Hospitality's Digital Disconnect
What we miss when we think AI can do everything
The not-quite-happy birthday dinner experience
It was my birthday last week. (Thanks for your belated congratulations.)
I like to tell people that I identify as 48 and a half. I will consent to adding a half year to my age every time the calendar hits March 26. That way, I can keep my dream of retiring at 65 alive.
To celebrate the occasion, which the Danes would say was a half-round birthday, Kirsten and I booked a table at a well-known, upscale restaurant.
In the booking app (yes, this Boomer uses apps to book tables, please applaud), I ticked the “birthday” box. In the field where you can write a note to the restaurant, I wrote “Celebrating my 65th birthday”.
A hostess greeted us on arrival and asked us to have a seat while reassuring us that our table would soon be available.
A couple of minutes later, she called out from behind the counter, “Who’s birthday is it?” I raised my hand and she said, “Oh. Happy Birthday.”
A second hostess showed us to our table. On the way, she asked, “Is this your first time dining at this restaurant?”
We’re not regulars, but we had previously booked it ten times on OpenTable and dropped in a few times without reservations.
We weren’t seated in the restaurant proper, which is a great spot for a romantic, celebratory evening.
Instead, we were taken through the bar area to a patio that was enclosed by plastic to keep the not-quite Spring-yet weather out.
Our server was new and was being shadowed by a more experienced person. Without commenting, we corrected minor mistakes like forgetting to ask how we would like our meat cooked and not offering a dessert menu.
After we caught the server’s attention to ask if they would like to know how we would like our meat cooked, the “Shadow” came by and said,
“Your server’s new. I’m just shadowing him this evening.”
Thanks for the info.
The meal was great, but our experience wasn’t.
It’s the manager’s fault, not the server’s!
Restaurants, hotels, and other hospitality businesses promise people memorable moments and exceptional experiences, but they can’t deliver them.
Only their employees can.
OpenTable, the app we used to book our evening out, provides a wealth of data that restaurants can use to personalize the service they provide. According to their website, the “shift overview” section highlights important reservation information including:
Guest Requests
Visit Notes
General Notes
Special Relationship
Special Events
Seating Preferences
Food & Drink Preferences
Managers can ensure that a note is provided for staff working the relevant shift.
Never has so much information been available to assist employees. In addition to the items listed above, hotel and restaurant systems can track guest visits, how much they spend, how often they cancel, how often they don’t show up without cancelling, and what they often order.
It should be easy, right?
How come it doesn’t work?
It’s not the system. It’s not the technology. It’s relying on technology without training staff to use the information provided.
Guests who use technology to make bookings, special requests, or provide pertinent information to the restaurants or hotels they use trust that the information will help give them the exceptional, personalized service the hospitality company’s marketing campaigns promise them.
When they arrive full of excitement and expectation, they are often let down as employees follow the same old script…
From the “Is this your first time dining with us?” welcome to the “Got any plans for the rest of the evening?” goodbye, hospitality businesses are leaving guests unimpressed while bored employees wonder how many times they have to repeat the same inauthentic greeting.
Be a better manager for less than $20.00 per employee
We wrote “Spin the Bottle Service - Hospitality in the Age of AI” during the pandemic.
It’s a collection of real-life experiences and stories that show how easy it is for people who genuinely care about their guests, their colleagues, and their profession to provide personal service.
If you’re a hospitality manager, give a copy to every team member. That’s not my idea. That’s a recommendation a server at one of our favourite restaurants came up with.
It’s an inexpensive way to make jobs more meaningful and turn your business into one your guests want to return to!
The book is available online and can be ordered by good bookstores everywhere.
To make it even easier for you, you can simply click the “Buy our Book” menu at the top of the page.
Or, if that’s too much of a challenge, just click the image of the book below. Sorry, I can’t make it any easier than that!
Post Script - the management response to our comments
Yes, we did write a comment to the management of the restaurant. People said that they usually gave a piece of cake to birthday guests. Would they invite me back for cake? Would they send me a gift card I could use for a piece of cake?

Unfortunately, I can’t answer those questions. The restaurant didn’t respond.
What do you think?
Is the digital disconnect affecting your travel, dining, or accommodation experiences?
What places have you been to where employees blow you away by making use of the technology that assists them with information to help them personalize the service you receive?
I promise to answer your questions and comments by using the notification technology Substack provides to alert me to subscribers and readers who care enough to engage!
Stay safe, Always Care

Hi! I’m Paul.
I was born, raised, and currently live in Canada. After high school, I embarked on a gap year in Europe. It lasted four decades. I went to university in Norway and started my hotel career in the basement of a five-star hotel in Oslo. The manager who hired me told me I was too old, too educated, and had too many opinions to be a security guard. He also told me that the only other person who applied for the job didn’t want it.
Thirty years later, I left that same company. It had grown from a small regional hotel chain with twenty-something hotels in Scandinavia to become a large, multi-brand hotel group with over a thousand hotels in almost one hundred countries.
Along the way, I moved from Norway to Denmark to Belgium. Before I left, the company awarded me their highest individual honour for leadership, and security professional peers selected me as the world’s most influential corporate security executive.
I’m a hospitality professional. I’m a security professional. If you ask, I will tell you that security was my job, and hospitality was my business.
Today, I’m an educator and a consultant passionate about hotels, hospitality, and keeping people safe during their travels.
In addition to the Always Care Community, I also write for Risk Resiliency’s Keep Travel Safe. If safe, secure hospitality, hotels, and travel are important to you, please subscribe to KTS!
Written with the clarity of hindsight, the accuracy of a faded memory, and countless creative liberties, the Always Care Community is a newsletter of how life has made me an emigrant, an immigrant, and gifted me experiences I never dreamed possible.
Thanks for reading. Your support is my motivation and I’m genuinely grateful that you’re here. Please share, subscribe, and connect with me.
Happy belated birthday, Paul! What a terrible experience... it brings to mind very touristy areas where the restaurant service is bad because servers and managers know that few people make a second visit. It's always fresh loads of new tourists that go back there. Probably the worst is the lack of answer from the management... maybe send them a link to this post? :)
Sorry about your less than stellar birthday experience!