She had been leading for fifteen years. She had a strong track record, a loyal team, and a reputation that preceded her in every room. And yet, somewhere in the last eighteen months, she had started second-guessing almost everything.
“I don’t know if I’m reading situations correctly anymore,” she said. “I used to just know. Now I overthink every conversation.”
When Confidence Becomes Complicated
This pattern — the capable leader who suddenly loses trust in their own judgment — is more common than most leadership conversations acknowledge. And it almost never means what the leader fears it means.
It rarely means their instincts have failed. More often, it means the environment has changed in ways that their existing instincts weren’t built for. A new organisational context. A different stakeholder landscape. A team that needs something different from what previous teams needed.
The instincts aren’t broken. They’re just operating in unfamiliar terrain.
The Work of Recalibration
In coaching, we spent time separating three things that had become conflated in her mind: what she actually did, what she thought she did, and what she feared others thought she did.
When we got specific — really specific, conversation by conversation — a clearer picture emerged. Her instincts were, in most cases, sound. What had eroded was not her judgment but her confidence in her judgment. And that erosion had a source.
A period of sustained pressure. A significant setback that hadn’t been properly processed. A transition where the goalposts had shifted without explicit acknowledgment.
Rediscovering the Compass
The shift wasn’t dramatic. It was quiet. A gradual reacquaintance with what she actually believed, what she actually valued, what kind of leader she actually wanted to be — as distinct from who she thought she was supposed to be in this particular environment.
Her instincts didn’t need replacing. They needed trusting again — with eyes open to what had changed.
Coach’s Reflection: Self-doubt in a capable leader is not always a warning sign. Sometimes it is an invitation — to examine whether the environment has shifted, whether the role has evolved beyond the original brief, whether a recalibration is needed rather than a rescue.
Call to Reflection: Is there a leadership instinct you’ve stopped trusting that might be worth re-examining — with fresh eyes rather than fresh doubt?
Yatish Chandrasekhar is an Executive Coach and Leadership Consultant at The Yogi Compass. He works with senior leaders across industries to help them discover their True North. If this resonated, he’d love to hear from you.