Over time as that level of trust increased, I felt comfortable in asking my team what they thought I could be doing better to help them and the team.
The Importance of the One on One
Greg Thomas
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Stop wasting my time with your shitty one-on-one meetings.

1:1 meetings are the most important thing a lead of any team can be spending their time on. It’s not a trade-off against more important things. It is the important thing. How do you go from terrible meetings to good ones?Here’s the guide I give to my team leads to get them started…


One on ones are an opportunity to help guide and mentor. They are probably the most important thing you can be doing.

Here is a little guidance if you need some help getting better results from these meetings. If it feels awkward, weird, or forced at first — Get over it. Once it’s just How You Do Things and your team knows what to expect, it won’t be weird anymore.

Ask “What’s on your mind?” then “…And what else?”

This is their meeting; If they have burning questions or comments, now is the time to tackle them.

Ask “What’s your biggest challenge right now?” then “…And what else?”

Help figure out what’s getting in their way. Maybe they need advice, but more likely they need a push to take ownership over the real problem and do something about it.

Provide feedback on your written Individual Expectations. (It should be made explicit what you expect the team to value and what behaviors and skills they need to demonstrate.)

Do the hard part. If someone isn’t meeting your expectations in any of these areas, it needs to be said and you need to have a plan for tackling it. Do not put it off.

Ask for feedback on your written Lead Expectations (It should be made explicit what the team should expect from you and what you will expect from yourself.)

Don’t overwhelm them, pick one. Ask ‘Do you think I am…?’ Listen and look for things you can improve with curiosity. This is not the time to be defensive.

Ask about what motivates them. Some examples:

  • What single thing would you say has the largest impact on whether or not you have a good day or a bad one?
  • Who would you say has the largest day-to-day influence on your success?
  • What changes would increase your satisfaction at work?
  • What’s the most unclear part of what’s expected of you?
  • Are there any specific areas of our work as a team that you are not interested in?
  • When have you been most inspired?
  • Would you consider what you do now your best work?

Ask about the things that make them uncomfortable. Some examples:

  • What kind of feedback is most uncomfortable for you to hear? How can I help make it more valuable for you?
  • What are you are most concerned about your personal progress in? How can we work together to get you better feedback?
  • Name one area where you believe you should know more than you actually do?
  • What do you believe your most recent check-ins say about you?
  • What are you afraid… (…of getting blamed for? …that might happen? …being criticized for?)
  • What aspect of what you do are you least comfortable with?

Ask about things they have learned. Some examples:

  • What is one mistake you made recently and what lesson could you share with others?
  • What is one observation you have made recently that you think others could benefit from?
  • What are three mistakes you made this year? How did you correct them? How will you avoid them in the future? How will you help others to avoid them?

Help them build some artifacts that are useful:

  • A personal vision statement. What are they all about?
  • A personal development plan. Where are they going? How are they getting there?
  • A 90 day roadmap. Concrete goals they feel they can really commit to. (If not, why not?)

Help them to define what role they play on the team. Questions that might help:

  • What are you really good at?
  • What skills do other people recognize in you?
  • What do you believe you do better than most people?
  • What are you most often recognized for?
  • What about yourself are you most proud or satisfied with?
  • What resources, experiences or connections do you have that others might not?
  • What do you try to do that you can’t seem to master?
  • What do you do only because you have to?
  • What are one or two aspects of your personality that you feel hold you back?
  • What resources, experiences or connections do you feel you lack that others might have?

Help them to stretch their ideas of what seems possible. Some examples:

  • You have permission to think of any crazy stuff. No holds barred. What do you want to try?
  • What would you speak about at the next (big conference)?

Ask about ways you can improve teamwork. Examples:

  • Name one way we can make the team a safer place for honest discussion.
  • Name one way we can make the team a better place to share ideas.
  • Name one way we can make the team a better place to learn from the experience of others.
  • What problems do you see in the relationships between our teams?

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