If your executive team feels aligned, but there is something not quite right, ask yourself these leadership questions, starting with this one:
When was the last time you disagreed properly about something that mattered?
Many leadership teams mistake calm meetings, polite agreement, and steady activity for alignment. In reality, avoidance often looks like harmony. Silence gets misread as consensus. Motion gets mistaken for progress.
This article is not about culture or intent; nor is it about effort.
It is about the questions leadership teams know they should ask — and quietly avoid because the answers are disruptive, politically awkward, or financially uncomfortable.
Most leadership problems reduce to one of four things:
- A people and capability problem
- A strategy and direction problem
- A path and momentum problem
- A team and governance problem
The leadership questions below are designed to help you work out which one you are actually facing.
A. People & Capability Leadership Questions
1. Do we have the right people in the right roles — or just the least-bad compromise?
This question is rarely asked directly because it immediately raises uncomfortable follow-ups.
Legacy appointments. Loyal performers who have outgrown their role. Strong individuals placed into positions that no longer match the shape or maturity of the organisation.
Over time, leadership teams make quiet trade-offs:
- “They know the business.”
- “Now isn’t the right moment.”
- “Changing this would cause disruption.”
The result is not a people problem. It is a role-clarity and courage problem.
When the least-bad compromise becomes the default, the organisation slowly optimises around constraint rather than capability — and leadership effort quietly increases to compensate.
2. Where are we tolerating underperformance because dealing with it feels costly?
Every executive team can point to at least one area where standards have slipped — not because expectations are unclear, but because consequences are awkward.
Underperformance is most often tolerated when:
- The individual has political capital
- The role touches sensitive stakeholders
- The cost of intervention feels higher than the cost of drift
The tell is almost always financial.
Missed targets explained away as timing issues.
Margins eroded “temporarily”.
Forecast accuracy reframed as volatility rather than discipline.
When financial underperformance is consistently contextualised rather than confronted, accountability has already slipped — even if the numbers are technically being reported.
3. Who is carrying responsibility without authority?
This is one of the clearest indicators of structural failure.
When responsibility and authority are misaligned:
- Decisions escalate unnecessarily
- Capable people burn out
- Heroics replace leadership
Progress becomes dependent on individuals compensating for broken structures rather than the system working as designed.
Responsibility without authority is not empowerment.
It is abdication upstream — and it always shows up later in missed outcomes, not org charts.
B. Strategy & Direction Leadership Questions
4. What would we stop doing if this strategy were genuinely real?
Most strategies explain what the organisation will do more of.
Very few clearly state what will stop.
A strategy only becomes real when it forces choices.
Choices mean trade-offs. Trade-offs create consequences.
If the strategy were genuinely in charge, some activities would be paused, reduced, or cancelled.
Some teams would miss their targets as a result — by design.
If nothing would stop, nothing would fall short.
And if nothing would fall short, the strategy is not governing the business. It is simply being written down while finance records the outcome.
When stopping work feels harder than starting new initiatives, what you have is not a strategy.
It is permission to carry on as before.
5. What decision have we delayed that would clarify direction immediately?
Every leadership team knows the decision that would remove ambiguity — and almost always explains its absence as prudence.
“We need more data.”
“It’s too early.”
“Let’s see how the next quarter goes.”
In practice, delayed decisions rarely reflect uncertainty alone.
They reflect fear of consequence.
Clarity forces commitment.
Commitment forces accountability.
And accountability removes optionality.
That is why the decision keeps moving.
6. Where is activity masking the absence of choice?
Busy organisations can look decisive while avoiding direction entirely.
Scores of initiatives. Increased reporting. More daily, weekly, monthly meetings.
Dashboards often make this worse, not better.
When leadership attention focuses on activity metrics rather than outcome thresholds, teams quickly learn what really matters:
staying busy, staying green, and staying off the escalation list.
Metrics without consequence do not create control.
They create comfort, and ultimately failure.
C. Path & Momentum Leadership Questions
7. What evidence would tell us we’re on the wrong path — and are we listening for it?
Most organisations collect performance data.
Far fewer collect disconfirming evidence.
Leadership teams are often very good at reinforcing a chosen narrative and very poor at recognising signals that challenge it.
The most dangerous signals are rarely operational.
They are financial.
Slippage explained as seasonality.
Margin erosion treated as investment.
Forecast misses reframed as prudence.
When financial signals are continually normalised, leadership teams stop asking whether the path is wrong — and start asking how to endure it.
8. Where are we confusing persistence with progress?
Persistence is a leadership virtue — until it becomes an excuse.
Staying the course can look like conviction.
It can also look like sunk-cost bias with better language.
Progress should reduce uncertainty, not entrench it.
If effort increases while clarity does not, persistence may be protecting the wrong decision.
D. Team & Governance Questions
9. Where do we mistake agreement for alignment?
Agreement is easy to manufacture.
Alignment is not.
Alignment shows up after the meeting:
- In decisions made consistently
- In priorities that do not drift
- In behaviour that matches words
If conversations are calm but execution diverges, alignment has not been tested — it has been assumed.
Nodding is not commitment.
Silence is not consent.
10. What decisions are made in corridors rather than in the boardroom?
This is one of the most reliable indicators of weak governance.
When decisions migrate outside the room:
- Accountability blurs
- Informal power replaces formal authority
- Relationships are protected instead of outcomes
Corridor decisions do not indicate agility.
They indicate that the room is no longer trusted to hold consequence.
Closing: How leadership teams actually fix this
These problems do not get fixed with better language, more workshops, or another reporting layer.
They get fixed when leadership teams make five deliberate moves — and stick to them.
1. Re-anchor accountability to decisions, not roles
Stop asking who owns the function.
Start naming who owns the decision — and what happens if it misses.
If responsibility cannot be traced to a decision-maker with authority, the problem is structural, not personal.
2. Make strategy financially visible
Every strategic choice should create:
- Something that stops
- Something that loses funding
- Something that no longer gets protected
If strategy does not create financial consequences, it is not governing the business.
3. Redefine metrics as thresholds, not indicators
Metrics should answer one question:
What would we do differently if this went red?
If the answer is “review it”, “note it”, or “monitor it”, the metric is informational — not governing.
Leadership teams fix this by linking a small number of metrics to:
- Pre-agreed decisions
- Pre-agreed trade-offs
- Pre-agreed escalation rules
4. Move the hardest conversations back into the room
Softened truths, corridor decisions, and post-meeting reinterpretation are not cultural quirks.
They are governance failures.
The fix is not more candour.
It is restoring consequence to the room where authority sits.
5. Align resources to the strategy — or admit it isn’t one
Strategies fail most often at the handover from intent to execution.
Not because teams don’t care.
Because the work, people, and time were never re-aligned to match the choices that were made.
A real strategy requires leadership teams to actively rebalance:
People across teams
Time across priorities
Capacity across the year
If every team is still fully committed to last year’s priorities, the strategy is already compromised.
Alignment is not a cascade exercise. It is a reallocation decision. If leadership is unwilling to move resources — or to say what will now move slower, slip, or stop — then the strategy exists only on paper.
At that point, delivery failure is not an execution problem.
It is a leadership one.
The real test
Leadership maturity is not measured by how aligned a team sounds.
It is measured by how quickly it confronts the uncomfortable, financially real consequences of its own choices.
If this article felt uncomfortably familiar, that is not a signal to soften the questions.
It is a signal to start using them — properly.