The Board Pack Was Perfect. The Decision Was Not.
Thursday 8 October — Art of Leadership (I) · Boards
The table
The case
Subtitle: A fictional leadership case for discussion. Source: The owner's own case (Dražen Kapusta, 2026-09-13), verbatim — the eight questions are his
The board pack arrived three days early.
It contained an executive summary, market analysis, financial scenarios, an integration plan and a carefully structured risk register.
Management recommended acquiring a smaller competitor.
The target offered access to a new customer segment, technical expertise and a strong regional reputation. The financial model showed a plausible route to attractive returns.
AI had helped the deal team organise documents, compare information and prepare answers to likely board questions. The team had reviewed the final material.
At the meeting, the discussion was focused.
Directors asked about price, integration capacity and customer concentration. Management answered each question. The board approved the acquisition subject to final conditions.
There had been no failure to make a decision.
Six months later, the chair reopened the pack.
The information still looked impressive.
She now saw a question nobody had asked clearly enough.
What They Believed They Were Buying
The acquisition thesis rested on three ideas.
The target had loyal customers. Its specialist employees would strengthen the combined business. The buyer’s systems and commercial reach would help it grow.
Each claim had supporting evidence.
Customer retention had been strong. The technical team had a good reputation. The buyer had successfully expanded other business units.
What the pack explored less thoroughly was how those strengths depended on the target’s existing way of working.
Customers valued direct access to experienced people who could make commitments quickly. Employees valued discretion and a close relationship with the founder.
The integration plan would change both.
The buyer intended to centralise approvals, standardise offers and move customer communication into a shared service structure.
Those changes supported the projected efficiencies.
They also touched the reasons customers and employees had stayed.
Facts Inside the Wrong Frame
During due diligence, several customers had praised the target’s responsiveness.
The observation appeared in the commercial section as evidence of customer satisfaction.
Employee interviews highlighted autonomy and access to the founder.
That appeared in the people section as a cultural consideration.
The integration plan described standardisation as an operational benefit.
Each section was reasonable on its own.
The connection between them was weak.
Nobody had explicitly tested whether the planned efficiencies would erode the capabilities supporting the growth forecast.
The board had reviewed the facts through the frame management supplied: an attractive business that would perform better inside a larger platform.
An alternative frame received less attention: a valuable business whose strengths might be damaged by the proposed integration.
How the Recommendation Became More Convincing
The chair asked the deal team to reconstruct how the pack had developed.
The initial mandate had been to assess the acquisition.
As negotiations progressed, the work increasingly focused on completing the transaction and preparing an approval recommendation.
AI was asked to summarise evidence, refine the strategic case and strengthen explanations of the proposed benefits.
It performed those tasks well.
It was asked less often to construct the strongest case against the deal or identify evidence inconsistent with the integration thesis.
Qualifying language also became shorter as material moved into the executive summary. “Customers interviewed during diligence” became “customers.” A small set of positive conversations came to support a broader statement than the evidence justified.
A risk involving key employees remained in the pack, with retention measures listed beside it.
That made the issue look addressed. Whether the proposed measures would preserve the working conditions those employees valued remained uncertain.
The result was a coherent argument whose most consequential assumptions had not received equal attention.
When the Early Signals Arrived
After completion, the integration team met its first milestones.
Systems migrated. Reporting became more consistent. Procurement savings began to appear.
At the same time, some customer decisions took longer. Two experienced employees left. A major account delayed renewing its agreement.
The integration dashboard remained largely positive because it measured completion of the planned work.
The chair asked for a different view.
Were customers still receiving the responsiveness they valued? Could technical employees still make the decisions needed to serve them? Were the projected savings creating costs elsewhere?
Management began changing the integration approach.
The deal could still succeed. But recovering lost confidence would take work that the original plan had not anticipated.
Reopening the Decision with the Tribe
At a COTRUGLI COlab session, the chair brought an anonymised version of the case.
She asked alumni to work from the information available before approval.
One group acted as management. Another examined how the target’s strongest employees might experience the integration. A third considered the choice from the perspective of an important customer.
A fourth group built a credible account of how the acquisition could disappoint despite meeting its integration milestones.
AI helped organise the competing arguments and link claims to the supplied material. Participants checked those links and challenged inferences that went beyond the evidence.
The exercise exposed the central tension quickly.
The chair was cautious about hindsight. Knowing that problems had emerged made warning signs easier to spot.
She therefore asked which questions the board could reasonably have raised at the time.
At dinner, an alumnus who had sold his own company offered a perspective missing from the original discussion.
“You described the freedoms you planned to remove as inefficiencies,” he said. “Some may have been. Others were how the business served its customers.”
The chair wrote that down.
The Next Recommendation
The board would soon consider another major investment.
The chair wanted the next pack to make the decision easier to examine.
She proposed requiring management to identify the assumptions carrying the greatest weight, show the evidence supporting and challenging them, and explain what early results would weaken the investment thesis.
Directors would also examine a credible alternative use of the same resources.
She did not want every recommendation buried under more material. The discipline needed to sharpen attention.
The central task was to understand what had to remain true for the decision to make sense—and whether the company’s own actions could change it.
The CDayZ Leadership Challenge
You are the board reviewing the next major investment proposal.
Design a discussion that tests the recommendation’s underlying logic, the quality of its evidence and the effects of management’s planned actions.
Specify what belongs in the board pack, which perspectives should be heard and how the investment thesis will be reviewed after approval.
Discussion Questions
The owner's "Eight Questions for the Room":
- What was the most consequential assumption in the acquisition thesis?
- Which available facts should the board have considered together?
- How would you distinguish evidence from interpretation?
- How could AI strengthen or weaken this review?
- Whose perspective was missing from the decision?
- What could the board reasonably have challenged before approval?
- How would you use a COTRUGLI COlab session to test a major decision?
- What evidence should trigger a review after approval?
Explain how it connected customer loyalty, employee capability and the planned integration.
Identify the connections that were weakened by presenting information in separate sections.
What would you require management to show about sources, sample size, uncertainty and the reasoning behind important claims?
Compare using it to refine a recommendation with using it to challenge assumptions, surface contradictions and examine alternative explanations.
How would you bring customer, employee or operating experience into the discussion without treating a few voices as representative of everyone?
Separate a fair critique of the original process from conclusions made easier by knowing what happened later.
Define the roles, source material and challenge process needed to produce useful scrutiny while preserving confidentiality and decision ownership.
Choose indicators that test whether the investment thesis remains sound, alongside measures of implementation progress.
A Lesson for the Next COTRUGLI Generation
A persuasive recommendation can contain accurate facts and still connect them badly.
Leaders improve judgement by examining assumptions, inviting relevant perspectives and considering how their own actions may change the conditions on which a plan depends.
AI can support that work when it is asked to expose uncertainty and competing explanations. The COTRUGLI tribe adds lived experience and the trust needed to challenge an attractive story.
The board had approved a plan to make the business stronger.
Its next task was to understand more precisely what made the business strong in the first place.
Your comment on this chapter
A question for the table, a disagreement, what you would have done. The case lead reads every comment; the ones the table takes up enter the chapter as questions from the room, with your name.