How To Master One on One Meetings

Table of Contents:

As the great CEO and managerial innovator Andy Grove said, meetings are just a medium. It’s what gets done in them that actually matters.

Simply scheduling one-on-ones doesn’t make you a better manager or leader. But using them correctly can help you become a great one. This article will help you get there. We cover the following questions:

  • Why are one-on-one meetings important?
  • How long should my one-on-one meetings be?
  • How often should I have one-on-one meetings?
  • What should I say in one-on-one meetings?
  • How do I know if I’m doing one-on-ones right?
  • What if my team members don’t say much?

Let’s get started.

Why Are One on One Meetings Important?

When you’re busy — and particularly if you have lots of team members — making time for one on one meetings can seem like a hassle. But they’re almost certainly the most important meetings in your calendar.  

More importantly, the benefits of one on one meetings include:

  • Improving the way your team works collectively and individually
  • Developing your team’s careers
  • Gauging the well-being of your team
  • Providing constructive feedback
  • Building trust with your team members
  • Discussing day-to-day activities, employee performance, and the overall employee experience
  • Conducting check-ins and follow-ups

And you can get this all in the space of about 30 to 45 minutes.

Improving Work

One-on-ones are a unique opportunity to understand and affect how your team functions in a level of detail you won’t get anywhere else — even when you consider team meetings.

One-on-ones are your must-do meetings, your single best opportunity to listen, really listen, to the people on your team to make sure you understand their perspective on what’s working and what’s not working. - Kim Scott, Radical Candor

This level of detail enables you to make far better decisions about how to run your team, which unlocks higher performance.

Let’s say you have a one-on-one with your subordinate every two weeks, and it lasts one-and-a-half hours. Ninety minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours, and also upgrade your understanding of what he’s doing. - Andy Grove, former CEO, Intel (High Output Management)

If you’re alarmed at a 90-minute one on one meeting, don’t worry. They don’t always have to be 90 minutes. But Grove’s point is sound.

For the sake of 45 minutes of your time, you could gain insights and improve decisions that impact hours — if not days and weeks — of your team’s work.  Why wouldn’t you invest that time?

As Mike Krieger said when reflecting on his time as co-founder of Instagram:

Once you add a management realize that you were only aware of the top 5% of what needed to get done. Mike Krieger, Co-Founder, Instagram

Career Development

Regular one on one meetings don’t just inform better decision-making about how to run your team, but also how to develop your individual team members.

Through these meetings, you learn more about people’s strengths, weaknesses, career aspirations, and challenges. This is the information you will use to shape the assignments they work on, the people they meet the skills they build, and development goals. Without one-on-ones, you’re shooting in the dark, with significant opportunity costs for your team’s progress.

Professional development and personal development are crucial to team morale, employee retention, and employee engagement. Don’t leave the opportunity for open communication and development on the table.


The insights you gather in one on one meetings will help you improve the performance of your team, but it’s also where you’ll find out how your team is doing more generally. Are they happy? If not, where are the problems? What can you do to fix them?  

Because of their more personal nature, one on ones allow these details to emerge, and only through regular one on one meetings can you get a sense of your team’s overall well-being, psychological safety, and overall job satisfaction. Regular check-ins are a core component of building high-performing teams — something every manager and leader should strive to achieve.

The sound that surrounds a successful regimen of one-on-ones is silence. All of the listening, questioning, and discussion that happens during a one-on-one is managerial preventative maintenance. You’ll see when interest in a project begins to wane and take action before it becomes job dissatisfaction. You’ll hear about tension between two employees and moderate a discussion before it becomes a yelling match in a meeting. Your reward for a culture of healthy one-on-ones is a distinct lack of drama. - Michael Lopp, Engineering Leader, Apple

Building Trust

At the core of any great relationship between a manager and a team member is trust. Building trust is a famously tricky thing to establish, particularly early on. Many new managers look to the skies and wonder how they can possibly make a start on earning it from their team.

One way to help is one on one meetings.

Showing up for your one on ones is the most concrete way to demonstrate to your team that you’re invested in them and their progress — and a key tenet of performance management. And when we say “showing up,” we don’t just mean attending the meeting. You need to be engaged to conduct an effective one on one meeting, but more on this later.

Providing Constructive Feedback

Face-to-face, one on one conversations open the door to frank and candid discussion. During a one on one meeting, one of your talking points or meeting agenda should be employee feedback. Through honest feedback, you encourage employees to grow professionally and personally, address weaknesses, and build strengths. You can also add this component to your performance reviews.

Along with end-of-meeting questions, make sure to include feedback as part of your one on one meeting agenda. It can eliminate roadblocks in work and communication, while also giving your employee a takeaway from the meeting as a whole.

How Long Should My One on One Meetings Be?

Man pointing to his watch

If you go back to why one on one meetings are important, how long do you think it would take to have a meaningful conversation on these subjects? Generally, you should schedule at least 30 minutes, but preferably 45.  

A 1-on-1 meeting that’s any shorter generally doesn’t leave enough time if your team member wants to have a substantive conversation on a particular topic. Worse, by rushing, you’ll actually diminish the trust your team has in you.

In your 15-minute one on one, all you learn is that you don’t have time to care.       - Michael Lopp, Engineering Leader, Apple

How Often Should I Have One on One Meetings?

In short, there’s no rule (although some companies will make one). How often you hold one on one meetings depends on your individual team members and your availability. But they will typically happen on something like a weekly or bi-weekly schedule.

Consider Your Team Members

Remember why one on ones are important: improving work, career development, checking in, building trust, and giving feedback.

One on ones won’t be the only time you’ll interact with your team members and get signals on these topics. If you’re working daily with a team member and have an established relationship, you both may feel an additional weekly meeting to discuss the past week doesn’t add much value. More experienced team members may also prefer more infrequent meetings. Conversely, if your team member has something specific to discuss, you might spend more time.  

In short, schedule your next meeting so they’re most constructive. The unique benefits of dedicated one to one meetings mean that most managers and team members will typically schedule them on at least a bi-weekly basis.

Your Availability

By “your availability,” we don’t just mean “have you got a gap in your calendar.” We mean whether you’ve got the availability to genuinely dedicate that portion of time to your team members.

A good one on one meeting requires intense listening and understanding without multitasking or distractions — at least 30 minutes of your undivided attention (potentially with some prep before and note-taking after).  

In an ideal world, you could give that to your team members on their preferred schedule.  However, if you have many team members, you may need to compromise to ensure you are actually available to schedule one on ones.

If you can’t find 30 minutes per team member at least every two weeks, you probably have too many direct reports.

One-on-ones should be a natural bottleneck that determines how many direct reports a boss can have. Kim Scott, Radical Candor

What Should I Say in One on One Meetings?

You probably shouldn’t say very much. One on one meetings are an opportunity to learn from your team members about their work, think about how you can help them, and demonstrate your investment in their professional growth.

For these reasons, a team member will typically lead one on one meetings. For managers, attentive listening is far more vital for conducting an effective one on one than knowing what to say.

When you speak, it’s likely prompts and questions to draw out some of these insights and ensure your one-on-one doesn’t descend into silence — or worse — a status update. Neither party learns anything from either of these.

By listening intently to your team members talk about their work, their successes, and their challenges, you’ll usually spot some detail that can be drawn out into a useful discussion. For that reason, managers usually start their one on ones with an open-ended question like “How are you?” or “How has the week been?”

These questions sound basic, but they get the conversation flowing and your team member leading it. Depending on their thoughts, you can then evolve the discussion. You might use prompts like:

  • Can you tell me more about that?
  • I know you’re focusing on (insert skill) this quarter. Have these one on one meetings helped with that?
  • We’re trying to do more of (insert focus area) on the team. How do you think we’re doing?
  • What would you like to do more of?
  • What would you like to do less of?
  • Are you getting the right support from your colleagues?
  • Is there anything that I can help you with?
  • Can I put you in touch with anyone over the next month?
  • I know I’ve been busy this month with (insert task).  Were there times when I could have supported you better?

The last example includes an admission of fault on behalf of the manager. One on ones should be a place where team members can offer feedback to the manager, although it can take time for people to feel comfortable doing this.

You may have read articles with titles like “121 questions for your next one-on-one.”  Though these can be useful, they can also create the unhelpful impression that you’re doing a bad job if you don’t ask this full range, which is nonsense. Using lists like these can also come across as robotic and impersonal when you’re meant to be demonstrating how much you care!  

If you consistently find you’re not having productive one-on-ones, these lists can be useful for prompts and inspiration — so here’s a giant list if you find these things helpful.

Using a Meeting Agenda

You may see advice that all one on one meetings should have an agenda, pushing the idea that a meeting agenda template is a necessity. However, it’s the team members’ meeting, so it should be run however is most constructive for them, regardless of the agenda.

Some team members may really like the structure of an agenda. Others may find it constraining and unhelpful. If you haven’t tried an agenda before, it’s certainly something worth experimenting with. It can give the manager time to prepare and offer better answers to complex questions.

Am I Doing One on One Meetings Correctly?

Man and woman having a one on one meeting at a cafe

“How do I know if I’m doing this job right?” The question echoes in the minds of nearly every manager. Though initially difficult to identify, you’ll be able to spot a few signals if they’re not going well (these are nicely consolidated in this article on evaluating one on ones by Adrienne Lowe):

  • Cancellations: If your team member consistently stops showing up, it’s a fairly strong signal they don’t value the meeting!
  • All smiles: If you’re consistently discussing positive stories, that suggests your team member doesn’t trust you enough to discuss their real challenges, and you’re missing the key value of the meeting.
  • Status update: A one-on-one is not a project management meeting. However, a one on one meeting can be easy to slip into this, particularly if you haven’t spoken to the team member in a little while. Use status updates for other forums (typically emails) to avoid wasting valuable one-on-one time.

What If My Team Members Don’t Say Much?

This is a relatively common question from new managers, particularly in the early stages of building relationships with a team. This usually indicates one of two things:

  1. They’re unsure about how to use the one on one meeting, and what they should be discussing.
  2. They don’t trust you enough yet to discuss the issues that are most important to them.

You can usually resolve the first issue by ensuring that your first one on one meeting with a team member sets some context about how you see one-on-ones, their value, and how you hope your team member can get the most out of them.

Number two is more difficult and can simply take time. However, you can try a few things to shorten the time frame:

  • Keep showing up: Demonstrate your commitment to them by regularly holding engaging one on ones, even if they’re a little reluctant to come forward at first. Don’t be disheartened!
  • Tell some of your own stories: Show some vulnerability yourself and model behavior by speaking about some of the topics you’ve previously raised in one-on-ones. Doing so may encourage your team members to open up on similar topics.
  • Change the format: Some team members won’t enjoy another Zoom call. Consider going audio-only, or doing it on a walk during the workday.  For in-person settings (remember them?), meeting outside the office or over a meal/coffee can help the flow of conversation.
  • Ask: If you find that your team members are unresponsive to one on one meetings, ask them directly about what you could do differently.

6 Ways To Make Your One on One Meetings More Meaningful

Two women smiling uring a one on one meeting

On a long enough timeline, one on one meetings can feel shallow and formulaic, even though neither side wants them to be that way. Managers want more engagement from team members, subsequently bringing substantial topics to discuss. Conversely, team members wish their managers would take more interest in their careers.

In short, everyone wants a more meaningful conversation, but how to get there isn’t always clear. Rather than looking for the answer in another article on ‘how to have better 1:1s’, what if you broadened out the topic to just work out how to have better conversations full stop?  

Lucy Foulkes is a psychologist and lecturer at University College London and her recent piece for Psyche magazine on ‘How to have more meaningful conversations’ really resonates in the context of a manager.

Foulkes identifies six ways to make your conversations more meaningful:

  1. Recognize small talk as a necessary first step: Small talk can feel artificial and sometimes performative, but the reasoning behind its usage is sound. It helps set the scene and establish rapport before you tackle weightier topics. Try not to skip it too quickly.
  2. Ask better questions: Asking thoughtful questions demonstrates you’re not just interested in topics you’ve introduced, but what matters to the other person. You don’t need original questions. Oftentimes, you can just go deeper into the existing discussion, with phrases like “What was that like?”, “Why did you feel that was important?”, or “How did that make you feel?”.  Want some more evidence? A 2017 Harvard study found that people who ask questions tend to be better liked by their conversation partners.
  3. Listen to the answers: Many people don’t listen with the intent to understand. They listen with the intent to reply. The only surefire way to avoid this faux pas is to motivate yourself by curiosity rather than debate.
  4. Be willing to share something about yourself: Manager-team member relationships improve when managers are willing to share too. This reciprocity encourages team members to open up. If this feels daunting, share something small. Remember — the act of sharing will encourage your counterpart to share too.
  5. Come ready to learn: If you approach a one on one meeting as a routine or chore, then you’re not going to get the most out of it. The feeling and perception of insincerity is palpable to your employees as well. Make sure that you come ready to learn more about your employees, work situations, and more.
  6. Give and take: The other party and you should consider abiding by a simple rule: “I will give you the space to speak, and I will properly listen to what you have to sa.”

How To Avoid Awkard Silence in One on One Meetings

The standard advice for 1:1s is that it’s the team member’s meeting. It’s a dedicated space where they know they’re going to be heard — where they have time to discuss what’s most important to them.

That all sounds great. But what if they don’t say anything? This happens more often than some managers would care to admit.

To fix the issue, we first need to understand what the problem is. If you find that a team member consistently fails to bring things to discuss with you in one on one meetings, it’s a sign of one of the following:

  • They’re too busy or overwhelmed to reflect on their work: People get burned out. Even if they’re not burned out, busy times of the year can detract from having a constructive one on one meeting. You’re the manager, you control their workload. The fix for this isn’t complicated and their lack of engagement is a symptom that you should consider taking action.
  • They’re unsure how to best use the time: Sometimes, people are quiet because they’re new to the one on one format. If you think this might be the case, give the individual some examples of ways you’ve used one on one meetings to good effect in your career.
  • They don’t trust you as a manager: In the early stages of a manager-team member relationship, this isn’t a problem per se — building trust takes time. The key is matching the level of discussion to the level of trust. If you’ve only just met, the discussion of personal issues or long-term plans can feel uncomfortable to a team member, but you can break the silence by introducing less challenging topics.

How To Nail Your First One on One Meeting as a First-Time Manager

A man and a woman smiling during a one on one meeting

If you Google one on one meetings, you’ll find articles with some sound advice that generally assume you’ve already begun having one on one meetings or know how to start. Consequently, this information is inaccessible to new managers the first time they step into the meeting room.  

This is an issue because a lot of the advice for running great one on one meetings over time isn’t that relevant for that first meeting. That meeting isn’t your typical one on one.  

The meeting isn’t about removing roadblocks, avoiding status updates, or worrying about whether to use an agenda. It’s about first impressions, showing you care, and laying the first bricks in the foundation of a great working relationship.

First Impressions Matter

These two things can be true at once.

  1. Team members will give new managers some slack while they adapt to a new and challenging role.
  2. People like to work for brilliant managers who always seem to have the time for them.

If your first one on one meeting is a tad clumsy, the other person will understand. But team members will also really appreciate it if you ace it. Try to do the latter and adjust accordingly.

The first step to having a great first one on one meeting is appreciating the opportunity to set the tone for a new professional relationship. Just being here and reading this article suggests you’re on the right track, and don’t intend to squander it.

First impressions in the context of managerial relationships need to be defined. Most new managers are promoted within their existing company, either above their peers they’ve worked with before, or to a team who may have some knowledge of their professional reputation.

In this context, talking about first impressions seems odd, but it’s the right phrase. Regardless of how you knew someone before, being their manager is a big first.

Don’t Overcomplicate It

This is just your first meeting; you’ll have many more. A key mistake by anyone new to one on one meetings is feeling that they have to do everything in this first interaction.  

That’s understandable. As someone’s manager, discussion topics are endless — career ambitions, working relationships, strengths, weaknesses, personal lives, areas for support, and so on.

All these things are also complicated. They require dedicated time to discuss in detail, and often a level of trust that isn’t established.  

Instead, focus on running a meeting that:

  • Establishes that you’re personally invested in their success and are ready to support them.
  • Informs you about their working preferences so you can start to create a good working relationship.

How You Schedule Your First One-on-One

No one likes it when their boss just drops a meeting into their calendar. Even if you know there’s nothing to be concerned about, there’s always a nagging doubt about what’s going to be discussed right up until the moment you meet.

For your first one on one meeting, let them know in advance you’ll be putting some time in their calendar for a meetup. This initial invite is your first opportunity to set the tone. It’s only a couple of sentences, but it’s still a way to show your focus is on them.

Perhaps something like:

Over the next few days, I’m going to schedule our first one-on-one meeting. I find these meetings helpful for open discussion, career development, and understanding where I can best help you as your manager. No need to prepare anything. I just want to catch up and talk about how you think you’ll get most out of these meetings in future.

Plan on spending between 45 minutes to an hour for your first meeting and avoid rescheduling at all costs. Remember, it’s all about setting the tone.

Before the Meeting

Think back to some of the worst one on one meetings you’ve had with previous bosses. Excluding the ones that were canceled, they probably involved your boss being late, unprepared misinformed, or all of the above. Bottle those thoughts and use the frustration to think about how you should approach your first 1:1.

Don’t Be Late

Don’t be late, but also, don’t turn up on the minute looking rushed from your previous appointment. You should be attentive and engaged, which is hard to do if you’re switching directly from a different context.

Try to leave at least five minutes before the meeting starts to give yourself a break, reset, and reacquaint yourself again with how you’d like the meeting to go.  It will pay immediate dividends when the meeting starts.

Familiarize Yourself With the Team Member’s Work

One of the main aims of this meeting is to demonstrate your interest in supporting your team members’ success. You have no quicker way to puncture that balloon than by getting the basic facts of their career wrong.

If they’re an existing team member, ask yourself a few questions as part of your prep work:

  • What projects have they recently worked on?
  • How long have they been at the company?
  • Are they involved in any other initiatives?
  • If they’re new to the company, what did they do beforehand?
  • What companies have they worked at? What was their role?

Speak to previous bosses or peers to find out if you don’t know.

You can drop some of these details into your discussion later to show you’re already up to speed and thinking about their career.

What To Talk About

Two women having a one on one meeting at a coffeehouse

Ok, you might say, that’s all very well and good, but if I’m not meant to overcomplicate it and open up all those big discussions, what am I meant to talk about?

Some of these suggestions should steer you in the right direction, but style it as you see fit. You are not meant to ask all of them. The most important thing is that you run the meeting authentically, in your style, in your own words. The questions are just suggestions, some of which you might want to adapt if they fit with the type of conversation you’d like to have.

Small Talk

You don’t have to jump straight into the more serious stuff; You probably shouldn’t. Small talk at the start of a meeting can make for a much happier one.  It gets the other person talking and involved in the meeting in a low-pressure, open conversation.

Don’t be shy about spending five to 10 minutes asking about how their day is going, what they did that weekend, or any plans for that evening. After all, even if it takes 10 minutes, you’ve scheduled an hour so there’s plenty of time.

Professional Interests

First, let’s talk about what this isn’t. This isn’t the time to have a full conversation about their career goals. Instead, dedicate a specific meeting for that. In the interim, learn about what work they enjoy, what they don’t, and what motivates them so you can make sure you’re not giving them projects that are the wrong fit.

You may find some of these questions helpful:

  • Why did you decide to work here?
  • Are you particularly excited about any opportunities?
  • What projects do you like to work on?
  • What projects would you rather not do?
  • Are there any goals you’re working towards at the moment?
  • Any surprises since you’ve joined, good or bad, that I should know about?
  • Do you need my help with anything in the short term?

Working Preferences

As a new manager, the last thing you want to do is manage someone in a way that they dislike.   Some managers go through an incredibly painful process of trial and error, judgemental glances across meeting rooms, eye-rolls, and passive-aggressive behavior.

Instead, you could just ask some of the following questions:

  • How do you like to receive feedback? Do you prefer it in writing so you have time to digest it or are you comfortable with less formal feedback?
  • How do you like to be praised for great work? In public or just in private?
  • Are there any manager behaviors that you know you hate?
  • What’s your ideal working environment?
  • When and where do you find you do your best work?

Any Questions?

This should be more than enough for one meeting but make sure to leave 10 minutes at the end of the meeting to ask if your team member has any questions. Again, it reinforces the impression that you’re there to help them.

Next Steps

Congratulations! You’ve completed your first one-on-one. Now to wrap it all up:

  • Schedule future one on ones: Depending on how your discussion went, make sure to schedule a set of recurring meetings for future one-on-ones. If you and/or your team member like using a collaborative agenda, set up a process to do that.
  • Set up a career goals conversation: To properly guide your team members’ careers, learn more about where they’re aiming. If you haven’t had this conversation yet, pencil it in.  
  • Take some notes: Take 15 mins to jot down everything that could be useful in the future.

Moving Beyond One on One Meetings

One on one meetings are just one of many meetings you face over your career as a manager. Just as soon as you feel like you’re mastering one on one meetings, another meeting, crisis, or issue arises.

Both veteran and first-time managers struggle with these problems from time to time. As a result, a holistic approach to management and the desire to become a leader is crucial to your success and the success of your team members.

Enter the world of Unicorn Labs. Our entire goal is to help you master the six levels of Unicorn leadership that instill psychological safety, reverence, and success in your team. With retreats, coaching, and self-guided courses, Unicorn Labs can take your management and leadership skills to unicorn levels.

Schedule a one on one meeting with us to learn more about how we can help you.

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