The Leadership Skill AI Can't Fake: Dr Paul Redmond on Leading Five Generations

Someone in the team loses a relative. The leader opens an AI tool, asks it to write a condolence note and sends what comes back. It reads beautifully, with no spelling mistakes and every sentence in the right place. And the person who receives it knows straight away.

Dr Paul Redmond has come across this in real organisations. "People know it's AI," he says, "and that can have a huge detrimental effect on team morale." It's a small act of outsourcing that tells a grieving employee something no leader would say out loud: this wasn't worth your time.

Redmond is one of the UK's leading voices on generations at work, delivering 70 to 80 keynotes a year for organisations including Google, the NHS and Royal London. His latest book is Leadership in an Age of AI: How to remain fearlessly human. In conversation with James Vincent on the ActionCOACH podcast, he made a case that connects two of the biggest pressures on leaders right now. Leading five generations in one workforce and adapting to AI look like separate problems. Both, he argues, test whether a leader is still willing to listen and do the human work themselves.

Every Generation Needs to Feel Wanted at Work

Redmond's starting point with any organisation is making it safe for every generation to feel wanted. The group he most often finds feeling unwanted may surprise business owners: the boomers. When they leave, they take decades of organisational backstory with them, much of it never written down.

At the other end, he hears constant criticism of Gen Z. They want promotion quickly, they question working hours and they ask awkward questions. Redmond's response is to understand those differences instead of complaining about them, while avoiding stereotypes. "Your generation isn't a straitjacket," he says. What it does shape is how people view the world.

Why Senior Leaders Stop Listening to Younger Voices

One of his more uncomfortable observations is that the more senior and successful a leader becomes, the harder it is to listen. "You think you're listening, but what you're really doing is waiting to interrupt."

Meetings are where this shows most. Research he cites suggests Gen Z speak the most in just 3% of meetings, so their ideas often go unheard. His suggestions for changing that, from who chairs the meeting to how reverse mentoring can work, are some of the most practical moments in the conversation.

He illustrates the cost of not listening with Blockbuster Video, which turned away the young founders of Netflix when they explained that people would one day download films instead of renting them. "They just couldn't see that things were going to change," he says.

For leaders, the shift is one of mindset. When Redmond started work, a manager would never admit to not knowing the answer. Now, he says, "vulnerability is a strength", and asking a younger colleague "What do you think?" is one of the most powerful things a leader can do.

People Quit Managers Who Avoid Honest Conversations

When organisations tell Redmond they're losing their Gen Z talent, he often finds the same root cause: a manager avoiding an open, honest conversation. Senior leaders tell him they didn't know there was a problem until the key people had already left.

For Redmond, the worst option is not having the conversation at all. He shares how he approaches feedback that is direct but supportive, and why British reluctance to "grumble" makes the choice of words even more important. The detail is worth hearing in full on the episode.

Staying Fearlessly Human When AI Can Do the Writing

This brings the conversation back to the condolence letter. Redmond has found many leaders effectively delegating their leadership to AI, using it to write strategy, send difficult emails and even make serious decisions. The appeal is obvious. The risk is a loss of trust, and a loss of accountability when things go wrong and nobody can say who made the decision.

His alternative is deliberately imperfect. A personal note, written by the leader, typos and all, carries something AI can't. The human skills he believes leaders are in danger of losing include courage and curiosity, and their value is only growing.

He also points to what he calls relational intelligence: getting on with people, handling conflict and working through difficult situations. These are the skills leaders will increasingly be judged on, because they remain the things AI can't do for us.

A Simple Daily Habit for More Human Leadership

Asked for one action listeners could take, Redmond kept it simple. Protect the first 30 minutes of the working day, which he calls "golden time". No phone, no laptop, just pen and paper and a plan for the day. "Do that every day and I promise you it will transform your career."

It's a small habit, and it reflects the whole conversation. The leader who protects time to think, who lets younger colleagues be heard and who writes the clumsy note themselves is making the same choice each time: to stay present with people when a faster option is available. For a workforce spanning five generations, that is the part of leadership nobody else can do for you.

Listen to the full conversation with Dr Paul Redmond on the ActionCOACH podcast, and find more of his thinking in Leadership in an Age of AI: How to remain fearlessly human.

Listen to the latest ActionCOACH UK Podcast here