Who is sharpening your thinking?
How challenge slowly disappears
Who is sharpening your thinking? Not just disagreeing for the sake of it, but provoking you to see new solutions, question untested assumptions, or see the problems you haven't even spotted yet.
I spoke to a CEO last week who realised, at the end of our conversation, that I had provided a level of challenge she wasn’t getting elsewhere. Including from her current executive coach.
I often talk with leaders where this shift has happened subtly. The level of scrutiny their thinking is exposed to has quietly reduced over time in a way they hadn't noticed.
If it were obvious, they'd have spotted it. We’ve all seen the films where powerful leaders surround themselves with ‘yes people’. It reinforces their sense of authority and power, but leads to poor decisions because no one is willing to question them.
But the reality is more subtle than the version on screen, so a lack of challenge can be hard to spot.
Three ways challenge fades
In my experience, this often shows up in one of three ways:
No time for challenge: The pace is so high that robust debate feels like a luxury. Decisions get made, but thinking isn’t fully tested.
Shared assumptions: The team is aligned, but in a way that limits perspective. No one sees an alternative because everyone is looking through the same lens.
Unspoken caution: The team holds back. Not necessarily out of fear, but because the cost of pushing too hard feels too high.
Where a trusted advisor comes in
One of the most valuable roles of an executive coach or trusted advisor is to break through this. To sharpen the thinking. To slow it down. To see what others can't. And to have the courage to ask the questions others won’t; to speak truth to power.
If you already have an executive coach: Are they still challenging you? Or has the relationship become too comfortable?
Or if you don’t have a coach at the moment:
Who is challenging your thinking?
I work one-to-one with senior leaders, helping them build strategies to tackle complex challenges. If you'd like to explore what that could look like for you, you can find out more here.
This post was originally shared with my email list. Want to receive weekly reflections on strategy, leadership and high-stakes decision-making delivered straight to your inbox? Sign up here.
Comments