How to run a great one-on-one meeting (hint: you probably aren't!)

Looking for some support? If now is the time to consider coaching, reach out here.

I know this sounds crazy, but when we started this thing I did not really think about what it would feel like to have all these employees around. - Me, 2014

I made the statement above to my co-founder during one of our daily walks around the block in the year our startup really started to blow up. A few months prior, it had been just us founders. Every lunch was a company all-hands. Now, things were changing fast, and I was unprepared.

Although I was a CEO of a fast-growing startup, I had never managed anyone before. I had no idea how much I did not know.

As a coach, I hear similar sentiments from CEOs all the time. Many founders are first-time managers, as are many of the young managers on their growing teams.

One of the most critical building blocks of great management — and one of the most misunderstood — is the one-on-one meeting.

What makes this meeting format so crucial while being so frequently misused? Let's look at the basics.

At our coaching firm, Sanity Labs, we train the key accountabilities of the CEO as follows:

• Hold the vision
• Recruit and retain the team needed to execute that vision
• Resource that team with capital, clarity, and care

But the CEO is not the only one accountable for providing clarity and care. Every manager is responsible for doing so for their reports or departments.

Most first-time managers have a sense of this, and they know that one-on-ones are a tool for it. But that’s often where the understanding ends.

Instead of using a thoughtful approach, many run ad-hoc meetings, fail to unlock value, or cancel them altogether.

Here are the four most common mistakes I see:

1. Believing the one-on-one is for the manager

Many managers use one-on-ones to alleviate their own anxiety about the business — bringing in their own questions and dumping them on their reports. That’s not the purpose. The goal is to provide clarity and care for the managee: to guide them on how their work maps to the needs of the team, to coach rather than direct, and to support them as humans through the inevitable ups and downs.

2. Using the meeting for updates

If you’re using one-on-ones for updates, it’s a sign of a larger operational issue: information isn’t flowing well in the company. Updates should be:

• Prepared in advance, in writing
• Data-supported
• Easily shared with others

That frees the one-on-one to focus on what matters most. Using your one-on-ones for updates is an expensive and ineffective band-aid.

3. Failing to set an agenda and keep notes

The structure of the meeting should be templated. The specific agenda should be set by the managee, who also keeps and shares notes from the meeting — including key next steps. This forces reflection before the meeting and ensures clarity beyond the meeting.

4. Holding rigidly to set time

A one-on-one should end when the agenda has been accomplished. Don't hold to an hour because you reserved an hour. The purpose isn’t to fill the time — it’s to create clarity and care.

My recommended one-on-one agenda

• Check-in — “What color are you? Red, yellow, or green?”
  • Green: I’m all good to go
  • Yellow: Here, but a bit stressed or distracted
  • Red: Physically here, but super distracted
  • Share context as desired but do not force it. More details on using check-ins to run great meetings is available here.
• Life outside work + work feelings — A space for connection and relationship-building. Ask what and how questions to learn about what's really going on for this person you are leading. Then listen.
• Biggest questions or challenges — What is keeping this person up at night? Manager listens, asks open questions, and explores solutions. Avoid jumping to directives. Be a coach, not a quarterback.
• Optional items from managee — What else would be helpful to explore?
• Requests for support — What is needed in the next days/weeks to succeed?

When we strip updates from one-on-ones, we create space for what really matters: supporting our people with clarity and care.

Give this a try — I’d love to hear how it lands for you and your team. It is not gospel; edit it as is helpful for your leadership style and your company's culture.

Looking for some support? If now is the time to consider coaching, reach out here.

Sending a big hug your way from my desk in LA.

-Matt

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