Emma: In my early 1-on-1 days, I thought to be a manager was to be some omniscient force, in total control, three chapters ahead of everyone else. But I was so, so insecure.

As a result, I was in constant performance anxiety. For 30 minutes per week(!) per direct report(!), I’d nod and jot notes, all the while scrambling to assess how I was doing: Is the conversation flowing? Are we having a good time? Did I answer that question right? I’m talking too much. Am I imparting wisdom and insight while demonstrating humility and charisma? Maybe I’m not talking enough? Say something smartfunny!

It was a never-ending string of Tinder dates-cum-job interviews.

Andy: Especially because I thought 1-on-1s were a bad-news delivery system: If anything was going to come up that I couldn’t handle, it was going to come up in that little room when I was absolutely on my own. No buying time to search the employee handbook, no Gchatting a friend, no pretending I was too busy. I’d have to answer.

Emma: Having to answer something that I do not know continues to be one of my greatest sources of dread. But there was one phrase I learned — Andy taught it to me — that felt like 1-on-1 armor.

It is: My first instinct is to say…

What a relief! It’s a verbal trick that allowed me to talk my way toward a conclusion, to give an answer that wasn’t necessarily The Answer, without sweating the pressure of being put on the spot. It meant I could even change my mind part way through without having to backtrack — the phrasing set me up for it. I have a whole cache of phrases like this. They’re little cheats to give me breathing room.

Phrases to Write at the Top of Your Notebook

This is some go-to language that has helped us look and feel capable, and answer honestly. Remember: You don’t actually have to have all the answers.

I Have No Clue

  • That’s a good question. Let me look into it.
  • I don’t know. I’ll find out.

External Processing

  • My first instinct is to say…
  • I can see this going a lot of directions.

Bop It Back

  • What’s your take?
  • If you knew the answer, what would it be?


  • Let’s talk this through together.
  • To the whiteboard!

Just Listening Is Enough

  • Thank you for telling me that.
  • I can see your point.
  • I feel ya.
  • Is there anything I can do?


I found that armor and relief in one rule: Never cancel. As long as I showed up for the meeting, I’d already gotten it right, even if it started going all wrong. I started to think of myself as a stand-up comic putting her time in on stage. I was going to bomb, and that was part of it.

I still always wanted to cancel. But not giving myself that option meant I was showing up.

My strategy today stems from that same rule. I show up relentlessly. Once a week. Thirty minutes. Every report I have. In any first 1-on-1, I share a Google doc with a few prompts: Best, Worst, Worries. (These are simple and hit on what’s great, what’s awful, and what’s scary to share.) Then, I go over my 1-on-1 rules: This is their time. I will never cancel. I won’t use 1-on-1s for project updates or deliverables. I’ll take notes as we go.

I find that this framework makes the meeting a real and safe space.

As the weeks go on, each 1-on-1 develops its own rhythm, topics, and styles. Like any relationship, they can sometimes stagnate and I reboot it with a new activity, new questions, or some straight talk: Our 1-on-1s are feeling a bit stagnant to me, do you feel that?

The 1-on-1 Topic Selector

These are all things we’ve discussed in 1-on-1s with our managers and with our reports. Share them with your team, now or when 1-on-1s start to fizzle. (Here’s a PDF version!)

Your best, your worst, your worries

How to prioritize (or delegate!) your workload

Your career goals, and how you can use this job to get there

Where are you at with your short-term goals?

AMA with your manager. What are their worries, their goals? What does success look like? What metrics are they paying attention to? What do they know about the future? What books have they read?

Announce your roadblocks

Ask for something. Need resources? Want access to a meeting? Think you are the right fit for that new project?

Give your manager feedback

Offer on-the-ground perspective with what’s going on with the team

Do you have challenges with other people or projects?

Get early feedback on a plan, a strategy, your work

Know something tough is coming up? Strategize about how you’ll tackle it.

Things that are too small to email about (clarifications, updates, etc.) Store them up and tackle them all.

1-on-1 project work

Post-mortem something that went wrong or went right

Workshop your next __________

Build a personal relationship: Ask/tell about life outside of work (within reason…)

What realizations and epiphanies have you had about your work?

Workstyle discussions: “This is how I like to work, here is what I’d like from you, here’s what motivates me.”

A look back: What topics were raised 3 months / 6 weeks ago? How did they resolve? Are they still going on? Do you need help? How have you grown?

Share time wasters (and ideas for how to delete them)

Create a work syllabus. What do you want to learn?

Vent session

Feedback on other team members — especially who’s killing it!



Emma: Yes! It’s all about finding that rhythm. And I approach 1-on-1s now with much more awareness that both people need to contribute. If I keep getting 10–15 minutes of progress updates and nothing else, it’s not because I’m failing as a manager to draw them into more meaningful conversation. That person may not know what to talk about or what they’re allowed to talk about. Maybe they don’t know what a good rhythm feels like. If I’m failing at anything, it’s setting good, clear expectations.

So I do. Sometimes, I’ll do it right in the moment with some of that generous, warm-hearted straight talk Andy mentioned: “These 1-on-1s are really for you — not for me to check up on your work. Let’s figure out some of the larger themes you care about.” If it’s a more pervasive problem, I might address a whole group together. What a perfect five-minute capstone to a monthly team meeting.

Good Boss Achievement Stickers: 1-on-1 Edition

The Bent Good Boss Achievement Stickers for never cancel a 1-on-1

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