Why the Cheshire Cat Is a Better Strategist Than Most Leaders

I don’t know about you, but there are seasons in my life when I get so wrapped up in, well, wrapping up projects, that I don’t think about what comes next, much less what’s coming in the next quarter or year. It’s so easy to get caught in the immediate day-to-day work that I forget to look at the overall direction I’m taking.

This reminds me of a passage from Alice in Wonderland that perfectly captures the importance of direction. When Alice asks the Cheshire Cat which way she ought to go, he replies, “That depends a good deal on where you want to get to.” When Alice says she doesn’t much care where, the Cat answers, “Then it doesn’t much matter which way you go.”

This is whimsical and clever. It’s also a brutal leadership lesson.

If we don't know where we're going, any road will get us there—and we’ll waste time, energy, and resources along the way.

Consider this your friendly reminder that the primary job of any leader is to set the destination for your team and then work together to get there. This requires intentional pauses. It requires leaders who lift their heads long enough to scan the horizon and say, “Here’s where we’re going.”

If you want to move beyond short-term work, here are some ideas to consider.

• Revisit priorities regularly. Strategy isn’t static—schedule time to reassess what deserves focus as conditions change. This can feel wildly indulgent when everyone else is “so busy.” Strategic thinking can look suspiciously like staring at a wall with a notebook. Resist the urge to apologize for it.

• Identify future risks. Look beyond today’s challenges to anticipate trends, constraints, or changes that could impact your organization.

• Align daily work with strategy. Ensure routine tasks and projects clearly support your long-term goals.

The Cheshire Cat was right. Direction matters. Where are you headed today—and tomorrow?