10 Key CEO Hiring Mistakes Board Members Regret

We analysed hundreds of conversations with Chairs, CEOs, investors and academics on CEO appointments boards later came to regret. The patterns were strikingly consistent.

The biggest mistakes were rarely about intelligence or experience. They were about judgment: how boards assessed people under uncertainty, pressure and incomplete information.

Below are 10 CEO hiring mistakes that board members repeatedly reflected on with hindsight.

What this article reveals at a glance

1. Consensus can create a dangerous illusion of certainty.
Boards often mistake alignment for rigour. When directors share similar backgrounds and assumptions, consensus can mask weak challenge and suppress alternative perspectives, particularly in CEO selection.

2. Charisma remains one of the most misleading hiring signals.
Engaging, persuasive candidates frequently outperform in interviews while underperforming in role. Board members repeatedly described how confidence and eloquence crowded out evidence of how candidates actually managed people.

3. Traditional interviews generate weak predictive data.
Hypothetical questions and polished answers feel rigorous but often produce “junk data.” What candidates say they would do rarely predicts what they actually do under pressure.

4. CEO failure often begins after you appointment them, not before.
Boards devote disproportionate effort to selection and far too little to onboarding. Several guests argued that insufficient transition support materially increases CEO failure risk.

5. Confidence is still rewarded in environments that demand learning.
In volatile contexts, leaders who project certainty can shut down dissent and learning. Boards increasingly regret backing CEOs who sounded sure but reduced psychological safety.

6. Tools cannot replace judgment about character.
Psychometrics and frameworks help, but over-reliance can create false reassurance. Character, humility and EQ remain difficult to measure, and costly to miss.

Taken together, these mistakes point to a deeper issue. CEO hiring decisions are often shaped by comfort, familiarity and surface-level signals rather than evidence of how leaders behave in reality. Boards that recognise this earlier make fewer regretful appointments.

Key hiring mistakes 

Lacking diversity of thought when hiring the CEO

“We had a group of people very similar in background and outlook, and that gave us a false sense of confidence … We went along with the consensus view. That wasn’t my finest hour.” Roger Parry CBE, Former Chair of Oxford Metrics, Director at the Donmar Warehouse, Partner at Stoneglade Capital 

Getting beguiled by charisma

“They were very engaging, very eloquent, and extremely persuasive in interviews. But over time it became apparent that they were doing things you would not expect in terms of managing people. That’s when you realise how easily you can be duped.” Stuart Roden, Chair / former Chair of Lansdowne Partners, Hetz Ventures, Lewis Advisors, Tresidor, the Design Museum and Unlocking Potential, NED at LSE and Trustee at the National Gallery and Centre for Social Justice

Over-reliance on hypothetical answers to hypothetical questions

“Many smart people interview candidates by asking the person how they would handle a certain situation … But the handbook of industrial and organisational behaviour did a large meta-analysis that found that asking hypothetical questions leads to hypothetical answers… The approach doesn’t have predictive validity. How someone answers a hypothetical question does not predict how they’re likely to actually behave on the job. It’s junk data.” Dr Geoff Smart, Chair and Founder of ghSMART, a global leadership advisory, which has published three bestselling books: Who? A Method for Hiring, The CEO Next Door, and PowerScore

Spending insufficient time onboarding a new CEO

“We spend 90% of the effort on selection and almost nothing on helping CEOs succeed once they’re in the role.” Navid Nazemian, PCC, ranked as the World’s #1 Executive Coach, Bestselling Author, Keynote Speaker, NED

Placing too much weight on interviews

“The interview process is a particularly false process: you’re on your best behaviour, and they’re on their best behaviour. You need to put a lot of time into it. Try to see people in different environments, because it’s quite tough to keep that mask up.” Lord Charles Allen, Baron Allen of Kensington, CBE, Chair of Moelis & Co, Balfour Beatty Plc, Global Media & Entertainment Group, and The Invictus Games

Treating psychology as a “vaccine”

“People tend to treat psychology… as a vaccine. I’ve read Daniel Kahneman’s book … Therefore, I’m immune from psychological biases. No… you can’t treat it as a vaccine, even if you’re perfectly aware of the trap.” Dan Gardner, best-selling author of Superforecasting, How Big Things Get Done, Risk and Future Babble

Confusing confidence with competence

“Don’t mistake confidence for competence because they are absolutely not the same thing… if you take people at their word, you're often going to hire the overconfident (but not necessarily as competent) man over his less confident, but highly competent female rival.” Mary Ann Sieghart, SID at Pantheon International plc, Remco Chair at Guardian Media Group and best-selling author of The Authority Gap

“When we select leaders, including CEOs, we play it by ear. We focus on style, not substance, and we end up with people who are overconfident rather than competent. The evidence shows that it takes competence to spot and stop incompetence.” Dr Tomas Chamorro-Premuzic, Chief Innovation Officer at Manpower Group and Professor of Business Psychology

Assuming “best in the room” means “right for the role now”

“Just because someone is the best candidate you’ve interviewed doesn’t necessarily make them the right person for the job. Sometimes you have to take a deep breath, dig into your pocket, and run the process again.” Nick Jenkins, Founder and former CEO of Moonpig, former Dragon on Dragon’s Den, Chair of Virtualstock, NED at Green Energy Options and Trustee at Operation Fistula

Rewarding certainty in an uncertain world

“Our brains are predisposed to seeing certainty where none exists. When leaders project that ‘we’ve got this’, it becomes much harder for others to speak up with dissenting views or worries. Boards often regret backing leaders who sounded confident but shut down learning.” Amy Edmondson, Professor of Leadership & Management at Harvard Business School, ranked #1 management thinker in the world by Thinkers50

Over-relying on psychometrics for character judgement

“I became sceptical about psychometrics because I’ve seen them miss things you’d hope they would pick up. Character and EQ matter enormously, but I’m careful about how much weight I put on those tools.” Angela Seymour-Jackson, Chair of PageGroup, Deputy Chair of Pikl, SID at Trustpilot Group, and NED at Future and Janus Henderson Group