Strategic planning retreats
A strategic planning retreat your team will actually execute.
The short answer
A strategic planning retreat takes a leadership team away to set direction for the next one to three years: where to focus, what to stop and who owns what. Most fail after the retreat, not during it: the plan is sound, but nothing changes in how the team works on Monday. Ours is built on our Planning focus area (the yearly plan, strategic direction, vision alignment), facilitated by James Carter, with every leader's one commitment reinforced for 30 days. From $35,000.
The real problem
Why most strategic plans die in the first month.
The plan usually is not the problem. Teams leave with good priorities, then return to an operating rhythm built for the old ones: the same meetings, the same reports, the same people deciding the same things. Within weeks the plan is a document.
So the retreat has two jobs: make the choices, and change the behaviors that will carry them out. We cover the second half in why leadership offsites don't stick.
Before you go
Decide these three things first.
- The one question. "If we could achieve only one thing at this retreat, what would it be?" Not five priorities. One.
- Who is in the room. Everyone who has to execute the plan, and nobody who is only there to observe. Usually 5 to 12 people.
- What everyone reads beforehand. The numbers, the customer data and a short pre-read, so the retreat is spent deciding rather than presenting.
A starting shape
A two-day strategic planning retreat agenda.
Day one: where we really are
- The one question, and what success looks like in a year
- An honest read of the business: what is working, what is not
- The choices: where to focus, where to stop
- The conversation the team has been avoiding
- Dinner, unstructured
Day two: owners and rhythm
- Three to five priorities, each with one owner
- The stop list, made explicit
- Changes to the meeting rhythm that will carry the plan
- One behavior per leader, said aloud to the team
- The 30 days of reinforcement begin
Format follows function
Strategy work alone, or strategy plus an experience?
If the team trusts each other and the issue is information and choices, a Focused retreat at a luxury venue with a ready Planning agenda is the efficient answer.
If the plan keeps stalling because the team does not trust each other, protects territory or avoids conflict, more planning will not fix it. That is when a shared experience earns its place: a remote lodge, real terrain or open water that shows the team how it actually operates under pressure, before the strategy sessions. See the formats.
"By the time US Holdings became Eagle Manufacturing Group and I moved from COO to CEO, we were no longer seven companies protecting our own territory. We were one company working toward the same outcome."
Ronn Page, former CEO, Eagle Manufacturing Group (revenue grew to $1.2B from $350M)Investment
What a strategic planning retreat costs.
All three include facilitation, venue, meals, activities and on-site coordination, exclusive of air travel. Every leader leaves with one behavior tied to the outcome. For 30 days they get a morning reminder and a 4 p.m. check-in, and the team gets a behavioral-change report at the end. That follow-through is what separates a retreat that changes how a team works from one that fades by the second Monday.
Straight answers
What is a strategic planning retreat?
A strategic planning retreat is one to three days away from the office where a leadership team sets direction for the next one to three years: priorities, what to stop, owners and the operating rhythm that will carry the plan.
How long should a strategic planning retreat be?
Two days suits most leadership teams: one to agree where the business really is and make the choices, one to assign owners and change the rhythm. Add a day when the team also needs to rebuild trust.
Who should attend a strategic planning retreat?
Everyone who must execute the plan, usually the CEO and direct reports, 5 to 12 people. Larger groups need a different design.
Do we need an outside facilitator?
If the CEO facilitates, the CEO cannot also argue a position, and the team will defer. An outside facilitator lets the whole team, the CEO included, do the work.
How much does a strategic planning retreat cost?
With Legendary Retreats, $35,000 to $50,000 for a Focused retreat built on the Planning focus area, $45,000 to $150,000 for a Signature retreat and $75,000 and up for bespoke, exclusive of air travel.
What is the difference between a strategic planning retreat and a strategy offsite?
Mostly the name. What matters is whether it ends with decisions, owners and a changed operating rhythm, or with a document. See offsite vs. executive retreat.
Keep reading
Bring the one question. We will build the retreat around it.
Fifteen minutes with James. You leave with a clear shape for the retreat: the outcome, the format and an honest range, whether or not we work together.