The Season Was Full, but the Destination Wanted More
Wednesday 7 October — Art of Trade · Hotels & tourism
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
On the last Saturday of August, the hotel owner walked through a full restaurant towards a terrace overlooking the sea.
The season had been strong. Her team had handled the busiest weeks well. Guest reviews were encouraging, and several families had already asked about returning the following summer.
At one table, a guest stopped her.
“We would love to come back in November. What would you put together for us?”
She began listing possibilities: food, wine, sailing when the weather allowed, nearby cultural sites.
“Could someone organise the whole stay?” he asked. “There might be twelve of us.”
She said yes before she knew exactly how.
On Monday, she called a restaurant owner, a guide and a friend who organised private transfers. Each liked the idea. Each asked different questions.
By Wednesday, she had become the unpaid coordinator of a small holiday programme.
By Friday, she was wondering why something so promising was so difficult to buy.
The Ambition Beyond August
At the next gathering of local business leaders, she told the story.
The room understood the opportunity immediately.
A restaurateur wanted enough predictable autumn business to retain more of his team. An experience operator had excellent guides who needed work beyond the summer peak. A local producer wanted visitors to spend time understanding his products, then remain customers after going home.
The hotel owner wanted guests who stayed longer and returned for reasons beyond the weather.
Nobody was proposing to abandon a successful summer season. They wanted to build on it.
The destination already had much of what it needed: capable people, distinctive places, good food, hospitality and stories worth travelling for.
What it lacked was an offer that those people could reliably deliver together.
“We all have something to sell,” the restaurateur said. “Who owns the experience between us?”
The Itinerary That Could Not Be Booked
The hotel’s marketing manager arrived at the next meeting with an AI-generated autumn itinerary.
It looked excellent.
There was a producer visit, a private dinner, a coastal excursion, a cultural programme and an evening designed around local music. Different versions addressed couples, executive groups and families.
Then the operators began checking it.
The producer did not receive visitors on the proposed day. The excursion depended on weather and needed a credible alternative. One dinner required a minimum group size. The transfer timings left no margin for delays.
The AI had helped them imagine and describe a coherent experience. The businesses had yet to make it real.
They revised the itinerary together.
This time, each element had an owner, actual availability and a clear price. They identified what could be personalised and what needed to remain fixed. They discussed who would answer a guest at nine in the evening if something changed.
The work was slower than generating the first proposal.
It also brought them closer to something a customer could confidently purchase.
Whose Guest Was It?
As the offer became more concrete, the commercial questions became harder.
The hotel would bring the first customers. Did that make it the natural coordinator?
The experience operator already knew how to manage bookings and changes. Should that business run the programme instead?
The restaurateur worried about being treated as an interchangeable supplier. The producer wanted a direct relationship with visitors who might later order from him.
One participant proposed a common brand. Another asked who would pay to build it.
They also disagreed about what success meant.
For the hotel, it might mean additional room nights. For the restaurant, profitable covers on otherwise quiet evenings. For the guide, enough confirmed work to plan ahead. For residents, a programme that respected daily life and brought worthwhile local activity.
An offer could succeed for one participant while disappointing another.
The hotel owner had convened the group. She now needed to help it become a working partnership without allowing the project to consume her own team.
Experiencing It Together
She invited two COTRUGLI classmates to spend a weekend testing the proposed programme alongside the local partners.
One led a business that regularly brought management teams together. The other had experience building partnerships across independent companies.
They arrived as participants, with permission to question everything.
Over two days, the group travelled together, ate together and watched how the experience connected. A conversation with a producer became the highlight of the afternoon. A supposedly essential stop felt rushed. An unplanned dinner discussion lasted much longer than the formal programme.
One classmate observed that the itinerary left too little time for guests to enjoy one another.
“You have filled every hour,” she said. “Where does the group become a group?”
The local partners saw it themselves. The shared table, the walk after dinner and the relaxed conversation on the transfer were part of what people would remember.
By Sunday, they had removed two activities and strengthened the remaining ones.
They had also learned how each partner behaved when plans changed. That experience gave their commercial discussion a firmer basis than another presentation would have done.
The First Commitment
The hotel owner proposed a small autumn programme aimed at leadership teams and groups travelling through trusted networks.
The first guests could come through COTRUGLI alumni introductions. The experience would still need to earn its price and stand on its own quality.
Before accepting bookings, the partners had to agree on coordination, payments, service standards, cancellations and the response when one element failed.
AI could support enquiries, tailor proposals and organise feedback using information the partners maintained. Someone still needed authority to confirm what the whole group could deliver.
They had two weeks to put that arrangement in place.
The original guest had written again.
“Have you had a chance to think about November?”
This time, the hotel owner wanted to answer with an offer her partners were ready to keep.
The CDayZ Leadership Challenge
You are the founding group behind the autumn programme.
Choose the first customer segment and design an experience that gives people a compelling reason to travel outside the main season.
Agree who coordinates delivery, how each partner benefits and what must be confirmed before the first booking. Your proposal should work at a small scale and reveal whether a broader destination partnership is worth building.
Discussion Questions
The owner's "Eight Questions for the Room":
- Who should be the first customer?
- What is the shared promise to that customer?
- Who should coordinate the offer?
- How would you make participation worthwhile for every partner?
- Where would AI make a useful contribution?
- How would you protect time for connection and shared experience?
- How could the COTRUGLI tribe help develop and test the offer?
- What would justify running a second season?
Which group has a strong reason to visit outside summer, and what would make the experience worth organising a trip around?
Describe the complete experience and identify which moments most strongly influence whether guests return or recommend it.
What authority, resources and compensation would that role need to manage independent partners reliably?
Address commercial returns, customer relationships and the work involved in preparing and delivering the programme.
What information must remain accurate, and which commitments should require confirmation from the people delivering them?
What role should meals, informal conversation, celebration and unstructured time play in the programme?
Which alumni could contribute as customers, hosts, partners or candid reviewers, and how would you turn their feedback into improvements?
Define success for guests, participating businesses and the destination, including how you would recognise uneven benefits or excessive coordination costs.
A Lesson for the Next COTRUGLI Generation
A successful season can create the confidence to pursue a larger ambition.
Building that ambition across a destination requires independent businesses to understand the experience they create together. Availability, handovers, shared standards and commercial agreements become part of hospitality.
The tribe grows through the same process. People learn how others work, share responsibility, solve problems and enjoy what they have made possible.
The guest’s question had sounded simple:
“Could someone organise the whole stay?”
Answering it well required the destination’s leaders to organise themselves.
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.