The Direct Report’s Guide to Meaningful One-on-Ones

How to have open and satisfying conversations with your manager

Bryan Ye
Bryan Ye
Oct 25 · 15 min read
Photo by Brooke Cagle on Unsplash

There are many guides for managers to run one-on-ones, but not many for direct reports. Managers get trained on how to be a manager, but nobody teaches a direct report on how to be an employee.

A manager’s job is to make sure their direct reports can do their jobs. One of the tools they use is the one-on-one: a meeting for just the manager and direct report. But if the meeting is for direct reports, doesn’t it make sense for them to learn what to do during the meeting too? There’s almost no information for direct reports; if you Google one-on-ones, everything you’ll find is for managers.

Due to a direct report’s misunderstanding of the purpose of a one-to-one, they often waste the potential of the meeting. If the direct report doesn’t know what the meeting is for, they don’t see the importance of opening up, and the meeting becomes just like any other meeting.

Nobody taught me how to have meaningful one-on-ones as a direct report. But I’m a self-experimenter, and I’ve figured some things out that might help you.


🤝 What Is a One-on-One?

One-on-ones appear to be a simple conversation between manager and employee, but it’s much more than that. It’s intimate, open-ended, and a safe place to talk through things you wouldn’t say around others. In The Hard Thing About Hard Things, Ben Horowitz says the one-on-one meeting is the most important meeting to have because they’re an opportunity for relationship-building.

If you want to, you can talk about work status and strategy conversations, but that isn’t the purpose of the meeting. You can discuss those things elsewhere. It’s often a place for coaching, unblocking, aligning, or even venting. If there’s any place to cry at work, a one-on-one meeting would be the least inappropriate place.

As a direct report, the one-on-one meeting is essential. If you don’t already schedule one-on-ones, talk to your manager to do so. Ask your manager: “can we schedule one-on-ones to talk about things I don’t feel comfortable talking about in the open?”

Knowing that there’s a place for me to talk about everything I couldn’t throughout the week is fundamental to my workplace health and productivity. Everything can go wrong, but I know there’s always a place to let it out. I see almost as a workplace therapy session: a place where worries are encouraged and celebrated.


🔁 Schedule a Recurring Meeting

There’s a lot of debate on how often you should have one-on-ones, but everyone agrees that they should be frequent, though that means different things to different people.

In High Output Management, Andy Grove recommends scheduling one-on-ones weekly to monthly, depending on the maturity of the direct report. But Mark Zuckerberg and Sheryl Sandberg still have one-on-ones every week — and Sheryl Sandberg is certainly mature.

If you haven’t had one-on-ones, schedule them once a week. The recurrence helps you get into the habit. Don’t lose the practice; you want to know that there’s a safe place for you to talk every week. No matter what happens, you can let it out at this one time in the week.

Ask your manager: “I want to have weekly one-on-ones so we can get into the habit of sharing information. It’s common practice in successful relationships between a manager and direct reports, like Mark Zuckerberg and Sheryl Sandberg. Can we do it?”

How long should the meeting be?

30 minutes to 1 hour. It can’t be any shorter because there’s no place for discussion. If something significant came up and you only had 10 minutes to talk about it, would you?

Make sure there’s enough time to talk about the awkward things — enough time to let everything out.

Where should the meeting be?

A one-on-one should be somewhere private. It should be a place where you can talk about things you can’t talk about in the open, like a simple meeting room. Some people go for a walk or to a cafe, but I don’t recommend this. You can’t open up in public places; other people might overhear you.

Don’t cancel one-on-ones

Canceling one-on-ones breaks — or at least damages — your habit. It’s already an awkward and challenging meeting, depending on your relationship with your manager. Don’t make it harder. (Luckily, most managers know this because they’re taught this in their training.)

Making sure you have the meeting is especially crucial if you don’t have a close relationship with your manager. It’s forced interaction, allowing you to build a better relationship.

Try not to reschedule one-on-ones; you want to signal that it’s important, and a repeatedly rescheduled meeting doesn’t appear important. But if you have to, then reschedule it in the rare case where it’s the only alternative to canceling.

I haven’t missed a single one-on-one since starting my current job unless my manager or I was on leave. If you don’t have time for a recurring one-on-one, you need to rethink your priorities.


👩‍🏫 Lead the One-on-One

One-on-ones are more of your manager’s responsibility, at least by job description. But you can help your manager do their job, which ultimately helps you.

If you’re used to your manager leading one-on-ones, you probably go into the meeting waiting for your manager to start talking. But one-on-ones are made to help the direct report, so why shouldn’t they lead it? One-on-ones are more effective when the direct report leads because they know what they need. Otherwise, managers have to use different tools to get them to open up, which is fine because they’ve taken training on how to do so. But you can save time by going straight to opening up.

As a direct report, you want to lead the one-to-one. Ask your manager: “I think it’s more effective if I lead our one-on-ones because I know what I want to talk through. Is it okay if I take ownership of the agenda? You can still add agenda items, but I’ll be the one deciding what to talk about.”

If you do this, you’ll be taking responsibility for the meeting. Leading the one-on-one isn’t about taking control; it’s about doing what’s best for the team. It doesn’t mean to delete your manager’s agenda items because you’re not comfortable talking about them, but rather, to prioritize what’s most important in the short time you have together.

Own the agenda

As a direct report, you should own the agenda. You know the details of your problems best. You should be able to tell your manager what you think is most important, and they should guide you.

Your manager can still put topics on the agenda, but you should be putting most of the things.

Before every one-on-one, create an agenda — even if it’s just a simple list. Unless your manager is a control freak, they’ll be glad you’re making their job easier.

Don’t let your manager take complete control

A common pitfall is letting the manager have complete control over the one-on-one. It’s easy to fall into because they’re comfortable with leading (that’s why they’re managers), and many direct reports don’t know what to do.

It’s the manager’s responsibility to make sure their team does their job, so they learn how to encourage even the shyest of direct reports to open up. But this means your manager comes to the meeting, they talk to you and spend time firing slings of questions, hoping they hit the target and get something out of you.

But you know what you need to talk about, and no matter how well-versed at the one-on-one your manager is, they might not ask the right questions. You might even hope your manager never asks that uncomfortable question that encourages your nervous but necessary thoughts to come out. Let this happen for too long, and it becomes a pattern. You’ll be so comfortable keeping your truest thoughts inside that you never be open.

Sharing awkward feelings was the scariest part of the one-on-one for me. I get it. Vulnerability is hard, and letting your manager see underneath your work persona is dangerous. At best, they can judge you; at worst, they can fire you. But the alternative is worse: you never do your job properly because you don’t have the resources, which leads to the same sort of judgment you feared from opening up.

Before I started leading one-on-ones, I entered them mindlessly. I knew my manager would do her job, and she would even do a good job. But it was never perfect. Sometimes I had topics to talk about that I couldn’t get out. Or more precisely, I chose not to — because I was comfortable letting my manager take complete control. After I started leading, I learned to talk about what I needed, which included the awkward affairs I had kept to myself. Being vulnerable has become a habit for me, and now I can talk about anything I need to — which means I can do my job better.


📄 Use a Shared Document

Use a shared doc to track everything for the one-on-one. Set the permissions so that both you and your manager can edit it. You can use this for the agenda, action items, things to remember, decisions, what the two of you discussed, what’s due, links to read later, etc. It’s a place for note-taking before, during, and after the one-on-one, and a place to align information.

Before I started having one-on-ones, I didn’t track them at all. My first manager was new, and no one had trained him. Not wanting to concentrate on remembering what we talked about every time, I started using a notebook to write things down. But I couldn’t give manager access to my notebook — it just isn’t feasible, and honestly, I didn’t want to: I like keeping my notebooks private. When I got a manager that used a shared doc, I immediately became relieved. Somehow, I had not thought of this simple but superb idea. It sounds so stupid and obvious now: use technology that provides shared editing.

Ask your manager: “I’m going to create a shared doc for our one-on-ones so we can track everything. I’ll put an agenda on it before we meet. Is that okay?”

Put the agenda on the doc

To own the agenda, you need a place to put it. Create a section in your shared doc for the agenda and add things to it throughout the week. Your manager can do the same.

Every time there’s something you need to talk about that you can’t get information on immediately, put it on the agenda. Writing down what you need to know frees up space in your mind. You won’t be scrambling to remember what you wanted to talk about if you know you can find it later.

Make sure your manager has access to the doc, so they can see what’s on the agenda so they can prepare to help you.

Structure of the doc

You determine the structure of your doc. Each individual works differently, and you should add to the structure depending on your needs.

If you want some sections to start, here are some I’ve found useful:

  • Agenda
  • Action items
  • Wins/losses

Shared documentation tool

If your organization already uses a shared documentation tool, use that. You don’t need anything fancy, just a doc that allows collaborative editing.

If you don’t know what to use, I recommend:

Avoid information overload

If there are purposeless sections in your doc, remove them. Useless structure is useless. It takes up space and distracts from what’s important. Strip away everything you don’t need to focus on what you do need. Don’t organize for the sake of organizing; organize to make your life better.

When I have sections in my one-to-one doc that I haven’t used in a while, I remove them. This felt scary at first but proved to be invaluable. It took some acceptance of the idea that I had control over the page.


🤐 What to Talk About

You can talk about everything, given you take into account your relationship with your manager. If you’re not close, it’s not a good idea to talk about less professional things.

There is one rule you should have: prioritize what you can’t talk about in the open. If you can talk about something outside of a one-on-one, don’t talk about it unless there’s spare time.

If you still don’t know, here are some things you might want to talk about:

Blockers

If something is blocking you from doing your work, you need to let your manager know as soon as possible. It’s your manager’s job to unblock you, or at least know you’re blocked so you can work on something else.

While talking about blockers, discuss whether you or your manager can do anything about it. If one of you can, create an action item on your shared doc and do it.

Ask yourself: “Is there anything stopping me from doing my work?”

Ask your manager: “X is stopping me from doing my work. Can we do something about it?”

Clarify confusion

You take in a lot of information at work. People are always talking to you, and sometimes you don’t have the time to clarify things. Topics can range from something simple like terminology to something complicated like a continuously discontinued project.

Before talking about it in your one-on-one, try to resolve what’s confusing — at least message people on Slack for more information. But sometimes it isn’t enough; sometimes, it’s so complicated that you need a longer explanation.

Ask your manager to clarify your confusion. If they don’t know, you’re both about to learn something together; at the very least, your manager should know who to talk to to get more information. If it confuses you, it probably confuses others, and you might also need to tell your team about what you’ve found out. Create an action item for any next steps.

Ask yourself: “Is there anything that’s confusing me?”

Ask your manager: “I learned about X this week, and I don’t understand it. Can you clarify it?”

Your struggles

Sometimes you need help facing a challenge; other times, you just need to be heard. The one-on-one is a safe place to talk about your feelings. You could be sad a coworker is leaving, scared you won’t finish your work by a deadline, or annoyed because your team keeps pivoting. Talk about it. Vulnerability is how we build relationships, and talking about your feelings is one of the most vulnerable things you can do.

Ask yourself: “Is there anything I’ve been struggling with lately?”

Ask your manager: “I feel X about Y. Can I get some help with it?”

Growth

One of the top reasons that employees quit is a lack of growth opportunities, so it’s fair to say that as a direct report, you care about your growth. Whether your goal is to develop your craft, learn more about the industry, or get promoted, your manager has resources to guide you.

If you already know what you want, the one-on-one is the time to talk about it. You might want to take on more work or need a more challenging project. Let your manager know how you feel about your current situation and, if possible, give a solution.

Don’t hesitate to talk about where you are in your career. It sometimes feels taboo to talk about career progression, and in some social situations, it is, but the one-on-one isn’t one of those situations.

Ask yourself: “Is there anything I want to help me grow?”

Ask your manager: “I want to get better at X. What are the steps I can take to do it?”

Information for your manager

Sometimes you receive information that feels out of place. Maybe there’s a new project that impacts your project, or perhaps the project you’re working on is pivoting.

Most of the time, your manager should know, but sometimes they’re working on such an abstract level that they don’t know what’s happening day-to-day. Miscommunication happens all the time, and the one-on-one is an excellent place to align.

Ask: “Is there anything odd that I found out that I think my manager should know?”

Ask your manager: “I found out X, and I think it affects Y. Do you know about this?”

Literally anything

The truth is: you can talk about anything you want. Talk to your manager about informal topics, especially if you have the relationship to support it.

It’s healthy to have meaningful work relationships, and one of the ways to create that is to bring your personal life into the conversation (with reasonable constraints on what’s professional). In The Making of a Manager, Julie Zhuo explains that a part of being a manager is to recognize their direct reports’ personal life. Similarly, it’s part of being a direct report to build a human-to-human relationship with their manager, not just a work relationship.

Talk about your hobbies. Talk about the new book you’re reading. Talk about how you didn’t get sleep last night because you stayed up playing a video game.

Ask: “Is there anything interesting I can share with my manager?”

Ask your manager: “I started doing X, and it’s awesome. Have you ever done something similar?”

“What caring means is understanding that we are not separate people at work and at home — sometimes the personal blends into the professional, and that’s ok.”

What not to talk about

I don’t want to impose any absolute rules, but there are some topics that — if you manage your communication channels well — don’t require the environment of a one-on-one for discussion. These things are, of course, anything you could discuss in the open. And the biggest culprit? Status updates. Status updates are like candy. You eat one, and it’s delicious; it even makes you feel good. But then you realize how easy and cheap it is to get that sweet dopamine hit, and then you another, and another, and another. All of a sudden, you can’t stop eating candy, so you get a sugar addiction, and before you know it, you have a severe sugar addiction, and by then, it’s too late.

Status updates are the same: they’re short and sweet, but also a dangerous slippery slope. If you keep talking about them, they become your fallback option for whenever you don’t feel comfortable talking about the awkward things. When that happens, you get into the habit of never talking about what you wanted to talk about. And so, you have unfulfilling one-on-ones.

When I started having one-on-ones, I only discussed status updates. I didn’t know what else to talk about. My first manager was inexperienced and didn’t understand the purpose of one-on-ones. But it wasn’t his fault: no one had trained him. Thankfully, times have changed. I now have a manager that encourages comfortable talking about the uncomfortable. I always have enough of the awkward things to talk about that I never have to bring out the nuclear option: status updates.


🦜 Give Your Manager Time to Talk

Even though you own the agenda, your manager should be able to put items on, too. Some topics your manager might be concerned with are KPIs or OKRs, workload management, and confusion about the details of your project.

Before your one-on-one, prepare for your manager’s agenda items. Make sure you have some understanding of the topic they want to know.

Leave time at the end of your one-on-one for your manager to talk about what they need from you. Make sure they get a chance to say something they want to. Any new information they give you will help you do your job.

Don’t take complete control

Most people will never have this problem. They have the opposite one I discussed earlier: letting their manager take complete control. But it can happen. Your manager might be happy if you lead, but if you take the lead too much, they might not ever get to say what they want to say.

You don’t want to miss important topics your manager wants to discuss. Remember: one-on-ones are a discussion, not a monologue.

When I started leading one-on-ones, I put too many things on the agenda, which gave no chance for my manager to talk. I now prioritize the most important things to make sure I don’t miss anything new information she wants to give.


The Results: A Better Working Relationship

You can ignore all my advice and let your manager take care of everything; to be honest, you’ll probably be fine. Managers get a lot of training on how to get you to talk, and they know the right topics to ask. But I encourage you to at least explore a little bit, trying taking the lead for once.

If you want to have satisfying one-on-ones, you’re going to have to do some of the work. But the meeting will reward you. Not just with the extra time you save by skipping information-stealing questions, but by being able to talk about what you want.

You also make your manager’s job easier. Your manager will never have to walk into a one-on-one with dread and anxiety, thinking, “What should I ask to get them to open up?” — because you open up without any help. The process will prepare you for greater leadership roles, and it will demonstrate that you are leadership material.

I’ve given you a template on how to lead one-on-ones, but you should explore what works for you. Take what you can get from this and make it your own.

Good luck with your one-on-ones.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

Bryan Ye

Written by

Bryan Ye

Words @Atlassian. Based in Sydney. I have a lot of thoughts; here are the less crazy ones. bryanyewriter@gmail.com

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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