Get the Most out of Your Strategic Planning Sessions

There’s a saying that you’re only as good as your last idea. This is especially true in business, as the best companies continually innovate their operations, offerings, brand, and view of the world. Most companies, therefore, follow some cadence for strategic planning/visioning, with leaders meeting quarterly or semi-annually to discuss the business, team, issues, opportunities, and ideas. 

The very best companies will even consider how they can innovate their planning and visioning process and sessions. 

At Gitwit, we lead 100+ stakeholder sessions each year, from strategic planning workshops to discovery sessions for new venture creations and kickoffs for new initiatives/projects. It is our job to intentionally design and lead these sessions to: 

• Break open new perspectives and ways of thinking 
• Push aside group think and business jargon
• Encourage dialogue and healthy argument
• Generate buy-in by involving stakeholders in the decision-making process 
• Provide clarity and kick-start momentum

We know that the success of a session depends upon four things: 

1. The expectations that you set for the session 
2. The questions that you ask 
3. How you ask the questions 
4. And who asks the questions 

Numbers 3 and 4 have the largest impact on the participation and answers that you elicit from stakeholders, and they are the difference between a good strategic session and a year-changing one. 

We’ve linked a deck with ideas for framing your next session and example exercises to include. But first, dive into our top two areas for creating challenging, productive, and fun sessions.

‍The Art of Question-Asking

This isn’t groundbreaking. We all know that how we ask a question changes the answers we get. 

Consider, as a basic example, asking someone about their favorite meal. You could go with a simple “What’s your favorite food?” or ask differently: “What is the most special meal you have ever had?”

In a business context, we could ask, “What are your goals for the product launch?” or prompt, “Imagine that it’s six months from now. The product launch has been successful. What headline would the New York Times write about it?” The latter typically gets people thinking much more big-picture and aspirationally than when trying to craft good “business goals.”

The instructions for how someone answers the questions also matter. Answers differ if you ask people to write down responses and share them individually rather than discuss them as a group or if you have everyone working in a collaborative document where they can see what others are typing rather than writing answers down on physical stickies.

Once we decide what we need and want to cover during a planning/visioning session, we spend a good amount of time brainstorming the different ways to ask the questions. Often, we intentionally include multiple exercises around the same question in different ways to elicit different responses or angles and use multiple formats (written, aloud, etc.) for answering questions in the same session.

Small frame shifts can yield big rewards in terms of the discussion and ideas that emerge from a session.

‍The Influence of the Inquisitor

The reality is that the person who asks you the question also influences your response. Imagine a friend asking you how fast you were driving. Now, imagine a police officer. The same goes in a business setting — team dynamics, power dynamics, reputation, etc., are at play. 

Sometimes, having an outside facilitator is reason enough for a team to hire Gitwit to lead planning sessions. If you are conducting your sessions internally, consider the effect of your session leader. Do you want a neutral facilitator who will not have an opinion on the decisions and outcomes of the conversation? Do you want a leader to help orient the group toward a specific focus? Do you want the facilitator to participate or simply facilitate? 

You could take the same session game plan and have two different facilitators use it with the same participants, likely having vastly different experiences/outcomes. 

‍Maximize Value from Time 

Strategic planning and vision sessions usually require the time of some of the most in-demand people inside your organization. A great session can shift the perception that this type of planning is a responsibility to an inspiration for the rest of their responsibilities. 

Getting people out of their comfort zone is key, and creating opportunities for frame-breaking thought and discussion/dissent is crucial. Ultimately, this type of session increases buy-in amongst stakeholders, because they feel that they have been a part of an important conversation, whether they agree with the direction or not. 

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