The 7 Questions I Use to Check In with My Team (Inspired by My Marriage)

Welcome to Peaceful Growth, where you will find actionable tips to grow your agency to $10M (without working overtime).

A few years ago, my wife and I started doing a monthly relationship check-in.

It was simple. We’d sit down, reflect on our past month together, and talk openly about what felt good, what didn’t, and what we wanted more of—or less of. It brought us closer and helped us clear up any small frustrations before they grew into big ones.

It worked so well in my personal life, I started using the same idea with my team at work.

Now, every year, I sit down for a 1-on-1 check-in with each of my direct reports. It’s part performance review, part career reflection, and part honest, human conversation.

And I’ve been doing this for the last 3 years.
It’s worked really well—for both me and my team.

Here’s how I run these meetings:

• I share the 7 questions (below) 1 week before the meeting.
  That gives the team time to reflect and write their answers.
• I block 60 to 90 minutes for each meeting—no rush, no pressure.
• I try to do these every 3 to 6 months, depending on the pace of the year.

And here are the 7 questions I ask:

1. What were the 3–5 big wins for you?

This opens things on a high note. It lets your team celebrate progress, achievements, and things they’re proud of. You’ll often hear about moments you might have missed.

2. What were the 3–5 big misses for you?

This creates space for honesty. We all mess up sometimes. But talking about it without blame helps build trust and a culture of learning.

3. What new did you learn last year?

It could be a skill, a mindset, or a life lesson. This question encourages reflection on growth—and shows you value more than just output.

4. Which areas of your life did you grow?

People are more than their job titles. Maybe they became more confident, more patient, or more present. This helps you see the full human.

5. What do you want to do less this year?

This helps reduce burnout. When people name what drains them, you can often help remove or reduce those things.

6. What do you want to do more this year?

This shows you care about what energizes them. Let people lean into their strengths and passions—it makes them more motivated and engaged.

7. Is there any concern from the last year that’s not been resolved?

This invites anything unspoken. It’s your chance to listen, understand, and make things right. Don’t skip this one.

Copy + Paste: The 7 Questions

If you’d like to try this with your team, here’s the full list for easy sharing:

Final Thought

These questions are simple—but powerful.
They’re not about performance ratings. They’re about connection.
And in the long run, connection builds trust.
And trust builds great teams.

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One More Thing...

A lot of you have asked about the tools I use to stay productive and grow my agency.

So, I put them all in one place—organized by category:

• Writing Tools ✍️
• Productivity Apps ⏳
• Skills and Courses for Founders 🎓

And more.

You can check them out here.

Hope it helps! 🚀