Strategic planning works better when everyone in the room can actually participate
I wrote a version of this post years ago, and after facilitating a lot more strategic planning sessions since then, I still believe the basic premise:
If your organization is going to invest the time to think seriously about its future, having someone from outside the organization lead the conversation can make a big difference.
Could you facilitate your own strategic planning process? Of course.
But there are some very good reasons not to.
1. Everyone gets to participate
This may be the simplest reason, but it is one of the most important.
If you are the CEO, Executive Director, Board Chair, or another organizational leader, you probably have thoughts about where the organization should go. You should be able to contribute those thoughts.
It is really difficult to fully participate in a conversation while also watching the clock, managing the agenda, making sure everyone is heard, redirecting the person who has been talking for 12 minutes, and figuring out what question needs to come next.
You can facilitate or you can fully participate.
Doing both well is hard.
2. Someone is responsible for the process
A good strategic planning facilitator is thinking about more than what question comes next.
They are looking at the entire process: what needs to happen before the session, what information people need, how the conversation should flow, where decisions need to be made, and what needs to happen afterward.
There is a reason I do not walk into a strategic planning session and simply ask, “So, where do you want to be in five years?”
The questions, exercises, pacing, and preparation should all be designed around what the organization actually needs to figure out.
3. An outsider can ask the questions insiders sometimes cannot
Every organization has assumptions.
“We have always done it this way.”
“That program is too important to change.”
“We tried that once.”
“That will never get Board support.”
An outside facilitator does not have the same history with those statements. That gives them permission to ask questions that may seem incredibly basic or occasionally even a little annoying.
Why?
What would happen if you stopped doing that?
Is this still a priority?
What problem are we actually trying to solve?
Sometimes the most useful question in a strategic planning session is the one everyone inside the organization stopped asking years ago.
4. The facilitator does not need a particular answer
I have opinions. Every facilitator does.
But my job in a strategic planning process is not to get the organization to adopt my strategy.
The Board and staff are the ones who have to live with the decisions.
That independence matters, particularly when there are strong personalities in the room, competing priorities, or some history behind the issues being discussed. A facilitator can push the conversation, test assumptions, make sure quieter voices are heard, and help the group work through disagreement without needing one particular idea to win.
5. It creates space to actually focus on strategy
We are all busy.
That means it is incredibly easy for a strategic planning conversation to become another Board meeting. You spend 20 minutes talking about an upcoming event, somebody raises a budget question, someone else remembers an operational issue that needs attention, and suddenly half the session is gone.
An outside facilitator can keep pulling the group back to the purpose of the conversation.
What are we trying to accomplish?
What choices need to be made?
What matters most over the next few years?
Not every good idea belongs in the strategic plan. Part of the work is figuring out what actually does.
6. The goal is progress, not just a good conversation
I love a good strategic conversation. But everyone leaving the room saying, “That was a really great discussion,” is not enough.
Something needs to happen because you had it.
A good facilitator helps move a group from ideas to choices, from choices to priorities, and eventually from priorities to action.
That does not mean every question gets resolved in one retreat. Strategic planning is a process, not a six-hour meeting.
But you should leave the process clearer about where you are going, what matters most, and what happens next.
The Bottom Line: You should be part of the conversation
Ultimately, that may be the biggest reason I recommend bringing in someone from the outside.
Your Board Chair should be thinking strategically, not worrying about facilitating the next exercise. Your CEO should be able to offer perspective rather than spending the day managing the room. Board members and staff should be able to challenge ideas, ask questions, disagree, and think.
Let someone else worry about the process.
That is what the facilitator is there to do.
And if your organization is beginning a strategic planning process, planning a Board retreat, or simply trying to figure out what comes next, I’m here to help. These are some of my favorite conversations to facilitate, especially when an organization has plenty of ideas and needs help turning them into a clearer direction.