It’s 1996. I take the tram for my monthly trip to the CD store.
I flip through the bins until I find Metallica. There it is: Load, their first new album in five years. But next to it are two older albums I don’t have yet. I can only afford one. The clerk lets me listen on headphones before I buy. I sit there, track after track, trying to choose. I walk out with the new album. The others will have to wait.
At home, I press play and study the photographs in the booklet. I read along with the lyrics while the music plays. And I listen to the album all the way to the end.
Today, I have more music in my pocket than that store ever held. It’s fantastic. And I wouldn’t go back.
But somewhere along the way, something disappeared. I call this the regression of progression.
Right now, many leadership teams are making two big changes at once: bringing AI into everything, and bringing people back to the office. Both come wrapped in advantages. Both carry costs that leaders don’t see, or don’t say out loud.
What ‘job’ was the CD really doing?
The late Clayton Christensen told a story about a fast-food chain that wanted to sell more milkshakes. It improved the flavor, but sales didn’t improve. Then researchers watched who actually bought them: mostly people on their way to work, early in the morning. They weren’t buying the milkshake for its taste. They bought it to make a long, boring commute bearable.
Christensen called this jobs to be done. We hire products to do a job for us. And often, we don’t know which jobs a thing is really doing.
Obviously, CDs were hired to play music. But it was also doing other jobs:
It gave me something to save for and look forward to.
It made me commit. I paid for it, so I gave it ten listens.
It turned listening into a journey, from the first track to the last.
It came with a human recommendation from the clerk behind the counter.
Spotify does the first job brilliantly. The others, it quietly fired.
These losses are hard to spot. They were side effects that nobody designed deliberately. So when you replace the old thing, you also fire it for all the jobs you never noticed.
Why the new thing always looks better
If every upgrade has a downgrade, why are we so bad at seeing it? It’s how we’re wired:
Our brains reward novelty. For our ancestors, exploring the unknown paid off. New territory meant new food. That reflex is still there: something new lights us up.
We decide at peak excitement. Our brains get most excited before we have the new thing, not after. And that’s exactly when we decide.
We compare promise to track record. The new thing is judged on its promise. The old thing is judged on its track record, flaws and all. That’s not a fair comparison.
We overestimate the impact. We expect a change to make a bigger difference, for longer, than it actually does. The gain fades into normal within weeks. The loss stays invisible.
In organizations, action looks like leadership. Launching something new is visible. Protecting what already works rarely gets you applause.
Put these together, and you get a predictable pattern. We buy the promise. We discover the price later. Right now, this pattern is playing out in two places at once.
AI: the price behind the promise
AI is the big development dominating almost every boardroom agenda right now. For good reason: its potential is enormous. But that’s exactly why we shouldn’t buy it blindly. Every AI rollout also takes something away, and few leaders name what that is.
Here are three places where organizations are racing ahead with AI. Let’s inspect the downgrade behind each upgrade.
1. More features, but a degraded experience
Last week, at a conference in Brussels, Alexey Krivitsky pointed out that companies have rushed to add AI features to their products. Then he asked the audience which product has actually gotten better because of it. Nobody could name one.
We got more bells and whistles, but the user experience suffered. Part of the reason: scarce development capacity used to force a hard conversation about what was worth building. AI makes development so cheap that the question “should we build this at all?” quietly disappears.
2. Cheaper customer care, but worse service
Contact centers often sit at the bottom of the organizational pyramid. Low status, high attrition. So replacing people with bots looks like an easy win. But a service call is one of the few moments a customer actually meets your company.
In early 2024, Klarna announced that its AI assistant was doing the work of 700 service reps. About a year later, its CEO admitted quality had dropped, and the company started hiring humans again.
A good service rep has the means to solve the problem, and the empathy to make an upset customer feel heard. When they go the extra mile on a complaint, customers can become more loyal than customers who never had a problem at all.
3. Instant strategy, but shallow understanding
Ask AI for a market analysis or a strategy draft, and you’ll have one before your coffee is cold. It may even be good. But writing is thinking. For a leadership team, the struggle of thinking it through together is the work. That’s where you build a deep, shared understanding, challenge each other’s assumptions, and put the puzzle together. It’s also where ownership is created. Skip it, and you get a strategy document nobody truly understands, or feels is theirs.
Return to office: the price nobody mentions
The second big change started in 2020, when COVID sent everyone home overnight. There was no choice. Remote work turned out to bring real, long-term benefits. But it also quietly took things from us: spontaneous conversations, juniors learning by watching experienced colleagues, a team that feels like a team.
Now the pendulum is swinging back. Many of the companies I work with are issuing return-to-office (RTO) mandates, usually for three days a week. This time, it’s a deliberate choice. So the question is: are we naming the trade-off?
When I read RTO announcements, I see the same few reasons. Collaboration. Culture. Creativity. Those are real. But flexible work was also doing jobs nobody wrote down:
It gave people back the hours they used to spend commuting.
It let people work when they have the most energy, not just from nine to five.
It gave families the flexibility to fit work around school runs and care.
It let companies hire beyond a 50-kilometer radius.
It told people: we trust you to work when and where you do it best.
In a tight talent market, each of these is a reason to stay. Or to leave.
In my Unblock book, I write about Even-Over statements: a way to make trade-offs explicit by saying “[this good thing] even over [that good thing].” An RTO announcement usually implies this one:
Connection even over Flexibility.
That’s a choice you can defend. But the Even-Overs people actually experience are often different:
Being at your desk even over Being at your best.
Oversight even over Trust.
Office days even over Family life.
The effect when done badly? People commute an hour to sit in a meeting booth doing video calls with colleagues who stayed home.
The gap between the announcement and the lived reality is exactly what employees feel. And it’s where engagement leaks away.
My advice: name the trade-offs out loud (more on this below). And don’t roll out RTO cookie-cutter style, one rule for every team regardless of the work. Instead, practice self-alignment: explain why you want people together, and let each team agree on how to make that happen.
A worksheet for your next upgrade
Before you roll out your next tool, structure, or policy, do two things.
First, name the trade-off. Write the honest Even-Over, not just the version in the announcement. What are you choosing, and what are you giving up?
Then, ask a ‘wicked question’. Inspired by the Liberating Structure, turn the tension into a design challenge: how can we have [what the new thing gives us] while keeping [what the old thing gave us]? For example: how can we have the speed of AI while keeping deep debates about what’s worth building?
Here is a short template to fill out with your leadership team:
We assume this change will get us _____. This matters because _____.
The old way was quietly also doing these jobs for us: _____.
By adopting this, we know we will lose _____.
We accept this loss because _____ matters more right now.
Our honest Even-Over: _____ even over _____.
Our wicked question: how can we have _____ while keeping _____ ?
To have both, we will launch the following experiment: _____.
We’ll know we’ve lost too much when _____.
We’ll revisit this decision on: _____.
Here’s what it looks like for a return-to-office decision made consciously:
We assume this change will get us more collaboration and creativity. This matters because we feel we’re losing speed and cohesion.
The old way was quietly also doing these jobs for us: showing people we trust them, letting them work when they have the most energy, giving families flexibility, and giving back commute hours.
By adopting this, we know we will lose some autonomy, some talent, and some engagement. We accept this loss because team cohesion matters more right now.
Our honest Even-Over: Connection even over Flexibility.
Our wicked question: how can we have real connection while keeping people’s autonomy? To have both, we will launch the following experiment: each team makes its own agreement about when and why they meet in person, instead of one rule for everyone.
We’ll know we’ve lost too much when good people start leaving, or when people commute to sit in video calls all day. We’ll revisit this decision on: a date 90 days from now.
The last two lines turn a one-way decision into an experiment. You’re not stuck with it forever; inspect and adapt.
Innovate with your eyes open
Standing still has a price too. So keep pursuing new technology and better ways of working. Just know the downgrade inside every upgrade, so you can choose what to keep.
Here’s a photo of me telling my favorite leadership story at a conference in Brussels, earlier this month. Contact me if you’d like me at your next event.
I’ll be joining the Global Peter Drucker Forum, Nov 4-5 in Vienna. See you there?
That’s it! To dive deeper, grab your copy of one of my books Formula X or Unblock. To get in touch, simply hit ‘reply’ or comment. I read every message.
