Your company is about to spend $20,000 or more on a leadership retreat. You have the venue booked, the dates on the calendar, and an agenda that looks solid on paper. The question worth asking before anyone boards a plane:
What is this retreat actually designed to produce?
A survey from MIT Sloan found that only 34% of executive teams report strong alignment on strategic priorities after their annual leadership offsite.
That means roughly 2 out of 3 leadership teams leave their retreat without the one thing it was supposed to create. Not because the people were disengaged. Because the retreat itself was planned like an event, rather than designed as a leadership intervention. After more than 20 years of facilitating leadership retreats, Mitch Simon has watched teams leave inspired and return to the same dynamics, the same unspoken tensions, the same strategic drift — not because the retreat failed, but because it was never designed to address those things in the first place.
The retreats that actually change organizations share a set of common ingredients. They are not about venue: they’re about what happens before, during, and after the room.
Ingredient 1: Outcomes Defined Before the Agenda Is Built
Most retreat agendas are built around topics. The best ones are built around outcomes.
A topic is “strategic planning.” An outcome is “every executive leaves with a shared vision they can describe in one sentence, and three commitments with owners and deadlines attached.”
One fills two days. The other changes the business.
Research on executive team effectiveness consistently shows that teams perform better when they share explicit, agreed-upon goals, not just a general direction. A retreat that opens without those outcomes named is, at best, an expensive discussion.
At Simon Leadership Alliance, our Retreat Assessment phase begins before a single agenda item is named: with a coaching call specifically designed to define what the organization needs to resolve, not just cover. The “resolve vs. discuss” distinction is critical.
Before your next retreat, ask: What does success look like 90 days from now? What needs to be resolved — not just raised — for this investment to be worth it?
Ingredient 2: Psychological Safety Established Before Anyone Arrives
The most important conversations at a leadership retreat are usually the ones that haven’t happened yet — because no one felt safe enough to start them.
Amy Edmondson’s research at Harvard identifies psychological safety as the single strongest predictor of team performance. Yet most retreats assume it exists simply because everyone showed up.
At Simon Leadership Alliance, psychological safety is built before the retreat begins: through an anonymous leadership team survey sent to every participant. The survey surfaces what people actually want, need, and won’t say out loud in a room with their CEO present.
The results shape the agenda.
In one recent retreat, Mitch sent a single pre-retreat question asking what emotional outcomes people wanted from being on the team.
Five out of six respondents said the same thing: appreciation. This aspect would never have surfaced without the survey, and changed everything about how the two days were designed.
Ingredient 3: A Facilitator Who Isn’t the CEO
When the CEO runs the retreat, the retreat runs for the CEO.
That is not a criticism; it is just physics. When the most senior person in the room is also steering the conversation, other voices self-censor. The real issues stay unspoken.
Research on group dynamics consistently shows that hierarchy suppresses candor even when leaders explicitly invite it.
An outside facilitator creates what the CEO cannot: an equal playing field. At SLA, facilitators are specifically trained to encourage open communication, navigate tough conversations, and keep the team on topic without the positional authority that distorts the discussion. The CEO becomes a participant — which is often where their best thinking happens anyway.
Ingredient 4: Candid Conversations by Design, Not by Accident
After 20 years of facilitating leadership retreats, Mitch Simon has found one theme at the core of every breakthrough retreat: CARE. What do leaders actually care about? What gets in the way of it? And is the team having those conversations — or carefully avoiding them?
Candor doesn’t happen because you asked for it. It happens because the retreat was structured to make it safer to tell the truth than to stay comfortable. That means building in the right questions, the right sequence, and a facilitator skilled enough to hold the room when the real issues surface.
The teams that get the most from a retreat are not the ones with the best agenda. They are the ones willing to have the conversation they’ve been postponing.
Ingredient 5: Decisions With Owners and Deadlines
Inspiration without commitment is just a good day out of the office.
McKinsey research on strategy execution consistently finds that the gap between strategy and results is almost never a knowledge problem. It’s an ownership problem. Someone needs to own each decision, with a deadline or specific objective attached, before the room empties.
At Simon Leadership Alliance, every retreat concludes with a written strategy document: vision, objectives, commitments, tasks, deadlines, and named accountable people. Not a recap. A contract the team made with itself.
Ingredient 6: A Follow-Through Plan within 90 Days
The retreat is not the goal. What happens in the 90 days after it is.
Behavioral research is unambiguous: without deliberate follow-through structures, new behaviors and commitments revert to baseline within 2-4 weeks — regardless of how energizing the retreat felt. The post-retreat period is where most executive offsites quietly fail.
SLA builds follow-through into the retreat design itself, not as an afterthought. In a team retreat case study, 100% of participants were still committed to their retreat commitments when surveyed one week later. That kind of accountability doesn’t happen by accident. It happens because the retreat was designed, from the start, to produce it.
Want the full framework?
The Leadership Retreat Playbook is now available on Amazon: a practical guide for CEOs, HR leaders, and facilitators who want their retreats to produce outcomes.
Get the Retreat Playbook Here ›A Venue Sets the Stage. A Facilitator Creates the Outcome.
The ingredients above are not complicated. But they require someone to design for them: before the first flight is booked, before the agenda is built, and long after the last session ends. The organizations that get the most from their retreats are the ones invested in making sure it was designed to change something — not those who found the best venue.
And yet environment itself does matter. Getting a leadership team out of their building, their city, and their routine is an ingredient, too. It shifts the conversation before anyone says a word.
San Diego is where Simon Leadership Alliance calls home, and our setting supports the work. If you’re planning an executive retreat and want it to produce real alignment, honest conversations, and commitments that hold 90 days later, we’ve spent two decades designing exactly that.
Schedule a complimentary retreat planning call or learn more about our approach:
→ Book a Retreat Planning Call
→ Get the Leadership Retreat Playbook on Amazon
