Management

How to Run Exceptional One-on-Ones

A practical guide for managers and their direct reports

Dave Bailey
Published in
11 min readJan 20, 2021

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How effective are your one-on-ones?

Most managers will say theirs are great. However, one study has shown that employees often leave one-on-ones less motivated than their managers. That concerns me.

Typical one-on-ones are 30 to 60-minute meetings between teammates and their managers to help the teammate achieve their goals. By this definition, short status updates don’t qualify as one-on-ones. But conversations about well-being do, so they’re certainly worth including in any effective one-on-one.

Even though one-on-ones focus on the teammate’s success, both parties benefit from the meeting. Managers can directly improve their team’s performance and teammates can have their voice heard by management.

In practice, it’s hard to improve someone’s performance — but so is sharing honest feedback with your manager. And when performance doesn’t improve — and teammates don’t feel listened to — both sides start to disengage.

Both parties need to show up

After a decade of running one-on-ones with direct reports in my own companies, I now run one-on-ones with venture-backed CEOs, as their coach. It’s helped me clarify what makes one-on-ones work and what really drives performance.

The output of a successful one-on-one is simply the one or two small actions a report can take to develop their capabilities and move forward in achieving their goals.

I’ve experimented with a wide variety of formats — from unstructured conversations to going through sets of formal questions — and I don’t think the format is as important as how both parties show up for the session. So in this essay, I’ll set out some principles that will help both managers and their reports get the most out of one-on-ones.

Advice for reports

Most one-on-one training is targeted at managers. However, it’s generally agreed that this is the report’s meeting, and they should own the agenda…

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