Enrollment Is the Missing Link in Strategic Planning

Your strategy failed because nobody was enrolled.

Why do strategies fail? It’s a popular business question with endless theories—frameworks, business models, competitive positioning, value creation.

I’ll leave that to HBR.

Here’s my thesis: companies minimize the need to enroll employees and stakeholders during the strategic process. So implementation falls short.

Enrollment isn’t a soft skill or HR buzzword. It’s the art of facilitating the behavioral, cultural, and human elements that need to be in place for people to make decisions and take action toward desired outcomes.

Without enrollment, you get a beautiful deck that sits on a shelf while everyone goes back to doing what they were doing before.

Work backward from success.

Let me visualize what success looks like and reverse-engineer it.

A successful strategy is executed by an accountable team with autonomy to experiment and make choices to achieve outcomes.

For a team to feel accountable, they need to be enrolled.

To be enrolled, they need to participate in strategic planning—or at minimum, the communication of the plan.

For teams to participate meaningfully, there needs to be executive commitment and a thoughtful strategic process design.

The chain looks like this:

Executive Commitment → Participation/Communication → Enrollment → Accountability

Break any link, and the strategy dies in PowerPoint.

The best strategies are narratives.

Great strategies are stories. They take stakeholders on a journey—historical perspective, present environment, future state—where humans execute choreographed tactics to achieve specific outcomes.

The operative word: human.

Management consultancies are incredibly competent at building strategic narratives. McKinsey can craft a story that makes your board weep with inspiration.

The challenge is turning that story into reality. And that requires enrollment from the people who actually have to execute it.

Embed internal teams early.

I advocate embedding an internal cross-functional, high-performance team with strategic leaders or third-party consultancies throughout the entire strategic process.

Short term, this adds complexity. It slows things down. It creates discomfort.

But that discomfort is where the magic happens. Suffering during the planning process is critical for enrollment.

Suffering forces cross-functional problem-solving among the practitioners within the organization—the people who will actually do the work. Without doers involved, strategy becomes academic. It becomes consultant theater that looks impressive but has no connection to operational reality.

Design the process intentionally.

Here’s my checklist for any strategic planning project:

1. Find and build a balanced internal team.

I identify this team during early stakeholder interviews. I probe: who are the high-potential employees? Who does everyone go to with questions?

Planning processes are excellent opportunities for people searching for stretch assignments. Find your A-players who want visibility and give them meaningful roles.

2. Keep everything visually in one place.

Ideally, a war room—an actual conference room where work lives on the walls. Or a virtual whiteboard like Miro.

Seeing the work develop enables strategic themes to emerge naturally. When everything is scattered across email threads and individual laptops, connections get missed.

3. Divide up the workstreams.

Create mini-teams to investigate and execute questions or issues derived from the planning group. Have them own and present their work.

Ownership creates accountability. If someone is responsible for customer segmentation analysis and has to present it to leadership, they’ll do better work than if they’re just “helping out.”

4. Facilitate and provide tools, knowledge, and coaching.

I embed myself on these teams as a player-coach. I help teams discover answers and provide guidance on executing workstreams.

For example, if a team has a customer segmentation workstream and struggles to get started, I offer methodologies and resources. But they do the work. They own the insights.

5. Over-communicate, especially with leadership.

Invite leaders into the war room—virtually or physically—and regularly walk through completed workstreams and learnings.

Be open to feedback. Make adjustments in real-time. This prevents the “big reveal” moment where leadership sees the strategy for the first time and hates it. By then, you’ve invested months and burned credibility.

6. Write the narrative before building the deck.

Before any PowerPoint, have the team write the narrative using only words. Walk through analyses, learnings, themes, initiatives, financials, and desired outcomes in prose.

Iterate. Get the entire team to sign off on the story.

Then—and only then—build the deck.

Most teams do this backward. They build slides and retrofit a narrative. The result is disjointed, jargon-heavy presentations that don’t tell a coherent story.

7. Let the team be your advocates.

I love when members of the planning team go back to their functional groups and present the strategy themselves.

If one of their own is enrolled and excited, it engenders commitment faster than any top-down mandate. Peer-to-peer communication is more credible than executive pronouncements.

8. Run a road show.

Review the strategy individually with the board, C-suite, senior leaders, and small intimate groups across the organization.

The goal: get maximum feedback and make adjustments as necessary.

Road shows grease the wheels for final plan approval and capital/resource requests. By the time you’re asking for formal approval, there should be no surprises. Everyone should have seen it, touched it, and influenced it.

Why this matters.

Adding these elements to your strategic planning process catalyzes participation, which enables enrollment, which drives accountability.

Execution succeeds when teams are enrolled and accountable.

Most strategic planning processes optimize for speed and polish. Get the consultants in. Build the deck. Present to the board. Announce the new strategy.

Then nothing changes.

That approach treats strategy like a product you deliver to the organization. “Here’s your new strategy. Now go execute it.”

But strategy isn’t a product. It’s a change in behavior across hundreds or thousands of people. And behavior change requires enrollment—not just communication.

The cost of skipping enrollment.

I’ve seen companies spend millions on strategic planning. Beautiful frameworks. Detailed financial models. Impressive decks with custom illustrations.

Then six months later, nobody can tell you what the strategy is. Teams are still operating under old priorities. Resources are allocated the same way they were before. Initiatives launch and die quietly.

Why? Because nobody was enrolled. The strategy was created in a conference room by executives and consultants, then announced to the organization as a fait accompli.

People don’t resist change. They resist being changed. When you involve teams early, let them suffer through the hard questions, give them ownership of workstreams—they become co-creators, not recipients.

Co-creators fight for the strategy. Recipients ignore it.

The takeaway.

Your strategy failed because it was built in isolation and delivered as a finished product.

Next time, slow down. Embed internal teams early. Let them struggle with the hard questions. Give them ownership. Over-communicate. Write the narrative before the deck. Turn them into advocates.

It’s messier. It’s slower. It’s harder to control.

But the strategy that emerges will be executable—because the people who have to execute it were enrolled from the beginning.

Enrollment isn’t optional. It’s the difference between strategy as theater and strategy as transformation.