Our Recipe for a Successful Strategic Leadership Offsite

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Taking time to pause and bring your team together is important and it’s also a huge investment that requires deliberate design and planning, especially now with the complexities of the pandemic. We’ve spent more than 20 years helping leaders and teams come together to create clarity and alignment, evolve strategy, drive execution, and catapult performance. Through our work with organizations large and small, facing many different opportunities and challenges, we have learned what matters most to ensure these events are highly productive and accelerate growth, whether it’s a C-team offsite, top 100 leader meeting, or whole organization summit.

The 3 essential ingredients critical to a successful leadership offsite

We’ve come to realize that the following three essential ingredients are critical to a successful leadership offsite. While the proportion of these ingredients may vary, the recipe always includes all three components.

Strategy

Almost always, the purpose of a leadership summit or offsite is to dig into questions of strategy. Sometimes it’s about revisiting the strategy, other times it’s about getting people aligned behind it, often it’s about getting clear on execution priorities within it. Regardless, it should always be about getting people engaged so they have an emotional connection to the strategy and a personal sense of accountability to execute it. It’s often said that a good strategy brilliantly executed is better than a great strategy poorly executed. With that premise in mind, dialogues should focus on making sure people are committed to execution excellence and that they understand how their work, priorities, choices, and goals connect to the broader business vision and strategy.

At some level, this requires a bit of top-down and bottom-up work. It’s not terribly inspiring to roll out a fully baked strategy in PowerPoint to a room full of leaders and just ask them to support it. Nor is it a great idea to ask a group of leaders where the organization should go and how it should get there without context or guidelines. The best of these meetings relies on something more in the middle. We often recommend that the senior team offer high-level direction and set guardrails, but leave it up to next-level leaders to answer execution questions in support of the high-level strategy. This ensures that the execution path is realistic. There are lots of tools and techniques for doing this kind of work and all of them focus on ensuring the quality of dialogue is high – this way, all voices are heard and people bring their best collective thinking to the process. Sometimes this is done through business simulations, other times Q&A, and often through actual planning using tools like design thinking.  The key is using an approach that both meets the needs of the audience and is appropriate for the kind of strategy you are pursuing. In all cases, it should be a set of dialogues, not a set of presentations. The value of having people face to face is the value of the conversation.

Relationship

In many organizations, leaders are geographically dispersed or primarily oriented to working with their own functional teams.  Rarely do they have the time to connect and get to know one another. Giving leaders the opportunity to do this, should always be a priority in these kinds of meetings. Collaboration and teamwork don’t happen by accident. People need to be connected to one another and feel comfortable in dialogue and debate with each other. All too often, we see that companies pack the agenda for leadership offsites so full that people barely have time to breathe, let alone talk. When there are breaks people go straight to their phones to catch up on email instead of talking with each other. We’ve seen 3-day events where people only connect with people they already know and then only briefly – and that’s an opportunity lost. We recommend that the breaks are long and that the design supports people talking, engaging, and meeting with one another. Often, that means people sitting in cross-functional teams or cross geography groups. Other times, that means the agenda includes dialogues to ensure people collaborate with people they don’t normally interact with. When relationship building is an intentional part of the design, people leave not only feeling connected to the strategy but also connected to each other and that makes all the difference.

Development

When you have a group of leaders together, it’s a unique opportunity to provide them with leadership skills, insights, and distinctions that will help them execute the strategy that’s being defined and/or planned. Almost all strategies will require something new or different from leaders. As it’s often said, “we can’t behave the way we did in the past and expect radically different results.” Meetings of this kind are a terrific opportunity for leaders to sit in the question of:

– What will this require of me and my team?

– How do I need to evolve as a leader?

– What new skills will I need?

– What new mindsets and orientations will I need?

When the offsite content supports the answering of these questions and is integrated with strategy and relationship dialogues, then the meeting is complete. Even more importantly, when development occurs in a strategic context with other leaders, it’s an incredible opportunity for peer-to-peer learning and for leaders to contextualize their development within the strategy, leading to richer learning and more actionable insights.

The best summit simultaneously enables leaders to get deeply connected to the future path, each other, and their own development journeys.  When that occurs, brilliant execution follows and magic happens.  The feedback we hear about a meeting designed and delivered using the above recipe often sounds like this: “I have been to many executive offsites and this was by far best meeting of its type I have ever experienced. Trium is a cut above…this was transformational for our business and for me as a leader.”

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