The 1:1 is the highest-leverage meeting on a founder's calendar and the most commonly wasted. Bad 1:1s are status updates the CEO could have read in Slack. Good 1:1s are where you build trust, spot problems six weeks early, and coach your team into better operators.
1. Personal check-in (5 min). How are you, actually. This is not filler. Founders who skip this section lose the ability to spot burnout before it becomes resignation. 2. Their agenda (10 min). Whatever they brought to talk about. If they did not bring anything, that is a signal — usually of overwhelm or disengagement. 3. Your agenda (10 min). Feedback, questions about their function, cross-team blockers you can help unstick. 4. Career and growth (5 min). Rotates weekly through skills, goals, and career direction.
1. What is the one thing this week that would make the biggest difference if it went well? 2. What is slowing you down that I could help remove? 3. What have you learned about the business this week that I should know? 4. What is one thing you would like more or less of from me?
Question four is the highest-signal question in a founder's toolkit. It surfaces coaching gaps, communication issues, and misaligned expectations before they compound.
Keep a running document per direct report. Each week, add three things: what they committed to, what you committed to, and one theme you noticed. Review the document before every 1:1. This turns 1:1s from repeated conversations into a visible arc of growth.
If the meeting feels flat for three weeks in a row, one of two things is true: the person needs a bigger scope (their work has become routine), or the relationship needs a reset. Ask directly: "our 1:1s feel like they are on autopilot — what would make this time more useful for you?"
A founder who runs excellent 1:1s builds a team that raises problems early, makes better decisions in the founder's absence, and stays two to three years longer than the industry norm.
