An Enter the Boardroom “Wrapped” Insight — drawn from conversations with world-class Chairs, NEDs, CEOs and governance leaders

Across our 2025 Enter the Boardroom conversations, leaders were unusually open about their mistakes: failed hires, acquisitions they should have questioned more closely, instincts they ignored, risks they underestimated, assumptions they trusted too readily, or conversations they didn’t have soon enough.

These moments rarely damaged careers. In fact, the opposite was true. They sharpened judgment, clarified values and strengthened the discipline directors now bring to the boardroom.

Here are the biggest judgment calls directors got wrong in 2025 and what they learned from them, shared directly by the leaders who lived them.

Failing to act quickly on a disruptive executive

Sir Douglas Flint delayed action on an executive who was valuable but deeply disruptive. The learning: “Take the action you know is right, even though it’s going to be difficult.”

Overestimating stakeholder alignment

Mark Winlow assumed a fellow board member was keeping major shareholders informed. They weren’t — causing unnecessary turbulence. The learning: stakeholder management is never done.

Backing the wrong candidate in a succession process

Angela Seymour-Jackson preferred a high-IQ, alpha-style candidate. The board chose someone else — who proved exceptional. The learning: team dynamics matter more than individual brilliance.

Investing when intuition said stop

Fred Destin invested further in a company despite his own instincts telling him not to. The learning: spreadsheets are tools, not truth. Intuition is a data point.

Letting a flawed project grow instead of stopping it

Jock Lennox allowed a project to expand despite underlying concerns. It became “a larger catastrophe.” The lesson: if something feels wrong, stop it early.

Not warning a CEO before challenging a recommendation in the boardroom

Rita Clifton challenged a proposal on the spot, catching the CEO off guard. The learning: challenge is essential, but pre-discussion builds trust and avoids unnecessary derailing.

Trusting “everything will be fine” from a CFO when instincts disagreed

Cindy Rampersaud accepted reassurances she later realised she should have tested. The lesson: when something feels off, probe harder.

Not intervening early enough during a cultural change initiative

Dame Marie Gabriel CBE felt uncomfortable with an approach but didn’t voice it soon enough. The learning: speak up even when your concern is still forming.

Staying in a doomed governance situation too long

Ali Parsa described not resigning early enough when forced to relinquish control of his own company. The learning: sometimes walking away sooner is the courageous choice.

Accepting a curated narrative instead of probing uncomfortable truth

Professor Alison Taylor allowed the “show-and-tell” to dominate instead of pushing for dilemmas upfront. The learning: ask for the messy truth early.

Allowing urgency to override judgment in a private equity hiring decision

Doug Gurr hired the wrong CEO due to time pressure. The learning: urgency is never a justification for compromising on talent.

Misjudging how a board member would react to a proposal

Louise Hill misread a key voice and didn’t do the relational prep. The learning: pre-prep is part of governance, not a shortcut around it.

Delegating a hiring specification he knew was wrong

Ian Phillips handed off a deputy headteacher brief despite misgivings. The learning: if the specification is flawed, fix it. Don’t pass it on.

Not getting on a plane soon enough to verify a problem on location 

Fiona Hathorn’s reflection from the Asian financial crisis remains one of the year’s most resonant lessons: Sometimes the only way to know the truth is to go and see.

What These Mistakes Reveal About Board Leadership in 2025

1. The biggest failures come from hesitation, not action.

Across the dataset, directors regretted waiting far more than doing.

2. People decisions are the hardest and the most consequential.

Many mistakes involved hiring, firing, succession or stakeholder management.

3. Instinct matters but only when paired with courage.

Directors repeatedly said they knew something was wrong earlier than they acted.

4. Transparency is a governance virtue.

Several mistakes came from trusting curated narratives instead of demanding clarity.

5. Learning from failure is a hallmark of the modern chair or NED.

Mistakes didn’t break these leaders. They sharpened them.