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.

The 25 most popular icebreaker questions based on four years of data

If you need a get-to-know-you question for team-building at work that isn’t trite and terrible, here are 25 to try out…

If you winced at the word, “icebreaker,” I don’t blame you. Get-to-know-you questions and games tend to feel cheesy. We’ve all been victim to a terribly trite icebreaker with coworkers that made us roll our eyes. I know I have.

However reluctantly, you may have realized that you need to break the ice at work. A new employee just joined your team, and you want to make sure they feel welcome. Or, you need to find a way to warm up a conference call between remote team members, and ask some get-to-know you questions for team-building.

After all, it’s always hard to work well with folks you don’t have a rapport with (not to mention, it’s less fun). Trust is the oil of the machine in the team. The more you have of it, the more things run smoothly. And the key to building trust within your team is to ask questions that help everyone get to know each other.

Given this, at Know Your Team, we put a lot of thought (over four years worth of research and fine-tuning!) into crafting get-to-know-you questions that would be as non-cheesy as possible, and elicit meaningful and memorable responses from the team. I get emails all the time from CEOs who’ll tell me, “Wow, Claire, I had no idea this question would get such a reaction from our team.”

Among the hundreds of get-to-know-you questions our software has, I wanted to share with you the top twenty-five…


#1: What was your first job?

By far, this question has prompted the most interesting responses for the companies we work with. Employees are always find it hilarious to learn that their boss’ first job was as a pool boy, or find it fascinating that a coworker’s first job was working in her mom’s doctor’s office. While it’s an unassuming question, the responses stand out.

#2: Have you ever met anyone famous?

This question is a fun one, as it taps into the people that your coworkers admire. Folks bond over a mutual love for Jude Law, or have a laugh when a manager shares her story about meeting LeBron James at a gas station.

#3: What are you reading right now?

People are always looking for something new to read — and so swapping book recommendations are a great way for people to know each other. Learning what others are reading also provides insights into coworkers’ interests. David Heinemeier Hansson, CTO of Basecamp, shared his answer to this question here.

#4: If you could pick up a new skill in an instant what would it be?

With this question, you’ll learn how your coworkers want to grow or what they aspire to do. For instance, you might learn that a coworker would love to be able to pick up Italian instantly, or that your boss has always wanted to get good at woodworking.

#5: Who’s someone you really admire?

Understanding who someone looks up to reveals a significant amount about a person’s influences, preferences, and outlook on life. This is a great question to ask to help get a sense of what and who a person values.

#6: Seen any good movies lately you’d recommend?

Perhaps you’ve asked this question before — but don’t overlook it. Movies are a great shared conversation topic. It never fails to be one that people like to answer and like to see other people’s answer to. Often times, people will end up going to see them movies that are recommended and talking about it over lunch, etc.

#7: Got any favorite quotes?

Personally, I’m a sucker for a good quote. I think it can provide a fascinating look into a person’s point-of-view. Asking about a person’s favorite quote is a great way to break the ice and get to know them better.

#8: Been pleasantly surprised by anything lately?

While this question may seem vague, the answers to this question are often a delight and intriguing to read. Someone might share an excellent customer service experience that surpassed their expectations, or share a funny story about them liking squash soup despite their initial reservations. This is especially a great question to ask to a group of folks who might know each other a little better already.

#9: What was your favorite band 10 years ago?

This question always elicits a chuckle or two. You’ll find out that you shared a embarrassing favorite band from years ago, and also find the generational difference between coworkers humorous as well.

#10: What’s your earliest memory?

This is typically something that’s not shared even between close friends — so asking about it creates a special connection between folks. Hearing about an intimate, early part of someone’s life says a lot about who they are.

#11: Been anywhere recently for the first time?

Sharing a new, novel experience is a wonderful way to create a sense of connection between people. You’ll learn about a new restaurant, a fun out-of-the-city getaway, or a never-heard-about bookstore you might find interesting.

#12: What’s your favorite family tradition?

Cooking Korean dumplings together around the holidays is one of mine. When you ask this question, you get an inside look into your coworkers family’s heritage and the things that bring their family together.

#13: Who had the most influence on you growing up?

A mother, a sports hero, a grandparent, an elementary school teacher… This question is touching to hear the answer to. You’ll gain a sense of respect about who has shaped your coworkers.

#14: What was the first thing you bought with your own money?

Maybe it was a goldfish as a pet or a pair of Air Jordans. This is another great question that fosters a sense of nostalgia and provides insights into people’s interests of the past and what they valued when they were younger.

#15: What’s something you want to do in the next year that you’ve never done before?

I love asking this question instead of the stale, “Do you have any goals this year?” Rather, this is a great aspirational question that exposes people’s dreams and hopes they’d love to pursue.

#16: Seen anything lately that made you smile?

The answers from this question are often unexpectedly lovely. You’ll find yourself nodding your head as a coworker talks about his kids, or about a beautiful tree she saw on her walk recently.

#17: What’s your favorite place you’ve ever visited?

Responses to this are varied and fun — you’ll find that some folks have the same “favorite place” in Spain that they’ve visited, or a place that happens to be just 20 minutes from where you live.

#18: Have you had your 15 minutes of fame yet?

This is a cheeky question that turns up a variety of answers and interpretations. You might be impressed about how a coworker was in the newspaper one time or get a good laugh about how they were on the evening news.

#19: What’s the best advice you’ve ever heard?

I’m a big fan of this question, as you’re essentially asking a person about what wisdom they personally find most valuable. The best advice I’ve ever received, myself? “Trust yourself.”

#20: How do you like your eggs?

Our customers who ask this question are always shocked by how popular the answers to it are. They discover that colleagues are immensely passionate about scrambled eggs or are sunny-side-up diehards.

#21: Do you have a favorite charity you wish more people knew about?

This is a fantastic question to ask. One company I know took it as a way to make a small donation to each charity mentioned.

#22: Got any phobias you’d like to break?

Spiders, heights, the ocean… Sharing fears is always a great way to feel closer to someone.

#23: Have you returned anything you’ve purchased recently? Why?

Ask this question and you’ll unearth some interesting observations on why people buy things — and what they find unsatisfactory.

#24: Do you collect anything?

Skip the boring question, “What are your hobbies?” and ask this instead. You might find that someone is unexpectedly avid butterfly collector (my uncle does this), or enjoys finding a new postcard every time she travels (my mom does this). Regardless, it’s a more unique way to learn about a person’s interest.

#25: What’s your favorite breakfast cereal?

This question continually (and surprisingly) blows people away with the response when they ask it. One customer of ours had such an enthusiastic response on this from her staff, she created a Cereal Day for her team.

I’ve used these questions to get to know a new employee, kick-off group meetings for boards I sit on, and even in one-on-one coffee meetings when I’m meeting someone for the first time. Give ’em a shot. Think you’ll be pleasantly surprised by the results.


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 do you fire someone well?

I don’t think a “best way” to fire someone exists — but here’s a stab at trying to do it with dignity, grace, and respect.

I fired someone last year.

Ugh. It was gut-wrenching. I’ve fired people before — but it doesn’t matter how many times you do it, it always feels downright terrible.

To prepare for the difficult conversation, I asked a few mentors for advice. I also posed the question to The Watercooler in Know Your Team, our community of leaders from all over the world, to learn how others handle letting someone go.

From almost 1,000 CEOs, managers, and executives, I compiled six recommendations on how to handle firing someone with dignity, grace and respect that I thought I’d share with you here:

Privacy, please.

Choose a conference room that’s away from the team, ideally that’s close to the exits. Or, if you’re a remote team, make sure you’re in a place that’s private when you make your Skype or Google Hangout call. Make sure your phone is turned off and door is closed so you’re not interrupted. And never ever do it in a public place, like a coffee shop.

The “optimal” time doesn’t exist.

Everyone has different opinions about whether you should let someone go on Friday end-of-day, or earlier in the week — but really, it’s moot. Once the decision has been made, it’s best to let the person go as fast as possible. There never is an “optimal” time to fire someone. Don’t let time or day or day of week become an excuse to delay. The longer you wait, the more your interactions with that person become disingenuous and uncomfortable in the days and hours leading up to you telling them they’re being let go.

Cut to the chase.

Don’t dawdle or make small talk. Your opening sentence should be delivered in 5 seconds or less. For example, one Watercooler member suggested you say, “Claire, I’m letting you go effective immediately.” Be clear, succinct, and direct. Nothing you can say will soften the blow so don’t try to sugar coat your message or ask about how a project is going, etc.

It’s a decision, not a conversation.

Don’t get drawn into an extensive conversation or argument — it’s a decision that’s been made, not something that’s up for debate. Make that clear. One Watercooler member suggested that after stating that you’re letting this person go, your second sentence should articulate terms (severance, impact to equity, etc), and your third sentence should indicate this is non-negotiable. Listen to their reaction, answer questions as you see fit, but try not to get pulled into defending your decision for hours on end.

This sucks for you, but sucks way worse for them.

Another Watercooler member cautioned that you may be tempted to offer comfort by saying something like, “This is a difficult decision” or “I really don’t want to do this.” But the last thing you want to do is indulge and pontificate on how you’re personally feeling. To be frank, the other person doesn’t care how difficult the decision was for you — you made it, regardless. And, if you really didn’t want to do it, you wouldn’t have. Of course it sucks for you, but that’s not for you to impose on the person you’re firing. Find someone else to confide your pain in, and keep in mind that the decision you’re making is on behalf of the team, the company, and their best interest.

Communicate the decision to your team with grace.

Ask how the person being let go prefers to break the news to the team. Their preference might be to send a farewell note themselves, or personally tell the team members they are closest with. Other times, they’ll ask you to simply relay the news for them. If it’s the latter, share the news with respect and mindfulness. Even if the person was fired for performance reasons that were 100% their own fault, thoughtfully consider what is appropriate to disclose. Imagine if the person fired were to overhear you sharing the news with the team: Would they feel it was fair? Use this as a benchmark for how to communicate the decision to your team.

No matter how you do it, letting someone go is one of the hardest things to do as a leader. There truly is no “best way” — but hopefully these tips will be helpful should you face this situation in the future.

I know it’s helped 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.

Looking for a new job? Don’t be boring

The best advice for someone who’s on the job hunt this new year

“Don’t be boring.”

When I asked Amanda Lannert, CEO of Jellyvision, what advice she had for people who are looking to get a job, that’s the answer she gave.

As a CEO of a rapidly growing 400-person company, soon to be 500 people, Lannert has done her fair share of hiring.

“It feels like companies hire people, but in fact people hire people,” she explained. “By and large, recruiters are bored. People play it safe. They commodify themselves into just a bullet-point list of skills and experience.”

By not being boring, Lannert pointed out how you’ll catch a recruiter’s eye, and make yourself much more likely to land that initial phone call or interview.

At the same time, it’s also a great way to assess the fit of the role for you, as a prospective employee. When you show who you are as a candidate — what you value, what environment you work best in — and don’t get a call back, that company may be saving you some time and energy.

How do you not be boring? Here are five things to try:

Focus on the cover letter, not the resume.

At Jellyvision, Lannert shared how they place supreme emphasis on the cover letter. “There’s nothing more refreshing than seeing someone who takes a chance to be incredibly human in a cover letter or an outreach, to put themselves forward,” she says.

This means language that’s real, down to earth — not stiff, business jargon-y, and cut from some googled job site template. As someone who’s reviewed thousands of applicants for jobs for Know Your Team, I’d often set aside an application when the person would start their cover letter with, “I’m interested in X role. Please see my resume attached.” Everybody writes that in their cover letter — focus on saying something different.

Show, don’t tell.

A few years ago, a friend of mine wanted to land a job at Trunk Club, a company he’d been dreaming to work for some time. The only problem was that they weren’t hiring at the time. I suggested that he show them what he had to offer the company — not just tell them. So my friend whipped up a 50-slide PowerPoint presentation detailing ideas, suggestions, and projects for exactly how he could improve their online presence and user experience. He did the work of showing how he’d be an asset to the team — not just telling. Lo and behold, they created a role for him and offered him a job.

Get creative.

As a CEO myself, when I was hiring Know Your Team’s first full-time programmer several years ago, I’ll never forget how one applicant wrote me a poem — yes, a poem — perhaps 20 lines long that described who he was and why he desired the role. While we didn’t end up selecting him (he lived outside the United States and we required that the person live stateside), I remember that application so vividly even years later. He took a chance, got creative, and stood out from the 400+ applications we received in the first 72 hours alone. He was far from boring, and it worked.

Demonstrate you want this job, not just any job.

Another way to not be boring is to make it clear: “I want to work here, nowhere else.” This past year, when we were hiring for our Chief Technology Officer role, someone took the time to build a custom software application, just for Know Your Team. He’d replicated the Know Your Team software to the best of their ability, using what he’d gathered from screenshots he’d seen online. His intention was to demonstrate that he was technically up to snuff for the role.

My greatest takeaway was that it showed he wanted to work here, and nowhere else. I was impressed by him wanting this job, not just any job, and that caught my attention.

Sound like yourself.

Perhaps most importantly, you should make sure you sound like yourself. Don’t try to write a poem if you’re not good at writing poems. Don’t try to be funny in your application if you’re not funny. Be thoughtful in portraying the truest version of yourself — not what you think the employer wants to read.

If you’re concerned about how to do this, the key is simply to take put a little time and care into your application. Don’t rush your writing your cover letter. Think about how you can thoughtfully show who you are and what you can bring to the company. When you pour considered thought and energy into something, your true self will come through. Being not boring is about being yourself, more than anything else.

Keep this credo of “Don’t be boring” in mind, as you apply for a job. Dare to be different, and stand out from the sea of bullet-pointed list resumes and bland cover letters. The less boring you are, the more memorable you are. And the more memorable you are, the more likely you’ll land the job you want.


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.

This article was originally published for Inc.com.

How transparent should you be as a leader?

Two things I’ve found helpful to consider when trying to decide what to share with my team – and what to keep to myself.

How transparent should you be as a leader?

This is a question many leaders struggle with — including myself. Do you share financials with the company? Or how about salary? How open should you be about why someone was fired?

From open-book management to making compensation public within the company, the concept of transparency in the workplace is more popular than ever.

Understandably (and rightfully) so. As a concept, transparency makes sense: If you want your team to behave the way that you would behave, they need access to the same information that you have. And, the more transparent you are, the more you’re likely to build trust within your team.

But what about the unintended consequences? Can transparency backfire? Do you inadvertently cause panic in a company when you reveal what the monthly burn rate is? Do you encourage resentment from more junior employees when you reveal how much senior employees in the company are making?

As a leader, how do you decide what to share with the rest of the team and what not to?

A few months ago, I spoke with the insightful Des Traynor, Co-founder of Intercom, on this topic. For Des, deciding how transparent he should be was one of the hardest lessons to learn as a leader. And as a CEO myself, I couldn’t agree more.

In our conversation, Des shared with me two things to consider when deciding how transparent you should be in your company:

Transparency requires context.

“The key thing people forget in transparency is it’s not about opening up the Google Drive and making sure that everyone can read everything,” says Des. “It’s about transparency of context as well.” Many of the CEOs who are a part of our leadership community in Know Your Team, The Watercooler, echo this sentiment as well. One CEO remarked how he had shared revenue numbers once, and “things had gone sideways with individuals who just don’t understand or appreciate all that goes into starting and operating a business.”

In other words, the negative reaction came from the lack of context about the revenue numbers. What that CEO wished he would’ve done was share more context. If you share revenue numbers without context of monthly spend, people start wondering, “Where’s all that money going?” So for example, at my company, we share revenue numbers, within the context of also our profit margin and expenses — so it’s understood how revenue supports our business as a whole, and not just “here’s the pile of money we’re making.”

Transparency is a spectrum.

Transparency isn’t all or nothing — things don’t have to be either completely open or completely a secret. Des emphasizes this, saying, “I think it’s worth having a critical threshold to decide what’s actually good for everyone to know, what’s not a secret but needs context, and what actually genuinely might be a secret because you don’t want everyone panicking about something.” Transparency is a spectrum, and if you indiscriminately just make everything 100 percent public, you could be wasting people’s time, confusing them, or causing them strife. Everyone has a capacity of information, and overloading folks with every detail of what’s happening in marketing, support, design, engineering — it can be too much. As a leader it’s important to ask yourself: In what cases is transparency appropriate and helpful, and in what other cases is it distracting or a burden? Are you being transparent, just for the sake of being transparent, or are you truly trying to help people make better decisions, and feel a greater sense of trust?

At the end of the day, transparency is truly a positive force. When it does backfire or causes fallout, it’s often because a leader hasn’t often taken the time to consider these two things: Transparency requires context, and transparency is a spectrum.

As you think through what you should be transparent about in your company, keep in mind these two things. Hopefully, they’re things you won’t have to learn the hard way.


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.

This article was originally published for Inc.com.

How to tell if a CEO is worth working for

If you’re looking to leave your company to work for another, you’ll want to consider this.

A few months ago, someone asked me for advice about potentially leaving one company to go work for another. He was curious what factors he should consider before making the decision.

He’d already vetted the role, the company, and the offer itself — all important aspects to consider. But I told him, in my opinion, the most crucial thing to vet is the CEO.

If you’re about to join a new company, you must figure out:

“Do I believe in the CEO?”

No company is successful with a CEO who can’t communicate, who can’t get everyone on the same page, who can’t hire well, and who can’t chart out a vision.

Personally, I remember interviewing at one of my first job out of college, and I remember it being really hard to tell if a CEO is “good” or not.

Plenty of CEOs sound like they’d be a good CEO. They’re charismatic, they’re articulate — but does sounding like a good CEO really make it true?

After almost four years of researching and observing hundreds of CEOs, I’ve learned to ask these four questions to discern whether or not a CEO is a good CEO:

#1: “When have you had to sugar-coat the truth — or avoid telling the truth — to your team?”

How a CEO answers this question reveals her barometer for integrity. Your CEO might laugh and say, “Oh, all the time,” a little too flippantly — signaling that she intentionally misguides employees habitually. On the other hand, if a CEO is too hesitant to admit anything substantial, that’s a red flag as well. It’s likely she’s holding something back. Ideally you’re looking for a CEO to level with you and admit in a nuanced, considerate way when she’s chosen to not be transparent with the team, and why.

#2: “What do you think is your own greatest leadership blindspot?”

This is a take on the classic, “What do you think your greatest weakness is” question — but with a twist. The word “blindspot” implies that the CEO has a weakness she might often overlook. So her answer to this will reveal her self-awareness. Does she have a hard time giving you a straight answer? Or is it clear that this is something that she’s thought a lot about, self-reflected upon, and perhaps even talked about with peers or an executive coach. If it’s the latter, it signifies that this leader has the humility and self-perceptiveness you’re looking for.

#3: “What does ‘success’ for the company look like to you?”

This may seem like an unassuming question to ask — perhaps it’s one you’ve asked the CEO already. However, we often don’t listen closely enough to the answer. If all the CEO is focused on is “winning” and “making money” and “dominating the competition” in her answer, I can guarantee that’s 100% what the work environment is going to revolve around. On the contrary, if she also talks about creating a sustainable, healthy culture, and making sure people feel fulfilled, challenged and supported in their jobs — you can bet that the work environment is going to reflect that. The answer to this question makes is crystal clear what a CEO’s priorities are.

#4: “What would an employee who’s left the company say it’s like to work for you?”

This may feel like a tough question to ask you prospective CEO — especially if they haven’t hired you yet. But it potentially is the most important question. The answer to it demonstrates how cognizant the CEO is of how they’ve treated employees in the past, and how willing they are to admit if they’d haven’t been the ideal leader. Be wary of CEOs who say only positive things, as it shows their refusal to recognize their shortcomings, or failure to understand how their own leadership behavior may have driven the other person away.

If you’re worried that asking these questions — particularly the last one — might offend your prospective CEO, that in itself is a sign that the CEO might not be who you’d hope for. The best leaders welcome tough questions, and will be impressed by your desire to better understand how they lead.

If anything, asking these questions will make you look better in their eyes. And, it gives you all the information you need to decide if they’re a CEO worth working for.

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.

This article was originally published for Inc.com where I write a column on leadership.