Climbing a hill with a friend recently offered one of those troubling moments of doubt that grows into a bigger reflection.

We are both from the North West of England, but from different corners of it. As we reached the top of the hill, the view opened up: the coastline, towns in the distance, industrial clusters on the horizon.

I spotted familiar sights – Blackpool Tower and the wide sandy beaches of Southport. To the left, we could see industrial structures. Could this be the docks of Bootle, near to Liverpool? My friend, who grew up closer to Liverpool, wasn’t so sure.

We stood there, both trying to make sense of the same scene. Each of us had some knowledge, some landmarks, but neither of us felt completely confident in judging the distance, scale, or even what we were actually looking at.

It wasn’t until we checked the map later that we confirmed: Yes, they were Bootle docks.

That moment reminded me of leadership. How often do we find ourselves in situations where we think we know the lay of the land?

We bring our experience, our past knowledge, and we make assumptions. Sometimes those assumptions are right, but sometimes the gap between perception and reality is bigger than we realize – and at times smaller.

Equally, even when you stand alongside someone with a different (and perhaps closer) perspective, they may not have full certainty either. No single view is complete.

Context matters, but so does the willingness to exercise humility: Recognizing that what looks obvious to us might be misleading, and what feels unclear to others might be a crucial clue we’ve overlooked.

In leadership, judging the “distance” – how far a project might stretch us, how difficult a transformation will be, how close or far we are from success – is rarely straightforward. Landmarks help, but they don’t always tell the whole story.

Our assumptions can anchor us, but they can also mislead.

The takeaway for me is this: Don’t rely solely on your own line of sight, even when it feels familiar. Seek multiple perspectives. Compare notes. And when in doubt, check the map. In organizational terms, that might mean data, feedback, or the voices of people on the ground.

Leadership isn’t about always knowing the answer from the top of the hill. It’s about creating enough clarity to move forward, even when certainty isn’t possible — and being willing to admit that sometimes we need to stop, look closer, and realign our view.

Without wishing to sound defensive, it was a pretty cloudy day. And just as days can be cloudy and the view vague, so can our perspective and understanding of our organizational and ecosystem be similarly challenging to discern.