Leadership Library

Manager Tool · 4 min read

Better 1:1 Questions

Twenty questions that move a check-in past status updates and into the things that actually matter.

CoachingLeading Others

A 1:1 that is only a status update is a meeting you could have replaced with a message. These questions are for the other kind — the half hour where someone thinks out loud and leaves clearer than they arrived.

Opening the conversation

Start wider than the work. The first question sets how honest the rest will be.

  • What is on your mind this week that we have not talked about?
  • What has your energy been like?
  • What is the most useful thing we could spend this half hour on?
  • What has been better than expected lately?
  • What is taking more out of you than it should?

Understanding the work

Move from what is happening to what it is like to be inside it.

  • Where are you stuck in a way you have not said out loud?
  • What decision are you sitting on?
  • What would you do if it were entirely your call?
  • What is the risk you are most worried about?
  • What is one thing I could take off your plate?

Growth and direction

Ask these monthly, not weekly. They need room to be answered honestly.

  • What part of the job do you want more of?
  • What are you learning right now?
  • Where do you want to be stretched in the next six months?
  • What skill would make the biggest difference to you this year?
  • Whose work do you admire here, and why?

Feedback in both directions

These questions are the ones most managers skip. They are also the ones that change how you lead.

  • What am I doing that is helping?
  • What am I doing that is getting in the way?
  • What have I missed?
  • Where do you need me to be clearer?
  • What should we do differently in these conversations?

You do not need twenty questions. You need one good one, asked slowly, followed by the patience to hear a real answer.

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