Why Most Strategy Sessions Fail, and How the Best Ones Get It Right

Next week, somewhere in Scottsdale or Palm Beach, a group of executives will gather in a beautiful resort hotel. There will be branded notebooks and a view meant to inspire big thinking. The CEO will kick things off with a few words about opportunity. Someone will joke about being off email for a day. The slides will be polished. The conversation will feel important.

A few weeks later, almost nothing will have changed.

That’s the quiet truth about most strategy sessions: they feel productive, but they rarely move the business forward.

The reason isn’t bad leadership or a lack of effort. It’s that most teams mistake talking about the business for working on the business. A great strategy session isn’t a meeting to review the present. It’s a reset. It’s that rare moment to step back and ask, “What’s changing around us that should change what we focus on next?”

And that question has never mattered more.

In an era when AI, regulation, and global volatility are reshaping every market, the world is moving faster than any single leader can track. You can’t predict it, but you can fall behind it. When teams don’t pause and reset together, focus drifts, resources scatter, and the company starts reacting to the world instead of shaping it.

My teammates and I have spent over three decades helping executive teams design and facilitate strategy conversations that actually move companies forward. That kind of progress doesn’t happen by accident or charisma. It happens by design—and the design starts before anyone walks into the room.

Here are five principles you can use for yourself.

1. Set the Challenge Before You Meet

Most strategy sessions fail before they start. The agenda looks smart, but the problem is fuzzy.

Teams can burn up a whole day debating what the real problem is without ever getting to solutions. That’s why the most successful sessions start with a sharp, agreed-upon challenge. Is growth stalling? Has a new competitor emerged? Are costs out of line? You can’t fix everything at once. Focus your team’s energy on the issues that matter most.

Do that work in advance. Use data, voice-of-customer insights, and stakeholder interviews to define the core problem. Ask your managers what’s really getting in the way of progress; they often know better than anyone. That way, when your team finally comes together, every minute is spent working on the solution, not defining the problem.

2. Invite Both Deciders and Disruptors

The biggest decision you’ll make about your strategy session is who’s in the room.

Most companies default to hierarchy: senior vice presidents, direct reports, the usual faces. But the org chart is a terrible map for solving problems.

You need both deciders and disruptors. The deciders are the leaders who can make calls and carry the work forward. The disruptors are those who challenge assumptions and stretch the team’s thinking. Sometimes they’re one or two levels down. Sometimes they’re experts closer to your customer, or people who see the system differently.

At Jump, we’ve watched this mix change the entire energy of a session. When you include disruptors—those who think differently, see differently, or simply care differently—you don’t just get new ideas. You get a new conversation.

The goal isn’t diversity for its own sake. It’s about ensuring the team doesn’t end up designing tomorrow with yesterday’s perspectives.

3. Find a Hybrid Facilitator

Even great musicians need a conductor. The same goes for leadership teams.

It’s a rare skill to draw out each participant’s perspective and move everyone toward a shared outcome, and many CEOs assume it’s their job to lead the meeting. But even if they’re good at it, that puts them in an impossible position: you can’t facilitate the conversation and fully participate in it at the same time.

So, get someone to facilitate. But not just anyone who knows how to run meetings. Working sessions aren’t about managing airtime; they’re about shaping thinking.

That’s why the most effective approach is to find someone who’s both a facilitator and a strategist: someone who can guide the discussion with objectivity while understanding the business deeply enough to push the team’s thinking. They’re not just keeping time or summarizing notes; they’re helping the group see patterns, test assumptions, and make sharper decisions.

4. Get People Leaning Forward

The biggest red flag in any executive session is when people start leaning back.

You’ve seen it: the lights dim, the PowerPoint begins, and a room full of capable leaders becomes an audience. They’re no longer co-creators; they’re critics. And once that happens, the meeting’s over.

Executive time is too expensive for passive consumption. It should be used for what can only be done in the same room: thinking together. A great strategy session isn’t a show; it’s an immersive experience.

Successful sessions change the energy in the room by making information physical and visual. They cover the walls with bold data, future scenarios, customer stories, and key trends. They surround people with the forces shaping their business so they can see the big picture—literally. Then they get people to walk the room, react, and make choices together.

When people engage with information this way—circulating, debating, pointing, deciding—they connect their minds and their bodies to the work. They think and decide differently. And the payoff goes beyond engagement. They notice patterns they’d miss from behind a laptop. They shift from analysis to ownership. And that shift builds both conviction and alignment PowerPoint never could.

5. Force Choices, Ideas, and Action

Left unchecked, strategy conversations drift into abstraction. The language gets lofty, the statements agreeable, and everyone leaves with a version of alignment that dissolves in daylight.

Great sessions make choices visible, concrete, and unavoidable.

Start by giving people something tangible to react to. Rather than asking abstract questions like: What kind of company do we want to be? Show them five different future customer personas and make them pick which one they’d most want to serve. Then ask why. Or present three possible growth stories for the next decade and push the group to decide which version of the future feels both bold and believable.

Once participants have made their initial picks, push further. Ask: What trade-offs would this choice require? What capabilities would we need to build? What risks are we willing to take? The conversation shifts from speculation to strategy. When people have to stand behind a choice, they think harder and commit faster.

Great facilitators help the group move from options to ownership. They clarify what’s being chosen, who owns it, and what it means to say no to the alternatives. Then they capture those decisions in simple language that everyone can carry forward.

The best sessions don’t just talk about ideas. They force decisions, surface conviction, and send leaders home knowing exactly what future they’ve chosen to create.

The Real Work of Alignment

Peter Drucker famously said that culture eats strategy for breakfast. He was right, but that’s only half the story. Culture and strategy don’t compete; they depend on each other. The most successful sessions strengthen both at once.

New technologies, shifting markets, and global volatility mean yesterday’s alignment may already be obsolete. Leaders can’t afford to waste opportunities to create focus, conviction, and action.

When leaders step back from the noise, face hard truths, and make real choices together, they’re not just aligning on a plan. They’re building the trust and conviction that make execution possible. A strategy conversation should leave people not just clearer, but more connected: to each other, to the mission, and to the future they’re choosing to create.

When you’re living in a world of constant change, the real outcome of a great strategy session isn’t a slide deck. It’s a team that knows where it’s headed and still believes in that direction when the next disruption hits.