How Do I Know If I Have the Right People in My Leadership Team?

Start with the role, not the person

This is essential. Ask:

“What does this leadership role need now?”

Not:

“How do we make this role fit the person who currently has it?”

Those are very different questions. The business should define the role. Then you assess whether the person can carry it.

Yesterday's right person may not be today's right person

That is not an insult. The business may have changed dramatically. A person who was excellent when the business had ten employees may struggle when it has fifty. A manager who could run one location may not be able to lead five. A functional expert may struggle with enterprise-wide leadership. Growth changes the job.

Loyalty matters — but it cannot answer every question

Long service is valuable. History matters. Trust matters. But leadership roles also carry consequences. If the business now requires something the person cannot provide, loyalty alone does not solve the gap. You can value someone's contribution and still need an honest role conversation.

Ask what the seat requires

For each leadership role, define: what outcomes it owns; what decisions it needs to make; what level of judgement is required; what leadership behaviour is expected; what capability it must build below. That gives you something real to assess against.

Do not assess leadership only by technical competence

A technically brilliant person can still be the wrong senior leader. Leadership needs more. Can they: make decisions; develop people; handle difficult conversations; work across functions; use evidence; challenge appropriately; think about the whole business? That is a different test.

Ask whether they think business-first

This is one of the strongest indicators. Do they ask:

“What is best for the business?”

Or mainly:

“What is best for my department?”

A leadership-team member has two jobs. Lead the function. Lead the business.

Watch the language

Language gives clues.

“They won't let us.”

“Finance's problem.”

“Operations should fix it.”

versus:

“Here is the part we own.”

“Here is the business impact.”

“Here is what I recommend.”

The second sounds like leadership.

Ask whether they can carry decisions

Do they decide within their authority? Or constantly wait for the CEO? A leadership role should carry significant judgement. If the person still needs permission for ordinary decisions, something needs developing.

Ask whether the quality of escalation is rising

Senior leaders will still escalate. But the level should rise. They should bring: complexity; high consequence; real strategic trade-offs. Not ordinary operational decisions they should reasonably own.

Ask whether they bring problems or thinking

A strong leadership-team member says:

“Here is the issue. Here is the evidence. These are the options. This is what I recommend.”

That is very different from:

“What do you want me to do?”

Ask whether they can disagree with the CEO

This matters. If somebody will never challenge you, are you getting their leadership judgement? Or merely their compliance? Strong leaders should be able to say:

“I don't agree, and here's why.”

Professionally. With evidence.

Ask whether they can receive challenge

The reverse matters too. When questioned, do they: listen; consider; change their mind where appropriate? Or become defensive? Leadership teams need people who can both give and receive challenge.

Ask whether they challenge peers directly

Do they address issues with each other? Or bring every disagreement to the CEO? A mature leadership team needs horizontal relationships. Not constant triangulation.

Ask whether they support decisions afterwards

Challenge before. Alignment after. A leader who disagrees in the room and then professionally supports the agreed decision can be very strong. A leader who says nothing, then undermines it later, is damaging.

Ask whether they keep commitments

This sounds simple. It is enormous. Do they do what they said they would do, by when they said they would do it? Reliability at leadership level matters. If senior leaders are casual with commitments, the culture below will notice.

Look at preparation

Do they come to leadership meetings prepared? Evidence? Thinking? Recommendations? Or do they arrive and improvise? Preparation is a leadership behaviour.

Ask whether they can see patterns

Strong leaders do more than respond to incidents. They ask: Why does this keep happening? What system is weak? What are we learning? That is increasingly important at senior level.

Ask whether they develop people

Who is stronger because this leader manages them? Who can carry more? Who has grown? Who could succeed them? Leadership is not simply personal delivery.

Look beneath them

This is one of the best tests. Strong beneath them? Or permanent dependency? If every decision still needs the leader, they may be producing results but not building capability.

Ask whether they build successors

Nobody should deliberately make themselves irreplaceable. A good leader should be building shoulders beneath them. That creates resilience.

Ask what happens when they are away

Does the function continue? Or does everything stop? Absence reveals the structure beneath the leader.

Ask whether they hold standards

Do they address poor performance? Or tolerate it? Do they allow exceptions for favourites? Do they protect the good people? Senior leaders shape culture through what they accept.

Ask whether they have difficult conversations

A leadership title does not remove this responsibility. Can they address: performance; behaviour; conflict; missed commitments? Or does the CEO eventually have to do it for them?

Ask whether they use evidence

Strong senior leaders should increasingly move away from:

“I feel like…”

towards:

“Here is what the evidence shows.”

That improves decision quality.

Ask whether they know their numbers

They do not need to be accountants. But they should understand the measures that matter in their area. Performance. Drivers. Risk. A leader who does not know whether their function is healthy is operating blind.

Ask whether they understand commercial consequence

Senior leadership requires commercial thinking. How does the decision affect: margin; cash; customer; capacity; risk? Not every leader starts with that skill. But they should develop it.

Ask whether they can prioritise

Growing businesses generate endless work. Can the leader distinguish: important; urgent; noise? Or does everything become top priority? Senior leaders need judgement about focus.

Ask whether they create clarity beneath them

Do their people know: what matters; what good looks like; who owns what; what decisions they can make? A leader's team often reflects the clarity of the leader.

Ask whether their function creates constant friction

Every function has issues. But if one area continually produces: confusion; missed handovers; conflict; surprises; ask what is happening at leadership level. The problem may not be the leader. But it deserves investigation.

Ask whether the CEO is compensating for them

This is a major clue. What are you doing because this leader is not doing it? Making their decisions? Managing their people? Fixing relationships? Checking their work? Running their meetings? If you are continually compensating, the role may not be fully carried.

Ask whether peers are compensating too

Perhaps the CEO is not rescuing. Another leader is. Finance keeps fixing Sales. Operations keeps compensating for Customer Service. The strongest leaders quietly carry the gap. That can hide the real issue for a long time.

Ask what the rest of the team knows

Sometimes everybody knows one leadership seat is weak. Except nobody says it. The awkward silence is information. This does not mean gossip should decide careers. But recurring peer concerns with evidence deserve attention.

Distinguish personality from capability

You do not need a leadership team full of identical personalities. Quiet can be strong. Direct can be strong. Analytical. Creative. Different is useful. The question is whether the person can carry the role.

Beware charisma

Confidence can be persuasive. So can fluent language. But ask for evidence. What have they built? What has improved? Who have they developed? What decisions have they carried well? Leadership is more than presence.

Beware the invisible strong leader too

The opposite mistake happens. Some people are not flashy. But they are: reliable; thoughtful; commercial; calm; good with people; trusted. Do not overlook substance because it is quieter.

Ask whether they care enough

Skill matters. So does willingness. Do they give a fuck? Do they prepare? Follow through? Learn? Take responsibility? You can develop a lot. It is much harder to develop care.

Distinguish can’t from won’t

A person may be willing but currently not capable. That can be developed. Another may be capable but not willing to carry the leadership standard. That is different. Know which problem you have.

Ask whether they are learning

The right leader does not need to know everything. But they should be growing. Can they take feedback? Apply it? Change behaviour? Leadership roles evolve. Learning matters.

Look at defensiveness

Everyone gets defensive sometimes. The question is pattern. Does feedback become: excuses; blame; counterattack; withdrawal? Or eventually: reflection; ownership; change? That tells you something.

Ask whether they can admit they were wrong

This is powerful. A leader who can say:

“I got that wrong.”

and change course may be stronger than one who never appears wrong because they never admit it.

Ask whether they make the business calmer

Strong leaders tend to create: clarity; reliability; fewer surprises; better decisions. Weak leadership often creates repeated noise around the role. That is worth noticing.

Do not confuse firefighting with strength

A leader may constantly save the day. Why does the day keep need saving? Look at whether the underlying function is becoming stronger.

Ask whether results depend too much on personal heroics

Strong quarter. But achieved through: late nights; constant intervention; key-person dependence. That may not be sustainable leadership.

Sustainable performance matters

Good leadership should gradually create systems and capability that survive normal pressure. Not only exceptional effort.

The right person should be able to grow with the seat

Ask:

“What will this role require two years from now?”

Can the person plausibly grow into that? That helps you look forward, not only backward.

Potential matters, but evidence matters too

Do not make major leadership decisions entirely on hope. What evidence suggests the person can grow? How have they responded to previous stretch? That creates a more grounded view.

Stretch before promotion where possible

Give someone a larger decision. Cross-functional project. Meeting leadership. Additional authority. Observe. That gives real evidence before permanently changing the seat.

Give development a fair chance

If the gap is developmental: make expectations clear; provide coaching; give support; set a timeframe; review evidence. Do not expect instant transformation. But do not leave development open forever This is where CEOs often get stuck.

“We're still working on it.”

For how long? What specifically should be different? By when? What evidence will show progress? Development needs a destination.

Define What Success Looks Like

For each leadership role: results; behaviours; management expectations; decision quality; people development. Make it explicit. Then both sides know the bargain.

Use evidence over time

A single bad month does not define someone. Nor does one brilliant presentation. Look for patterns. That creates fairer decisions.

Do not wait until you are furious

If doubts exist, address them early. Otherwise the CEO may compensate for years and then suddenly decide:

“I can't take this anymore.”

That is not a good process.

Have the conversation while improvement is still possible

Clear. Evidence-based. Respectful.

“This is what the role requires. This is where I see the gap.”

Then agree what needs to change.

Wrong seat does not always mean wrong person

Important. Someone may be valuable to the business but wrong for the current leadership role. Could they move? Take a specialist role? Carry different scope? Do not force a binary answer too quickly.

But do not invent meaningless roles Sometimes businesses create a vague special role simply to avoid a difficult people decision. Be careful. A role should exist because the business needs it.

Leadership-team seats are expensive

Not merely salary. They affect: decisions; culture; execution; staff; customers; CEO capacity. A weak senior seat has a large multiplier.

Ask whether the business has outgrown the seat design

Sometimes the person is not the main problem. The role has become impossible. Too broad. Conflicting responsibilities. Insufficient authority. Fix the structure before blaming the individual.

Assess the whole team, not only individuals

Perhaps each leader is competent individually. But collectively: no challenge; no trust; no shared ownership. That is still a leadership-team problem.

Look at the balance of capability

Does the team collectively have enough: commercial judgement; operational strength; people leadership; financial understanding; strategy; execution? You do not need everyone to have everything. The team needs enough of what the business requires.

Diversity of thinking is useful

You do not want five versions of the CEO. Different perspectives improve decisions. Provided everyone can operate within the same leadership standard.

Avoid surrounding yourself with people who always agree

Comfortable. Dangerous. You need people capable of challenging your assumptions. And avoid building a team that only fights Constant conflict is not proof of healthy challenge. The goal is constructive disagreement that leads to better decisions.

Trust matters

Can leaders rely on each other? Do they believe commitments? Can they speak directly? Do they share information? Leadership quality is partly relational.

Ask whether they act like a team outside the meeting

Do they support each other? Solve things directly? Or operate as separate kingdoms? The latter will keep the CEO in the middle.

A practical leadership-seat test

For each person ask: Can they carry the results of the role? Do they make sound decisions? Do they think business-first? Do they bring recommendations? Can they challenge and be challenged? Do they keep commitments? Do they develop people? Do they address poor performance? Do they improve systems?

Can their function operate without them? Are they becoming less dependent on the CEO? Are they growing fast enough for what the role will require? That is a serious leadership test.