One Question That Changed the Conversation
The analogy of a crab outgrowing its shell is a relatable one. For humans, though, it’s a little less obvious when we have outgrown something—whether a role, a way of leading, or a mindset that once served us well.
Recently, I was moved by a coaching conversation in which a high-performing leader realized that the very mindset that had helped him advance in his firm was now limiting his future path there.
We had just two sessions as part of a broader leadership development program, yet the insights were powerful enough to shift how he approached his next chapter there.
This leader had built a profitable global business within a much larger firm and was deeply respected by his clients and team. A few years earlier, critical feedback had prompted him to invest more deeply in developing and mentoring his team. His most recent feedback reflected just how far he had come, with colleagues offering detailed, positive accounts of his leadership and impact.
It was a meaningful evolution, and one worth celebrating.
So what was the problem?
On the surface, there didn’t seem to be one.
His manager, however, was highly territorial and political. My client had learned to accommodate his manager’s need for visibility; he had built a highly profitable business under his manager’s purview without drawing too much attention to himself.
Somewhat unconsciously, he had also continued to manage his business at a more granular level than his team required to stay out of his boss’s way.
Increasingly, however, my client wanted to explore new business opportunities beyond his existing business and step out from under his shadow . He had not done so, however, due to assumptions (below) he held about what would happen if he did so:
If I build something new, my manager will ultimately take the credit, ownership, and upside. So why should I put forth any effort?
Rather than debate whether his assessment of his manager was right or wrong or discuss how he might maneuver politically, I found myself stepping back to consider the broader future at stake.
I found myself asking him a simple question:
“Two years from now, if you are still in the same role, how will that feel for you?”
The question stopped him in his tracks.
Until then, he had been focused on what his boss would gain if he did all the heavy lifting in a new direction. This question shifted his attention to what he might lose by staying exactly where he was.
He acknowledged the irony: the status quo would keep him valued by the firm and well compensated, even if he was unlikely to feel as if he was fulfilling his potential. Furthermore, he realized that the process of studying the market would be an enjoyable learning journey in of itself, regardless of the commercial outcome.
By the end of our second conversation, he felt motivated to hand off more responsibility to his team and explore business opportunities adjacent to his current business
It wasn’t a perfect solution. He would still be operating within boundaries that were comfortable for his boss, but it was a more expansive path than growing bored in his current role.
The conversation was a good reminder that no matter how self-aware or high-performing or valued a leader may be, there are always blind spots and opportunities to uncover. Sometimes, the very assumptions that have helped us navigate our careers begin to constrain our thinking and behavior.
The challenge is recognizing when our most reliable strategies don’t serve us any more. The question that shifted him was one that had him imagine a future that was static to the present, and only then did he confront the real opportunity cost.
What might you or someone else you know be holding onto for the sake of comfort, security, or success that is no longer serving you or them?
