Planning for Planning: How to Organize a Successful Strategic Planning Retreat

Planning for Planning: How to Organize a Successful Strategic Planning Retreat

Strategic planning is the bedrock of responsible business. At its best, it allows you to diagnose your present opportunities and risks, then reach into the future to tinker with the possibilities and create a long-term roadmap for success. It involves brains and imaginations coming together in a space to formulate goals and envision the long journey toward them.

But all of that planning takes – well – planning. Organizing a strategic planning retreat is a lot like strategic planning itself. You have to reconcile present realities with future goals. You need to dream big. Furthermore, you have to take a methodical, exhaustive approach to fit all the pieces together.

Here’s how to organize a successful strategic planning retreat.

Determine the Event Logistics First, with Plenty of Lead Time

Let’s dispense with the nitty gritty first. As with any corporate event, a strategic planning retreat works best with time and consideration on its side.

Depending on the size of the retreat, you may need to earmark 40 or more hours for logistical planning. During this time, you’ll begin with an outline of event objectives, gradually moving toward specific items. A few logistical concerns to tackle are:

  • Establishing a budget
  • Choosing a date
  • Choosing a venue
  • Creating and finalizing a guest list
  • Engaging vendors and suppliers
  • Coordinating with the venue on AV, conference spaces, etc.
  • Coordinating accommodations (if applicable).

These are the basic considerations for a strategic planning retreat. However, feel free to fill in the gaps with items specific to your organization or event.

Prioritize Collaboration over Command 

There are two ways to undertake strategic planning for a retreat. You can create the strategic objectives in advance, making the retreat more about top-down communication than anything. Additionally, you can use the retreat as a launchpad for collaborating on strategic planning.

Unless your business is in crisis mode, the latter option is better. You’ve gathered diverse talent, perspectives, and specializations in one room, away from the stuffy confines of an office. Thus, you might as well leverage the opportunity to create something special.

Hire a Futurist Consultant or Keynote Speaker

Strategic planning isn’t just about looking to the quarter ahead. It should be a profoundly brave exercise in looking far into the future. To accomplish this, consider hiring a futurist.

Futurist speakers and consultants don’t just facilitate strategic planning. They foster strategic foresight. They help you imagine the countless possible futures your company may encounter. There are an innumerable combination of risks, opportunities, disruptions, and market shifts in your industry. Thus, they encourage you to create provisions for the world ahead.

According to the eminent futurist speaker Nikolas Badminton of, “Reigniting our imaginations… is as important to the discipline of strategy and foresight as any of the frameworks that we use. Reigniting our curiosity… and encouraging everyone to be open with their thoughts and feelings on multiple futures are essential to the work that we do.”Consider a futurist keynote or consultant to help spark and lead the conversation at your next planning retreat.

Have Fun

Lastly, a strategic planning retreat is still a retreat. It should function, at least secondarily, as a way for your team to blow off some steam and enjoy one another’s company.

Fun can be part of the planning process. For instance, a spirited brainstorming session with a futurist shouldn’t need to be dry. Additionally, it can absolutely be fun. But you might also plan events and activities around the work. Valuing the humanity and joy in your talented team is equally important to your overall corporate strategy as the specific action plans you walk away with.

If you’re planning a strategic planning retreat, remember these straightforward tips. Thus, you should be prepared, flexible, fun, and bold enough to imagine far into the future. If you can balance these demands, you should pull off a strategic planning retreat that bears fruit for years (possibly decades) to come.

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