A couple of years ago, one of my mentees called me.
He had just joined a new company. Bigger title, leadership role and a larger team. It was a clear step up compared to his previous role.
He asked me, – “It’s a bigger role now. How should I navigate this situation and succeed? ”
I listened to the context, culture, people, expectations.
Then I told him what I felt he needed to change — not just better product management or strategy skills, but behaviour.
How he showed up, style of communication, aligning very senior stakeholders. How leadership at that level was less about doing and more about influencing.
He nodded and thanked me.
Eight months later, he called again.
This time, his voice was heavy. Things weren’t going well and he felt stuck and under pressure.
Ironically, I had forgotten our earlier conversation. So I started sharing my thoughts — what he needed to shift, how he needed to adapt, what he should stop doing.
When I finished, there was silence.
Then he said, “You told me the exact same thing a year back. I didn’t understand it then. But I understand it fully now.”
That line stayed with me.
Back then, he consciously agreed with me but unconsciously believed that his old methods would work. After all, they had worked before. He didn’t grasp that the role demanded a different way of operating.
By the time he truly understood what needs to change in him, it was too late to turn things around in that company. He eventually exited.
The good part? He did very well in his next role because this time, the learning had already sunk in.
That episode reminded me of 2 simple things:
1. Learning happens only when we are ready.
2. Experience & failures have a way of teaching what mentors cannot. Because failure creates the emotional space required for that learning to enter — especially when the growth demanded is steep and not incremental.
Interestingly, what I had told him originally were lessons I had learnt after my own failure — lessons I only appreciated when something didn’t go my way.
As mentors, managers, or leaders, we sometimes get frustrated when people don’t act on what we tell them. But maybe the timing isn’t right yet or they haven’t felt the pain strongly enough.
And as professionals, we resist change until reality forces us to confront ourselves.
Looking back at your own journey —What is something you were told early in your career that only made sense after a failure?
