How to Lead a Strategic Planning Retreat

There is no substitute for getting your team (and your whole organization) working toward the same goals. A strategic planning retreat can pull everyone’s heads out of the office, so you can look at the bigger picture together.

We have learned some important lessons that make the difference between success and failure in strategic planning efforts. If you’ve already decided that you want to lead your own retreat (instead of bringing in an expert facilitator), you can increase your odds of success by paying attention to these keys.

#1: Measure your Mountain

When I lived in Africa, a massive and beautiful plateau rose 3,500 feet above us just a few miles from our home. Since I was in fairly good shape from running and riding my bike, I didn’t really need any preparation to hike up to the top. But when a friend challenged me to climb Mt. Kilimanjaro with him (19,341 feet!), I knew it would take a lot of work to get ready.

Before your strategic planning retreat, you need to measure your mountain to understand what you are trying to accomplish. Do you want to come out with a full 3-5 year Strategic Plan? A more limited Annual Plan? Or just a review and refresh of a plan you already have? Once you decide, make sure to set expectations by letting your team know exactly what you want to get done on the retreat.

Keep in mind: the bigger your mountain, the more work you need to do in advance.

#2: Assemble the right questions

A common pitfall in strategic planning is not digging deep enough to uncover the real issues. If you ask superficial questions, you will end up producing a plan that looks remarkably like what you are already doing but with bigger numbers. If you want to get past that, you’ve got to ask the right questions.

The right questions are not only difficult to answer, they can be difficult to think of. Here are a few to get you started:

Instead of…Ask…
What are our core values?

(or) Do we still like our core values?

What do our current actions say about what we actually value around here?

What actions and decisions would show that our core values are real and not just aspirational?

Do we have the right people?What do the right people look like, and how would we recognize them if they showed up?

Who do we have onboard today that we know is not aligned with our mission and values? What can we do to help them change or move on?

Are we structured correctly for success?What are our key processes, and does each of them have a clear owner who is responsible?


#3: Share responsibility for preparation with your team

Sharing responsibility is not just good leadership, it’s also smart. Let people choose areas of ownership (or make assignments). They will accomplish more preparation than you could alone, and they will be more invested in the process. That’s two big wins for you.

What areas does your team need to prepare in advance?

  1. Logistics. This includes arranging the venue, meals and snacks, materials on site (projector, easel charts or whiteboards, and markers), calendar invitations, and reminders.
  2. Research. Someone needs to collect relevant information like recent financial reports, any available market information, and the last set of written plans or goals that you have.
  3. Employee survey results. Don’t take the risk of having your wonderful new plan blown off by your employees because you didn’t consult them. A simple survey can give you a feel for what employees are seeing and raise issues for discussion at the strategic planning retreat.
  4. Agenda and schedule. You need an agenda to follow that will guide your discussion at the retreat. A schedule and a dedicated timekeeper help you stay on task and make progress. If your team knows what is on the agenda, they can prepare to discuss items in their own areas.

#4: Stay in your role

Since you have chosen to facilitate the retreat, your team needs you to stay in that role. Here is what happens when you don’t have good facilitation:

  • The group gets sidetracked and chases rabbits
  • Discussions go long and do not conclude with specific actions or decisions
  • Quiet people watch and don’t give their input
  • Loud people talk too much and dominate

Committing to the facilitator role is difficult for most CEOs or owners/presidents. You can facilitate, or you can participate, but you can’t do both at the same time. The facilitator doesn’t answer questions—he or she asks them and follows up with more questions to get the team to really think.

Once you start championing an idea, you have become a participant, and it’s hard (or impossible) to facilitate discussion of the alternatives. If you switch roles mid-retreat, your team may get confused or disengage.

“You can facilitate, or you can participate, but you can’t do both.”

A strategic planning retreat could be just what your team needs to create alignment and break through obstacles.

Have questions?   Reach out and talk to us about how you can plan and lead a successful strategic planning retreat for your team.

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