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Executive Leadership Coaching

3 minute read

No More Boondoggles: The 5 Essential Elements of a Productive Leadership Retreat

Oct 2, 2019

Written by: Shawn Sweeney

When you hear the words “leadership retreat,” do you immediately think “boondoggle”?

It doesn’t have to be! In fact, it shouldn’t be. And with careful attention to the five essential elements of a productive leadership retreat, it won’t be.

I’ve attended, led, or planned dozens of leadership retreats in my career. I've seen my fair share of dos and don'ts. And I've learned a lot about the benefits of a leadership retreat — and why it's important.

Top 3 Reasons Why a Leadership Retreat Is Important

Why is it important to make a leadership retreat a priority for your leadership team? Based on my experience, here are my top 3 reasons:

  1. HEAD SPACE: A leadership retreat is a unique opportunity for your leadership team to completely detach from running the business, so they have a clear head to think about new ideas from new perspectives. (Tip: Host your retreat in new surroundings — not too close to the office!)
  2. DEEP THOUGHTS: A leadership retreat offers the dedicated time and space for your leadership team to think deeply about important topics, like long-range plans and ideas for new products.
  3. REAL CONNECTIONS: A leadership retreat creates the environment for your leadership team to build meaningful connections, strengthen relationships, and get to know each other outside the typical work environment — all of which is critical for building true trust. Trust is mission-critical to your organization — it boosts engagement, productivity, and satisfaction.

“Designed well, offsite leadership retreats can end up being transformational moments for the organization,” innovation and leadership development thought leader Robert B. Tucker recently wrote in a Forbes.com article on leadership retreats. “The best ones build trust among top team members and create greater buy-in and alignment around a common vision of the future.”

5 Essential Elements of a Productive Leadership Retreat

The most powerful retreats I’ve been part of all share these five essential elements of a productive leadership retreat. If your leadership retreat doesn’t check the box on all five, you’re at risk of ending up with a boondoggle.

  1. PLAN AHEAD — WAY AHEAD: You can’t pull together a meaningful leadership retreat by planning the week before, or by spending only an hour or two thinking about the agenda. Invest the time to think about what you really want — and need — to accomplish with your leadership team, how to design an agenda to effectively meet your goals, and who should attend or not attend. Ideally you can share the plan with the team several months ahead of time, to set expectations, be transparent, and kick-start thinking around what you’ll be focusing on during the retreat.
  2. ASSIGN PRE-WORK: If you wait until the retreat to get things rolling, you aren’t going to make the best use of your time together. Most leadership retreats are two to three days, which limits what you can truly accomplish. So you really need to be focused — and prepared. The pre-work will help the team come ready to dive into the bigger, more challenging topics. Helpful pre-work can include an assessment of the previous year’s performance, or a SWOT analysis.
  3. GET A FACILITATOR: If you try to lead your retreat yourself, you can expect sub-par performance. That’s not a knock against you at all. It’s difficult to facilitate your own group. And it’s nearly impossible to fully immerse yourself in the conversations and make valuable contributions if you’re worrying about managing the agenda and time. The right facilitator will make the difference.
  4. DON’T RUSH: It’s critical that you allow enough time and space for discussions — real discussions. This isn’t the time to try to rush through 20 topics in two days. Choose a few topics, and then spend plenty of time on both divergent and convergent thinking. If you’re coming out of a fast-paced work environment (aren’t we all?!), make time at the beginning of your time together for people to decompress and down-shift into a different gear for the retreat.
  5. WRAP UP WITH AN ACTION PLAN: Before you leave the leadership retreat, develop an action plan. Once you all walk out that door, what needs to happen next? You may have had great conversations, but if you don’t commit to doing something, all of those great ideas and a-ha moments will be lost as soon as you step foot back in the office. Commit to a detailed action plan, with specific owners and milestones, before you leave. And make it a priority to follow up on that plan at least quarterly.

Just say “no” to boondoggles. Will your next leadership retreat be transformational — or trivial? A productive leadership retreat will make a huge impact on your organization. Do your due diligence to make it worth everyone’s while and set your team up for success.

At Spinnaker, we’re the go-to resource for the real-time results you need now, and the lasting impact you depend on to strengthen your business in the future. Our expertise, agility, and first-hand business knowledge move your business forward. To find out more, connect with us today.