The Hardest CEO Conversations Boards Avoid

Across hundreds of conversations on Enter the Boardroom, Chairs and directors repeatedly described moments when they knew a conversation needed to happen but hesitated.

Boards often delay these conversations because they feel personal, awkward or destabilising. But later, they reflect on their omissions as key turning points. 

What follows are the hardest CEO conversations our guests said boards most commonly avoid. 

What this article reveals at a glance

1. The most difficult conversations are avoided precisely because they feel “non-technical.”
Boards are generally comfortable discussing numbers, strategy and structure. They are far less comfortable addressing behaviour, emotions, power and ethics, even when those issues pose the greatest risk.

2. Delay turns manageable issues into structural problems.
Guests repeatedly emphasised that early, direct conversations, when issues are still small, are far more effective than late interventions after trust has eroded.

3. High performance can mask deeper risk.
Several contributors warned that boards often avoid challenge when results are strong, even though success can hide leadership bottlenecks, cultural damage or strategic overreach.

4. Many of these conversations test the board as much as the CEO.
In some cases, the issue is not the CEO’s behaviour but the board’s willingness to confront its own shortcomings.

Taken together, these insights suggest that board effectiveness is often revealed not in routine oversight, but in the conversations directors are willing to initiate when it feels uncomfortable to do so.

The Conversations Boards Avoid

Addressing violations of boundaries

"If you’ve clearly set boundaries - whether financial, ethical, or behavioural - then violations should be addressed as soon as possible. Don’t wait for big violations. Nip it in the bud. Hold up the mirror, give that feedback. It's not mean. It's clear. We're forward-looking: the aim is to ensure future success, not punish past mistakes." Amy Edmondson, Professor of Leadership & Management at Harvard Business School, ranked #1 management thinker in the world by Thinkers50 in 2023

Calling out excessive information requests

"It's very tempting if you are a board director to just rattle off a request for a set of pieces of analysis from the management which you may not realize are going to take multiple days of someone’s time to put together. I’ll often encourage CEOs to have an open discussion on the subject of information requests, where there'll be a set of criteria that are agreed for what counts as the right trigger." Tim Jackson, Founder of QXL and a General Partner at Walking Ventures

Raising personal challenges

"The chair actually talked to the CEO about how he was feeling, had a feelings conversation, and shared how he had behaved when new in his executive role. That allowed a much more honest conversation about what was going on. The CEO was then given a coach, and they were able to discuss what he wanted from the chair in their relationship. They started to have a much more human-to-human conversation." Joy Harcup, executive coach and board reviewer at Praesta Partners and author of The Art & Psychology of Board Relationships

Recognising when the business has outgrown the founder

“The CEO-Founder who starts the company may not always be able to grow in the same way, like the company is growing … every chair of a startup should be aware that this will come sooner or later.” Mienhard F. Schmidt, Principal & Managing Director at ONYX Enterprises LLC, plural Board Member and Chair with more than 25 years’ experience across Healthcare, Diagnostics & MedTech. 

“I think a good founder should be able to recognise when it’s time to jump, not wait to be pushed. That’s a very difficult conversation, but it’s one that boards sometimes need to have.” 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

Distinguishing between strategy and implementation (and the respective roles of the executive and non-executives) 

“Not everybody agrees what is strategic and what is implementation. And that’s where the grey areas start.” Gillian Wilmot, Chair of ZOO Digital Group plc, Jisp and SYNALOGiK Innovative Solutions Ltd

Admitting when board directors are the problem

“If an investor claims a board seat but doesn’t prepare, doesn’t show up and doesn’t help, something is seriously wrong.” Marta Krupinska, CEO & Co-Founder of CUR8, Chair of YBI and NED at ACUA Ocean 

Questioning a successful CEO when everything looks fine

“If everything seems to be going right, that’s exactly when the board should be asking what might go wrong, and we didn’t do that enough.” Roger Parry CBE, Former Chair of Oxford Metrics, Director at the Donmar Warehouse, Partner at Stoneglade Capital 

“The business was going great at the time, and I was the miserable person in the corner saying, ‘but what about this?’ That’s not what people want to hear when everything looks fine.” Baroness Helena Morrissey, Former/Chair of Altum Group, Fidelis Insurance Group, Investment Industry Diversity Project, AJ Bell and The Investment Association

Addressing leadership bottlenecks created by the CEO

“If the CEO is making all the decisions, the organisation can’t scale.” Shellye Archambeau, Fortune 500 board director, strategic advisor, former CEO and author

Challenging the assumption that growth always equals value

“Expansion may not make sense strategically, even if incentives push the CEO to pursue it.”
Hamilton Helmer, Co-Founder at Strategy Capital, former Lecturer in Business Strategy at Stanford, author of “7 Powers: The Foundations of Business Strategy”

Confronting brilliant but damaging leaders

“Good board leaders will deal with high performers who are toxic, and they will exit them.” Anne Francke OBE, CEO, Chartered Management Institute

Admitting when the CEO is the wrong messenger

“In the NHS world, I couldn’t do the pitch. It had to be a doctor.” Wais Shaifta, Chief Growth Officer at The Co-op, NED at The Gym Group, former NED at Reach plc, Senior Independent Trustee at Football Foundation, Samaipata and Ex-CEO Push Doctor

Questioning whether the remuneration model is fit for purpose

“My argument was simply that I didn’t properly understand the fees. And if I couldn’t understand them, how could clients? That’s a very uncomfortable conversation to have.” Baroness Helena Morrissey, Former/Chair of Altum Group, Fidelis Insurance Group, Investment Industry Diversity Project, AJ Bell and The Investment Association

Being realistic about fat-tail IT risks

“IT projects are so ubiquitous we tend to treat them as not being terribly dangerous. No, in fact, they are more dangerous than most project categories… Statistically, IT ranks just a hair above nuclear power. That’s how dangerous it is.” Dan Gardner, best-selling author of Superforecasting, How Big Things Get Done, Risk and Future Babble  

Challenging ambition that has tipped into recklessness

“The problem comes when vision fades and ambition and aggression take over and become not a means to an end, but the end themselves. That’s when healthy culture gets distorted into something darker, and boards often avoid calling that out until it’s too late.” Gerry Brown, Chair of NovaQuest Capital Management and G Brown Associates, co-author of Disaster in the Boardroom

Calling out disengagement before it becomes mistrust

“If the CEO is not engaging with the board, you first need to understand what is really happening. After that, either the chair raises it directly, or the board discusses it collectively and decides how to address it.” Professor Stanislav Shekshnia, Professor at INSEAD, where he directs board development programs, and Chair of TechnoEnergy AG 

Scrutinising internal CEO successors

“Boards often say they have a succession plan, but what they really have is a PowerPoint with some high performers on it. Then something happens and nobody is ready. That’s when panic sets in.” Angela Seymour-Jackson, Chair of PageGroup, Deputy Chair of Pikl, SID at Trustpilot Group, and NED at Future and Janus Henderson Group

“Every board member that I’ve spoken with will privately say that they’re not comfortable raising the topic of CEO succession with a successful CEO. And so when they do, the conversations [are] really uncomfortable.” Elena Botelho, Co-author, The CEO Next Door, Partner at ghSMART

Asking internal candidates what they would do differently

“The tough question for internal candidates is: what would you do differently from your current boss? That’s challenging because there’s a lot of co-ownership of the existing strategy, but it’s not about criticism — it’s about what the future needs.” Gerry Murphy, Chair of Tesco and Burberry, Trustee at Burberry Foundation, Senior Advisor at Perella Weinberg and Mentor at J&A Mentoring

Ethics (as a strategic issue, not a procedural one)

“I think the first thing I would say is ethics is seen as a procedural process, policy question, and not as a core strategic question. Those tensions really show up at the board level, but they’re often avoided or delegated instead of confronted directly.” Professor Alison Taylor, Clinical Associate Professor at NYU Stern School of Business and author of Higher Ground: How Business Can Do the Right Thing in a Turbulent World