Find Your Trailhead

If you’re a hiker, you might know that in addition to finding a trail that matches what you’re looking for, you need to know exactly where the trailhead is—otherwise you may never get a chance to enjoy that great trail you’ve discovered, and you’ll almost definitely leave frustrated instead.


Failing to make sure that you know the geo coordinates of your trailhead is an apt analogy for a fundamental mistake that lots of people make when embarking on a strategy journey. They’re armed with a mountain of research and great arguments for where they should be taking their organization, but lack an accurate understanding of where they are actually beginning. In other words, they don’t have an honest accounting of exactly where they are starting so they can make the right critical moves to get where they want to go. 

This may seem like a simple problem, perhaps a reflection of insufficient diligence during the strategic planning process. But this is not a data or information problem; it is an interpretation problem. As a leader—in whatever formal seat you may have—you need to be clear-eyed and confident about where you really are at any point in a change process, but especially at the beginning. 

So before you embark upon your strategic hike, find your trailhead. Do whatever it takes to find out exactly where you stand. Seek disconfirming information. Ask critics for input. Test assumptions. Look internally at your leadership team to ensure you really know where your capabilities are strong and weak. Unless you undertake the effort required to clarify your trailhead, you can expect to spend a lot of time wandering around in frustration.