What Makes a Great Executive Retreat

After a two-year hiatus, the annual executive retreat is making a comeback. In theory, the CEO gathers company executives off-site to focus on strategy, and the team returns with clear goals and a sense of camaraderie. In reality, wall-to-wall PowerPoint presentations are often the order of the day. Information flows in one direction, followed by improvised, open-mic Q&As. Executives fight for their individual fiefdoms. Teamwork is often notable by its absence. The ultimate output is a list of ambiguous messages that are scarcely actionable and rarely followed up. In short, retreats are often an expensive waste of time. The author presents a more creative approach CEOs can take to make the most of this annual opportunity with their executive teams.

The executive retreat, a well-established corporate staple, is making a comeback after more than two years of virtual gatherings. The traditional format is simple: The CEO takes the company’s executive leaders away from the office for a day or two of debate and strategic contemplation. The team returns with a clear idea of ​​what they’re doing and a renewed sense of working as a team with their colleagues.

That’s the theory. In practice, wall-to-wall PowerPoint presentations are often the order of the day. Information flows in one direction, followed by improvised, open-mic Q&As. Executives fight for their individual fiefdoms. Teamwork is often notable by its absence. The ultimate output is a list of ambiguous messages that are scarcely actionable and rarely followed up. In short, retreats are often an expensive waste of time.

Based on my decade of experience designing and facilitating strategy retreats in small and large companies around the world, there’s a more creative approach CEOs can take to make the most of this annual opportunity with their executive teams.

A Reimagined Format

One of the first retreats I ran was for a 5,000-person telecommunications company we’ll call TelCo. The CEO had the novel idea of ​​challenging the team of 25 executives by changing the traditional format. Out went the endless presentations. The CEO renamed the internal annual meeting “TelCo Investor Day.”

The executives were expected to pitch their strategies and plans for the next three years as if they were in front of a group of challenging investors. To support this role-play exercise, the CEO prepared a set of questions that were unusual for the annual internal retreat, such as:

  • What type of player do you want to be in three years?
  • What’s your execution plan to get to your objectives?
  • Which are your differentiating factors that make you think that you’ll be able to win the market?
  • We’re a utility and have never built anything like this before. What are you doing to be credible in this business?
  • It’s important to communicate that we’re serious about sustainability. How credible is your ESG story? How do you plan to bring it to life?
  • To sum up, what’s your sustainable business strategy in 50 words?

The CEO didn’t share the questions with the executives in advance. Instead, two weeks before TelCo Investor Day, executives were informed that they had to prepare a 10-minute pitch about their three-year strategy — and PowerPoint slides were out. I met with each executive twice, the first time for a high-level briefing, the second time for rehearsal.

At the retreat, the role-play exercise turned out to be particularly effective. It is truly engaged the audience. For the first time in our consulting experience, a colleague and I participated in a two-day strategy plan meeting where executives were the leaders, actively contributing to the discussion and not checking their emails. They were eager to challenge themselves in a constructive way. As one executive commented, “Retreats have been traditionally the only time in the year we got together and saw one another. This is the first time we are connecting in a more constructive way. Also, I feel I have a clearer understanding of the strategic goals and ambition of my peers and how we can collaborate better together.”

The format offered the executives the opportunity to change their perspectives and adopt an investor view. It put them in the shoes of external people who were not emotionally attached to the company and its individual businesses. This allowed a free flow of questions and information, which sets the basis for a fair, open, and constructive feedback exchange. Each executive had to fight hard to convince the CEO and their peers — who were playing the investors’ role — about the value creation proposition and soundness of their proposed business strategy.

Three Lessons for a Successful Executive Retreat

As we debriefed with the CEO after the retreat, we identified three lessons for making this one-of-a-kind retreat a repeatable routine in the future:

Turn the audience into the facilitators.

Executives aren’t there just to attend a meeting they’ve been invited to — they need to be actively engaged throughout the retreat. When creating the event agenda, don’t over-plan. To get the most out of the time and keep the executives involved, leave enough time for a real exchange of ideas and meaningful strategy conversations.

Once the retreat is over, it’s common for executive teams to be secretive about their time away. But they should be reporting both positive and negative feedback back to their teams. Encourage executives to make it a regular practice to share a one-page memo, not a deck, with employees. Who better to build on the feedback than your own direct reports, who are the ones helping you make your strategy and investor pitch real?

Help executives prepare and rehearse.

You can’t improvise meaningful discussions. A successful retreat is not a jamming session. Give executives the time and support to prepare and practice how to deliver their investor pitches quickly, on the spot, and under pressure. Help them empathize with a broader set of stakeholders by thinking outside the roster of their usual suspects. Ask unexpected questions about employee value (engagement, DEI, wellbeing, and so on) or social value (external and regulatory relations, human rights impact, carbon footprint, and more) of their strategy. The pitch is an invaluable opportunity to exercise executives’ storytelling muscles while fostering a more transparent and open approach to strategy formulation.

Encourage candid strategy discussions.

While companies understand the importance of encouraging a culture of psychological safety, very few executives want to or are able to make themselves vulnerable — especially at the annual strategy offsite. This retreat is a good example of how executives can practice honest, constructive feedback in the moment, while also communicating empathy. At the event, make sure that a few “be candid with care” rules are clear to all participants in the room. To start building your checklist, here are four rules that have proven particularly effective for explaining what candor means at retreats:

  • Express your disagreement in a healthy way. It’s not about being nice; it’s about being frank and respectful.
  • Be open to challenging questions.
  • It’s not about you. It’s about having learning-oriented conversations.
  • It’s okay not to have all the answers.

The most important takeaway is that even the most traditional, deeply rooted practices in large organizations can be innovated — especially those that you might think cannot be changed because it’s the way things have always been done. Sometimes great strategy needs a bit of creativity.

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