Why does the same issue return in every leadership meeting?

“We have discussed this three times”

Someone says this in the meeting, usually with a mixture of irritation and hope.

There are nods around the table. The CEO asks for closure. A decision is recorded. Owners and dates are added. Six weeks later, the issue returns with slightly different slides.

Perhaps your recurring topic is pricing discipline. Sales wants room to respond to the market. Finance wants margin protection. Delivery wants fewer custom promises. Each meeting produces another approval rule, and each approval rule creates another exception.

Or perhaps the topic is empowerment. Leaders agree that decisions should move closer to the customer. The next avoidable mistake sends authority straight back to the centre.

The team has discussed the issue. It has not resolved the dilemma inside the issue.

What makes something a dilemma?

A problem can usually be solved once the cause is understood. A dilemma contains two legitimate needs that pull in different directions.

Companies need speed and quality. They need common standards and local judgement. They need control and empowerment. They need to invest for growth and protect profitability.

Choosing either side permanently would be foolish in most situations. Refusing to choose under specific conditions is equally costly.

This is why experienced leaders can spend months circling the same subject. Each person can produce good evidence for their position. Sales can show the deal that was lost because an approval arrived late. Finance can show the margin lost through accumulated exceptions. The debate gets louder while the underlying question remains unnamed: Under which conditions does speed matter more, and what risk are we prepared to carry?

Why ordinary meeting discipline does not settle it

Better agendas, pre-reads and action trackers are useful. They cannot decide how a company wants to operate.

Recurring dilemmas tend to survive meetings for five reasons.

The team debates examples instead of the operating rule

One customer discount is approved. Another is rejected. Both decisions may be correct. Nobody extracts the principle that connects them.

The next request arrives with a new set of facts, and the debate begins again.

Ask, “What rule would help a capable leader make the next five decisions without bringing each one to this room?” The answer will reveal whether the team is building an organisation or handling a queue.

Leaders defend their functions

The sales leader is expected to protect growth. The finance leader is expected to protect economics. Their disagreement can be useful.

It becomes unproductive when the CEO acts as a permanent referee. Each function presents its case, the CEO chooses, and the broader leadership team learns very little about making enterprise decisions together.

The question for both leaders is, “What would you recommend if you were accountable for the whole company?” Both retain their functional expertise and use it at enterprise level.

Abstract words conceal the cost

Agility, excellence, customer centricity, empowerment and ownership are difficult to oppose. They are also difficult to operate.

A serious choice has a cost. Faster decisions may produce more variation. Higher quality may extend turnaround time. Local freedom may make the customer experience less consistent. A standard process may reject a promising exception.

If every value in the discussion sounds positive, the team has probably avoided the choice.

Consensus is treated as proof of alignment

People agree for several reasons. They may support the decision. They may trust the person making it. They may be tired. They may intend to reinterpret it later.

Before closing the discussion, ask each leader what the decision means for their function. What will they stop doing? Which request will they now refuse? What will they explain differently to their teams?

Differences in interpretation are easier to address in the meeting than three levels below it.

The action list arrives too early

Teams often rush from debate to tasks because tasks feel productive. Draft the policy. Create the communication. Update the dashboard. Train the managers.

Those activities will faithfully spread whatever ambiguity remains in the room.

Resolve the operating choice first. The action list should carry that choice into roles, processes, measures and behaviour.

A practical way to resolve a recurring dilemma

Take an issue that has appeared in at least three leadership meetings. Give it 60 minutes and work through the following questions.

1. Name the two legitimate needs

Avoid labels that make one side sound irresponsible. “Customer focus versus bureaucracy” has already chosen a winner. “Customer responsiveness versus delivery consistency” allows a real discussion.

The language matters because leaders will struggle to examine a choice if their position has been turned into a character flaw.

2. Describe the cost of overusing each side

What happens when customer responsiveness dominates every decision? What happens when delivery consistency dominates?

Use examples from your own company. You are looking for the point where a strength starts producing damage.

3. Decide which side leads in which context

The answer may depend on customer segment, financial threshold, regulatory risk, reversibility or stage of growth.

For example:

• Standard offerings follow the published delivery model.

• Strategic accounts can request exceptions within an agreed cost and capacity range.

• Exceptions beyond that range require a named business owner to accept the margin and delivery consequences.

• The leadership team reviews patterns monthly instead of approving individual requests.

Now the company has a rule that can travel.

4. Build the choice into the system

Who has authority? What information must be visible? Which metric might expose overuse? When will the rule be reviewed? What behaviour should leaders demonstrate when an outcome goes wrong?

If authority is delegated and the first imperfect result leads to public criticism, the formal rule will lose to the lived one.

5. Test the rule against awkward cases

Easy examples create false confidence. Use the large customer with poor margins, the high performer who ignores a process, the urgent hire who falls outside the salary band, or the market opportunity that does not fit the strategy.

If the rule survives awkward cases, it may be ready for the organisation.

Sixty dilemmas, each with consequences

Over more than ten years of work with leadership teams, we developed the Dilemmas Resolution Framework. It maps sixty organisational dilemmas across strategy, execution, people, culture, communication and governance.

The framework deliberately leaves room for context. A high-growth founder-led company may choose more central involvement for a period. A mature multi-location business may move the same decision closer to its units. Its value lies in making the choice conscious, explaining it and connecting it to the way work gets done.

The framework is also the basis of our book, Hope Is Not A Strategy, which describes a deliberate process for building alignment and culture.

For your next leadership meeting, resist the urge to add another agenda item. Pick the issue that keeps returning. Write the two legitimate needs on a board. Ask where each one should lead, what it will cost and how the choice will appear in an actual decision.

If the team cannot answer those questions, another action tracker will keep you organised while the issue survives.

The Execution Readiness Assessment can help identify the dilemmas slowing execution in your leadership team.