Ten Tips on How to Lead a Strategic Planning Session

Whether you’re just beginning your strategic planning or in the middle of a process, these tips can help you create the best possible plan for your organization:

how to lead a strategic planning session1. Get ready. Deciding what information you need to make meaningful decisions is the key to a successful planning process. Prepare a full picture of your current situation. This picture doesn’t have to be deep, but it should be broad. I recommend that you go outside the four walls of your organization and the tribe’s knowledge. Gather feedback from employees, clients, consumers, partners, suppliers, etc. Prepare the internal information so critical to framing strategic issues – financial and client trends, your comparative standing to other organizations that have a similar mission and/or service delivery scope. Usually, the staff and planning consultant is best suited to take the lead on gathering and preparing this information. Build a 360‐degree view that will help you determine what your organization does well and identify opportunities for the future.

2. Start meeting after you get ready. If I could change one thing about the traditional planning process, it would be when the planning committee starts the meeting. In my experience, the most effective use of a planning committee is to have an initial meeting where the timeline and planning process is reviewed and agreed upon. After you are ready (see the above paragraph), hold the planning retreat, where you get the collective input and ideas that inform the committee’s work. Then the committee meets, usually two to four times to bring the plan together.

3. Allow time for big‐picture thinking together. Many times board and staff try to squeeze the big, strategic discussions into a half‐day retreat. I get it; we’re all busy and there are plenty of tempting reasons why there is never enough time. And, it’s worth it to make the time. To create a strategic plan, you need time to digest information, bring everyone up to speed, and think big with your planning group. Whenever possible, carve out a day and a half for your kick‐off planning session. If that truly isn’t possible, another option is to use regularly scheduled team and/or board meetings to prepare everyone for a full or half‐day session. Add on an extra hour onto your regularly scheduled board meeting, or re‐structure several of your board agendas for presentations on stakeholder feedback, financial and service trends.

4. Ask the hard questions. This is easy to say, more difficult to do. Usually one of the toughest moments of a planning process is when I ask groups to not only think about what they need to stop doing but to actually commit to stop doing it. Here are some questions to think about: What are our Sacred Cows? If we were only going to do one or two things really well, what would they be? Does this organization need to exist the way it’s structured? What assumptions are we making that prevent us from seeing a different approach to better achieve our mission?

5. Concentrate on what moves the dial. Not every organization needs big, hairy audacious goals (BHAG). They sound good on paper but can be unrealistic to achieve. Instead, identify the handful of strategies that – if you courageously commit and allocate resources to – will move your organization significantly forward.

how to lead a strategic planning session washington6. Allow for open and free discussion regardless of each person’s position within the organization. It’s really tough to lead planning sessions with a facilitator from ‘the inside’ — no matter how well you think you can do it. If you can, hire an outside facilitator – someone who doesn’t have any stake in your success. This frees up the conversation and creates the space to challenge assumptions and sacred cows. It is also the best way to encourage active participation, without letting any one person dominate the session.

7. Don’t write your plan in stone. Good strategic plans are fluid, not rigid and unbending. They allow you to adapt to changes in the marketplace. Don’t be afraid to change your plan as necessary.

8. Keep it simple and clear. I favor plans that don’t get too granular. Every plan needs goals, key action steps, and accountabilities — but avoid getting in the weeds with multi‐year operational activities, deadlines and assignments. I suggest no more than a one‐year operational plan, prepared by staff, to accompany the initial strategic plan.

9. Make strategy a habit, not just a retreat. Embed a practice to work the plan and maintain a rigor around implementation. Otherwise none of it is worth doing and is a waste of everyone’s time. One way to do this is to develop a strategic agenda for your leadership meetings. This agenda leverages the strategic plan to inform your meeting agendas and plan time for review of performance achievements (I suggest quarterly and at least bi‐annually). Focus on accountability for results, lessons learned, and changes to be made.

10. Have Fun! Strategic planning is a time to build cohesion among board and staff. Leverage your planning time so that it’s also relationship time. Plan your ice breakers and team activities around your planning goals. For example, create a Did You Know Quiz based on key facts about your organization. It’s a great way to reinforce important information with board members and can help educate newer board members.

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