Effective One-On-Ones: A Strategy Guide

Effective One-On-Ones

Effective one-on-ones are crucial to being a manager that people can depend on, but they’re not only for managers. Tech leads, squad leads, or leads of any kind should take advantage of one-on-ones to ensure they stay on the same page with their team. They can be intimidating for someone who hasn’t held one before, but the following guide will point out a few things you can do to make it less awkward.

Frequency and Duration

A good rule of thumb is that you should aim for at least one hour every two weeks. Whether that is one hour every other week, or 30 minutes once a week, is up to you. If you or the person you’re meeting with is in a brand new role, you should consider meeting once a week for an hour. While that may sound like a lot for someone who isn’t accustomed to one-on-ones, you’ll find that you will easily be able to fill that time with valuable conversation.

Speaking of “filling time”, don’t feel like you need to take up the entire hour every time you meet. It’s ok to end early if you truly feel like you’ve discussed all you need to. Its ok to cancel your scheduled one-on-one every once in awhile, but avoid ever canceling more than one in a row. Ideally, the suggestion to skip a one-on-one should come from the person you have it scheduled with, not you.

Schedule your one-on-ones deliberately. Make them as predictable as possible, holding them at the same time every week (or every other week, if necessary). Although you shouldn’t necessarily wait for your one-on-one to chat about something important, making it predictable brings a sense of normalcy to a sometimes hectic job.

If you’re in a situation where a one-on-one feels awkward, just call it a “sync up”. It sounds silly, but calling it something different can have a pretty big effect on how it is perceived. Syncing up is something that peers do. A one-on-one is more along the lines of what a manager does (dedicates time) for their reports.


It doesn’t matter where you meet, so long as it is private. Make sure you are able to talk freely, without having to worry about prying eyes or ears.

You may need to be creative about where you meet if you’re working with someone who is hesitant to really open up, or when it seems like they’re just telling you what they think you want to hear. Don’t be afraid to change it up at times. You’ll find that meeting in a cafe or grabbing lunch is much more likely to get someone to open up than meeting in a stuffy conference room.

If you’re not able to step away for lunch, try going on a walk around the office. Even if things are going well, experiment with mixing things up every once in awhile to break out of any rut you may be in.

Always Come Prepared

Avoid the temptation to just show up at your next one-on-one. Make sure that you take at least 10 minutes before you meet to look through your notes from the previous meeting, and think through any problems you suspect they may be having. If you just show up, you’re doing little more than going through the motions. They’ll know this, and they’ll be much more hesitant to open up about their challenges.

What I do is sit down at the beginning of each day and look at who I’ll be meeting with that day. I take my notebook and prepare notes about what I want to discuss and ask about first thing in the morning. That gives me the entire day to reflect on my notes during slow moments and refine my message or questions.

There’s tremendous value in having time between when you jot down your notes, and when you use them. Giving your thoughts a chance to marinade helps you ensure that you are articulating them accurately. You’re much less likely to regret your words or stick your foot in your mouth if you have a chance to think them through.

Deliberately Shut Down Any Distractions

You send a powerful and clear message when you close your laptop, turn off your phone, or otherwise shut down any distractions when you meet for your one-on-one. I do that deliberately, but subtly, in every one-on-one. Although I don’t even need to bring my laptop to any of these meetings, I make an effort to arrive first, and explicitly close my laptop and stick my phone on the desk upside-down when they enter.

Your one-on-one is their time, not your time. Making yourself completely available during these meetings is crucial. Avoid the temptation to check your phone or even look at your watch. Its only an hour once a week. You’ll be ok without checking your email for a bit.

Take Notes

No matter how good you think your memory is, you’ll forget half of what is discussed. Taking notes is crucial. Don’t take notes on your laptop, because despite your best intentions, it will look like you’re distracted.

I have had success using small notebooks (like Field Notes notebooks), one for each person. Having a dedicated notebook for each individual makes catching up before the meeting easy, and keeps all my notes about that person in one place.

Be careful about the notes you take. Assume that at some point you’ll lose that notebook, and someone else would pick it up and read through it. While your conversations with that individual are confidential, don’t assume that your notes will be. Avoid gossip or negative notes. Just focus on getting your job done and this will help you stick to the facts instead of bringing in unnecessary emotion. If the other person needs to vent, that’s fine. Just keep it out of your notes.

Its Their Time

Your one-on-one is not a time for you to preach. Its their time, not yours. Start with whatever they brought to the meeting to discuss. If you have something you need to talk about, make sure that their concerns have been fully addressed first.

This is why its critical that you avoid canceling if at all possible. When you do, you are potentially robbing them of their time to talk about their concerns. If a time doesn’t work out, reschedule it as soon as possible.

Coach by Asking Questions

It will be tempting to want to solve every problem that is mentioned right then and there. You need to be careful though, because you need to make sure that “solving” the problem is really what they’re asking for. Sometimes people just need to vent. Help them to avoid gossip by not adding fuel to the fire when they do vent, but make a point to empathize about their frustration. Empathize with the situation, but avoid taking sides.

If you simply solve their problems, you’re also missing an opportunity to teach. Even when the answer seems clear to you, the best way to teach is by helping the other person arrive at their own conclusions. You can do this by asking thoughtful questions that guide the conversation. This takes practice to master, but when you do, you’ll find that results are much longer lasting.

For example, when someone comes to you with a problem like “I feel like I’m being left out of a lot of meetings that I should be involved in”, you can lead them in the right direction by asking something like “What are your thoughts on how to change that?”. Give them a chance to propose their own solution instead of telling them what to do. If they continue to struggle, continue to ask questions to guide them in the right direction.

If they are completely stuck, give them a little hint to help move them along. In this example, if the other person was at a total loss as to what they should do, you could ask a leading question like “Do you think it would help to talk to Jane about that?” See what they think and continue to ask additional questions as needed. When you feel like they’ve finally reached the correct result, validate that with something like “That makes sense. I agree and think that’s worth a shot”.

As the well-known (and very wise) Chinese proverb says, “Give a man a fish and you feed him for a day. Teach a man to fish and you feed him for a lifetime.” The way you teach someone to fish is by asking questions and teaching them that they can arrive at their own correct conclusions by just thinking it through a little more.

Don’t Sugarcoat Difficult Conversations

While you certainly want everyone to feel important and taken care of, this is not the time to shoot the breeze or gossip. Take a little time to get to know them a little better each time, but don’t let that drag on. You’re there to be their manager or their leader, not their friend. Be kind and caring, but get to business quickly. After all, we’re paid to solve problems, not chit chat.

Encourage an atmosphere of trust and open discussion. Your conversation should be a safe place, where both of you feel comfortable voicing your true thoughts and feelings, not just what you think the other person wants to hear. Practice Radical Candor by avoiding any sort of sugarcoating when it comes to difficult conversations. It may take a little bit to get there — you won’t be able to do this without a healthy amount of trust — but an atmosphere of trust and openness should be your ultimate goal.

Commit to Action Items

If there are things you can or should to in follow-up to your conversation, commit to them by writing them down and repeating them at the end of your meeting. It is absolutely crucial that you follow-up quickly and decisively. If you don’t, you lose credibility, and people will simply stop bringing you their concerns. While this could feel like people are simply learning to deal with their own problems, it could be that they simply don’t trust you to make a difference. This can be a death-blow to any manager, and is very difficult to overcome.

When you do drop the ball or forget something, admit to it and make it right. When possible, bring it up before they do. If you took good notes and try to come prepared, you should notice that you missed something before you meet.

Don’t Wait to Have Important Conversations

Avoid the temptation to wait until your next one-on-one to have important conversations. If you want to be seen as a leader who gets things done, have the conversation as soon as you need to. If you take an action item away from a one-on-one, knock it out as quickly as possible, and let the other person know right away. This improves your reputation as someone that gets things done, and also sets an expectation that you want the same from them.


In the end, the most important thing you can do is to make your one-on-ones predictable, dependable, and sincere. Take them seriously, and you will send a clear signal that you care about each individual, and the work they do. They will pay you back with loyalty, accountability, and a much tighter feedback loop.

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  • Alan says:

    Regarding the idea that the conversation name (like “one-on-one”) can affect the participants, that’s true of “sync up” as well. At least in engineering-heavy circles, “sync up” is alongside “get on the same page” and “I hope this email finds you well” – it’s widely considered a cliched phrase that’s used in lieu of actual content.

    If your audience or company includes engineers, consider calling it what it is, such as “Recurring meeting” or “Occasional chat.”

    • Retrospective.co says:

      A very good point. My thought with calling it something like a “sync up” is to make it less intimidating when someone might . I’ve found that using a cliched phrase helps some people from putting their defenses up, because it seems more benign.

      I think your point is definitely valid: Call it whatever you think is best for your company’s culture. What works for us won’t necessarily work for everyone, so you know best.

  • Nick says:

    TONS of great points in this, but I have a few opposing viewpoints. First, even if you think you have nothing to talk about, I think you should take the full hour. There is always something to discuss and the more time you spend together, the quicker and stronger the bond between you will be built.

    Secondly, while I’m not totally against taking notes (I don’t do it myself), I would strongly suggest not doing it during your meeting. You should be fully engaged in what they’re saying and actively listening. Also, if someone is writing down things that I’m saying, I’m much less likely to be forthcoming and open up.

    Finally, this probably goes without saying, but it shouldn’t be all about business. Some (if not most) of the 1×1 should be about their personal lives. In my experience, showing that you sincerely care about the person (and not just the employee) is the absolute best way to build trust. But of course, be respectful of their boundaries and let them lead the conversation. Don’t invite yourself into parts of their lives that they don’t want to discuss.

    As usual, great article!

    • Retrospective.co says:

      Thanks Nick. Great points. I particularly appreciate you taking the time to offer alternative/opposing viewpoints!

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