Are You Going to Be Sears or Walmart? A Harvard Professor's AI Question for Tour Operators
Last week I watched an interview with Karim Lakhani, a Harvard Business School professor who runs AI experiments with thousands of workers at companies like Procter & Gamble. About 47 minutes in, he tells a retail story I keep coming back to.
When Amazon showed up in the late ’90s, most retailers laughed it off. “Oh, how cute,” is how Lakhani puts it. Jeff Bezos rethought retail from the inside out, while Kmart and Sears added a website to their product database and never adjusted. Walmart struggled for a long time, then figured it out, and today it’s as competitive as it ever was.
Then he asks the question he now puts to every established company: “Are you going to be Walmart or are you going to be Kmart?”
His reasoning matters for us. A company is a bundle of expertise: people who know how to answer a guest, price a tour, build a schedule, close the month. AI is pushing the cost of a lot of that expertise toward zero. When that happens, the businesses that bolt the new tool onto the old way of working fall behind the ones that rebuild around it.
You can watch the full interview here.
What the Sears move looks like in a tour business
The Sears move is opening ChatGPT or Claude a few times a week to write a social post or tidy up an email. It helps, and you save twenty minutes here and there. Nobody’s role changes, though. The inbox is still yours at 9 pm, month-end still eats a day, and the business runs the way it did in 2022.
Most operators I talk to are here. That’s where everyone starts, and it’s the AI equivalent of Sears putting its catalogue online.
What the Walmart move looks like
Walmart didn’t copy Amazon’s warehouses. It used the asset it already had, thousands of stores, and rebuilt the systems behind them so each store could fill online orders.
Your asset is already there too: your guides, your reputation and the experience guests come for. The Walmart move is rebuilding the work behind it, so your team hands the repetitive part of each role to AI every day. Guest emails, booking changes, schedules, reports, follow-ups, and all the copying and pasting between your booking system and your inbox.
Here’s what that has looked like for operators who’ve been through our training:
- Andrea Dominguez, Discovery Pisa, built a scheduler that folds four calendars into one, counts heads and assigns guides. Month-end now takes 10 minutes, and she gets about three hours a day back in high season.
- Jason Capps, Jason’s Journeys, had AI search his old enquiry emails for warm leads. One filled the last two spots on his Puglia trip, which he puts at “about 16,000 in added revenue.”
- Christian Hoeffel, Vineyard Voyages, has AI posting to social media three times a week, and his rosters and waivers move into Xola on their own. In his words: “I feel like I’m finally the CEO of my business.”
None of them rebuilt the whole company at once. Each picked one recurring job, handed it over properly, and then moved to the next.
Three questions to find out which one you are
- If you were away for a week, which jobs would pile up? Those are your first candidates, because they’re the ones only you are doing.
- Does anyone on your team use AI for more than writing? If AI only drafts text in your business, you’re on the Sears side for now.
- Does your AI know your business? If everyone starts from a blank chat and re-explains your tours, policies and tone every time, the setup is costing you more time than it saves.
Where we’re putting our effort
Over the past decade we’ve coached 2,500+ tour, activity and attraction businesses. Guest Focus is now an AI training company for experience businesses, and the best place to start is our 1-Week AI Bootcamp.
- Three live sessions: Tue Nov 10, Thu Nov 12 and Tue Nov 17, noon to 1:30 pm Eastern (9 am Los Angeles, 5 pm London), with replays
- See what operators have handed to AI, and how we run Guest Focus with it
- Leave with two AI employees set up for your business: an Inbox Manager that drafts your guest replies, and one that helps ChatGPT, Claude and Gemini recommend you
- From $97, and you can bring your team for $97 a person
- Session 1 guarantee: come to Session 1 live or watch the replay, and if it isn’t right for you, email [email protected] before Session 2 starts for a full refund
Registration closes Monday, Nov 9 at 11:59 pm Vancouver time.



