Start with the end—A shot of fearless culture #432

Your weekly dose of culture insights and exercises, one topic at a time.

Jul 08, 2026

“This makes me feel uncomfortable and nervous,” a team leader emailed me after receiving the pre-work for an offsite I was hired to facilitate.

To me, that’s usually a good sign.

Most leaders expect an offsite to be a break from work. A chance to reconnect, relax, and spend time together outside the office.

And yes, there should be moments like that.

But a great offsite is more than a reset.

It’s a rare chance to step away from day-to-day execution. To address the issues that keep resurfacing. To challenge assumptions. It’s a commitment to becoming a better team.

That’s why I make the pre-work challenging.

It sets the tone before anyone walks into the room. It tells people this isn’t another meeting. There’s no growth without real work.

The best offsites don’t start with an agenda. They start with the outcome.

In my latest article, I share how to keep your offsite from turning into another pointless meeting.

Explore this week’s newsletter:

→ 7 Reasons Team Offsites Fail (And What to Do Instead)

→ Exercises and practical resources

Stay fearless, my friend.

Gustavo

In Case You Missed It

→ How to Run an Effective Team Offsite: Success Metrics Explained

Ask Your Team This

What would make our upcoming offsite a waste of time?

⚠️ Try This: Offsite Expectations

Before planning your next offsite, ask each team member to reflect on previous retreats they’ve attended, whether with your current team or another organization.

First, write down:

What worked well?
What didn’t work?

Then complete these prompts for your next offsite:

I like… (something I’d like our next offsite to include)
I wish… (something I’d like us to do better)
What if… (an idea we’ve never tried before)

Share everyone’s responses and integrate them into a brief for your next offsite. This is not a wishlist. The goal is to improve the experience, not to please everybody.