7 Reasons Executive Offsites Flounder And Fail
Coauthored with Mark Nevins. Originally published April 21, 2025 on Forbes
In our collective 50 years working with leaders, we’ve designed and facilitated executive team offsites for more than 100 organizations, across almost every industry, from high-growth privately held companies to large public ones. In that time, we’ve learned a great deal about what does and doesn’t work.
The biggest lesson we've learned is that there's no formulaic way to run a successful executive team offsite. What works well in one situation can bomb in the next, even if the meeting objectives are ostensibly similar.
The reason there’s no “perfect offsite” formula, of course, is people. Executive teams are complex constellations of personalities, styles, strengths, weaknesses, goals, fears, hopes, and dreams. The best offsites accommodate all of these things without being dominated by any one of them. That means the best offsites have to be collaboratively conceived, flexibly designed, and dynamically facilitated.
Here are seven reasons why executive team offsites fail and how to address each:
1. CEO or top leader doesn’t own the meeting
An offsite is a critical tool to align a team with the leader’s agenda. While elements of meeting planning will inevitably be delegated, the team leader must take direct ownership for the entire experience. That lead executive should work closely with the designer/facilitator to define the objectives, pressure-test the agenda, and explicitly design the meeting to achieve the desired outcomes. During the offsite, the chief executive should collaborate closely with the facilitators to make sure the meeting stays on track and achieves its goals. The best offsites aren’t rote performances of an agenda; they’re thoughtful improvisations, like a jazz performance.
2. The purpose of the meeting is not clear
Every executive walking into an offsite should be clear on the intended outcomes of the meetings and the strategy for achieving them. “Build trust” or “clarify strategy” are not clear outcomes; they’re too vague and cliche to be useful. Meeting leaders need to be crystal clear about why the meeting is being held. Meetings without clear objectives invariably fail, even if the participants don’t realize it at the time. When well-intentioned leaders ask their teams to submit agenda items, the outcome is inevitably a dog’s breakfast. Every meeting should have a clear purpose and set of objectives, not just a list of topics masquerading as an agenda. The meeting objectives should be meaningful and attainable, and the group should not waste time debating or reporting on anything unrelated to these objectives.
3. Design is rushed or poorly planned
Most ineffective offsites fail in the design phase, before anyone even steps foot into the room. Short lead time is the most common cause. We receive frequent requests to design and facilitate offsites with just two or three weeks lead time. This is a glaring red flag that the work to be done is not high-priority. If the offsite is strategically significant, we recommend at least 8-12 weeks of lead time, especially for C-suite teams. As facilitators, we use this lead time to form clear objectives with the chief executive, interview all the offsite participants, and develop a current state assessment report that informs a tight design. If facilitators don’t prepare at this level, they can’t facilitate strategically.
4. Over-indexing on team dynamics to the detriment of strategy
Team dynamics play a role in effective execution, but the work of the team is to drive results, not merely act like a happy team. As many business writers have observed, artificial harmony can mask much dysfunction. The best facilitators weave strategy, execution, team dynamics, and honest assessment of the current state into the work of the offsite, all while modeling and inviting the trust and open discussion that’s essential to guiding the team through the process of making difficult strategic decisions together. Make sure your facilitator is someone the team respects as a business strategist, not just a curator of fun exercises.
5. Too many talking heads and not enough dialogue
In-person executive team time is precious. It shouldn’t be wasted on overwrought PowerPoint decks or things that don’t require a meeting. Use pre-work to get informational content on the table instead of burning through offsite time reporting out to get everyone up to speed. Set the expectation that presentations, spreadsheets, and reports will be reviewed in advance. Reserve the offsite itself for tough topics that require dialogue and debate. A skilled facilitator will manage the extroverts so they don’t take over, draw valuable input from introverts, bring the challenging questions to the fore, and help drive from insight to impact, including: “What are we going to do post-offsite to see real benefit and results?”
6. Unwillingness to change course mid-meeting if needed
Good facilitators create space for difficult conversations, which can raise issues that have previously been left unaddressed or even outright avoided. Sometimes it makes sense to table these issues and revisit them later. However, sometimes it makes more sense to dig deeper in the moment. When that happens, facilitators need to move with courage and confidence to shift the meeting plan and make room for that work immediately. Facilitators and leaders in the room should be willing to ask themselves and each other, what’s the most important thing for us to discuss right now? When the answer to that question changes during a meeting, don’t hesitate to redesign the time together right then.
7. One-and-done mentality
No single offsite should carry the burden of overcoming all the challenges that an executive team is facing. Unfortunately, we see executives approach offsites with this mentality all the time: they somehow expect that gnarly challenges created over months or years can somehow get sorted in a couple days and, presto, high-performing team. It doesn’t happen. Just like high-performing sports teams don’t declare themselves in top form after one training camp, high-performing executive teams shouldn’t do so after one offsite. Work at the offsite should be brought back onsite, advanced, and serve as the foundation for subsequent time together. A succession of well-designed meetings and offsites over time are key to a teams growth and success. The best offsites are the ones where the work, mindset, and collaboration follow the team back to the office and become the work that the team is most focused on.
Avoiding these pitfalls is essential to delivering executive team offsites that accomplish strategic objectives, clarify the path forward, and energize the team for the work ahead. When leaders partner with their offsite designers and facilitators to create a forum for real work, not just a fun get-away truly excellent things can happen.