Too often, strategic planning is treated as an annual box to check—a few days away from daily operations, followed by a slide deck and, if you're lucky, a dose of renewed optimism. But without a structured process that extends well beyond the offsite, even the strongest strategic plans risk fading into the background. It’s a familiar cycle: big goals are set, enthusiasm runs high, and then execution is overtaken by the urgency of business as usual.

After working with hundreds of leadership teams over the last two decades, we’ve seen a consistent pattern: what separates companies that achieve sustained growth from those that stall isn’t the quality of their plans—it’s the quality of their strategic rhythm.

It Starts Before the Offsite

The most effective strategy work begins before anyone walks into the room. Strong pre-work ensures that the offsite isn’t spent brainstorming from scratch, but refining real insights. One-on-one conversations with each team member and thoughtful pre-work create space for honest perspectives—on the business, on the challenges, and on what truly matters in the year ahead.

At the same time, the CEO works with a facilitator to develop what we call a CEO deck—a clear articulation of strategic direction, top priorities, and the questions that need the team’s best thinking. While strategy should be collaborative, it also requires strong leadership. I call this a “stake in the sand.” It is a starting point, but the team can move it around together which drives alignment. This clear point-of-view anchors the discussion and elevates the conversation from tactical to strategic right away.

The Offsite: Sharpening and Aligning Strategy

By the time the team arrives at the offsite, they’ve already done the work to surface and propose key priorities. That means the session can be used not for broad ideation, but for focused refinement and real decision-making.

A few core principles shape this process:

• Debate and synthesis: Teams split to evaluate and sharpen proposed goals, then reconvene to synthesize insights and align on direction. This has an added benefit of hearing everyone’s voice.
  
• Measurable targets: A strategy without success metrics is just a wish. Each goal is paired with clear indicators that define what success looks like.
  
• Shared ownership: Goals don’t live or die with the CEO. They’re owned by cross-functional teams throughout the organization who drive progress throughout the year.
  
• Governance: Execution doesn’t happen by accident. Teams agree on how they’ll meet, track, and adjust progress over time.
  
  

From Offsite to Action: Making Strategy Stick

No matter how strong the plan, it’s what happens after the offsite that determines impact. What keeps strategy alive is rhythm—a cadence of team check-ins, goal reviews, and focused conversations that tie strategy to daily execution.

Monthly team meetings. Strategy days with the leadership team every other month. Scorecards that surface what’s working and what’s not. These rituals create the structure to revisit and refine strategy continuously—because staying the course often requires deliberate recalibration.

Great Strategy Is Ongoing Work

Strategic planning isn’t an event—it’s a way of leading. It demands preparation, clarity, debate, follow-through, and course correction. The companies that thrive are the ones that treat it as a discipline, not a document.

This is the core philosophy behind the Strategic Ascent System we’ve developed at Katahdin Group. It’s a system for turning strategy into action—repeatedly, sustainably, and together.