Last week, our team at Katahdin Group held a strategic planning offsite using our Strategic Ascent system to get our goals in place for 2026. This time we weren’t just facilitators, but participants in the process. It was a powerful reminder of what makes strategic planning both challenging and deeply rewarding. Here are a few insights gained while they are fresh in my mind.

The Power of Taking a Stand

One of the biggest takeaways was how essential it is for a CEO to take a clear point of view. Strategic planning starts with the leader laying out their vision for what the business could look like in three or five years. That means doing your homework and coming to the table ready to say, “Here’s where I think we need to go.”

This was uncomfortable for me. I was nervous about my vision for where I saw the business going. The night before we got together, I slept restlessly, alternating between concern that I was being too aggressive and concern that I was being a wimp. Had I chosen the right goals? Would my team think me smart or crazy? This team is exceptional, with a lot of experience, and I did not want to let them down.

Clearly articulating a vision requires vulnerability and a willingness to let others push around your ideas. But without that initial point of view, everyone else is left guessing. By putting a stake in the ground, the CEO gives the team something concrete to react to, test, and improve. Over our two days together, that direction was edited by people who understand the business and care deeply about its success. This alignment shifted the strategy to a shared responsibility. At the end of the second day, I felt an enormous burden lightened by the team.

The Importance of Writing It Down

Equally important is writing that point of view down. There is real power in a written artifact—whether a PowerPoint or, even better, a long-form memo. Writing forces clarity. It shows how the logic connects across time horizons, financial history, and future goals.

A verbal strategy is open to interpretation and memory. A written strategy allows critical comparison. Teams can look at a three-year direction alongside historical performance and proposed goals and decide whether the logic holds together. When everything lives in one place, people can come to the same conclusion—or challenge it productively. That shared reference point dramatically raised the quality of our conversations and the level of alignment we were able to achieve.

A System to Keep You Moving Along the Road

Strategic planning is uncomfortable because it asks leaders to commit to change and to goals that are not business as usual. That discomfort is precisely why a system matters. A good strategic planning process acts as a traffic cop, ensuring traffic keeps moving even when the day-to-day work in the business creates congestion. It also provides guardrails to avoid veering off course along the way.

Going through Strategic Ascent ourselves, I could see that structure at work. Even when we got pulled into details or competing priorities, the process kept bringing us back to the choices we had to make and the commitments we were putting on the table.

Without a system, even the strongest ideas tend to fade. With one, the organization can stay aligned and accountable long after the initial planning session ends.

Inviting the Team’s Input

Finally, the process reinforced how important it is to hear from everyone around the table. When the CEO’s written point of view is open for debate, teams engage more deeply. They see how their input shapes the strategy, which increases collaboration, ownership and commitment.

I saw that happen repeatedly over our two days together. As the team pushed on my thinking and added their own perspectives, the strategy became stronger and more complete than what I had brought in on my own.

This is also uncomfortable, because a good CEO needs to listen and may have to make commitments they were not considering making. It pushes the envelope, but I would argue that flexibility and aggressiveness together are what make good CEOs great CEOs.

Strategic planning, done well, is exhausting and uncomfortable. It is also essential. Our experience going through Strategic Ascent just as our clients do reaffirmed that clarity, vulnerability, and a disciplined system are not optional—they are the work required to build a stronger, more resilient business.

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