Most CEOs I talk to have tried to run their own strategic planning process at some point. And most of them came away frustrated, not because they weren't capable, but because facilitating effective and efficient strategic planning is more challenging than it appears from the outside.
For years, I ran strategic planning myself without a real system. Since joining Katahdin Group, I've had the opportunity to experience strategic planning from both sides of the table: as a CEO participating in the process and as a facilitator guiding leadership teams through it. Those experiences reinforced something I didn't fully appreciate before: creating a great strategic plan requires a level of discipline, structure, and facilitation that most leaders underestimate.
Strategic planning is the most critical meeting each year where the CEO needs to hear the team clearly. That means listening hard, sitting with disagreement, and being open to having their thinking changed. None of that is possible when the CEO is also managing the clock, watching the energy in the room, collecting feedback, and deciding what gets discussed next.
I've been on both sides of this. When I was running my own offsites, I was the one keeping things moving, and I missed signals from my team I should have caught. When I went through Strategic Ascent as a participant and the CEO, I could finally just be in the conversation.
When the CEO is facilitating the discussion, the dynamic in the room changes. Most leadership teams won't challenge the CEO the same way they would challenge a third-party facilitator. People become more cautious about pushing back, questioning assumptions, or introducing ideas that run counter to where they think the CEO wants the conversation to go.
The result is often a form of alignment that looks stronger than it really is. The team agrees, but they haven't necessarily worked through the disagreements, concerns, and tradeoffs required to build true commitment. Strategic planning only works when the entire leadership team is fully engaged in shaping the outcome.
Good strategic planning starts with the CEO putting forward a clear point of view: “Here's where I think we need to go.” That point of view needs to be pushed on, hard, by the team.
When the CEO is running the meeting, that pushback rarely happens with the intensity it needs. People defer. The strategy that comes out the other side looks like the strategy that went in, which is the opposite of what you want. The whole point is for the team's perspective and active collaboration to make it stronger.
Most leadership teams can identify more opportunities than they can realistically execute. The difficult part of strategic planning is not generating ideas. It’s deciding what matters most and having the discipline to leave other good ideas behind.
When CEOs run the process themselves, it becomes much easier for the plan to expand beyond what the organization can actually handle. The team convinces itself that eight priorities are manageable instead of five. Initiatives stay on the list because nobody wants to argue against something that feels valuable. And if the CEO feels strongly about keeping something in the plan, most teams will only push back so far.
A strong facilitator creates discipline around those decisions. They keep the team focused on the reality that strategy is ultimately about tradeoffs. Not because the additional ideas are bad, but because too many priorities almost always weaken execution.
The goal is not to leave the room with the longest list of important initiatives. It’s to leave with a focused set of priorities the organization can realistically execute.
Once the offsite ends, operational urgency takes over. The same CEO who was responsible for facilitating the planning process is now responsible for sales, customers, talent, operations, and everything else demanding attention.
Strategic work gradually gets pushed aside, not because it isn't important, but because the day-to-day demands of running the business inevitably compete for the CEO's attention. The plan loses momentum when no one is left to insist that the strategic work stays on the calendar.
Most CEOs who facilitate their own strategic planning process do it for good reasons. They know the business deeply, care about the outcome, want to save some pennies, and aren’t always convinced an outside facilitator will produce a meaningfully better outcome.
What’s easy to underestimate is how much the quality of the conversation changes when the CEO is also responsible for managing the process. The discussion often becomes less candid, the hardest decisions get softened, and priorities gradually expand instead of narrow. The team may leave the room aligned at the surface level, but without the kind of real commitment that comes from fully working through difficult decisions together.
I’ve seen firsthand how different those conversations become when someone else owns the facilitation with one clear responsibility: protecting the process so the leadership team can do its best strategic thinking. That creates space for more honest debate, sharper prioritization, and true alignment around a small number of goals the organization can realistically execute well.
The difference is not just a better offsite. It’s a tighter strategy, stronger leadership alignment, less time sitting in meetings and a much greater likelihood that the plan actually drives meaningful change in the business.
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