Coaching: The Edge in High-Stakes Decisions

“I need to talk things through”, he said.

6/10/20251 min read

silhouette of road signage during golden hour
silhouette of road signage during golden hour

“I need to talk things through”, he said, “with someone who has no agenda, is free of bias – just sharp questions to keep me on course. Don’t hold back.”

He was the founder and right in the middle of a £50 million fundraise. Excited during the day – sleepless at night.

We started exploring: the investors, the scenarios, the risks, the opportunities, priorities, process, corporate value, behavioural values, gain and loss of autonomy, ethics and much more.

Some time and a full whiteboard later the picture became clear. Anyone could have walked into the room and would have understood the situation.

Mission accomplished? Not quite.

We took a short break – ready to wrap up – when the magic happened.

As he reviewed (prompted by more questions) something flipped. The initial approach was suddenly turned on its head. Unexpected, yet undeniable – the result of coaching with no bias – just relentless clarity and space to see the unseen.

By week’s end, the first signed term sheet arrived. The coaching didn’t land the deal, but the confidence and strategic clarity to navigate uncertainty undeniably did.

How did coaching create that breakthrough?

In the noise of high-stakes decisions, the right conversation can change the trajectory entirely. That’s the power of coaching done well.

What changed? The initial approach towards investors would have killed the deal. The new approach provided the insights needed to interact confidently with potential investors and the perspective how to impact the own team in times of uncertainty and growth.

The learnings:

  • Sometimes one more question can unlock the missing 10% and move it from good to great.

  • Cherish the break. As in elite sports, breakthroughs often come in recovery – not in exertion. That pause between exercises – just enough to regain strength – is where the insight poured out.

  • Never underestimate the impact a CEO with clarity and healthy energy can have on their surroundings.