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9 one-on-one meeting tips

Introduction

Matt Szaszko

Matt Szaszko

Matt is an experienced Product Manager who worked on machine learning solutions that got him to Y Combinator. He launched and grew a mobile app to 1 million users and transitioned companies to become agile. He comes from a background in psychology.


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One on One Meetings

9 one-on-one meeting tips

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9 one on one meeting tips

Is it tips for your one-on-one meeting you’re looking for? You’ve come to the right place. But before we jump in, let’s set the scene. The one-on-one meeting is possibly the most lightweight management tool you can use in your fledging company. We wrote at length here about what a one on one meeting is, why you should have it and some general one on one tips. In this post, we’ll go through best practices in more detail.

What is a one-on-one meeting?

Classically, the one-on-one meeting is a consistently recurring, timeboxed meeting between a manager and a direct report. However, since one-on-ones are so useful. I’ve seen companies as small as just two co-founders having them and there the relationship is more horizontal rather than vertical. So don’t get too hung up on the hierarchy of people in a one-on-one meeting. It doesn’t change their purpose and general structure.

One-on-one meetings help the flow of information from top to down and from down to up. As a manager you can share or explain the vision of the company or a shift in the market. You can talk about how the organization is growing and what challenges it faces. As an employee, you can share your aspirations and frustrations, motivations and barriers. One-onones are designed to be a space where candid conversations can happen about mostly work but also life and everything else in-between.

Therefore the one-on-one meeting provides a constant informal pulse of your organization, something that is invaluable as a manager. Imagine if you wouldn’t keep your finger on this pulse, you’d only get to know about problems when they are too late. You’d have to communicate changes in vision, strategy or the organization in a formal, top-down manner, something that has been proven to yield worse results. But you already know this and convinced you should start having one-on-ones. Or you are already doing them and just interested in some one-on-one tips. Whichever it might be, let’s get started.

One-on-one meeting tips

1. Set up a recurring meeting for the same time each week

When you become a manager of people, your day immediately gets busier. Even if it doesn’t it’ll sure look like it to anyone else. This means that people will have a hard time scheduling ad hoc meetings with you and might not even try. Set your one-on-one meetings up in advance for the same time each week. A good practice as a manger is to block off an entire day for one-on-ones. This will also help you avoid some of the other pitfalls we’ll discuss below.

2. Dedicate at least 30 minutes

As your company scales like crazy you might be tempted to think that you could optimize the time you spend on management by cutting down on people’s one-on-one time and get it over with with 10-15 minutes each. You’ve got 10 people working for you, that’s more than 2 hours potentially saved each week. No, they don’t work for you, as a manager, you’re working for them. Any meaningful conversation takes longer than 15 minutes.

A good rule of thumb is to dedicate at least 30 minutes to your one-on-one s and leave a 15 minute buffer after for any other meetings or tasks you might have coming up. If everything is smooth sailing you can use the extra 15 minutes to reflect on the one-on-one you just had or get some quick tasks off your plate or to grab a coffee and walk around a bit to relax.

3. Don’t cut the meeting short

This should go without saying since we talked about setting up a recurring meeting and dedicating a fixed time for it and the benefits of these approaches. However, I’ve seen this happen all too often so I think it’s important to mention. Do not cut a one-on-one meeting short because of something short of an outright emergency.

When you cut a one-on-one short it signals to the other person that whatever was the reason is more important to you than them. Even worse, it might signal that you’re incompetent at your job since you can’t even plan to set aside a set amount of time for something this personal and important. If all lights are green and there’s nothing to worry about, your team member might initiate to end the one-on-one early. This is fine and it’s okay to go along with it. But you shouldn’t be the one to propose this.

4. Never skip a one-on-one meeting

It seems easy to bail on a one-on-one in the face of other burning issues. After all, you talk every week, right? What can just one week delay cause? While one-on-one meetings might seem less directly mission critical when you’re in the tranches fighting fires, getting on calls with angry customers, talking to disinterested investors and trying to still make time for that one task you still need to do, don’t skip one on ones.

Just think about it, every time you skip a one-on-one meeting you send a clear message to your team member, “You don’t matter”. At least not as much as that quarterly investor update that you knew was coming up but you didn’t do it because you hate it. Every time you skip a one on one you become less in the eyes of your team. Don’t do it.

5. Start with “How are you?”

This is the perfect opener for any one-on-one. “How are you?” is a simple question where the answer is often very complicated. And that is where the one-on-one begins, with the answer. Depending on the tone and content of the answer you’ll decide where to go from there. Everything okay and you’re just checking in on each other? Is there a lingering issue that need to be solved so that value creation can continue unhindered? Is there a showstopper disaster that needs your undivided attention? It all starts with “How are you?”

This is also why you need at least 30 minutes for your discussion. Both of you needs to leave the daily grind of the business behind for a bit and reflect. A good way to start is by acknowledging how we’re feeling and then examine what are the likely causes of those feelings. If one has an idea on how to mitigate or reinforce the causes it’s great to bring it up. However, remember that you shouldn’t try to jump on everything and try to offer a seemingly quick solution. Just listen first, acknowledge how the other person is feeling and go from there. A lot of times, just sharing hardships can help or make the person realize the course of action they should take.

6. It’s not a status update

“How are you?” is also a great way to avoid another pitfall of one-on-one meetings, them turning into a status update. Because what a one-on-one is not is a way to keep on top of the to dos of the other person, to report on progress or to ask for the status of tasks. Pay attention to this as it is easy to fall back into this pattern if there is not much to talk about or if the team member doesn’t feel comfortable to talk about something. It is your job as a manager to make them feel comfortable to share. And while it might be easier for both of you to just talk about the status of ongoing things, don’t be tempted by it.

7. Don’t issue work tasks

Just like you shouldn’t turn a one-on-one meeting into a status update, you should also not use them to issue tasks related to daily operations. It is okay if based on your conversation your direct report comes up with stuff to do on their own, but you shouldn’t be the one instructing them in this meeting.

As far as one-on-one tips go, this one has an exception and it is when the task relates to an issue you’re discussing. Let’s say the person complains that the dev team is always frustrated that not all edge cases are covered on user stories and it brews resentment towards them, the PO and they are unsure how to deal with this. While you might know a great way to solve this, instead of outright instructing the person to use your method, you should gently guide them towards coming up with the solution themselves. This could mean that an action item for the next one on one meeting is to do some research on this problem and come up with a proposal. Note that this is not about what to do, but rather how things are done.

8. Follow up on your action items

As a manager it is your job to make sure your team can maximize their potential and deliver the most amount of value to users and to the business. In most of the cases you as the manager will end up with a lot of action items after a one-on-one meeting. One of the most important one-on-one tips is that you should make sure you either have completed or have something credible to show on the next one-on-one relating to your action items.

9. Keep things confidential

As far as one-on-one meeting tips go, this one is probably the most important. For successful one-on-one meetings, trust is very important. A lot of these one-on-one tips centered around building and keeping that trust. But a surefire way to damage it, maybe even permanently is to not keep something that was shared in private confidential.

So before you think about sharing some feedback with another team member for example, do ask for permission from the person who shared it. And when it comes to personal matters, it’s probably best not to even ask and just keep them between you two. Nobody wants to hear on an All Hands meeting that the company is giving everybody Headspace subscriptions because they had a panic attack at work.

Takeaways from these one-on-one meeting tips

I think you can spot a pattern here, people expect managers to be responsible, organized, accountable, trustworthy but relatable. It is not easy to pull all of this off and still keep the boundary between manager and team members. This is where I hope these 9 one-on-one tips help.

Do you have some one-on-one tips of your own? Do share them in the comments below.

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Matt Szaszko

Matt Szaszko

Matt is an experienced Product Manager who worked on machine learning solutions that got him to Y Combinator. He launched and grew a mobile app to 1 million users and transitioned companies to become agile. He comes from a background in psychology.

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