All Notes

1:1s are for personal connection, not project updates

Last updated

Apr 15, 2025

I use recurring 1:1s as a space for me to reflect with my reports about their life at work. I want to surface sensitive frustrations, feelings about the team, the managerial relationship, and the company, and to get to know my reports personally.

I learned all this from Sue Odio, our COO at Stellate. Andreas Klinger also wrote about his 1:1 philosophy, which is similar.

My script for the first 1:1 with a new direct report

1:1s are a space for us to reflect about how you’re feeling about your life at work.

I ask the same standard questions that flow from you to the company every time (see my template below), which are really just there to prompt your mind and surface potentially interesting reflections, feelings, and discussion topics.

We won’t go through all of them every time, nor will we always have something to talk about for each one. Feel free to come prepared with discussion topics or questions if you have something on your mind.

What we talk about and what we don’t talk about is fuzzy, but there are two things that I will never bring up in a 1:1 to ensure it stays a safe place for us to reflect:

  1. Project or status check-ins

  2. Performance conversations (e.g., performance improvement plan or promotion)

Of course, if you have something that’s on your mind regarding a project, your performance, your career, or similar comes up, I’d love to talk about it. But, as the manager, I need to make sure that I have dedicated other spaces for project and performance conversations.

Template: 1:1 questions

  1. Direct report personally

  2. Direct report at work

  3. Our managerial relationship

  4. The team

  5. The company

The questions:

  • What’s top-of-mind for you?

  • Personally

    • How are you feeling?

      • How are you feeling, really?
    • How are you doing (outside of work)?

    • What are you excited about in life right now?

  • Personally at work

    • How do you feel about the value that you bring to the company?

    • What are you spending your time on that depletes your energy?

    • What are you spending your time on that is energizing?

  • The managerial relationship

    • Are you getting enough feedback from me?

    • What can I do to better support you & be a partner to you?

  • The team

    • How are you feeling about the team?

    • What can we do to improve our team dynamic?

    • Anything you long for, for our team?

  • The company

    • How are you feeling about the company?

    • Do you have clarity on our Vision/Mission/Values?

    • Do you have clarity on our strategy?

Other notes about Company Building

  • 🌿
    How to be better at making decisions

    What can I do before, during, and after making decisions to be better at making them?

  • 🌿
    How to present to executives

    1. Know all your details Know and be able to speak to all the details. Review your own work and ask yourself what somebody else might ask you about it, then make sure you have a solid answer to all those questions. Even things that are technically ou...

  • 🌿
    Developer tools startups are playing on hard mode

    How do you build a business selling tools to people who can technically build anything you can?

  • 🌲
    Being unreasonably responsive has made my projects more successful

    Creators who respond to feedback quickly unlock two virtuous cycles that allow them to build better solutions more quickly.

  • 🌿
    Message me whenever

    Send me messages whenever inspiration strikes or when it makes sense for your workflow. I'll respond when I'm back online. This isn't about being "always on," quite the opposite: it's about respecting that we each know how to structure our own work l...

  • 🌱
    How I manage my todos as a CEO

    Kanban board with five columns: Inbox, Backlog, Blocked, Delegated, Done Most importantly: GTD-style “if it takes less than 2 minutes, do it immediately.” Create todos for everything (and I mean, everything, including replying to people) that go in...

  • 🌱
    How to run recurring virtual meetings efficiently

    Start with a checkin question for connection (10% of the meeting length) Capture decisions made Capture open action items and check in on open ones every time, otherwise they get lost/forgotten due to poor personal execution Align on discussion ...

  • 🌿
    How I run gratitude circles

    Credit to Sue Ko who taught me this many years ago. Gratitude circles are a beautiful way to get team members feel seen by their peers. I run them in-person at least once a year with each of my teams. Quote from one of my engineers after their first ...

  • 🌿
    How we make brainstorming work

    Brainstorming usually fails. But, I noticed a pattern in the times that it worked exceptionally well. Here's how to make it work.

  • 🌿
    How we foster deeper connections in our remote team

    I believe that teams that are more connected perform better and that remote teams have worse connections. How can we improve that?

  • 🌲
    Why I'm vigorous about giving feedback

    Every day, you will find me hunting down a founder's email to send them feedback about my experience with their product. Why?