How to Have a Great One-on-One Meeting

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Are you having weekly one-on-ones with your team?

Are you having weekly one-on-ones that people dread or ones that they look forward to?

These days, most managers are doing some form of weekly check-in with their direct reports. But how do you know if you’re doing them well?  It turns out that most managers are using their one-on-one meeting time to check-in on tasks, and missing an opportunity to focus on the larger and more meaningful personal growth themes that lead to real engagement.

Let’s be clear about what we mean by personal growth. We’re not talking about the personal content of your employee’s life—but about how they are showing up as a person in their work life.

How do you go there in your one-on-one meeting? Here’s a step-by-step guide for how to structure and deliver this new kind of one-on-one:

Step 1: Establish the Context

Before you invite your employee to a one-on-one meeting, it’s best to explain the purpose first. Nobody wants to get an invite to a meeting with their boss without knowing in advance what it’s about. Start by pulling this person aside in an off moment (in person or by phone, better not over email). Tell them that you’d like to put a new kind of meeting on the books — or reset one you already have scheduled.

Here are the key points you want to make sure to get across in this first conversation:

  • The purpose of this meeting is to create a relaxed and consistent venue where you can talk about ongoing personal development, NOT current tasks, and deadlines.
  • Your goal is to develop (or restore) mutual trust — that, so long as it’s done respectfully, they feel safe to offer you feedback as their manager as well.
  • You want to meet EVERY week for 30 minutes so you’re not rushed, and you can come back to big themes over time.

Once you’ve agreed with them on the “Why?” of this new meeting, send them an invite for a time that works consistently for both of you on an ongoing basis.  That’s it for step 1. It’s natural to be nervous or wonder how it’s going to go. No time like the present to take the first step!

Step 2: Starting The First Meeting

Before you dive into a conversation about what you’re seeing and what you want them to work on, take a few minutes to reset the context. You may be clear on what the meeting is about, but they’re likely still nervous or feeling defensive in some way. The conversation you had in the hallway might have been mostly a blur for them and they’ve spent the last four days worrying about it. Do whatever comes naturally for you to make the space safe.

Here are the key things you want them to get (and for you to remember!) every week from here on out:

  • This is NOT a check-in about current projects or status updates (there are other meetings for that).
  • This is NOT your time to nitpick on isolated mistakes or micromanage them
  • This IS a time to talk about themes and patterns that need improvement
  • This IS a time to develop trust between the two of you — to get real with each other against the grain of all of our business conditioning.
  • This IS a place for each of you to slow down and own or come back around on things that happened between meetings (an overreaction you realized you had, a mistake you’ve been afraid to talk about).

Step 3: Deliver With Care

When you feel you’re both settled and clear on the purpose of this ongoing meeting, it’s time to introduce the main topic for today’s meeting. You’ll have to find your own words, but here’s an example of what it might sound like:

“Okay, _______, so here’s where I’d like to start. There’s something I’ve been noticing lately that I’d like to talk with you about. I’m not sure what it means, I could be misreading things or not seeing the whole story, but you seem to be struggling with _________________________(Give them at least one, and ideally two or three specific examples to ground what you’re talking about). Do you have a sense of what I’m talking about?”

That’s all you need to begin. Now, wait for their response and let the conversation go wherever it needs for as long as it needs. When the time is right — trust your intuition — move on to the next step.

Step 4: Help Them See The Impacts

The most effective way you can help someone else grow is by helping them see how their behavior is impacting others. You gave some answers to these questions in the guide, but now is NOT the time to share those. Now is the time to ask them those questions and give them the space to come up with the answers for themselves:

“I’d like to close this meeting today with a little assignment for you to do at some point over the next few days. Don’t rush it — find a time when you have at least 15 minutes with no distractions — and see what answers you get to these four questions:

  1. When you struggle with ____________________ how does it make more/harder work for your teammates?
  2. When you struggle with ____________________ how does it adversely impact our customers
  3. When you struggle with ____________________ how does it make it harder for me, as your manager?
  4. When you struggle with____________________ how does it hold you back, in terms of becoming the kind of person you want to become?

(Tip: copy these questions into an email and send them to your employee after the meeting).

Let them know you’re there to help, but that the next step is theirs to take:

“You can send me an email with what you come up with if you want. But, either way, we’ll talk about whatever you come up with in next week’s meeting, okay?”

Step 5: Close With An Opening

Leave some time at the end of the meeting to find out how it’s been for them.  Here are some questions you can ask to guide you:

  • How was this for you to talk in this new way?
  • Was it more or less what you expected when I first brought up this idea or did something surprise you?
  • Is there anything we didn’t get to today that you’d like to spend some time talking about next time?

Three More Best Practices

  1. Personalize the conversation. Frame your meeting according to your current level of concern, frustration or worry by finding a way to be transparent about what you’re thinking. Conversely, if you realize you’re bringing up a subject you should’ve brought up a while ago, be sure to name that at the outset and own the meeting for yourself in that way.
  2. The Power of the Pen. One of the most powerful things I ever learned was in law school where I decided to rewrite ALL of my notes from the year in preparation for my final exam, and the consolidated them down over and over until I had internalized everything. You can try that by rewriting your 1×1 meeting plan in your own words.
  3. Make it about them.This is the most important part and you probably won’t get it right in the first meeting. The key to great employee meetings is to make it clear to your employee that it’s about their growth, and NOT fundamentally about the business or any particular result. When you get there, you’ll know it because they’ll tell you. The feeling of having a boss who genuinely cares about you is unmistakable.
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