Why I stopped believing that the best thing I could give my clients was another strategic planning retreat.
The pattern I couldn’t ignore.
For years, organizations hired me to facilitate strategic planning. They flew me across the country, brought their people together, and paid me well to help them understand their situation, choose a direction, and decide what to do next. Some invited me back every year—sometimes more often.
From a consulting-business perspective, repeat clients are wonderful. But eventually I began to feel uneasy about what those repeat engagements revealed.
My clients were relying on me to do something I believed they could learn to do themselves.
They weren’t lacking intelligence, commitment, or knowledge of their organizations. Often they understood their own work far better than I ever could. What they lacked was a reliable way to help their people think together, make consequential decisions, and adapt when circumstances changed.
And I was being paid to supply that capacity temporarily, rather than help them develop it permanently.
The advantage of being on the inside.
Much of my consulting work was with National Park Service leaders and teams. After working with so many of them, I knew their language, acronyms, procedures, constraints, and recurring challenges. That familiarity made me a far more effective facilitator. I didn’t have to spend the first part of an engagement learning what everyone meant or how their world worked.
But it also taught me something larger: context matters. A great deal.
The people who work inside an organization know its history, relationships, unspoken tensions, responsibilities, and daily realities. They notice things an occasional visitor may never see. If they also know how to facilitate collective inquiry, direction-setting, decisions, and learning, they may be better positioned to help their organization navigate than even a highly skilled outsider.
I knew this from the other side, too. I had navigated consequential change as an employee, in nonprofits and businesses, and as a business owner. The hard work doesn’t happen only when everyone gathers in a room to write a plan. It happens in the weeks and months afterward, when reality answers back.
A retreat is an event. A crossing is lived.
A good retreat can be useful. It can create space to think, bring perspectives together, and make decisions. A good strategic plan can be useful, too. But neither one is the same thing as an organization’s ability to navigate consequential change.
Conditions shift. New information appears. People disagree. An opportunity emerges that no one anticipated. A decision that looked sound in February needs reconsideration in June.
If every significant turn requires calling the facilitator back, what capacity has the organization actually gained?
The question isn’t whether an outside facilitator can help produce a plan. It’s whether the people who must live with the consequences can keep finding their way once that facilitator leaves.
“We need someone to manage the personalities”
I’ve also heard another familiar reason for bringing in an outsider: “We need someone who can manage the personalities.” I understand the concern. Groups can be difficult. Strategic conversations touch resources, identity, influence, and uncertainty; people naturally protect what matters to them.
But too often, what gets called a personality problem is a problem of process and working agreements. Who has a voice? What decision are we actually making? How do we distinguish exploration from commitment? What happens when someone dominates, withdraws, or breaks an agreement?
Facilitators learn to provide structure for the group and boundaries for participation. Leaders can learn those skills, too. In fact, I think they should. They need them long after the retreat ends.
There are exceptions. Severe conflict, compromised trust, power imbalances, or a need for genuine independence may make an outside facilitator or mediator the responsible choice. But hiring someone to hold the boundaries we are unwilling to hold ourselves doesn’t make that leadership responsibility disappear.
Outside help can be valuable. Dependence is a different matter.
I’m not arguing that organizations should never hire consultants. Specialized expertise, an independent assessment, mediation, or temporary capacity can be exactly what a situation requires. I know brilliant facilitators whose work makes a real difference.
What I question is the default assumption that leading a consequential process must be outsourced—and that a successful engagement is one that ends with a polished deliverable.
What if we measured success differently? What if the organization emerged not only with direction, but with people more capable of noticing change, asking better questions, making decisions, coordinating action, and learning together?
A different kind of investment.
This is the thinking behind Trailbreaker at Wayfinding School. Rather than hiring someone to lead your people through one planning event, you learn to facilitate a consequential crossing with your actual people, through actual decisions, while developing the collective’s capacity to navigate together.
You don’t need to know the whole way. You need to know how to help your people find their way.
Before you commission the next retreat or strategic planning engagement, I’d ask one question: Are we purchasing help for this moment—or developing the capacity we’ll need for what comes next?
Want to think that decision through?
Download Before You Hire a Facilitator: A Decision Guide for Leaders Facing Consequential Change. It will help you distinguish the kinds of support you may need, examine the capacity your people already have, and decide what should remain in-house. [INSERT EMAIL SIGNUP / DOWNLOAD LINK]
If you’re ready to explore developing that capacity while advancing a real crossing, learn about Trailbreaker.