“I’m stuck.”

(This is how most of my coaching sessions started.)

It’s 2017 and we are preparing for our annual offsite/2018 planning. Our strategic pivot wasn’t really working.

I was losing my mojo and I think my exec team could tell. I felt like I had a clear sense of where to go next but was trigger shy.

2 years earlier, I had sold 25% of the company and pivoted the entire strategy and well… it wasn’t working!

In frustration, I said, “These planning sessions feel like a waste of time. They don’t really change anything and they pull us away from our work.”

Dave’s reply: “Well Jesse, have you considered maybe you don’t know how to run a great offsite?”

As I usually did in my coaching sessions, I got defensive at first.

But then realized he was totally right. No one had ever taught me to do it and I never truly believed in the value.

Lucky for me, Dave had facilitated a ton and taught me.

Lucky for you, today I’m going to share a simple approach to run killer planning offsites!

Before I start any offsite, I want to think about the group coming. I close my eyes and go to the END of the offsite.

I imagine each member of the team calling their significant other or mom and that person asking, “So how did it go?”

I get clear with what I want them to THINK, FEEL and DO at the end?

I may want them to think: “We have an exciting plan for next year!” or “I really like my colleagues” or “I can rely on my team.”

Feelings can range from excitement to joy (celebration) or even feeling some sadness of letting go of the old plan.

What specific actions will they take 48 hours after leaving the room? Are they hiring new people? Changing their priorities? Get clear on what you want happening as the offsite ends.

1/3rd Trust Building

I believe one of the most important functions of a team get-together is trust building.

Team performance has almost NOTHING to do with individual talent and EVERYTHING to do with psychological safety.

This gets built in both formal and informal ways during an offsite.

One of my favorite exercises: "If You Really Knew Me…"

We get in a circle and each persons says, “If you really knew me…” and fills it in any way they like.

“If you really knew me, you’d know that I went skiing with my kids this weekend.”

I recommend 3 rounds of it (e.g., If you REALLY really knew me…).

It will feel awkward at first (that’s normal) but usually one person keeps taking it deeper each round.

By the end of 3 rounds everyone is openly sharing their deep, dark secrets.

Vulnerability, play and touch bond groups in unique ways and this hits on that first category.

A good dinner, hike or a bunch of celebratory high fives also goes a long way.

I like to sprinkle these throughout the offsite.

“Sprinkle” of inspiration

For GrowthAssistant, I always recommend that Adriane have at least 3 people join us:

• client

• Growth Assistant

• luminary/advisor type person

Schedules can be challenging but I think that grouping makes sense.

The client talks about how VALUABLE the service is for them and their business. This brings it all to life for the team who works all the time but rarely is upfront with the customer.

The luminary hits on something like AI or how hard it is to build a business and the team feels seen and inspired.

And of course, the Growth Assistant talks about how their career and life have been changed by GA.

Put that all together and the team is RUNNING out of the session to keep building.

1/3rd Business Planning

A ton goes into this section but the most important thing you can do as a leader is think deeply about where the team and company are and ensure the discussions are helpful and relevant.

I like to push for clarity, alignment and prioritization in this part.

A little preview for how I start each business section:

As a leader, you MUST present your vision FIRST.

We just did the Bootstrapped Giants offsite. Andrew walked in saying “what do you all think we should do?”

I stopped him. I said (as Dave once told me): “You are the CEO. You are the leader and we stand behind you. Start with your vision and then we will align to it.”

The Traditional Approach:

Open brainstorming + group discussion = chaos.

It’s usually unproductive and actually leaves people feeling frustrated.

My (Dave’s really) simple but highly effective process:

My approach:

Leader shares their vision (or what I call: Desired Future State). A clear articulation on where we are in 3 and 1 year.

Numbers, employees, customers, other product details, etc. Your DREAM. Your DESIRE.

Then you, the leader, ask the “WHAT” question: “On a scale of 0-10, how aligned are you to this vision?”

Avoid the HOW questions for now. To help frame that, I’ll say to the team: “For now, lets just agree on if we’re scaling a mountain or going scuba diving, not on what equipment we need.”

Everyone goes around with their score. Then you ask (starting with the lowest score), “Give me 2-3 reasons you are that number and NOT a zero.” (I.e. why do you agree with this vision?)

DO NOT SKIP THIS PART. This gets everyone seeing all the stuff they agree with, that creates productive vibes

Then you ask: “What are 2-3 things it would take to MAKE you a 10/10?”

Notice the frame of that question. It isn’t what don’t you like. It forces productive conversation.

Think of it almost like a negotiation. “If you simply add these 2 things, I agree with the plan!”

I’ve seen this turn days long debates in 45 minutes with everyone being MORE aligned.

After you ask the WHAT 0-10, do a HOW 0-10. “How LIKELY are we to accomplish this plan?”

Now the real fun comes in. Same prompts as above but what you’ll likely find is some common themes/issues that pop up for why the team doubts you can attain that DFS.

It could be resourcing, a gap in customer service or competitive issues or something else!

Whatever it is should be the focus of your “business” problem solving on the offsite.

1/3rd Skill Building

I always love to have some time towards intentional, group skill building. Could be our feedback skills. Could be selling. Or maybe it’s a creative brainstorm.

Something where we actually improve ourselves and learn things.

At our annual Ampush offsite, I’d always have more tenured people break out and teach more junior people a skill.

One of my favorites was the McKinsey approach to Problem Solving.

This is where you use a thing called an “issue tree” and break down the problem into specific, digestible chunks.

First, I taught it at our offsite, then I had our director levels teach it.

The result: everyone in the company spoke the same language and learned the same system for thinking. It was powerful.

I've run this formula across dozens of offsites at Ampush and Gateway X.

Teams that dedicate equal time to trust, planning, and skills simply perform better.

The difference between good and great offsites lies in this equation:

At Ampush, the best insights emerged after someone let their guard down. That starts with you, the leader.

One moment of vulnerability. One personal story. Suddenly, trust shot through the roof.

It’s science. Trust and alignment amplify results like compound interest.

So, here’s your first test:

On a scale of 0-10, how confident are you in your current offsite approach?

Reply with your score and why. I read every response.

-jesse

PS. My coach Dave Kashen has loads of team building activities. He recently had us do Car & Driver.

How it works: We paired up. One person was the “driver” and the other the “car.”

We started by having the car close their eyes while the driver places hands on their shoulders to guide them around the space.

Check out the expression on Nak’s face as he “drove” me around the park.