The Art of the Awkward 1:1

Embrace the Awkward

  1. Don’t talk about any topic that you could discuss in the open, among your team desks or in the cafe. If it’s safe enough to be overheard — it’s not the right content for a 1:1. Email it, send it in Slack, discuss among the desks, say it at a meeting, anything but a 1:1.
  2. Commit to saying one rather awkward thing every 1:1, and get the other person to commit too. Agreeing in advance and getting permission makes it feel way more safe. Committing creates peer pressure to be real. It works.

The Awkward Awakens

  • Get started and commit. A common complaint is that setting up the agreement to be awkward in a 1:1 series itself feels really awkward. Great! That satisfies your quota for the next meeting. Commit to awkwardness to someone (your peer, manager, a friend) and follow through.
  • Fix your other communication. If it’s hard to get to the real stuff in 1:1s, your other communication channels might suck. Get all your updates, easy questions, simple feedback done some other way: email, team meeting, Slack msg, text, whatever your company does. Whatever you do, don’t waste the 1:1.
  • Plan to be awkward. Spend a few minutes at the beginning of the week thinking what would be great to get off your chest and what you’d love to hear about from your coworkers. Plan how to be awkward rather than how to avoid it.

The Awkward List

Meta & Feelings (Occasional)

  • Talk about emotions. Label one you’re feeling, or what you sense from other person. Boom, instant awkward and great discussion.
  • Any meta-conversation about your conversations. We never talk about Topic A, we just always talk Topic B. Why is that? When I tell you about Topic A, you always react like this, and that’s why I don’t tell you that stuff. When I bring up Topic B, how do you feel? Why is that?
  • Ask for their fears. What are they afraid of (for their career, the project, an upcoming tough meeting)? Why? Share your own.
  • Trust check. How easy is it for both of you to share intimate things with each other? Why? What would make it easier? Discuss.

Extra Honest Feedback (All the time)

  • Are they acting like the best manager / report / partner you could wish for? Are you? Why or why not? Discuss.
  • What have you already told someone else about this person (or heard others say)? Share with them. Discuss.
  • What is everyone around neglecting to tell this person? What’s the work equivalent of this person having mustard on their face after lunch? Be a good friend / coworker and tell them.

Humble Advice Seeking (All the time)

  • Tell them a growth area you’re working on currently. Tell them why you picked it (even if it was one of those “not-really-optional” ones!). Ask for advice.
  • Check for your own role in a weird situation. Pick a thing you’ve recently complained about. Ask them — “What could I’ve done differently in that situation?”
  • Ask for feedback on how to be better. Then, skip the fluffy answer and ask again until you get something real.
  • Admit a fault or a mistake. Ask for support and advice. Ask them if they noticed you making it or not.




Eng & Product VP @ FB. Loves: awesome managers, people who grow, tech, food, design, sports. Follow me as @mrabkin.

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Mark Rabkin

Mark Rabkin

Eng & Product VP @ FB. Loves: awesome managers, people who grow, tech, food, design, sports. Follow me as @mrabkin.

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