We all know of a local company, even if it is a local pub or a brewery that has existed for hundreds of years. These companies are tied to traditions and go back generations, shaping the town’s culture and traditions.
But they often fall into the same trap when it comes to innovation and digitalization. These businesses are used to making something in a particular way, and that has been like that for years. Now someone is telling them to open up their Google Business profile or share content on social media, and it is hard.
Digitalizing a legacy business might be even harder than starting a brand new digital business from scratch. Think about it. A startup can choose modern software, design everything around mobile users, and change direction without high costs or worrying about what happens to their 200 stores and decades of customer records in an old system.
Let’s find out how legacy businesses are adapting to modern times.
The First Mistake Is Treating Digital as a Separate Business
Most companies fail to realize that customers do not actually think in terms of “online” and “offline.” They simply want the product and want the easiest and most convenient way for them to get it.
Walmart is a perfect example. The company that began with physical discount stores now describes itself as a technology-powered omnichannel retailer. Its stores increasingly double as fulfillment centers, which allows orders placed digitally to be picked locally and delivered quickly all around the U.S.
The business is the same; it only adapted with time. We have the same thing happening with horse racing. Back in the day, the only way you could have placed a bet on a popular race was by physically going there. But right now, there are plenty of betting apps with online horse betting promotions that allow people to place a bet from their mobile phones.
Customers don’t go, “Oh, now horse racing is digital.” They just see the same business, only with a more convenient way for them to engage with it. So, the first transformation comes when you see the digitalization of a legacy business as the same thing.
A Good Digital Experience Removes Friction Nobody Misses
Traditional businesses sometimes become emotionally attached to processes simply because those processes have existed for decades.
Appointments are arranged between 9:00 and 4:30, except Wednesdays, for reasons lost to history.
Customers generally feel considerably less nostalgic.
Lloyds Banking Group offers a good example of what happens when a traditional service business starts redesigning those interactions around digital behavior.
The British banking group reported 23.6 million digitally active users in 2025 and around 21.5 million app users. It also said roughly 85 percent of current-account openings during the year happened through mobile channels, with the process capable of taking around seven minutes.
The important improvement is not that banking suddenly has prettier buttons.
It is that an activity which once required travel, paperwork, and a conversation across a desk can happen while somebody is sitting on their sofa.
Digital Transformation Often Starts in Very Unexciting Places
The glamorous version of transformation involves artificial intelligence, augmented reality, and dramatic presentations containing phrases such as “reimagining the customer journey.”
Modernizing software that six people understand, and three of them are considering retirement.
The LEGO Group offers a useful example.
LEGO is one of the most physical products imaginable. Its entire appeal revolves around pieces of plastic that people touch, combine, and occasionally step on at night.
Yet the company has invested heavily in modernizing the technology underneath the business. Its 2025 annual report describes multi-year programs covering enterprise software, data management, product lifecycle systems, membership platforms, security, and digital tools for both consumers and retail partners.
Newspapers Learned This Lesson the Hard Way
Few industries demonstrate the problem more clearly than newspapers.
For generations, the business model was wonderfully physical.
Journalists produced stories. Printing presses created newspapers. Trucks distributed them. People bought copies.
Then the internet arrived and politely removed several assumptions underneath the entire model.
The New York Times responded by gradually turning itself from a newspaper company with a website into a digital subscription business that still happens to print newspapers.
By the end of June 2026, The Times had about 12.8 million digital-only subscribers. Its digital offering now stretches beyond traditional news into products such as The Athletic, Cooking, Games, Audio, and Wirecutter.
Old Technology Is Often the Real Enemy
One of the strangest problems legacy businesses face is that successful companies accumulate technology.
A system gets added. Then another system talks to that system. Then somebody builds a workaround because the two systems do not quite agree.
Twenty years later, changing a password somehow affects payroll in Belgium.
Lloyds has openly described reducing and modernizing its legacy technology estate as part of its digital strategy. The bank says around half of its applications have moved onto cloud infrastructure and that it has reduced the number of data centers it operates.
Customers may never notice that an ancient backend system disappeared.
So, yes, digitalizing a legacy business that had the same procedures for hundreds of years is hard, but not impossible. You just have to approach it with an open mind, do it step-by-step, and value the old stuff just as much as the new digital advancements.
