How Do I Get My Leadership Team to Challenge Each Other Instead of Leaving It All to Me?

Horizontal accountability matters

Most organisations are comfortable with vertical accountability. Manager challenges employee. CEO challenges manager. That is familiar. The next level is horizontal accountability. Peer to peer. One leader saying to another:

“You committed to that. What happened?”

Or:

“I don’t think the evidence supports your conclusion.”

Or:

“I think this creates a problem for the business.”

That is not disloyalty. That is leadership.

The CEO cannot be the only adult in the room

If every difficult point waits for you, the team is not yet carrying collective responsibility. You become: referee; challenger; truth-teller; decision-maker; and enforcement mechanism. That is exhausting. And it also lets everybody else stay relatively comfortable.

Ask why they are not challenging each other

There are several common reasons. They do not trust each other. They fear conflict. They do not want to damage relationships. They think challenge belongs to the CEO. They are unsure whether they have the right. They do not want challenge coming back at them. Or the culture has previously punished disagreement. You need to understand which of those is operating.

Make challenge part of the job

If someone sits on the leadership team, their responsibility is not merely to report on their own function. They are there to improve the quality of leadership decisions. That means speaking when something does not make sense. Bringing evidence. Asking the uncomfortable question. Challenge is part of the role.

Define what good challenge looks like

Good challenge is: specific; evidence-based; business-first; respectful; direct. Not: sarcastic; personal; territorial; political. A useful distinction is: challenge the thinking, not the person.

Use business-first language

Instead of:

“Sales always does this.”

Try:

“I think this decision creates a downstream problem for Operations. Can we look at that?”

Instead of:

“Finance is being difficult again.”

Try:

“What is the commercial risk Finance is trying to protect us from?”

The language changes the quality of the debate.

Challenge belongs in the room

If someone leaves the meeting and says: “I completely disagreed with that,” ask:

“Did you say so in the meeting?”

If not, why not? The useful challenge belongs where the decision can still improve. Not in the corridor afterwards.

Stop rewarding silence

If the quiet leader is praised for being “easy to work with” while the person who challenges is labelled difficult, people learn the wrong lesson. You want thoughtful challenge. Recognise it when it improves the decision. But do not reward combative behaviour Challenge is not a licence to dominate.

The objective is not to win. It is to improve the thinking. A leader who challenges everything for status is not necessarily adding value.

Ask the quietest voice

Sometimes the same two people dominate. The CEO can say:

“We’ve heard from Sales and Finance. Operations, what do you think?”

That invites broader contribution. Over time, the team should need less prompting.

Ask peers to respond before you do

This is a useful leadership habit. A manager presents a recommendation. Do not immediately give your view. Ask:

“What do the rest of you think?”

Now the team has to engage. That begins shifting challenge sideways.

Hold back deliberately

This may feel slower. Especially when you know exactly what you think. But if you answer first, everyone tends to react to you. If you hold back, they have to think. That is development.

Ask who sees a risk

When a proposal sounds too easy, ask:

“Who sees a risk we haven’t discussed?”

That legitimises dissent. It tells the room that disagreement is useful.

Ask for the opposite case

If everyone quickly agrees, ask:

“What is the strongest argument against this?”

You are not creating conflict for sport. You are testing the decision.

Build enough trust for disagreement

People will not challenge honestly if they believe the relationship cannot survive it. Trust means: we can disagree; we can question; we can say something uncomfortable; and still work together afterwards. That is a stronger form of trust than politeness.

Do not confuse niceness with trust

A very pleasant leadership team can still be weak. Everyone is cordial. Nobody says what they really think. The meeting looks harmonious. The real opinions emerge later. That is not trust. That is avoidance.

Give permission explicitly

Sometimes senior managers genuinely think peer challenge is inappropriate. Say:

“If you see something that does not stack up, I expect you to say so. You are not here only to protect your own function.”

Make the expectation visible.

Challenge should move across functions

Sales should be able to challenge Operations. Operations should be able to challenge Finance. Finance should be able to challenge Sales. Not because everyone knows everyone else’s job. Because everyone shares responsibility for the business.

Stay curious across functions

A good challenge can sound like:

“Help me understand why that matters operationally.”

Or:

“What assumption is sitting underneath that number?”

Curiosity often produces better debate than accusation.

Make evidence the common ground

Challenge becomes personal when everything is opinion. Use evidence. What does the data show? What was agreed? What actually happened? What pattern exists? Now disagreement has somewhere to land.

Use the scoreboard

A shared scoreboard helps the team challenge reality rather than personalities. If margin is off track, the question is not:

“Whose fault is this?”

It is:

“What is driving this and what do we need to do?”

Evidence creates a common problem to solve.

Peer accountability should include commitments

If one leader promised something, another leader should be able to ask:

“Where is that up to?”

That should not require the CEO. The commitment belongs to the team.

Make commitments visible

Horizontal accountability is much easier when actions are recorded. Owner. Date. Definition of done. Status. Now peer challenge is not random. It is grounded in the shared system.

The CEO should not monopolise follow-up

If only you review the Action Register, everyone else can remain passive. Ask different leaders to review sections. Invite them to challenge misses. Build shared ownership of execution.

Watch for nervous laughter

When one leader challenges another, teams sometimes respond with awkward humour. That is data. It may indicate that direct challenge still feels unusual. Keep normalising it.

Do not rescue the room from tension too quickly

This matters. Two leaders disagree. The CEO jumps in to settle it immediately. Why? Perhaps the tension was actually productive. Let them work through it. If the conversation remains professional, some discomfort is useful. But intervene if challenge becomes personal There is a line. If it becomes:

dismissive; aggressive; humiliating; or targeted at character, step in. The standard is robust thinking, not interpersonal damage.

Teach people how to challenge

Useful phrases include:

“I see it differently because…”

“What evidence supports that?”

“What are we assuming here?”

“What happens downstream if we do this?”

“I’m not convinced this is best for the business.”

“What risk are we accepting?”

These are practical.

Teach people how to receive challenge

This matters just as much. A leader who receives challenge by becoming defensive will quickly shut the behaviour down. The better response is:

“Tell me more.”

“What are you seeing that I’m missing?”

“What evidence do you have?”

That keeps the conversation useful.

Do not punish challenge later

This destroys trust. Someone disagrees respectfully in the meeting. Later they are excluded, criticised or labelled difficult. Everyone notices. If you want honest debate, people need to know it will not be held against them.

Leaders should be able to change their mind

A mature response is:

“You’ve convinced me.”

That does not reduce authority. It strengthens decision quality.

Stop turning every disagreement into consensus

Teams sometimes avoid peer challenge because they believe they must all leave equally happy. No. You need enough debate to improve the decision. Then clarity about what happens next. Debate before. Alignment after. Challenge should be strongest before the decision.

Once a legitimate decision is made, the team needs to support it professionally. That creates both rigour and cohesion.

Watch for passive resistance afterwards

A leader may say nothing in the meeting. Then quietly undermine implementation. That is far more damaging than respectful disagreement earlier. Make it clear: speak now; then align. Ask whether they challenge only when their own department is affected This is revealing.

A true leadership-team member challenges because the business issue matters. Not only because their own function loses something. Business-first challenge has a wider lens.

Challenge can protect the CEO too

The CEO is not always right. A strong team should be able to say:

“I think you’re missing something.”

If nobody can challenge the CEO, you do not have full leadership capability. You have deference.

Invite challenge of your own thinking

Ask:

“What am I missing?”

“Who disagrees with me?”

“What is the risk in my position?”

Then do not punish the answer. That models the culture.

Do not answer your own question

This happens. CEO asks:

“What am I missing?”

Three seconds pass. Then CEO explains why the idea is still right. Stop. Wait. Let the team speak.

The CEO’s status magnifies everything

A casual comment from the CEO can shut down debate.

“I think this is obvious.”

Now who wants to disagree? Be aware of your weight in the room.

Use structured challenge if needed

For important decisions, deliberately assign someone to test the recommendation. Not as permanent devil’s advocate theatre. Just as a discipline. What are the risks? What assumptions are weak? What would make this fail? That can improve thinking.

Rotate who leads parts of the meeting

This can also build ownership. Let different leaders: present the score; chair a section; lead a decision; review commitments. The team becomes less CEO-centric.

Make peer accountability part of leadership development

If a manager can challenge employees but not peers, they still have development work to do. Senior leadership requires influencing sideways as well as downward.

Ask what stops them

In one-on-ones, ask:

“Where are you holding back from challenging the leadership team?”

The answer may be revealing. Fear? Trust? Politics? Uncertainty? Then develop the gap.

Recognise good peer challenge

When somebody respectfully raises an important point, say:

“That was useful challenge.”

It signals that the behaviour is wanted.

Recognise people who change their view too

The receiver matters.

“I appreciated that you listened and changed your position when the evidence changed.”

That reinforces maturity at both ends.

Build shared standards

A leadership-team code might include: Business first. Challenge directly. Bring evidence. Say what needs saying in the room. Support decisions afterwards. Hold commitments. No triangulation. Now peer accountability has a shared base.

Stop triangulation

Triangulation is when A has a problem with B but takes it to C. Leadership teams can become full of it. Encourage: A talks to B. Directly. If help is genuinely needed, fine. But do not become the permanent intermediary. Ask: have you spoken to them? This may be one of the CEO’s most useful questions. When a leader complains about another leader:

“Have you spoken to them?”

If not:

“Why not?”

That pushes accountability back sideways.

Do not become the complaint desk

If senior managers know they can vent to you instead of resolving issues with each other, they will. Listening is sometimes appropriate. But do not let complaint replace action.