Chapter 1. Advanced PeopleOps—One-on-One Retrospectives

Marcus Blankenship

Carmen’s heart sunk as she looked at her calendar. Back-to-back one-on-one meetings filled her day, overflowing into the next.

“Ugh…maybe I could call in sick. Or make up an excuse to work from home. My boss wouldn’t care. My team would be thrilled to skip them.”

“It’s not too late, you can still call in sick,” she thought as she stood in the Starbucks line, “But then what kind of boss would you be? It sucks, and everyone hates it, but you have to do it.”

“Sheesh, what are we gonna talk about? I guess I’ll just ask people what they’re working on this week, and hopefully, I can get each one done in five minutes. Oh! Or maybe we could do them in small groups! That would take soooooo much less time.”

“I’d better order an extra-large coffee with quad shots…I’m going to need it.”

Apply What You Already Know

I’m going to share a head-smackingly simple lesson that has served me well. Ready?

Make every fourth one-on-one meeting a retrospective to discuss improvements to your one-on-ones.

This is similar to a sprint retrospective, and you can use the same format. The point of a sprint retrospective is for the team to improve. The point of this retrospective is to improve your one-on-ones, making them more valuable for both of you.

That’s it. Go do it.

But, if you need a nudge…

Here are five steps to help you start:

  1. Let each team member know that the next one-on-one meeting will be used to discuss your one-on-one meetings.

  2. Ask them to write down what’s working for them, what’s not working, and ideas for change. You will do the same.

  3. During the meeting, discuss what you both wrote, just like in a normal retrospective.

  4. Brainstorm a list together of possible actions that will improve the meetings.

  5. Choose a few actions, again together, to try for the next three meetings, and then discuss them in your next one-on-one retrospective.

Simply start talking about your one-on-ones with the other person and discuss how they could be better.

What If You’re Not the Boss?

What can you do to improve a one-on-one that is inflicted on you? Here are some simple, but maybe not easy, ways to broach the subject with your boss:

  • Forward this article to your boss, with a note that you’d like to try one-on-one retrospectives.

  • In your next one-on-one meeting, ask if you can take a few minutes to discuss how the meeting can be improved.

  • Brainstorm a retro-style “glad-sad-mad” list about the meeting and bring it to the next meeting.

  • Ask your boss what the real goal of the meeting is and whether they feel this format is working.

  • Let your boss know that the current meeting format frustrates you and that you’d like to discuss changing it.

  • Tell your boss the way you feel about your one-on-one meetings, and then ask how they feel about them.

Talk about what’s really happening. Stop pretending that your one-on-ones are great, or that they can’t be changed, or that you’re benefiting from them as much as you could be.

Best case: the meetings will improve, your boss will appreciate your initiative, and you’ll do better work.

Worst case: your boss says, “No, things are fine as is. How dare you suggest they could be improved? Just give me your status update.”

(If the worst case happens, you have bigger problems than crummy one-on-one meetings.)

What Kinds of Things Can Be Changed About a 1:1 Meeting?

It’s easy to fall into a rut with your one-on-one meetings, like an old married couple can fall into a pattern about how they spend Friday nights. Here are 10 things about your one-on-ones that you could change but might not have considered. (There are surely many more, but this should get your creative juices flowing.)

  • How often you meet (it doesn’t have to be the same frequency with each person)

  • What time you meet (it doesn’t have to always be at the same time)

  • Who runs the meeting (how could you take turns running the meeting?)

  • Where you meet (consider a walking meeting or a breakfast meeting)

  • What preparation both of you do for the meeting (try more, or less, prep)

  • The agenda for the meeting

  • The goal of the meeting

  • The length of the meeting

  • The communication medium (face-to-face, telephone, Slack, Skype, etc.)

  • What you could combine it with (a meal, a walk, a commute, etc.)

Do You Wait Too Long to Consider a Change?

When I begin to feel in a rut, I ask myself some questions. In particular, I ask whether my current practices still fit with my current situation or reality. Often, I find that this one question allows me to be more agile, more creative, and less judging. It lets me see new possibilities that I’d been missing.

For example, if I were dreading my one-on-ones, I might ask questions such as these:

  • What is my secret goal for these meetings?

  • What is my spoken goal for them?

  • What is the other person’s goal for them?

  • What is the company’s goal for them?

  • What would happen if we stopped doing them?

  • What parts are valuable to me and which feel like a waste?

  • What parts are valuable to them and which feel like a waste?

  • What is the least we could do and still have a valuable one-on-one meeting?

  • What do we need to add, subtract, change?

Grandma’s Ham

Albert Einstein summed it up pretty well when he said, “The important thing is not to stop questioning.”

Jane asked her mother, “Why do you cut the ends off the ham before baking it?”

Her mother answered, “Because that’s how your grandma taught me to do it. Ask Grandma.”

When Jane asked her Grandma, she replied, “My roasting pan was small, so I had to cut the ends off the ham to fit it in the pan.”

It’s difficult to question the status quo.

Not just because you want to avoid looking dumb or rocking the boat or breaking tradition, but because you might not realize there’s a question to ask.

New possibilities are wonderful. New choices and options do exist about how we work together. New possibilities bring hope that the future doesn’t need to be like the past and that we can grow and improve.

What a great thought!

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