The Situation:
“I’m a seasoned executive coach who has been working with a high-performing client for six months. During a recent session, the client revealed that they’re struggling with making choices because they believe their previous decisions led to a failed business venture 10 years ago. Though outwardly successful now, they’ve been operating from a place of fear and self-doubt, taking the ‘safe’ route in decisions. They’re aware that this is holding them back but feel paralyzed by the past. How can I help this client move forward?”
Response:
Let’s talk about the ghosts in the boardroom. Not spooky ones, but the ghosts of decisions past. You know the ones. They whisper reminders of that one time, 10 years ago, when a business venture went south. Now, even
though they’re a high-performing executive, they find themself playing it safe, paralyzed by the fear of history repeating itself.
I once coached a brilliant leader who was haunted by this very ghost. On the surface, they were the picture of success. But in our sessions, they admitted to being stuck, which took incredible vulnerability. Every major decision was filtered through the lens of a 20-year-old failure, leaving them choosing the “safe” but uninspiring path. This fear was their silent co-pilot, and it was steering them away from incredible opportunities.
It reminds me of my own spectacular failure in a speaking engagement. A colleague asked me to step in and present his material, which I did not know well. The dull, glazed and un- responsive gazes made me think I’d never do another speech again. The memory of that speech kept me from even trying to prepare another speech for a long time. It was silly, but the fear of a repeat disaster felt very real.
So, how do we exorcise these ghosts? As a coach, the first step is to reframe the narrative. That failed venture of the executive, and mine, wasn’t a life sentence; it was a masterclass. We must unpack the lessons learned. What did that experience teach about resilience, market timing, team dynamics, or preparation?
We transform the story from “I failed” to “I learned.” Bring your own humility and great questions to the table to help your client banish those ghosts.
Next, we take small, calculated risks. We don’t jump straight to betting the farm. Instead, we identify low-stakes decisions where you can practice trusting your judgment again.
Think of it as business-decision physiotherapy. Each small win rebuilds the muscle of confidence that has atrophied over time. We might create a “decision journal” to track outcomes, proving that your instincts are sharp and the past is not a pre- dictor of the future.
By helping your client separate the past event from their current identity, they can start leading from a place of strength and wisdom, not fear. Author Roy T. Bennett says it best: “The past is a place of reference, not a place of residence.
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Published in, and reproduced with permission from, choice, the magazine of professional coaching www.choice-online.com