Issue 9: Who Dares to Disagree with the CEO?

⏱ 5-minute read

Why constructive challenge is essential to effective leadership and better boardroom decisions.

The Boardroom Question

When did someone last challenge a decision you were making — and how did you respond?

It’s an interesting question for any CEO or senior leader.

Most executives would probably say they welcome different opinions. But how comfortable are the people around them about expressing those opinions?

Do they feel confident questioning a decision, suggesting an alternative or pointing out something the CEO may have overlooked?

Or is it easier simply to agree?

A boardroom where everyone agrees might appear harmonious and effective. But agreement isn’t always evidence of good decision-making.

Sometimes, the most valuable person around the table is the one prepared to say:

“I don’t agree — and here’s why.”

Why Constructive Challenge in Leadership Matters

Strong leadership isn’t about having all the answers.

It’s about creating an environment where the right questions are asked, different perspectives are considered and decisions are made with the benefit of collective experience.

Constructive challenge in leadership isn’t about encouraging conflict or undermining authority. It’s about ensuring that assumptions are tested, risks are considered and alternative approaches are explored before important decisions are made.

A confident CEO should be able to explain their thinking, listen to opposing views and occasionally change their mind.

That doesn’t mean every decision needs unanimous agreement.

Ultimately, someone must take responsibility and make the call.

But there’s an important difference between making a decision after listening to different perspectives and making one because nobody felt comfortable questioning it.

The strongest leadership teams don’t necessarily agree on everything. They trust one another enough to disagree.

The Danger of Everyone Agreeing

There’s a well-established concept known as groupthink.

It occurs when the desire for harmony or consensus within a group begins to outweigh independent thinking and critical evaluation.

In a boardroom, this can be particularly dangerous.

A respected CEO may express a strong preference early in a discussion. Other executives, consciously or unconsciously, may begin aligning their views with that position.

Someone with reservations might decide not to raise them.

Another might assume that because nobody else is questioning the proposal, their concerns are probably unfounded

Before long, what appears to be a unanimous decision may simply reflect an absence of challenge.

The danger isn’t necessarily that the CEO has made the wrong decision.

It’s that the organisation hasn’t properly tested whether it’s the right one.

Saying You Welcome Challenge Isn’t Enough

Many leaders describe themselves as approachable, collaborative and open to different opinions.

But the real test comes when somebody disagrees with them.

Do they listen without interrupting?

Do they ask questions to understand the opposing view?

Do they thank someone for raising an uncomfortable issue?

Or do they become defensive, dismiss the concern or make it clear that further discussion isn’t welcome?

People notice these reactions.

And they remember them.

If challenging the CEO results in embarrassment, frustration or exclusion, colleagues quickly learn that agreement is the safer option.

On the other hand, when a senior leader responds thoughtfully to a different perspective, it sends a powerful message.

The CIPD’s guidance on employee voice reinforces the importance of giving people opportunities to express their views and ensuring those views are genuinely considered.

It’s safe to speak up here.

That confidence is central to what organisational researchers describe as psychological safety — an environment in which people feel able to raise concerns, ask questions and acknowledge mistakes without fear of humiliation or punishment.

Psychological safety doesn’t mean avoiding accountability or difficult conversations.

Quite the opposite.

It creates the conditions for those conversations to happen.

Constructive Challenge Is Not Confrontation

There is, of course, a difference between healthy disagreement and persistent negativity.

A leadership team where every proposal becomes an argument can be just as ineffective as one where nobody speaks up.

Constructive challenge should be thoughtful, respectful and focused on improving the outcome.

It might involve asking:

• What assumptions are we making?
• What evidence supports this approach?
• What could go wrong?
• Have we considered another perspective?
• What would change our minds?
• Are we overlooking something because it’s uncomfortable to discuss?

These aren’t necessarily difficult questions.

But they can lead to difficult — and valuable — conversations.

The objective isn’t to win an argument.

It’s to reach a better decision.

Does the CEO Have Too Much Influence?

The CEO’s influence within an organisation is considerable.

Even when they don’t intend it, their views can carry more weight than those of others.

Their tone, body language and reactions can influence whether people contribute openly.

A CEO who announces their preferred solution at the beginning of a meeting may unintentionally discourage alternative suggestions.

Sometimes a simple change in approach can make a significant difference.

Rather than starting with an opinion, the CEO might ask others to share theirs first.

Rather than immediately defending a proposal, they might invite colleagues to identify its weaknesses.

And rather than treating disagreement as resistance, they can recognise it as an important contribution to the decision-making process.

The more senior the leader, the greater their responsibility to make room for other voices.

Publishing: The Value of Different Perspectives

Publishing is an industry built on creativity, judgement, relationships and commercial decisions.

Editorial instinct and experience are enormously valuable.

But publishing businesses also need to respond to changing reader behaviour, new formats, emerging technologies, evolving routes to market and commercial pressures.

That makes constructive challenge particularly important.

An established publishing approach may have delivered excellent results for many years.

But does that automatically make it the right approach for the next five?

Could someone from sales, marketing, digital, rights or finance see an opportunity — or a risk — that others have missed?

Could a newer member of the senior team question an assumption that has become so familiar nobody thinks to challenge it?

Publishing businesses benefit from strong editorial conviction.

They also benefit from an environment where that conviction can be tested against different commercial and strategic perspectives.

The challenge is to combine experience with curiosity rather than allowing one to silence the other.

Financial Services: Challenge as Part of Good Governance

In Financial Services, constructive challenge has an additional dimension.

Effective governance depends on appropriate scrutiny, clear accountability and a willingness to question decisions that may expose an organisation or its customers to risk.

Risk, compliance, finance, operations and commercial leaders may understandably approach the same proposal from different perspectives.

Those differences should be an organisational strength.

A commercial opportunity may look attractive from a growth perspective but raise legitimate questions about operational capacity, customer outcomes or regulatory requirements.

The purpose of challenge isn’t necessarily to stop the organisation moving forward.

It’s to help ensure that decisions are informed, proportionate and sustainable.

In a well-functioning senior team, differing professional perspectives should improve decisions rather than create unnecessary divisions.

Are You Recruiting People Who Will Challenge You?

There is also an interesting connection with how organisations appoint senior executives.

When assessing candidates, it’s natural to consider whether they will fit the culture and work effectively with the existing leadership team.

But what does cultural fit really mean?

Does it mean someone who shares the organisation’s values and can collaborate effectively?

Or does it sometimes become shorthand for someone who thinks and behaves like the people already around the table?

There is a difference.

A senior appointment can be an opportunity to introduce fresh thinking, different experiences and new perspectives.

But only if the organisation is genuinely willing to listen to them.

Recruiting someone because they bring a different perspective, then expecting them to conform to established thinking, rather defeats the purpose.

The best addition to a leadership team isn’t always someone who fits comfortably into every existing conversation.

Sometimes it’s someone who helps the organisation have better conversations.

Five Questions for Your Next Leadership Meeting

1. When did someone last openly disagree with the CEO or another senior leader?
2. How do we respond when someone challenges an established view?
3. Are there people around the table who rarely contribute — and do we understand why?
4. Do our meetings encourage genuine discussion, or are decisions effectively made before everyone arrives?
5. Are we surrounding ourselves with people who bring different perspectives, or people who reinforce our existing thinking?

The answers may reveal more about the effectiveness of a senior team than the number of meetings it holds or the speed at which decisions are made.

Key Takeaways

• Constructive challenge strengthens decision-making by testing assumptions and encouraging different perspectives.
• Agreement isn’t always evidence of alignment; sometimes it reflects a reluctance to speak up.
• CEOs and senior leaders set the tone through how they respond to disagreement.
• Psychological safety and accountability should work together, not against one another.
• Healthy disagreement should focus on improving outcomes rather than winning arguments.
• Different professional backgrounds and experiences can make senior teams more effective.
• Recruiting people with fresh perspectives only adds value if the organisation is prepared to hear them.

A Final Thought

At Mosaic Executive Search, we’ve spent more than 25 years working with senior executives and organisations across Publishing and Financial Services.

One of the things we’ve consistently valued is the ability of strong leaders to combine confidence in their own judgement with respect for the experience and perspectives of others.

When identifying senior talent, technical expertise and commercial achievements matter enormously.

But so do judgement, integrity, communication and the confidence to challenge established thinking constructively.

Equally important is whether an organisation creates the environment for those qualities to flourish.

Because appointing capable people is only part of building an effective leadership team.

The strongest leaders don’t surround themselves with people who always agree. They create the confidence for others to challenge them — and the wisdom to listen.

Further Reading

Boardroom Insights | Issue 07
Experience vs Potential: What Matters When Hiring Leaders?

Boardroom Insights | Issue 08
Would Your Rising Stars Choose You?