5 Tips for Better Strategic Planning Sessions

Spencer Harris, Director of Operations at Mostly Serious explains what it takes to improve a company's strategic planning session and how to re-engage participants.

By guest blogger Spencer Harris, Ph.D

May 03 2018 at 1:12 p.m.

Strategic planning sessions are the organizational double-edged sword. Done properly, the discussions can set a clear path for success and energize your team. Most employees, though, loathe even the idea of long meetings, and many planning sessions often devolve into competitive silence, with participants trying to be more quiet than their peers. These sessions, then, warrant special consideration and preparation. After facilitating and participating in nearly 50 of these types of discussions in the last three years, I’ve developed a list of five elements that make for the best strategic planning sessions.  

1. Prepare and share a detailed agenda in advance. 

The best strategy sessions start well before the discussion actually begins. In order to generate effective conversations, provide an agenda well in advance of the meeting that clearly identifies the topics for discussion, any pre-work or research that participants need to do in preparation, and the structure of the conversation. Be sure to build in time for breaks and, if possible, list the ideal outcomes for the day so that participants understand the goals of the session.

2. Use a “Parking Lot.”

Providing an agenda for a structured conversation is only half the battle. The other half is maintaining that structure (and, importantly, knowing when to shed it). One common obstacle to staying on schedule is the rabbit hole, a discussion (germane or otherwise) that sends participants down a winding path of possibilities with little end in sight. To guard against the ever-present risk of the rabbit hole, try implementing a “Parking Lot,” a hypothetical space to capture issues that require follow-up but warrant time outside of the current session. Then, at the conclusion of your discussion, schedule a time to follow up on Parking Lot items. 

3. Start with big picture items, but end with specific details. 

Often, the most difficult part of a strategy discussion is determining how to choose between any of the paths your organization could take. After all, in a conversation about the future, nearly everything could be the best idea. One method for giving participants a way to evaluate competing suggestions is to start the session by generating longer-term big picture goals for the company. Starting with the end in mind (he said, consulting his copy of 7 Habits) provides clarity on what the organization should achieve. All future suggestions, then, can be filtered through a simple question, “Which of these approaches is most likely to help us get to that end goal?”

But, don’t stop there. Once you’ve identified which plans are best, create manageable goals for the next year (with tangible outcomes and metrics for success), and develop 90-day action items that will move you down that path. Finally, before you leave that conversation, identify which team member is accountable for ensuring that each of those yearly goals and 90-day action items gets implemented. 

4. Create clarity by illustrating the conversation.

Good strategic planning sessions necessarily require participants to engage some ambiguity. The future is, by definition, undefined. Therefore, creating clarity in the conversation is critical. To accomplish this, help participants visualize the discussion by illustrating as much as possible. Write on whiteboards and use flip charts or those obnoxiously large sticky easel pads. Draw pictures, make lists, use different colors to distinguish between “big picture items,” short-term goals, and SWOT items. Creating a visual “map” of the conversation can be as important as the substance of the discussion.

5. Get up, move around, and interact.

Planning sessions are, typically, longer affairs. Most are at least three hours, and many are full day (if not multiple day) sessions. And, participants’ energy often reflect the effects of such duration. Many people start the day with unbridled enthusiasm but, by the midway point, are comfortable (if not restless), and beginning to mentally check out. Scheduled breaks are useful, but are not the only method for manufacturing energy. 

One way to re-engage participants and restore energy to the conversation is to have people get out of their chairs and move as part of the structured discussion. For example, after generating a list of “Strengths” during the SWOT portion of the session, encourage participants to take a moment and identify the top three strengths from that conversation. Then, give them each a different color writing utensil and ask them to get up and mark their choices on the larger list. This breaks the lull of sitting in a chair, and can create a meaningful discussion if the participants have wildly different perceptions of the organization’s most significant strengths. 

Remember, the best planning sessions don’t rely exclusively on the conversation in the room. Rather, they begin long before people walk into the room with an agenda, emphasize structure and facilitation tools to move the conversation forward, and require participants to think big and move around. Use these 5 tips to make your planning sessions the best part of your year, not your team’s least favorite day. 

Spencer Harris (Ph.D) is the Director of Operations at Mostly Serious, an agency that specializes in strategy, digital products, and online marketing. You can learn more about Mostly Serious on Twitter, Facebook, Instagram, or by visiting