The Activation Gap Opens Before the Retreat Ends

There is a strategy activation gap sitting in most organizations. The data is unflinching. A study published by MIT’s Sloan review found that typically, only 28% of an organization’s executives and senior managers — those responsible for executing the strategy — can even identify the top strategic priorities, let alone use them to guide action. The numbers become ever more dismal with every step down in seniority. Strategic alignment drops from 51% at the top team to 22% among their direct reports. It’s hard not to picture the strategy doing a grand jeté out of the retreat, stumbling and staggering into a ditch.

So, why doesn’t the brilliance of the retreat survive its migration beyond that inner sanctum?

I came at that question sideways, and not by studying the numbers.

The Eye-Rollers Were Right

We think about almost everything before a strategy retreat: The site, attendees, experience, snacks, scorecard. Everything! Right?

I was on a call with a few other strategy consultants when one of them described how transformative their last retreat had been. I felt myself mentally roll my eyes. It reminded me of the people in the back row on day one of many retreats I’ve led — the ones rolling their eyes too (sometimes not just mentally).

By the end of the three days, they too are usually inspired and excited, their cynicism forgotten. The breakthroughs are real — palpable.

But my own cynicism came as a shock, one I had to explore.

What had changed for me? It wasn’t the retreats. Instead, it was that I started coaching founders after them. Once I saw what happens — surprisingly soon after the retreat — I couldn’t unsee it. In retreat after retreat — including the extraordinary ones, including mine — the eye-rollers’ comments echoed: “I’ve been to a million of these, and they make no difference.”

But why not?

Here’s what I see. A founder and team leave the retreat elated — the refined value proposition, the projects, accountability, a scorecard! Yay!! The projects have names on them and milestones. Then our coaching calls fill with the shrinking runway, irksome investors, the essential contract that depends on a new and unplanned feature.

Sometimes the projects stall for lack of bandwidth. Sometimes they get done — and it changes nothing, because they were just more work, never really tied to the breakthrough strategy. It’s not that the strategy gets rejected. It becomes a side conversation, or a never-tackled task, and quietly fades.

That pattern is not a failure of any particular retreat. It is built in to how we plan them.

Retreat Planning 101

This isn’t what anyone intends. But it’s an inevitable result of the strategic planning mental model.

Leaders hold strategic planning retreats to fix something. It can be flagging results, the ambition to grow, a new competitor or technology — or simply to revise the strategic plan from five years ago. They believe the new plan will be transformative — that the experience will alter the organization’s approach and how the team sees things.

Decision made, they delegate the retreat to a consultant or a team member.

All the attention shifts to the retreat.

What result do we want?

• It must produce a strategic plan.
• And it should inspire, motivate, create cohesion and energy.

Who should attend? There will be a debate, but eventually a group gets selected.

Someone asks about execution. Well, obviously!

• There will be projects, with owners and milestones. KPIs, OKRs, a scorecard.

Finally, logistics.

• How long, and do we leave town?
• And the event will have great food, bottomless coffee, entertainment, social time.

I’m sure this is familiar to you. It’s everything, right? The quality of the retreat, the accountability … and the coffee. What else could there be?

We Picture the Room, Not the Result

To see what’s missing, we must step back into the wider view.

We don’t hold a retreat to produce a plan. We hold it to transform the organization — not into something unrecognizable, but into something qualitatively altered.

Yes, transformation sounds mystical and grand. But it happens all the time. Someone unfit begins an exercise program and sticks to it. They get stronger and leaner. But they also start to see things differently. Their habits and priorities shift. They plan their weeks, their diets, and their outfits differently. Recipes and routines change.

Our gymgoer is transformed — just from this extra habit.

That is an individual transformation. The one we want for our organization involves more people and more coordination. But they are of a kind.

We have the retreat to transform the organization.

Whether the strategy is a wholesale reinvention or an incremental shift, we are crafting it to cause a transformation. Yet we never consider the transformation as we plan the retreat.

We never ask what it would take for the output — the strategy — to become the new direction. We never ask how anyone will make decisions or alter their current work once the new orientation has been decided.

It would be easy to say that the KPIs and OKRs will do that. But as the Sloan numbers show, they don’t.

Ask Early and Aloud

There isn’t one answer. But it begins with this inquiry: Why don’t we worry about this when we plan a strategy retreat? How come the choice of snacks and dry-erase marker colors ranks higher than translating strategy into daily decisions and judgments?

I know why I never considered it. Because I thought it was handled. Handled by a scorecard. Handled by projects and accountability. Handled by whoever owned that scorecard once my engagement was over.

Until I was as involved with my clients after the retreat as I had been prior to it, the gap was invisible to me. But when I was face to face, week in and week out with the CEO’s reality, I saw what happened. The strategy became remote — aspirational at best — a memento at worst.

Just knowing that we failed to ask the question gives us the first corrective step.

Ask the question! Ask it early — before we decide who attends and whether to have nuts and fruit or muffins.

What does it even mean for a strategy to have fully penetrated and become activated?

It doesn’t mean that you hit all the milestones, or even that projects are on track for completion. Those are neither necessary nor sufficient.

At the Four Seasons, it means that the valet moves the objects off the passenger seat before bringing the car, because he noticed that the driver had a guest with him.

For one of my SaaS clients, it means her sales rep will solve his prospect’s problem with the current product. He won’t ask the engineers to make a new feature that his prospect thinks she needs.

A shared PowerPoint distributes bullet points. How do you distribute judgment?

Ask the question and craft a plan. It doesn’t guarantee you will succeed. But focusing on the precarious intersection of new strategy and existing reality before the retreat increases the likelihood of strategic success.