Strategy Retreat Questions: 3 Different Ones Consider

Different Strategy Retreat Questions to Consider
Most strategy retreats aim to produce a sharp, credible, and actionable plan that positions the executive team — and the organization — for its next stage of growth. These sessions can create powerful momentum for alignment and strengthen the leadership team’s cohesion, but those benefits rarely materialize unless the group is willing to surface the real issues and engage in candid debate. While the final output often takes the form of a concise set of high-impact strategic priorities — ideally captured in a one-page strategy communication map — too many leadership teams fall short because they don’t push themselves to ask fundamentally different questions. The result is a plan built on familiar assumptions rather than the deeper insights needed to shape a more competitive future.

The Importance of Strategic Clarity
Too many leadership teams do not invest the time required to create an aligned and winning strategy.  That is a mistake.  Strategies matter.

• Our organizational alignment research found that strategic clarity accounts for up to 31% of the difference between high and low performing organizations in terms of revenue growth, profitability, customer loyalty, and employee engagement.
• Strategic clarity however, is not as easy as it sounds.  Our research also found that while most agree that a winning strategy is of utmost importance, two-thirds disagree about or misunderstand the specific next steps necessary to execute it at their own organization.

Ask Different Strategy Retreat Questions to Get It Right
If you are in charge of Strategic Planning Retreat Facilitation or for developing a strategy for your team or company, invest enough time with the right stakeholders to ask and answer different strategy retreat questions to ensure your team:

• clearly understands the strategic priorities and plan
• has no doubt that leadership is fully committed to the strategy
• is consistently implementing the plan across the organization
• is ready to be highly responsive to change at work

Three Different Strategy Retreat Questions to Consider
Here are three different strategy retreat questions to consider at your next strategic planning session to shake things up a bit:

1. What Would Someone from the Outside Do If They Were in Charge?
   This question cuts through organizational blind spots with remarkable precision. Picture a new leader stepping in — or an outside company taking the helm. With no attachment to legacy decisions, no loyalty to long-standing practices, and no emotional investment in “how we’ve always done it,” what would they immediately start, stop, or continue?

   Most organizations become deeply conditioned by their routines. Over time, familiar processes harden into unspoken rules, and even outdated approaches start to feel non-negotiable. That makes it harder to reimagine how to tackle complex strategic issues or rethink decisions that were made under very different circumstances.

   Stepping into an outsider’s mindset forces a reset. It compels leaders to articulate the underlying logic for current systems, norms, and structures — and to confront where that logic no longer holds. Assumptions that once made sense may now be slowing strategy execution, dulling innovation, or diverting resources from strategic priorities that actually matter.

   By deliberately breaking from the established code, leaders open space for new insights and more imaginative solutions. This kind of disciplined challenge often reveals that some long-standing choices have quietly become obsolete or ineffective. And once those constraints are surfaced, teams can design a path forward that reflects today’s realities rather than yesterday’s rationale.

2. What Part of the Business Does Not Fit?
   Step back and take a hard, holistic look at every major element of the business — partnerships, products, services, delivery channels, and even long-standing operational choices. They should reinforce one another in a way that strengthens your unique value proposition and supports how you win in the market. When something feels out of sync with your go-to-market strategy or doesn’t clearly advance your differentiation, that misalignment is telling you something.

   Once you spot a potential mismatch, examine its true contribution relative to everything else the organization is trying to accomplish. Some offerings or activities may have made sense years ago but now dilute focus, slow execution, or distract from priorities that matter more. In many cases, the business would operate with greater clarity and efficiency without them — and the costs of maintaining them quietly outweigh the benefits.

   At the same time, look for what’s missing. Are there capabilities, partnerships, or underutilized assets that could dramatically strengthen the strategy if they were developed or elevated? Strategic clarity isn’t only about cutting; it’s also about surfacing gaps that limit your ability to compete with speed and precision.

   Effective strategy is, by design, selective. No organization can pursue every opportunity or sustain every legacy initiative while performing at a high level. The best strategies channel energy, talent, and investment into the few areas with the greatest potential for impact. In our experience, once you move beyond two or three major bets, focus starts to erode — and performance tends to follow.

3. Is Our Corporate Culture Helping or Hindering Our Strategic Ambitions?
   Every strategy ultimately runs through culture. It determines how work gets done — the shared beliefs, habits, and unwritten rules that shape daily behavior. Whether intentionally shaped or left to evolve on its own, culture exists in every organization, and its influence on strategic execution is unavoidable.

   Leaders have a responsibility to understand their current culture and whether it accelerates or obstructs the strategy they are trying to advance. The most effective leadership teams are deliberate about this connection. They assess their culture across the key research-supported dimensions that influence performance, and they actively cultivate the behaviors that will reinforce their strategic direction rather than work against it.

   When culture and strategy are aligned, the organization gains coherence and momentum. Decisions are made faster, teams pull in the same direction, and people understand not only what needs to be achieved but how to behave in pursuit of those goals. But when the two diverge, friction builds — sometimes subtly, sometimes dramatically. A strategy that demands rapid innovation, for example, will stall inside a culture that only greenlights new offerings after competitors have proven the model. Likewise, a strategy that requires bold moves will be undermined by a culture that insists on eliminating every risk before taking action.

   These mismatches are not abstract. They show up in missed opportunities, slower execution, and persistent internal tension. Surfacing them — honestly and early — gives leaders the chance to realign expectations, reshape behaviors, and create the cultural conditions necessary for the strategy to succeed.

The Bottom Line
If you want your next strategy retreat to drive meaningful alignment and a sharper path forward, broaden the conversation. Push beyond familiar reviews and challenge your team with different, more courageous questions. That’s how you uncover the issues that truly matter and build a strategy that can — and will — be successfully executed.

If this made you question the effectiveness of your last strategy retreat, download Should You Facilitate Your Own Strategy Retreat?