• Learn how to challenge the Chair without damaging your relationship
• Discover the emotional and political risks of speaking up (and how to live with them)
• Get practical strategies for timing, tone and framing your message
One of the things I'm loving most about my The Real Math of Business™ podcast is the questions I'm getting from listeners.
This week I got a particularly juicy one from a CFO:
"How do I hold the CEO accountable when the rest of the exec team won't?"
And it really made me think.
Because while this particular question came from a CFO, the theme is universal. Whether you're a CEO dealing with a Chair tolerating an ineffective board, or a graduate trying to push back on a well-intentioned but overwhelmed line manager, the challenge of speaking up when no one else will is something most leaders will face sooner or later.
A tale as old as time
We all know the story of The Emperor's New Clothes. The emperor, hoodwinked by his greedy tailor and surrounded by sycophants, walks through the streets naked while his staff and citizens pretend that he is wrapped in finery. No one wants to be the one to speak up. Except one little boy.
The story speaks to something that lives deep within us all. Most of us like to think that we are a person who can be relied upon to tell the truth, no matter how uncomfortable, even when those around us remain silent. But given the nature of power dynamics in the workplace and the fact that, whether we like it or not, our career is tethered to the relationships around us, it's often not that simple. Especially when the person you need to challenge is the person who signs off on your bonus.
If you've ever been in this position, or suspect you might find yourself in one soon, read on.
1. Understand why others won't speak up
It's interesting that in both the 1837 Hans Christian-Anderson version of the story, and the original Spanish telling from five centuries before, both of the truth sayers (a young child in the 1837 version and a man of low social standing in the 1335 version) are those with little political capital to protect.
It is hardly a surprise that those with the most to lose would be the least likely to speak up. But there are deeper, less obvious reasons why we don't speak up when we know we should.
Psychologist Irving Janis's work on groupthink shows how strong team cohesion can suppress dissent. When a team values harmony above healthy tension, the cost of disagreement becomes social and emotional, not just professional.
And neuroscience backs this up: the brain processes social threat e.g. fear of exclusion, disapproval, loss of status, the same way it processes physical pain. The brain is wired to perceive speaking up as, quite literally, dangerous to our wellbeing.
As Patrick Lencioni put it in The Five Dysfunctions of a Team:
"The ultimate dysfunction of a team is the tendency of members to seek artificial harmony over constructive conflict."
There are all sorts of reasons that the rest of the board might stay quiet: self-preservation, groupthink, exhaustion, lack of psychological safety, or simply learned helplessness. But that doesn't mean you should too.
You can't control their reasons. But you can decide whether you're willing to uphold your own standard of leadership, even if you're doing it alone.
2. Get clear on your intent
Before you act, be brutally honest with yourself. Ask:
• Am I reacting emotionally?
• Is this part of a pattern, or a one-off?
• Am I trying to protect the business? Or just win an argument?
• What outcome am I seeking?
Once you're crystal clear on the fact that your aim isn't to score points or take the moral high ground, it's simply to help the Chair make better decisions aligned with the long-term health of the business, move onto the next step.
3. Use your proximity wisely
Don't underestimate the power of a private, well-timed conversation.
When you raise your concern:
• Be clear about your intent.
• Frame the issue in terms of strategic or reputational risk.
• Anchor your concern in data, commercial outcomes, or shareholder expectations.
Avoid emotional language or anything that could sound like personal criticism. Focus on impact, not the Chair's personality or motives.
Instead of saying:
"This is a bad idea and no one agrees with it."
Try:
"Here's where I see potential risk, and how it might play out in the long term. I know you've got good reasons for your point of view, but I think it's worth pressure-testing before we move ahead."
Tone, timing, and trust matter here. Use them well.
4. Be honest about the risks
Let's not sugar-coat it: speaking up has consequences. And those risks are not just professional. There are social and emotional risks at play here too.
You might:
• Damage trust with individual directors
• Lose influence in future discussions
• Be seen as difficult or overly assertive
• Or (and as the perfectionist eldest daughter this is the one that scares me the most) be wrong
The reality is though that even if all these things were to come to pass, shame is just a feeling. It can't kill you.
You can recover from awkwardness. Much easier than a business can recover from a misstep that costs time, money or creates reputational damage.
Before you speak up, ask yourself: What consequences can I live with?
If you're raising something with ethical, financial, or reputational consequences, you may need to escalate your concerns to the regulator. Would this be a red line for you? Decide in advance how far you're willing to go so you can act with intention from the get-go.
5. Don't take it personally.
The Chair might ignore your advice. That's their prerogative.
Your role is to raise the issue calmly and respectfully. If it's dismissed, let it go. Don't let resentment or cynicism creep in. That's like drinking poison and expecting the other person to die.
And if your intervention doesn't change anything? You've still done your job.
At the end of the day, no, it's not fair that the rest of the board stayed silent while you carried all the risk. No, it's not fair that you're the one losing time in your already busy day to documenting activity and convening meetings that nobody else is willing to have. But you'll sleep better knowing you did the right, courageous thing.
Best case? The Chair thanks you and has a new found appreciation for the depth of your integrity and your loyalty to the business. Your example might even give the rest of the board the courage to follow suit. Worst case? You gain clarity on who is really in the trenches alongside you.
Either way, it's valuable data.
The inglorious satisfaction of speaking up
In business, as in life, there is typically no applause for doing the right thing.
No one remembers the little boy in The Emperor's New Clothes. The story is about the emperor and the lickspittles that surrounded him. The story was never about the boy.
But the boy spoke up anyway. And he was right.
So my question to you is this:
"What would you want your executive team to do if you were the one making the wrong call?"
And...
"Are you willing to do the same for your board?"
I'd love to hear your thoughts.
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