4 Tips to get the older generation on board with digital transformation

My brother recently said that when I speak, it’s like I’m the Pied Piper and the “olde” folks just seem to follow. The truth? They don’t. It’s a lot of back-and-forth, building trust, and cultivating authentic relationships before I can even begin to nudge the needle of change. What I’m about to share isn’t from a textbook (though books might give it fancier names and order things differently). This is my personal approach. Maybe, just maybe, you’ll find a nugget or two worth pocketing.

When I start any transformation project, the first thing I do is meet with stakeholders. I want to understand their pain points and hear their ideas for solutions. This is critical—not just to grasp the issues but to get a sense of the people. Who’s for me? Who’s against me? Who needs extra attention to come around? Who requires a nudge from someone they trust? Think of it as reconnaissance of the culture, the people, and, frankly, the problems. Sometimes the pain points aren’t even in my scope, and that’s okay. I pass them on to the relevant teams, letting everyone know their feedback is being heard and acted upon.

Being upfront about what I’m doing and why helps. Yes, sometimes I get the cynical “This is just for the company” spiel. Well, of course, it is. If the company doesn’t thrive, none of us have jobs! But you’re not here for a rallying cry to the masses. You want to know how to win over the gogos (grandmothers, in case you’re wondering) and the grey-haired gurus who may see the digital world as a bit, well, daunting.

So, let me share 4 tips to get the older generation on board with digital transformation.

1. Respect Their Experience

No need to kneel (unless you’re feeling dramatic), but do acknowledge that these folks have seen and done things. They’ve weathered storms and steered ships long before you were in nappies. Respect their wisdom and the fact that, even in areas where they may lack technical knowledge, they bring invaluable insights. People are more likely to listen if they feel their contributions are valued.

T4L Tip: You don’t have all the answers—no one does!

2. Speak Their Language

Forget the tech jargon. The older generation doesn’t want to know the inner workings of an app; they want to know why it matters to them. Focus on tangible benefits. If you’re introducing a new application, say things like: “This app saves time—you’ll never have to queue at the canteen again!”

T4L Tip: If there’s one thing you take away from me, it’s this: Lead with the “why,” not the “how.” That’s what gets the wheels turning.

3. Show, Don’t Just Tell

This might be hard—I know when I’m excited about a new change, I want to drone on and on about how amazing it is. Instead of simply telling the world how brilliant it is, show them. This approach has been a game changer for me, and it also gives me direct feedback about what might need tweaking as I watch stakeholders interact with a new system or process.

T4L Tip: This does require patience. You’ll need to walk them through it step by step. I also create guides with pictures for them to reference later. It works like magic!

4. Leverage Social Circles

Sometimes, all it takes is a friend, colleague, or even a boss leading the charge. I love tracking outcomes—preferably using something like a Power BI dashboard—and getting people into some friendly competition or camaraderie. That can be just the nudge they need.

T4L Tip: Encouraging their peers to join the digital journey together makes it sweeter and much easier to bring everyone along.

At the end of the day, helping the older generation embrace digital transformation is about meeting them where they are, respecting their journey, and gently guiding them into the possibilities of a tech-enabled future. And who knows? Once they’re on board, they might surprise you with how much they can teach you—life experience, after all, isn’t something you can download.

Check out Transformation Leader (T4L) free Transformation Leadership course ideal for anyone who wants to assess their leadership gaps to implement lasting change in their organisation. https://www.t4leader.com/challenge-page/transformational-leadership?programId=d4e58ca0-f0e6-4f12-b2a8-9dc5fcf6e335