Ask the Right Questions for Strategic Planning Success

By Dana Gillis, Executive Coach – For the past several Fearless blog posts, we’ve focused our sights on strategic planning. The exploration started with using the power of storytelling to make your plan more compelling. Next was a roadmap of the strategic planning process, followed by a cautionary note on common strategic planning mistakes. You’ve now pulled together your team to engage in the strategic planning process … so what’s next?

Asking the right questions can help the strategic planning process be less difficult and more successful.Consultant, educator and author Peter Drucker gives a great clue in his quote, “The most serious mistakes are not being made as a result of wrong answers.  The true dangerous thing is asking the wrong question.”

In thinking about a strategic plan, the question that comes to mind is, what is a strategic plan and what does it do? A good strategic plan serves as a roadmap for allocating resources to achieve an overarching organizational vision. At a fundamental level, a strategic plan is an organizational response to a series of interconnected questions. What are our goals? What resources are needed? What’s the timeline? Who is responsible for individual actions in attaining the goal? Dr. Drucker’s cautionary statement reminds us that the answers to many basic, but essential questions are at the core of an impactful strategic plan.

The key to ensuring that your organization’s strategic plan leads to success is to ask the right questions at the beginning of the process.

Most strategic planning starts with a historical look at an organization’s most recent performance as a foundation for mapping its future course. While an important step, the successful strategic plan should be focused on “what’s next?” If innovation is an indicator of success, would it be much of a leap to claim that advancement is the result of the search for the best answers to intriguing questions? It is the question that sets the course for the best answer.

In his book, A More Beautiful Question, journalist Warren Berger writes on the, “role questioning plays in enabling people to innovate, solve problems, and move ahead in their careers and lives.” The same can be said of organizations.

The foundation for a sound strategic plan is not about asking only the most difficult questions. With a good strategic plan, you ask  the right questions.  So how do you get to the right questions? A good exercise for jump-starting the strategic planning process is to have your team look one year into your organization’s future, visualizing a bleak outcome. Have your team list everything that could have gone wrong to lead to such an unfortunate result. And now the question, “What are all the things the team/organization needs to do to avoid that undesirable consequence?”

In his book, Berger posits that better questioning leads to the success sought by leaders and organizations. Asking, Why? What if…? and How? serves as a mechanism to help leaders keep planning efforts fixed on a strategic rather than tactical focus.

The strategic planning process doesn’t have to be a difficult task. It can be an impactful exercise if you ask the right questions to get to a plan leading to success.