Don’t solve the problem.

What makes a great manager isn’t the problems they solve, but the questions they ask. Start with these 16 questions here.

An employee comes to you and says, “I have a problem.” If you’re trying to be a great manager, what do you do?

Your initial instinct might be to roll up your sleeves. “Time to be the boss,” you think to yourself. You’re ready to step in, solve the problem and save the day.

Or something like that. You just want to be helpful.

In reality, your instinct is the opposite of helpful. Startlingly, when you jump in to solve a problem as a manager, it’s one of the biggest leadership mistakes you can make.

Keep reading “Don’t solve the problem.”

The 3 most effective ways to build trust as a leader

Based on data from 597 people, the best ways to build trust as a leader aren’t what you think they are.

How do you build trust as a leader? The answer seems intuitive enough.

For many of us, we hold company off-sites and run team-building activities. Informal lunches, monthly social get-togethers, and one-on-one meetings are part of how we build trust at work.

We also thank our team publicly and give employee recognition for a job well done. And, we strive to be transparent with company information during all-team meetings.

These are among the most popular ways to build trust because they work… Right?

Wrong.

Keep reading “The 3 most effective ways to build trust as a leader”

Delegate outcomes, not activities.

When it comes to delegating, invite your team into both the thinking and the doing.

Do you consider yourself “a doer”?

That person who enjoys doing the work, fine-tuning the details, meddling in the weeds of how it’ll all work? Then you probably have trouble delegating as a leader.

I know I do.

For so many managers and leaders — especially those of us who are used to be the person doingthe work and are now handing off the work to others — learning to delegate is, well, tricky, if not painful.

Keep reading “Delegate outcomes, not activities.”

The mindset shift of a manager

Becoming a new manager isn’t merely a change in what you do — it’s a change in how you think.

Becoming a manager for the first time is deceptively difficult.

No matter how many leadership books you’ve read or conversations you’ve had with mentors — the transition to becoming a manager is precarious.

Talk to any leader, and they’ll affirm this. “I was a terrible manager when I first started,” most will say. Myself included!

Keep reading “The mindset shift of a manager”

How to deal with a micromanaging boss

The 5 reasons why people tend to micromanage in the workplace – and how to manage up, and around them.

I’ve heard the phrase, “I have a micromanaging boss,” more times than I can remember.

I heard it again, just last week. This person asked me, “What do I do? Is there anything I can say to a micromanager? How do I manage up?”

Here’s what I recommended to him…

Keep reading “How to deal with a micromanaging boss”

Leaders, doing what you’re good at hurts your team.

Playing to your strengths as a leader doesn’t make you a good manager. Here’s why.

Of all the tips to be a good manager, “leaning into your strengths” has got to be one of the most frequently cited.

“Do what you’re good at. Focus on your strengths.” That’s the conventional advice we all receive. There’s no shortage of StrengthsFinders assessments and personality tests urging us to triangulate which strengths we should zoom in on.

However, I recently had a conversation with Peldi Guilizzoni, CEO of Balsamiq, on The Heartbeat. His insight on this topic turned my head sideways… in a good way. Peldi asserted:

“Doing what you’re good at hurts the team.”

Huh? Let me explain.

Keep reading “Leaders, doing what you’re good at hurts your team.”

Stop being so nice all the time.

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

Leaders, stop being so nice all the time.

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

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

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

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

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

He’s not the only one.

Have you ever found yourself in one of these situations?

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

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

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

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

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

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

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

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

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

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

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


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

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

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

You’re not prepared.

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

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

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

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

#1: Get up-to-speed.

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

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

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

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

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

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

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

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

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

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

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

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

Questions that uncover concerns / issues…

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

Questions that elicit feedback about work performance…

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

Questions that help provide career direction…

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

Questions that foster a sense of personal connection…

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

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

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

#4: Calibrate your mindset.

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

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


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

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

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

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

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

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

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

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

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

#1: “How’s it going?”

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

What should you ask instead?

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

#2: “What’s the latest on __?”

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

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

What should you ask instead?

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

#3: “How can I help you?”

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

What should you ask instead?

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

#4: “How can we improve?”

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

What should you ask instead?

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


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

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

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


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