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.

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.

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.

Managers, screw the Golden Rule

Don’t treat employees the way you want to be treated. Here’s why.

“Treat others the way you’d like to be treated.”

This is The Golden Rule we all learned growing up. As a manager or CEO in a company, you’d think it would make sense to follow it too. Managers should treat their employees the way they’d like to be treated, right?

Not quite.

In a recent interview I did with David Heinemeier Hansson (DHH), the Creator of the popular web framework Ruby on Rails and Chief Technology Officer at Basecamp, he shared this insight: You shouldn’t treat other people the way you want to be treated because the other person isn’t you.

The other person has different preferences (beliefs, ideas, and experiences) and is going to react to a situation differently than you. You might think something is reasonable or fair, but that’s you thinking that, not the other person. You cannot assume that the way she would like to be treated is the same as the way you’d like to be treated.

David admits to being guilty of this as much as anyone, saying that when he does this, “I’m trying to be empathetic to my own mirror image, which is not actually a very good definition of empathy.”

In fact, it’s self-centered in many ways to assume that if you treat others the way you’d like to be treated, other people will like it too.

One of the most memorable examples for me of this is when I talked with another CEO a few months ago. He told me how his company had implemented an unlimited vacation policy recently. In theory, he thought it was going to work great. It’s what he had always wanted when he’d worked at other companies himself — unlimited vacation, what could be better?

But then something interesting at his company happened: No one in his company took vacation. Maybe a day or two off here and there, but people took less vacation with the unlimited vacation policy than they had in years before.

I was a little shocked when he first told me this. What went wrong? The CEO learned is that none of the employees wanted to be seen as “the slacker” or “letting the team down.” Everyone else was afraid of taking vacation, so no one went on one.

After realizing this, the CEO replaced the unlimited vacation policy with a requirement that people take at least two weeks off of paid vacation during a year. It’s not what he would have necessarily wanted, but that’s not the point. If you’re a great manager or leader, you shouldn’t be operating from the point-of-view of what you want, you should be operating from the point-of-view of what others want.

Instead of practicing The Golden Rule and assuming other people are just like you, what should you do?

The answer is deceptively simple. Ask.

Ask your employees what type of vacation policy they’d prefer or what work environment they’d like to be in. Here are some examples of things you can specifically ask:

  • How do you prefer I give you feedback? In-person or in writing?
  • When you are most productive in a day? During the morning or the afternoon? Or even at night?
  • How much social interaction is important to you? Should we plan more team-bonding outings or have more regular company lunches?
  • How often would you like to get together for one-on-ones? Once a week, once a month or once a quarter?
  • How would you like to recognized for your work? Do prefer verbal praise in front of others, or more privately? Are small gifts or tokens of appreciation a good way to signify gratitude?
  • How much direction or context do you like before kicking off a project? Do you need space to gather your thoughts initially, or do you like having a lot of suggestions from me upfront?

Don’t just assume their answers are the same as yours. Ask, listen, and then act accordingly. The Golden Rule need not apply.


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 influence culture when you’re not the CEO

“Culture starts from the top,” it’s often said.

But is that really true?

Surely, it is easier to influence company culture when you’re at the top. As a CEO, founder, or business owner, people are already looking to you for example and guidance around what’s important within the team. (I wrote a bit about how you can influence culture as a leader here.)

However, being a leader in the company is not required to influence company culture. If you’re an employee or a middle manager and you’re frustrated with the status quo in your company, all is not lost.

Culture has nothing to do with what your job title on your business card says. It has everything to do with your beliefs, words, and actions as an individual.

Culture is made up of people after all — people who decide what artifacts, espoused values and beliefs, and basic underlying assumptions are true for a team. Any one person can influence culture, not just the CEO.

Regardless of what position you hold in the company, here are few ways you can create an environment for the culture you want to take form:

Model what you’d like to be true of your team.

Let’s say your CEO isn’t great about being responsive to emails and showing that she’s listening. If responsiveness is something you think should be a part of your company’s culture… the question is, how well do you respond to your own emails? When in a one-on-one or a meeting with your team, do you yourself do a good job yourself of listening to and responding to others’ requests? Look at yourself, first and foremost, as a starting point for the kind of company culture you aspire to have.

The power of modeling what you’d like your company culture to be is two-fold: (1) You make it known and visible what can be improved. And (2) if things start going well and your colleagues are really loving what you’re doing, someone — the CEO, founder, or business owner — is going to notice. She’s going to say, “Hmm maybe we all should start doing what you’re doing.”

In other words: Show what you’d like to better in the organization — don’t just wait for it to happen.

Dissent is a responsibility.

If there’s something you think could be better in the organization that the team should adopt to improve the culture, speak up. As an employee, dissent is a responsibility. Voice it respectfully, especially when the opportunity to give feedback presents itself. For example, in your last one-one-one meeting, when your manager or CEO asked you what could be improved, did you share a thoughtful answer?

Culture can only be intentionally shifted if it’s intentionally talked about.

It’s important to do this in private — no leader likes to be “blasted” in front of the company about what you think she is falling short of. (You can read more about how to give difficult feedback to your boss here.)

It’s also important to share your suggestion in the context of the team — and not just your own individual interests. For instance, it’s easy to say that you think the culture should be more open, especially around financials, because you think it’d help you better negotiate a raise. But instead, if you can share why transparent financials would help everyone on the team feel more bought on to what the company is trying to accomplish, the likelihood of others embracing what you’re looking to change increases.

Give space, grace, and gratitude to leaders.

It may take time for the rest of your company to catch on to how you’re trying to influence the company culture for the better. You may even get questions or resistance for why you’re doing things a certain way. Don’t be deterred. Understand that change takes time — especially cultural change, not to mention change that happens from the bottom up. Understand that your leaders are juggling many priorities, and that it may take repeated action for them to take note.

You can also thank your leaders in the meantime for the things they do that already reinforce and support the kind of culture you desire as an employee. There’s a lot of talk of the importance of employee recognition — but manager recognition is just as important. Leaders aren’t thanked very often, so it goes a long way to help solidify the culture you’re want to have, when you show appreciation for the things you already think are headed in the right direction.


Influencing culture from the bottom-up, and not just the top-down, is possible. Though, it may be more difficult and take more time to manifest, it’s an important route to seek as an employee or middle manager. If you can slowly yet steadily put energy behind shifting the culture, you not only make things better for yourself, but for others as well.

As an employee or middle manager, a better company culture can start with you.


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.

How to influence company culture

“How do you actually influence company culture?”

This is the big, hairy question I often get asked by CEOs, managers, and employees alike. The other week, I posed it at the end of my most recent piece, The Culture Cliché.

In that piece, I shared how the fundamental, core element of culture are our basic underlying assumptions. That is, the things we actually believe — but might not always say or outwardly show — are what determines our company culture.

As a result, the key to influencing culture is tapping into those basic underlying assumptions: Listening to them, responding to them, and acting according to them.

But what does that tangibly mean? Can you affect or influence others’ basic underlying assumptions, to begin with?

Yes and no.

Yes, basic underlying assumptions can be affected.

But no, they can’t be outright changed. You can’t manipulate someone else’s basic underlying assumptions. Employees are not malleable objects for leaders to shape. Each person has her own intrinsic, worthwhile desires and beliefs — and that’s not for you as a leader to try to mess with.

Instead, what you can do is to focus on creating an environment where employees can choose to shift their basic underlying assumptions in line with what feels right to them.

Let’s talk about what this practically looks like.

There are three parts to creating an environment where the kind of basic underlying assumptions you want — and ultimately, the kind of company culture you want — can come into fruition:

Personal accountability

You must model the behaviors and basic underlying assumptions you want to be true. One of the greatest shortcomings of a leader is wanting others to do something when she doesn’t practice it herself. For instance, a manager often doesn’t admit her own weaknesses, but expects employees to be upfront and forthcoming about mistakes that happen in the company. See the disconnect? Whatever basic underlying assumptions you desire to be deeply rooted in your company, you must exhibit those basic underlying assumptions yourself, first.

As the leader, you should be the living embodiment of the basic underlying assumptions you want your culture to have. You should be consciously and intentionally speaking and acting in a way that shows people, “This is important to me.”

Consistency

Your desired basic underlying assumptions won’t be made true unless they are consistent. Basic underlying assumptions are solidified when you act consistently upon them.

Say you want honesty and transparency to be a basic underlying assumptions within your company’s culture. You decide to hold an all-hands meeting every month where you cover high-level financials, company goals, accomplishments, and answer employees’ questions. Seems like it’d be an effective initiative to establish that honesty and transparency are a basic underlying assumptions within the company.

But here’s the missing piece: Is it consistent? Do you hold those all-hands meetings every month, regularly? Or has the frequency of those meetings tapered off so now it’s every 2 or 3 months…or just whenever you remember to have them.

If it’s the latter, you’re falling short of creating an environment where those basic underlying assumptions can be strengthened.

Consistency determines whether or not this tenet of your culture is fleeting, or here to stay.

Richness

Being consistent alone in how you demonstrate your basic underlying assumptions isn’t enough. You must think about the richness of how you’re communicating these basic underlying assumptions. Are you using a variety of channels, means, and mediums to show that this is something that’s important for the team to embrace and embody? Or are you just relying on one?

For example, it’s not enough to just hold the all-hands meetings and assume that’s the only way to foster honesty and transparency within the company. Consider that some people might not feel comfortable speaking up in front of the rest of the company… so you’ll want to make sure you’re also doing one-on-ones. But don’t also merely assume that a one-on-one is enough of an opportunity for someone to speak their mind. Perhaps that person doesn’t always feel comfortable directly addressing that particular manager. Make sure you provide other opportunities for your employees to speak up, be it at group lunches, coffees get-togethers, CEO office hours, or an all-company survey.

The richness of how you communicate, the varying formats and mediums, helps dictate if the basic underlying assumption is truly what it should be: foundational.

Now this is no grand formula by any means for creating the culture that you want. Shaping a company’s culture and tapping into a team’s basic underlying assumptions is more art than it is science.

But consider these three elements — personal accountability, consistency, and richness — in how you’re upholding the basic underlying assumptions you want to make more real.

Pick one, commit to it, and see progress build over time. Slowly, but surely, you’ll see the difference.


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.

Cereal Day

Something as small as breakfast cereal– yes, cereal — can improve employee engagement. Here’s why.

The executive director of a prominent nonprofit called iMentor Chicago reached out to me the other week. Her name is Halleemah Nash.

“A question I asked my team a few months ago really caught me off guard,” Nash shared with me.

“I thought it was honestly kind of a silly question — something I’d never answer myself, personally. But I thought, ‘Oh what the heck, let’s ask it and see what happens.’”

The question was:

“What’s your favorite breakfast cereal?”

She asked this question to her staff, expecting nothing much to come of it.

The opposite happened. Almost every single person on her staff responded — enthusiastically, humorously. It got the whole office talking, laughing, joking with one another.

Nash took notice. She saw the collegiality it spurred, and wanted to encourage that positive spirit even more.

Once a month, she decided to plan a “Cereal Day,” when she’d bring in everyone’s favorite cereal. She had “Cereal Day” take place on the day of her team’s monthly strategic planning meeting — no doubt a tough, intense day for the staff.

Her staff absolutely loved it. Nash was stunned. “Who knew that cereal would get people pumped for a strategic planning conversation,” she wrote to me candidly in an email.

While it’s endearing to think that breakfast cereal is “the thing” that flips a switch for a team’s employee engagement, there’s something deeper going on here. Nash’s “Cereal Day” works as a means to boost her team’s morale for specific reasons.

Here’s what we can all learn from it as leaders:

Great leaders bring levity to a team, not just the load of work.

Let’s be real: Work feels serious a majority of the time. Everyone’s busy, there are deadlines flying around, a thousand decisions to be made — it’s easy to get your head stuck in the weeds of work. We all need a break, at some point.

Nash understands this, and so intentionally chose her strategic planning meeting day as the day to hold “Cereal Day,” as a result. She knew how in moments of stress or intensity, people do better work when they can step away, have a laugh, and just lighten up a bit.

As a leader, yes, it’s your job to press the gas pedal to make sure folks are focused. But you also want to give people permission to be people — to have fun, be silly, be expressive. Don’t get frustrated if you notice your team members cracking jokes during a meeting. Don’t be bitter when an employee takes an extra long lunch with a co-worker. Take it as a sign that they might need that levity. Like Nash, if there is a particularly tense time of year, use it as an opportunity to bring lightness to that meeting or season.

Great leaders find a way to connect everyone, not just some.

“Cereal Day” was effective at bringing together Nash’s team because, frankly, it’s unlike a lot of other team-bonding events: It involved everyone. Think about it.

At a happy hour, typically the same folks congregate and talk to one another. During a one-on-one coffee conversation, you only get to know that one particular person. It’s rare to have moments in the company where everyone gets to interact with everyone else — but that’s what “Cereal Day” did. Nash’s “Cereal Day” is the antidote to the silos that pop up in organizations.

Take an honest look at your own company’s current team-bonding events and see if they’re a common touch point for everyone, or just for some. You may be accidentally reinforcing the silos in your company you’re working so hard to dissolve. You may have to get creative — or even better, ask your employees about their personal tastes and interests — so you can tailor company outings, events, and activities to be a shared, common touch point for everyone.

Even if it’s about breakfast cereal — the fact that it’s something everyone can participate is what matters.


Whether you try to engage your employees as a leader with cereal or not, that’s totally up to you. But “Cereal Day” is an important reminder for us as leaders that employee engagement isn’t just about the big, grand gestures of extending vacation time or big pay raises.

True employee engagement is about caring enough to ask even the seemingly small, trivial questions to your team — and paying close attention to the answers.


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.

This article was originally published for Inc.com.

Excuses we tell ourselves as leaders to avoid honest employee feedback

I was on the phone with a CEO the other week. He wanted my advice for how he could cultivate a more open, transparent company culture for his team.

This CEO seemed to be already doing a lot of the right things. He held monthly all-hands meetings to get everyone on the same page. He also regularly asked questions to his employees about what could be better in the company.

However, when I recommended one question that he ask his employees, he was a bit taken aback.

“You want me to ask my team: ‘Are there any benefits we don’t offer that you think we should?’ Hmm, I dunno, Claire,” he told me.

This CEO assured me that he welcomed and valued feedback from employees. But asking about company benefits? And asking about them so publicly? He started to feel nervous about it.

“I don’t want the feedback to be a distraction,” he shared. “There’s so much we already do around benefits — I think this could set the wrong expectations and derail people from getting their work done.”

He continued:

“And, I don’t think we’re ready to act on that feedback. If we ask that question, it implies we need to implement something. But it might not be cost-effective. If we can’t do it, I don’t want to let people down.”

I get it. I’m a CEO myself. No CEO wants her employees to be distracted. No CEO wants to make false promises.

Here’s the reality, though: If you dig deeper, those two statements are actually excuses that are keeping you from building the open, transparent company culture you’re keen on.

Let’s take a look.

Excuse #1: “I don’t want feedback to be a distraction.”

Any feedback your employee might have already exists, whether or not you choose to ask about it. If someone has an idea to improve company benefits, that’s an idea that they’re already thinking about in their heads. So if you don’t ask about it — if you let that feedback sit and fester — it becomes a distraction. The longer you ignore it, the longer you don’t ask about it, the greater the distraction balloons. The way to nip the distraction in the bud is to ask about it. When you ask a question like, “Are there any benefits we don’t offer that you think the we should?”, you have an opportunity to clear the air, and help an employee feel heard. Asking for feedback isn’t the distraction — pretending that your employees don’t have feedback is.

Excuse #2: “I’m not ready to act on feedback.”

Popular management wisdom tells you that,”You shouldn’t ask for feedback unless you’re ready to act on it.” Sure, if you don’t do something with the feedback, you’ll look like you’re not following through on your word. But acting on feedback doesn’t necessarily mean implementing the actual piece of feedback. You can thank the person who gave you the feedback. You can explain why you’re not enacting the feedback, and provide context for the decision. Both routes show you’re listening, and that you value your employees’ feedback. Oftentimes, that recognition and explanation is all an employee is looking for. They’ll take notice.

If you’ve ever caught your own manager — or yourself — saying the above two excuses, then here’s my tip: Stop.

While you may mean well, you’re hindering yourself from creating the open, transparent company culture you’ve always wanted.


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.

This article was originally published for Inc.com.