One-on-ones 101: With whom and how often?

As a busy leader, you may be wondering how to fit one-on-ones into an already packed schedule. Here are some best practices selected from The Watercooler, our online community for leaders.

A frequent question I receive when it comes to having one-on-ones with employees is: With whom and how often? Everyone? Direct reports? A cross-section of employees from different departments? Once a week? Once a month? Bi-weekly? Quarterly? Once a year?

One-on-one meetings can be notably time-consuming — especially if you’ve got more than 50 employees. So figuring out how who you’re talking with and the right cadence of conversations is crucial.

To get a sense of what other successful leaders have implemented at their companies, I posed the question of one-on-one frequency and structure to The Watercooler, our online community in Know Your Team with 1,000+ leaders, managers and executives from around the world.

Here’s some of their best advice about one-on-ones:

  • With more than 100 employees, this content strategy leader can’t have one-on-ones with everyone. She holds one-on-ones with direct reports every two weeks, and she meets with peers and stakeholders in different teams and departments across the company every one-to-three months.
  • One leader of a 50-person-plus organization said she conducts one-on-ones with six managers and four or five employees selected at random. This gives her a good understanding of what’s going on in the company — and not just from a manager’s perspective. The frequency is one a month.
  • With a company of about 25 people, one leader said she meets with four direct reports weekly for 30 minutes, and twice each week for an hour with two different employees. This ensures that everyone has the opportunity to voice long-range items.
  • Another leader of a small team of about 10 people said she can still conduct one-on-ones with everyone. But rather than load up everyone’s calendars with meetings, she tries to be more present and aware about what’s happening in terms of attitudes and behaviors across the team, which allows her to actively react by scheduling more one-on-ones with those who may need it most.

How often do you hold your one-on-ones, and with whom? Share your experience in the comments below, or join us in The Watercooler and read what leaders from around the globe are discussing when it comes to leadership and employee engagement. Look forward to hearing from you!


Six tips to rock your one-on-ones

Quick, handy best practices to have effective, productive one-on-one meetings with your team


One-on-ones with employees are one of the most underrated tools for managers. If done properly, these meetings can be an incredibly effective way for managers to receive feedback, gauge employee satisfaction and productivity and even offer some insight into how team members are interacting and working together.

In fact, in a Watercooler AMA we hosted with Amir Salihefendic, Founder and CEO of Doist, he said that his biggest leadership lesson he wish he learned earlier was investing one-on-ones meetings. “We started to do one-on-ones very late,” admitted Amir. “I would even recommend them if you are a smaller company.”

Take it from Amir, first hand, and start investing more in your one-on-ones. Here are some tips to get the most out of your next one-on-one meeting…

Be present.

This means close your laptop. Turn the ringer off on your phone. Have a meaningful, purpose-driven conversation. We can all go 30 minutes away from email, text messages and phone calls to ensure a successful one-on-one meeting.

Be open.

This advice is for both parties, the manager and the employee. The employee, of course, has to be open to feedback from his or her manager on job performance, time management, conflict resolution and all those other topics we look to address during our one-on-ones. But, the manager also has to be open, as well. This time is just as much for the employee to offer feedback. What if that feedback is not 100 percent positive? Hint: See №5.

Be prepared.

This cannot be overstated. Being unprepared is not only a quick way to an ineffective meeting, but it also shows a blatant disregard for the other person’s time. Do everyone a favor and be as prepared for this meeting as you would be for your top client. Here are the eight best questions to ask during your one-on-one.

Be honest.

Didn’t we cover this in №2? Well, sort of. That was about receiving feedback. This one is about giving honest, constructive feedback. Has an employee ever turned to you during an annual evaluation and say that he or she was surprised by a deficiency you noted? Why wasn’t that in your one-on-ones? Your time is valuable. So is theirs. Use it wisely and honestly.

Receive feedback gracefully.

This is a topic I’ve tackled multiple times because it’s not always easy to do. Here are some more tips to mastering the art of receiving negative feedback in a productive manner.

Don’t leave empty-handed.

Did a conflict come up? If so, what are the action items to address the issue? Perhaps a new employee goal or a professional development opportunity surfaced — who is going to own this item to make sure it’s accomplished? It’s important to leave the meeting with clear expectations and action items so that both parties can be prepared for the next week (or two weeks, or however often you have them) to have another A+ one-on-one.


You may have noticed that I’ve been writing a bunch about one-on-ones lately… Well, I’m actually in the process of writing an in-depth guide to one-on-ones! If you’d like to get notified for when I publish the full guide , sign-up below and I’ll be sure to ping ya 👇

https://upscri.be/98d8ee/






P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @cjlew23.)

7 ways to prepare for an effective one-on-one meeting with your manager

Got an upcoming one-on-one meeting with your manager? Consider a few of these tips in preparation for it.

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

Yikes, really?

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

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

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

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

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

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

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

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

Share what’s been most motivating to you.

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

Reveal what’s been draining and demotivating to you.

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

Explain how you want to stretch and grow.

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

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

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

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

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

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

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

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

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

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

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

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


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

Here are six ways to get employees talking about what they really feel during a one-on-one meeting (and not what they think you want to hear)…

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

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

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

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

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

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

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

Make empathy your mission.

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

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

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

Ask questions to uncover two things: tension and energy.

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

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

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

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

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

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

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

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

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

Admit what you think you suck at.

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

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

Explain why you need their input.

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

Don’t get defensive.

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

Talk less.

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


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

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

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