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Planning tips from the Cheshire Cat

In the whimsical world of Lewis Carroll's "Alice in Wonderland," Alice finds herself lost in a bewildering forest. Seeking direction, she encounters the enigmatic Cheshire Cat, whose wisdom extends far beyond his grin. Uncertain of her destination, Alice asks the cat for guidance, in response he poses a pivotal question: "Where do you want to go?" Perplexed, Alice admits she's unsure. The Cheshire Cat sagely replies, "Then it doesn't really matter, does it?"

This simple exchange carries profound implications, especially in the realm of strategic planning. Much like Alice, organizations large and small often wander aimlessly without a clear destination in mind. The Cheshire Cat's words echo the essence of strategic planning – it's not just about the journey but having a well-defined destination.

Regardless of your work setting a clear destination is key. A destination permits you and your team to define specific, measurable, achievable, relevant, and time-bound (SMART) objectives. These objectives serve as roadside markers and allow you to chart your progress. Without them, businesses risk wandering into uncertainty, where decisions lack purpose and actions lack direction.

The Cheshire Cat nudged Alice to ponder her goals, strategic planning requires organizations to envision their future. A compelling vision statement encapsulates the organization's aspirations, inspiring teams, and stakeholders alike. It paints a vivid picture of the desired destination, guiding every decision and action taken.

Strategic planning acts as the map in a wonderland of business, and asks organization to have a goal. The work involves analyzing the terrain, understanding potential obstacles, and charting the most efficient course. Without a map, businesses risk becoming like Alice, unsure of where they're headed, and as the Cheshire Cat points out, without a clear destination, the path taken becomes inconsequential.

Just as Alice embraced the challenges of Wonderland, embracing the strategic planning process may be quite daunting and I often encounter resistance. Often, it’s because they envision a lengthy planning process that takes place over days or even weeks and eats up hours of staff time. However, the truth is, some of the best strategic planning sessions I’ve attended were completed in a single day! Regardless of the process you choose, a good plan requires an honest appreciation of your organizations strengths and weaknesses, and a clear understanding of your operating environment. By acknowledging the landscape, businesses can align their resources, optimize their strengths, address their weaknesses, and move forward towards a well understood goal.

Remember, in the words of the Cheshire Cat, "If you don't know where you're going, any road will take you there."

Norm Adams is a Certified Professional Business Coach with more than 25-years business experience in both Canada and the US. This month, Norm and Dave Fuller are preparing for Pivotleader's 7th Annual Strategic Planning Day on January 10, 2024 from 10:00 am to 2:30pm. Formal promotion of this event will start in November but if you'd like to receive some information now, feel free to email Norm at


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