Episode 48 – Leading with Vulnerability: The Power of Saying ‘I Don’t Know’

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

What happens when a CEO says “I don’t know” at the worst possible moment? In this episode Jeff looks back on the time when COVID shattered revenue. Jeff didn’t bluff; he admitted he was lost. That choice flipped a switch. The board stepped up with 11 bold scenarios, and set a course not just to survive, but to thrive. Jeff describes the response in his company: “frontline staff from help desk operators to managers to directors, were sitting there and all they wanted to do was help. I was the old lady that fell over. All they wanted to do is come and help me up.” Vulnerability, used with intent and authenticity, became the catalyst that unlocked scale, trust, and decisive action.

Jeff and Sam explore how transparency spreads across teams and client relationships. Instead of legal threats over unpaid invoices, Jeff’s team chose radical openness and ‘little and often’ repayments to keep suppliers alive. The response? Deeper trust, cleaner communication, and partnerships that were stronger coming out of the crisis than going in. If you’ve ever feared that honesty would erode your authority, this conversation shows the opposite: truth builds credibility, disarms critics, and invites your team to grow taller.

In 2026 Cloudfm Group celebrates its 15^th anniversary. 

Find out more about Cloudfm here.