These are not hostile questions. They are the questions a well-prepared client asks.
1
"You mentioned personalisation. You didn't mention the Advantage Card. Why?"
17 million active members. The most valuable asset Boots has in an AI context. The absence of this in the pitch is the first question to ask.
2
"Which of your three case studies involved a loyalty dataset above 10 million members?"
Scale matters. Personalisation at 50,000 customers and at 17 million are different engineering and governance problems.
3
"How do you handle AI recommendations that touch prescription or pharmacy services?"
Boots is not just a retailer. The compliance layer for anything touching pharmacy is significant. Has the agency thought about it?
4
"What's your governance model for working with Advantage Card data?"
Clean rooms, data sharing agreements, PII handling. If this isn't already scoped, that's a significant gap.
5
"How does the Walgreens Boots Alliance context affect your AI architecture?"
The parent company relationship has data and compliance implications. An agency working at this level should have asked the question before pitching.
6
"You pitched 'hyper-personalisation'. Name one AI output that Boots customers would receive differently based on their Advantage Card history."
One concrete example. If they can't give it, the personalisation narrative is aspiration.
7
"What does your AI do when a recommendation conflicts with a pharmacist's advice?"
This is a real edge case for Boots. A blank look is the wrong answer.
8
"Which health or pharmacy brands have you deployed AI for in a live, post-pilot environment?"
Not explored, not tested — deployed and live. Pilot case studies don't count.
9
"What's your unit cost model for personalised content at Boots' volume?"
At 17 million members, the economics of personalisation need to be in the brief. Was this covered?
10
"If we gave you the Advantage Card data under a governance agreement, what would you build first?"
The answer to this question tells you more than the rest of the pitch. It separates people who've thought about Boots specifically from people who've recycled a generic AI presentation.