Align teams in less than 90 minutes

Most leadership teams think they’re aligned, until you ask them to write things down.

That’s what happened with a founder-led B2B company we recently worked with.

When we ran a strategy session, we asked the team to answer 3 simple questions:

1. What does winning look like?
2. Where do we play?
3. How do we operate to win?

Each person answered them individually.

And the responses? Completely different.

→ Some focused on aspirational goals.
→ Others named customers.
→ A few zoomed straight into internal process issues

None of them were wrong. But all of them were misaligned.

This is what strategy drift looks like.

Most strategy problems are alignment problems

We used to think that strategy meant writing long documents.

Now, we know it’s about getting a leadership team to agree on a few critical things:

→ What are we focused on right now?
→ Why do we believe that’s the right focus?
→ What’s in our way, and how do we clear it?

That’s why we start every project with a tool called “Evaluating Our Strategy.”

It’s designed to surface exactly this kind of misalignment early → so we don’t waste time solving the wrong problems later.

What this tool looks like in practice

Here’s how it works:

We set up a 90-minute working session and give every leader the same prompt:

“Individually answer the following:

Each person writes their answers down.
Then we share and discuss as a group.

The goal?

Not to debate, just to compare.
It becomes immediately clear where there’s alignment and where there isn’t.

The real outcomes teams get from this

We’ve used this exact framework in over a dozen leadership sessions this year. Every time, the results are the same:

→ Leaders get clear on how their strategy is actually understood by others
→ The group sees where they’re duplicating effort or working at cross-purposes
→ They identify early which capabilities are helping or hurting execution

In one recent case, the session revealed:

→ The product team and sales team had completely different definitions of the “ideal customer”

→ Half the team was optimizing for short-term revenue, while others were focused on long-term retention

→ Nobody could clearly articulate how their go-to-market motion differed from key competitors

No one had seen it before, because they hadn’t stopped to ask.

Why this simple tool works

It forces teams to:

→ Step back from day-to-day problem solving
→ Share individual mental models
→ Spot pattern gaps before they become execution breakdowns

And because it takes less than an hour, it fits neatly into an existing offsite or planning sprint.

We’ve used it to:

→ Prep for strategic planning cycles
→ Align founder-operator teams during transitions
→ Clarify direction after org restructures

It’s become one of our go-to starting points.

Want to try it?

You can literally run this next week.

Here’s how:

→ Book 90 minutes with your leadership team.
→ Send them the 3 questions in advance.
→ Ask each person to write individual answers.
→ Use the session to share, not debate.

You’ll walk away with a heatmap of alignment gaps and a clearer sense of where your strategy actually lives (in people’s heads).

If you’re running a business and you’re not sure everyone’s rowing in the same direction, this is the fastest way to find out.

Whenever you’re ready, there are three ways we can help your team…

1. Strategy & Growth Blueprint: A market-grounded strategy, annual plan, and 90-day execution board the whole team owns.

2. Operations & Tech Reset: Bottlenecks mapped, future-state processes designed, and a phased tech roadmap ready to launch.

3. Manager+ Accelerator: Build core skills in delegation, feedback, goal-setting, and develop a plan to lead a stronger team.

If you’re tired of strategy discussions that go in circles,
👉 https://www.strengthsinsights.com/connect