Strategy consulting in Wonderland = Asking the right questions


This past year, I worked with a nonprofit organization to develop a strategic plan, and as part of the process, we at Wellspring Consulting facilitated a full-day retreat, bringing together key Board and staff members who were committed to the organization’s future. The President of the organization was a master storyteller. His reputation for exceptional tale-telling and side-splitting punchlines was known by all in his field. During the retreat, the President recounted a story that I had heard many times before, but within this context, I was able to hear it in a new way. Now, his gem of wisdom allows me to explain what outstanding strategy consulting is.

When introducing Wellspring at the Board retreat, the President started with a passage from Lewis Carroll’s Alice in Wonderland. [see here] At this point in the story, Alice has entered the woods and arrives at a fork in the road. She looks around to see if there are any clues as to where the paths might lead and is suddenly startled to see the Cheshire Cat sitting on the bough of a tree.

"Would you tell me, please, which way I ought to go from here?"

"That depends a good deal on where you want to get to," said the CheshireCat.

"I don’t much care where…" said Alice.

"Then it doesn’t matter which way you go," said the Cat.

“And this,” declared the President of the organization, “is why we have Wellspring with us.”

As the story unfolds, we see that the Cheshire Cat’s role in guiding Alice on her adventures was to pose the right questions. From the vantage point of his perch up in the tree, the Cat could see the landscape of Wonderland and could watch Alice traverse the terrain. At each vexing crossing, the Cat would pop into the scene to push her thinking again and again. As her guide, he enabled Alice to navigate her way through Wonderland by posing the right questions to elucidate the right insights. Though seemingly disorienting at times, his astute, logical line of questioning brought Alice through a process by probing further and further, allowing her capital-T Truth to rise to the surface, until Wonderland began to make sense to her.

This is what outstanding strategy consulting is. Excellent strategic planning entails asking the right questions, which in turn requires strong skills in logic, in analytics and in “organizational therapy,” the term I use to describe the process of reflecting on what is seen from an objective outsider’s perspective.

The Cheshire Cat’s extraordinarily talent in bringing Alice through a process by posing the right questions is no surprise given Lewis Carroll’s expertise as a mathematician, logician and teacher. Carroll understood how asking simple, mindless questions lead to simple, mindless answers, whereas asking great questions can invoke great answers and, in turn, lead to great decisions.

Pushing your thinking until the vision for where you want to go becomes clear is the power of outstanding strategic consulting. At its core, strategic consulting is about asking the right questions – ones that are nuanced and thoughtful – in order to make the right decisions. Through this process of questioning, a shared understanding among organizations’ leadership unfolds, and like Alice with her eventual new-found orientation, you can get to where you want to go.