  • Is it clear what needs to get done? How can I make the goals or expectations clearer?
  • Is the level of quality that’s required for this work clear? What examples or details can I provide to clarify the level of quality that’s needed?
  • Am I being respectful of the amount of time you have to accomplish something? Can I be doing a better job of protecting your time?
  • Do you feel you’re being set up to fail in any way? Are my expectations realistic? What am I asking that we should adjust so it’s more reasonable?
  • Do you have the tools and resources to do your job well?
  • Have I given you enough context about why this work is important, who the work is for, or any other information that is crucial to do your job well?
  • What’s irked you or rubbed you the wrong way about my management style? Does my tone come off the wrong way? Do I follow-up too frequently with you, not giving you space to breathe?

Ask these questions to look outward.

You’re trying to figure out: “What on the employee’s end is limiting them? What choices or capabilities of their own are keeping them from the results you want to see?”

  • How have you been feeling about your own performance lately? Where do you see opportunities to improve, if any?
  • What are you most enjoying about the work you’re doing? What part of the work is inspiring, motivating, and energizing, if any?
  • What part of the work do you feel stuck? What have you been trying the “crack the nut” on, but it feels like you’re banging your head?
  • What part of the work is “meh”? What tasks have you feeling bored or ambivalent about?
  • When’s the last time you got to talk to or connect with a customer who benefited from the work you did? Would you like more opportunities to do that, and should make that happen?
  • Do you feel you’re playing to your strengths in your role? Where do you feel like there is a steep learning curve for you?
  • Would you say you’re feeling optimistic, pessimistic or somewhere in the middle about the company’s future?

You’ll notice that none of these questions ask, “What do you think you’re doing wrong?” or “What do you think I’m doing wrong?” The point of these questions is not to end up in an accusatory place, either way. Your goal is to reach a place of better understanding.

By approaching the conversation with an underperforming employee with questions to ask, rather than answers or directives to insert, you create space for that employee to want to do something different. To actually change and improve.

That change, that improvement, is the goal, after all.


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 well do you know yourself?

Why self-awareness at work just might be the most underrated, overlooked element of a successful leader.

A few months ago, I asked Ben Congleton, CEO of Olark, what he wished he’d learned earlier as a leader. No, he didn’t mention learning a new business development hack, nor did he talk about the importance of hiring well. Rather, what Ben wishes he’d learned earlier was how to improve his self-awareness as a leader.

Self-awareness, really? After considering it for a moment, I caught myself nodding vigorously at his answer. How true!

In my head, I recalled all the moments I’ve personally lacked self-awareness as a leader: When I micromanaged someone yet had no idea, when I argued against a new idea because of my own bias… The list goes on. Each time, I’d shot myself in the foot.

The more I thought about it, the more I realized: Self-awareness at work just might be the most underrated, overlooked element of a successful leader.

Here’s why…

Why self-awareness is crucial for leaders

Fundamentally, self-awareness is about understanding your own mental state. It’s knowing about yourself: When are you energized? When are you in a bad mood? Where are you strong in, and where are you weak? What are you tendencies, your biases, and your leanings toward? What might your blindspots be?

This self-knowledge is irreplaceable. Without self-awareness, you can’t make informed decisions. You don’t know if you’re getting in your own way — if a strong irrational personal bias or misguided mental model is shaping your view on things.

Self-awareness is also critical as a leader because it means that you can build healthier relationships with your employees. Ben himself admits how his lack of self-awareness kept him from resolving an employee conflict as well as he’d like. He recalls:

“I remember there was one point where I was trying to resolve a conflict between two employees, and I just was like my head was somewhere else, my head was just like ‘This is the last thing on my to-do list, I just need to get this done, and then I can hop on a plane and go see my family.’”

Lastly, self-awareness is important for your growth and personal development as a leader. You can’t improve as a leader if you don’t know what to improve in. You have to see the current state of yourself clearly if you want to make any progress in getting better as a leader.

With self-awareness being so important, what are the ways you can actually improve your self-awareness in leadership?

How to improve your self-awareness as a leader

Assume positive intent.

One thing that Ben tries to keep in mind to improve his self-awareness as a leader is to assume good faith. When you feel yourself getting defensive and are not in a good mental state to receive feedback, stop and recognize it.Understand that the source of your resistance to what the other person is saying may be your poor assumption of the other person’s intention. You think they’re out to get you, or have ulterior motives. So assuming positive intent is a first step to bringing a sense of self-awareness to the situation: You may not being hearing things for what they are because you’re misreading the other person’s intention.

Hold up a mirror to yourself and your decisions.

Self-awareness naturally includes assessing yourself for your own mental models, biases, strengths and shortcomings, and the gaps in your perception of reality. Something that Peter Drucker, the well-known management expert, has recommended is: “Whenever you make a decision or take a key decision, write down what you expect will happen. Nine or 12 months later, compare the results with what you expected.” Warren Buffet, in fact, practices a version of this with his investment decisions. This active reflection process helps create a deeper understanding for yourself. And by reflecting on your decisions and the outcomes, you can reach a more objective understanding of what’s working for you as a leader, and what’s not.

It’s not all about you.

Self-awareness isn’t just about reflecting inward, and delving into what you’re personally feeling. You have to understand what’s going on with the other person, as well. How might what’s happening at home or something that a family member is struggling with be affecting her performance? Does this person have preferences and reactions drastically different from your own? Don’t assume that this person wants to be treated the way you want to be treated. Embracing this nuance that everyone is not like you is a cornerstone of self-awareness as a leader. It’s not all about you — you must seek out to understand others’ perspectives.

Ask your team the tough questions.

If you really want to become self-aware, there are few better ways to accomplish this than asking your team. This means asking questions that you may be even hesitant to know the answer to. For instance, try asking, “When’s the last time something I did or said frustrated you?” Or, ask, “When’s the last time you felt unsupported as a member of the team?” When you defer to them to shed light on your tendencies, not only will you get helpful information to give you greater self-awareness, but you show them a willingness to become better as a leader. That, in itself, helps strengthen your bond with the rest of your team. Not sure exactly what to ask your team? Try a few of these questions to uncover your leadership blindspots.

Find an accountability partner.

For Ben, the most effective way for him to develop greater self-awareness as a leader was to hire an executive coach. For Ben, this was helpful for two reasons: (1) It created an accountability partner for him, helping him put into the practice the things he wanted to improve, and (2) it forced him to have a time to reflect every week, causing him to set aside time to deliberately to become more self-aware. Without this third-party intervening to keep Ben actively focusing on his own self-awareness, he doubts he would have made the same progress he did as a leader. Now, I’m not saying you need to go out and hire an executive coach tomorrow. Rather, a third-party serving as an accountability partner could be a friend, mentor, spouse or anyone outside the company. You simply need a buddy to help make sure you’re walking the walk when it comes to becoming more self-aware.


I’m so grateful that Ben admitted that self-awareness was his greatest leadership lesson. It was the reminder I needed to double-down on my own personal self-awareness. Without self-awareness, we fly blind as leaders. Choosing to know ourselves is truly our first step to becoming a better leader.


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.

The 12 Signs: How to know when you’re slowly but surely becoming a bad manager

No one sets out to become a bad boss. Yet, slowly but surely, it’s easy to become the bad manager we all dread.

Times are stressful. You’re trying to make things happen. You notice your team isn’t as engaged as they should be. You can feel your patience getting shorter and shorter. You feel stuck and exasperated about leading your team. The more you do, the worse it seems to get.

Then, a sinking feeling hits you: You might be becoming a bad manager.

I’ve had that sinking feeling in my own stomach before, too. Especially in the early days of running Know Your Team, I was plagued with self-doubt. “Am I doing this right?” I wondered. “Am I falling into the trap of doing things that I’ve hated in other bosses?”

Since then, I recognized the early signs of a bad manager — the kind of manager I dreaded working for. Now, I’d like to share these signs with you, so you can hopefully avoid these pitfalls and get back on track to being the good manager you want to be.

Sign #1: You think an employee “should already know that.”

When you’re a leader, you benefit from having all the information. Yet we forget that the rest of the team does not have that same information. Don’t fall into the trap of assuming that employees “should already know that.” Instead, consider why your team doesn’t have the information they need, and own that shortcoming yourself. Good leaders know it’s on themselves to make sure the team knows what they need to know.

Sign #2: You find yourself saying “No” more often than “Why not?” or “Could this work later?”

In times of uncertainty, we as leaders have a bias against creativity. A great leader understands this, and adjusts for this bias. She knows that good ideas and suggestions take many forms — and saying “no” to something right away could be shortchanging your team. Not to mention, it’s demoralizing for your team to always have their ideas constantly turned down. Consider: Are you becoming a bad manager because you’re too closed off to new ideas?

Sign #3: You ask an employee to stay late without staying late yourself.

True leadership starts with walking the walk. Our actions set the example for our team. So if you ask someone to stay late at the office, but you don’t stay late yourself — that’s not a small, trivial thing. It’s a statement to your employee that you don’t value them or their time. Reexamine if you’re modeling the behavior yourself that you’d like your employees to exhibit.

Sign #4: You feel like you’re irreplaceable and are the only person who can do a certain part of the job.

Feeling like you’re irreplaceable isn’t a badge of honor — it can be your greatest downfall as a leader. Why? It’s often the reason we micromanage others or don’t delegate projects. When we accept that others can do parts of our job better than us, we are more willing to share responsibility, delegate tasks, and not breathe down our team’s neck. Wil Reynolds, Founder of SEER Interactive, has admitted how he’s fallen victim to this himself.

Sign #5: You think asking certain questions can be dangerous or a giant waste of time.

You’re worried that asking what an employee thinks about your benefits or compensation package are just huge distractions. While in the short-term this may feel like the case, the reality is that employees have feedback for you already, whether or not you ask about them. So by not asking questions, you’re simply letting a problem fester. If you want to be a good leader, you’ll gather the courage to ask questions and hear answers you may not want to hear. It’s better than not knowing the answer at all.

Sign #6: You think emotions have no place in the workplace.

Emotions are facts — the way we feel about our work affect how well we do our work. So we must accept our team’s emotions, just as we do our financials or design projects. Work is often seen as a logical, rational place, so considering people’s emotions can feel burdensome and complicated. But great leaders embrace that their team will feel a range of emotions, and that’s part of the day-to-day process of working together.

Sign #7: You think doing something yourself is easier because you can’t trust anyone else to get it done right.

Your reluctance to hand things off to your team is a telling sign that you’re slipping into becoming a bad manager. A great leader knows that the crux of teamwork is equipping others with the ability to do things right and trusting that they will. As the African proverb goes: “If you want to go fast, go alone. If you want to go far, go together.”

Sign #8: You think some people deserve your trust more than others — and you act on those hunches.

Few things turn a manager from good to bad as quickly as playing favorites. As unwilling as you might be to even call your actions “playing favorites,” the fact that you give some people on your team more leeway or grace than others is a recipe for resentment. Fairness is a critical trait of the best leaders.

Sign #9: You feel that you need your team to be close by or in the office in order for people to get work done.

You might find it strangely comforting to see an employee in front of a computer, at the office. That means they’re being productive, right? What a farce that is. Watching people get work done doesn’t mean the work actually gets done. Realize that your desire for proof of the work, instead of caring about the result, is a crutch and an attempt to control others. If anything, your desire to see people doing work is a burden to your team.

Sign #10: You think that if an employee has a problem, issue, question, or concern, they’ll simply come to you with it.

Open door policies in companies simply don’t work. We forget is that there is an inherent power dynamic when we’re the manager. When we’re “the boss,” we’re seen as the ones “in control” and with power. As a result, an employee is concerned with how she’ll come across to you, if you’ll treat her differently, or even fire her. There’s no incentive for her to be honest with you, if it’s not what you want to hear. So you’ve got to ask what problems, issues, or questions your team might have — you can’t expect them to come to you.

Sign #11: You “test” employees to make sure they’re prepared and working hard.

You catch yourself asking questions during meetings just to “make sure employees are paying attention.” Or, you assign small tasks just to make sure your team “is on their toes.” Stop. Trying to “test” your employees is counterproductive. You’re draining their morale, not building it up. If you’re ever tempted to try to test your employees — resist the urge. Ask yourself, “Why do I feel the urge to test them? What am I not doing to create an environment where they can perform their best?”

Sign #12: You spend more time thinking about trying to eliminate distractions in the workplace than trying to give people a reason to feel excited about coming to work.

As a manager, it’s tempting to focus on what your team should stop doing. They should stop taking such long lunches, or stop wasting time on Facebook. Rather, the best managers take an opposite approach: They focus on what they can to give their team so they feel motivated and engaged. For instance, instead of being preoccupied with how long your team’s coffee breaks are, consider, have you made it clear how their work is connected to the bigger picture?

All of us as leaders have fallen victim to one of these 12 signs, at one time or another. The key is to recognize it, when it happens. Don’t give yourself excuses for why it did. And don’t beat yourself up about it, either! Simply accept it, decide what you’d like to do differently, and move forward.

Being a good manager is hard for everyone. I only hope learning these 12 signs can help you, as much as it did me.


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.

The 8 best questions to put on your next one-on-one meeting agenda

I asked 1,000 leaders from all over the world what questions they ask during a one-on-one meeting. Here’s what they said…

That one-on-one meeting is scheduled on your calendar this week. So, what should you talk about?

As a manager, executive, or business owner, this is one of the most recurring and perplexing situations you’ll face. Should you prepare an one-on-one meeting agenda ahead of time? Does it feel too stiff to do so? Should you simply have general meetings topics ready to go? What are the questions you should asking during this one-on-one?

We posed this dilemma to The Watercooler, our online leadership community in Know Your Team with almost 1,000 leaders from all over the world, to see what they had to say. From that conversation, I’ve shared what these managers, business owners, and executives from The Watercooler have found to be the best questions to ask during a one-on-one meeting.

Take a look and see if you agree…


#1: How’s life?

On the surface, this doesn’t seem like a significant question to ask. After all, some managers default to asking this question as a crutch when they’re not sure how to open up a one-on-one meeting. However, this question can be actually quite powerful, if you can embrace a greater intention behind it: To build trust. When asked, most Watercooler members agreed on the importance of having trust and a strong personal rapport going into the one-on-one. The more you know about a coworker’s dreams, hobbies, pets, children’s names, etc., the greater the sense of trust is. And the greater the trust, the easier a tough conversation is. As a result, many managers from the Watercooler kick off their one-on-one with a “get-know-you” question like, “How’s life?” or “How’s [insert spouse’s name]?” or “What are you up to this weekend?”

One manager in particular emphasized the importance of talking about life outside of work way before you even have the one-on-one. That way, you build a foundation of trust to use if you need to bring up a difficult topic during your one-on-one. Prior to a one-on-one, here are some of the top 25 get-to-know you questions that can help with this.

#2: What are you worried about right now?

During a one-on-one, you want to figure if there’s anything bothering an employee, before it’s too late and they decide to leave or their performance is affected. Few questions do that an well as as this one. Recommended by a few of the Watercooler members (and a question I regularly asking during my one-on-ones), this question can help unearth the deep-seated concerns, confusion, or uncertainty an employee might be facing. A slight variation to this question that may unearth even more specific answers is: “When’s the last time you were worried about something?” This question is rooted in a specific moment of tension that can help make it more concrete for an employee when reflecting on if there’s something they might be worried about.

#3: What rumors are you hearing that you think I should know about?

Asking this question can bring to light rumors that you can dispel before they spin out of control. But on top of that, as one Watercooler member said: “What the rumor mill is saying is also often a compass pointing to places where people feel stressed.” Ask this question to uncover a deeper, disconcerting source of unease or frustration for employees. You’ll want to pay attention to that.

For one Watercooler member, asking this question had a direct effect on her entire team’s morale: She was able to nip a rumor in the bud very quickly about why an employee was fired.

#4: If you could be proud of one accomplishment between now and next year, what would it be?

To get a coworker thinking about their personal goals over the next six months, as well as their long-term careers, one manager in The Watercooler recommended asking this question. You may not get a meaningful response every single time from every employee you pose it to, as some employees may find it difficult to answer on-the-spot. However, it’s a great way to spark the initial conversation with an employee about future goals. Not to mention, it’s a more thoughtful question than simply asking, “What goals do you have for yourself?”

#5: What are your biggest time wasters?

No one likes to waste time. Few feelings are as stifling and demoralizing, especially in a work setting. As a result, asking this question during a one-on-one is imperative. Once you ask this question, be prepared to think on and follow with concrete ideas for how you think that person’s time won’t be wasted.

#6: Would you like more or less direction from me?

Feeling micromanaged is often another source of stress for an employee — and it’s one of the most common. As a manager, it can easily to unintentionally give an employee too much guidance. At the same time, employees find it equally frustrating when they’re hung out to dry with no support. When you ask this question, you can then adjust your management style and techniques. Furthermore, asking this question also signals to your coworker that you recognize the value of providing the right level of support as a manager. As a leader, this question shows you’re self-aware.

#7: Would you like more or less feedback on your work? If so, what additional feedback would you like?

Watercooler members suggest asking this question, because you’re most-likely going to get a resounding “yes.” After surveying hundreds of companies and thousands of employees through Know Your Team, we’ve found that 80% of employees say, “I want more feedback about my performance.” Your one-on-one is the perfect opportunity to figure out exactly what kind of feedback someone would like.

#8: Are there any decisions you’re hung up on?

One of the best ways to help coach an employee is to give them some support on a decision that they’re wrestling with. They could be quite distraught because they’re not sure with path to take — and you can help. Asking this question during the one-on-one is a wonderful way to alleviate the potential pain they may be feeling around a tough decision.

Whether your one-on-ones are weekly, once a month, or once a quarter, I’d highly encourage you to place one or two of these questions in your typical meeting agenda. Based on the experiences of Watercooler members who’ve asked these questions, you’re guaranteed to learn something new and create a stronger rapport with your team.


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.