In a recent video conversation with Kerry Cunningham and Matt Heinz, Kerry asked a deceptively simple question, why is it that

“People learn something once, and then they are stuck with that learning for the rest of their life or career.”

What really landed for me was Kerry’s next point

These people aren’t sitting in the lower ranks or stuck in middle management

Quite the opposite

They’re often at the very top of the organisation

Kerry went on to say that many of them learned their version of sales or marketing a long time ago

It worked

It got them promoted

It helped them succeed

And because it once worked, it became truth

Matt then added an important layer

Those approaches probably did work at the time

But senior leaders are no longer in the weeds

They’re removed from the day-to-day reality, so it’s easy to assume that what worked back then must still work now

Which leads to the familiar refrain Matt summed up perfectly, senior management then say:
“Why can’t people do it the way I did it?”

The problem, of course, is that the world has moved on

I wrote an article about bias yesterday, and this feels like a perfect example

Outdated beliefs, frozen in time by past success, quietly become organisational bias

And when those biases sit at the top of the house, they don’t just slow progress, they actively hold businesses back

Conclusion

Past success is a poor strategy for future growth if it’s never questioned

The real leadership challenge isn’t defending what once worked, but having the humility to relearn, unlearn, and adapt

In fast-moving markets, clinging to old truths doesn’t preserve excellence, it limits it