I like to ask other managers what kind of questions they ask during their one on ones. Everyone has their own style, so I often get some interesting responses. Getting good information out of your one on one conversations is something of an art. Given the amount of time over a career that you will spend during one on ones, it’s worth a small time investment to improve your skills.

Managing Humans

Schedule one-on-ones with direct reports, keep them on the same day and time, and never cancel them. - Lopp, Michael (Managing Humans)

This book is commonly held up as the work of God when it comes to managing people. Here are my blatant crib notes of the text.

  • Start with the question “How are you?”.
  • Your biggest job is to gauge mood.
  • Learn something from every one on one.
  • Status is not the point.
  • Three things that are working, three things that are not, what are we going to do about it?
  • Never cancel them, it sends a bad message.

When you’re stuck, Michael suggests some emergency topics.

  • Prepared points - i.e. context items from GTD.
  • Mini performance review.
  • Your current disaster.

Specific Questions

How is it going?

This is a variation on “How are you”? This does lead to a status update most times, so you often need to redirect. It’s important to lead with something that lets people talk about whatever they want.

How do you feel about coming to work every day?

More direct question to get at their mood/happiness.

How do you feel about working on project X?

Give the employee permission to say that they don’t like their current project, as well as implicitly tell them that it’s something we can change.

How is it going working with person X?

Is there some asshole that’s bothering you? Maybe I can help.

Who are your best friends at work?

For some people, work friend ships are critical.

Who are the top people outside the company who you want to work with again?

We should try to hire them.

What features would you add?

Are you thinking about the long-term future of the software? I care about what you think!

What could I be doing better?

I try to ask this as often as I can, but often forget.

How comfortable are you with uncertainty?

i.e. - how much insight into the sausage making can you stomach? Is that motivational for you, or counter-productive?

Other ideas

One thing I like to do is change the scenery of a one on one. Taking a walk outside is a great idea. I also like to do a one on one over lunch occasionally. On the other hand, you definitely want to be in a traditional conference room if you need to give hard feedback, or have a tough conversation.

The Coaching Habit

Recommended reading. The seven questions they recommend work well for one on ones, too:

  • What’s on your mind?
  • And what else?
  • What’s the real challenge here for you?
  • What do you want?
  • How can I help?
  • If you’re saying yes to this, what are you saying no to?
  • What was most useful for you?