How I Level Up Teams In 40 Days (And How You Can Too)

_{[Read time: 5 minutes]}

3 years ago, I took a risk.

I agreed to facilitate a strategic retreat for a small team (within a large organization). It wasn’t a service I offered. And I didn’t know much about the team.

Fast-forward to today. I’ve turned this risk into a viable revenue stream ($37,950 and counting), and all of the teams have asked me to return.

It turned out that not knowing what the team did was an advantage.

Facilitating is less about knowing the nuances of the team and more about connecting the dots.

Here’s why this matters…

If you’re trying to level up your services, know that many businesses and organizations already hold retreats…which means demand!

If you’re “the boss” running the retreat, know you can prevent it from falling flat.

I’ve uncovered 2 core issues:

• When the “boss runs it,” it feels like forced participation and suffocates discussion (no matter how “open” the team is)

• There is never enough time to prepare, making the live session lackluster at best

But I’ve cracked the code.

Here is a simple 4-part blueprint to ensure your next retreat is impactful and productive.

Two suggestions before getting to the blueprint:

→ Get super actionable and narrow: Get out of big-picture land. While talking about 30,000-foot-level, nice-to-haves feels good, get laser-focused on the juiciest, most impactful topic.

→ Use an objective facilitator to improve the outcomes. When someone on the team facilitates the retreat, you lose the regulator of the conversation. Two negatives emerge…too many rabbit holes, and everyone talks at the facilitator (not the rest of the group).

Your 4-Part Blueprint To A Successful Retreat:

1 — Ground the retreat with a “gravity” question.

I hold a 60-minute session to find the core topic with “the boss” (CEO, VP, team lead, or business owner).

Unless the retreat’s purpose is to learn as a group, leverage the boss's direction (because only one person is in a position to steer the ship).

I use Gary Keller’s focusing question as the basis of the session:

This question determines the highest leverage activity.

Once the topic of focus is set, we’ll reshape it into the gravity question using this structure:

Here’s an example:

Let’s say reducing employee turnover is the focus (because onboarding is time-intensive, costly, and takes away from compounding growth)

Here’s what a gravity question could look like:

What are the 3-5 actions the team can take over the next 6 months to improve margins by 18%, so we can allocate funds to increase compensation, build a retention fund, and hire an onboarding specialist?

(…something like that, very specific)

2 — Craft an outcome to demonstrate “tangible” progress.

Fast forward to the end.

Identify how to document the answer to the gravity question. It can be a single decision, a detailed action plan, or a whiteboard sketch. But it must demonstrate tangible progress.

But don’t just create takeaways → create momentum (otherwise, you risk signaling the retreat is a forgettable event).

Let’s revisit the example above to combat employee turnover and improve onboarding.

The tangible outcome? A detailed action plan, which may include:

• list of the 3-5 sub-actions

• the first step of each sub-action

• a metric to assess the impact of each sub-action

• a timeline or prioritization of sub-actions

• resources needed to support

• a feedback loop

With the gravity question and tangible outcome, you have the key points. Every other activity is about building the stepping stones in between.

3 — The secret is doing 80% of the work before the retreat (live session).

You want attendees to come prepared for the live session (because this may single-handedly drive an entire year’s worth of results).

Showing up unprepared can be avoided.

The retreat should start 30-40 days before the live session takes place.

I hold multiple 1×1 sessions with every attendee to:

• have “think out loud” sessions and mentally spar

• develop questions the others should consider

• identify blockers to the gravity question

It allows attendees:

• to earmark dedicated strategy time

• to think without being influenced by others

• a chance to vent in private (and get it out of the way)

For the facilitator, it identifies the important prompting questions.

(Side note → “brainstorming-type” retreats don’t create momentum — they create more thinking without action. There’s a time and place for them. Retreats are not that time.)

4 — Send a “prep” letter 2-5 days before to “prime” their minds.

This consolidates the important points from the 1×1 sessions (and other pre-work).

It allows each attendee to build on top of their baseline thoughts.

Think of the prep letter as the bumpers on the bowling alley. It prevents a gutterball (i.e., no impact) and increases the chances of a strike.

Everyone comes to the conversation fully primed, prepared, and super clear.

Use strategic retreats as launchpads of progress, not just forgettable events.

When the live session is done, a new normal should exist.

I’m not saying it revolutionizes everything, but if the topic is genuinely one thing that is “such that by doing it, everything else will be easier or unnecessary,”…then yeah, you’ll put a dent in progress.

That’s it for this week. Thank you for reading.

See you next week.

— Peter

P.S. If you’re planning (or want to plan) a retreat, I can help you in 2 ways.

1. Get the full breakdown of my process so you can better prepare for success

2. Have me run the process (so you don’t have to)

If either #1 or #2 sounds right, fill out this form.

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