Most CEOs I talk to have tried to run their own strategic planning process at some point. And mosts of them came away frustrated, not because they and their team wasn't capable, but because the work itself is harder than it looks from the outside.
For years, I ran strategic planning myself without a real system. And I've now gone through Strategic Ascent as the CEO of Katahdin Group, going through the same process we put our clients through. The experience reaffirmed something I had only half understood before: the parts of strategic planning that are hardest to get right are rarely the parts that look hard from the outside.
Here are the five challenges I've seen consistently get in the way when CEOs run the process on their own.
Strategic planning is the one meeting a 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, 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 the CEO, I could finally just be in the conversation.
When there's no proven structure, leadership teams spend a meaningful chunk of the offsite arguing about how to plan rather than what to plan. What should we cover first? How many goals are we trying to set? Why are we using this template?
That conversation isn't wasted, exactly. But it's the wrong conversation. The team's energy should be going into the strategy itself, not the scaffolding around it.
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 to make it stronger.
The offsite ends, the team goes back to their day jobs, and operational urgency takes over. Without someone outside the company protecting the cadence, the regular strategy days slip, the scorecard stops getting attention, and the plan quietly turns into the binder on the shelf.
This is the single most common failure I see. The plan doesn't die at the offsite. It dies in month three, when no one is left to insist that the strategic work stays on the calendar.
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.
Most CEOs who facilitate their own strategic planning process do it for good reasons. They know the business deeply, care about the outcome, want the team aligned around where the company is headed, 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, and a much greater likelihood that the plan actually drives meaningful change in the business.
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