The Leadership Retreat with Real Substance: Building Relationships While Solving Real Problems
One of my favorite types of projects? A leadership retreat with real substance. Not just a day of team building for the sake of it, but a session that tackles the problems teams have been bumping up against all year—while also building trust, clarity, and connection.
Recently, I had the opportunity to prepare a leadership retreat for a remote-first team. The initial ask was simple: “We just want to bring people together and build connection.” But as a facilitator, I know how important it is to ask the right questions before jumping into design. I don’t just say, “Yup, leave it to me, I’ll build you the best retreat.” Instead, I engage the client to really understand the context, frustrations, and challenges that need attention.
The Power of Asking the Right Questions
In this case, asking the right questions uncovered something critical: the team was struggling with role and responsibility clarity, and they were ready for some hard conversations. Suddenly, this retreat had a purpose—a very specific problem to solve.
The clarity changed everything. Now I could design a session that had substance. We’d work on relationship building and tackle the issue that was causing friction and slowing the team down.
My Process: Designing for Meaningful Impact
Start with Pre-Engagement
Before designing the retreat, I engage the people involved to understand what success looks like for them. What would make the retreat meaningful? What do they need from this time together? This step builds psychological safety early, giving people space to share their frustrations and hopes. It also saves time—when we arrive in person, every moment is well-used.Design with Intention
With the team’s input and a clear understanding of the problem, I design the session. The focus: solving the right problem while creating opportunities for real conversation, collaboration, and connection.Collaborate with Key Leaders
I share the plan with key leaders to get feedback. This step always surfaces additional insights and deeper nuance I can use to level up the session design. It ensures the retreat is aligned with what matters most for the group.Prepare the Tools—and Myself
Preparation is everything. From the tools I’ll use to the questions I’ll ask, the work is in the prep. That way, when I show up, I can be fully present and ready to meet the group where they are.
Showing Up: Being Ready to Pivot
A well-designed retreat has a plan—but great facilitation is about knowing when to adjust. The ability to pivot in the room is essential to meet the group’s energy, uncover what’s most important, and help people feel seen, heard, and engaged in the process.
The goal:
Solve the right problem.
Build the right conversations at the right time.
Help the team leave with clarity, alignment, and momentum.
Real Substance = Real Impact
A leadership retreat can’t just feel good—it has to be good. It needs to address what’s most important for the work, the outcomes, and the people. When done well, it strengthens relationships and moves the needle on real challenges.
If your team has been spinning its wheels on a challenge, consider this: Let’s design a retreat that helps you solve the problem and connect your team more deeply. Meaningful progress doesn’t happen by accident—it happens when we pause, reflect, and engage with intention.
Ready to slow down and accelerate? Let’s talk.
