The Leadership Blindspot Harming Your AI Transformation

Our guest author and Poppins partner, David Boyle, has coached hundreds of senior leaders on using AI in their work. He co-wrote the first practical ChatGPT guide and helps executives get started through Audience Strategies.

I recently coached a jeweller who makes luxury pieces with fine diamonds. They're brilliant at their craft, but struggled when asked to write about it. We found a simple fix: they record themselves talking while they work, then use AI to turn it into written content that they can fine tune. The joy (and relief) on their face when they realised AI could remove the drudgery from their day and amplify what they love most was something really special.

After hundreds of coaching sessions with leaders of all shapes and sizes, we keep seeing the same thing. Whether you’re in finance or law, in product or marketing, no matter how much expertise you’ve built up, there’s a way that AI can help bring out the best in you.

Because the biggest company barrier to AI transformation isn’t technology, strategy, or even resources, it’s the belief that AI is for the team, not the leader. But as the jeweller’s story shows, AI has value for everyone. And when leaders experience that firsthand, their understanding deepens, and their support for AI across the organisation grows exponentially.

When ChatGPT launched in late 2022, we published the first practical guide within three weeks. One of our key findings was that language models act as 'electric bikes for the mind'—they don't replace executive judgment but amplify it, allowing leaders to operate with the analytical power previously reserved for those with large research teams. Leaders across industries told us our book transformed their view of AI, yet for the first two years of ChatGPT, most executives said the same thing: "AI isn't for me—just train my team".

So when we sat down to discuss any training for their teams, we’d often pause and say, "Let us show you something first." We’d then demonstrate how AI could help with their own work. By the end of these quick sessions, their perspective (and resistance) had shifted. After seeing this happen again and again, we realised we were onto something—and our AI coaching was born.

In an off the record coaching session, we hear very different things compared to training sessions or even internal meetings. But what actually surprises me most is that senior leaders often feel more intimidated by AI than junior staff. In fact, only recently a CEO who'd led digital transformations for 20 years told me: "This is the first time I've felt behind on technology."

It’s across the spectrum of leading positions too. A legal officer comes in focused on risks. They leave thinking about opportunities. "I came here seeing all the dangers," one told me. "Now I think we need to speed up rollout."

Creative Directors will admit to their worry that AI is replacing their expertise. They then try it and quickly realise it helps them explore more ideas faster: "It's like having a team who never gets tired."

Every session we have run has one thing in common: there's always a way AI can amplify your expertise.

The best first applications are usually super simple. The jeweller talking into their phone. A CEO who dreads spending three hours on board updates now creating first drafts in 20 minutes (often better). A CFO getting help with presentations. Nothing fancy. Just useful use of AI to work that little bit better, quicker and happier.

The secret? These instances multiply. They multiply the impact of expertise. And when you start to implement many uses across your day, they collectively feel like having a superpower.

When you save 30 minutes on a board update, that's helpful. When they save 30 minutes on every piece of communication, every day? That's hours a week to focus on what only they can do. Even senior leaders get excited when they see how AI works for them too.

We worked with one company that had spent many months on their AI programme. Good infrastructure. Clear policies. Training for everyone. But AI usage across the company was flat.

So we coached their leadership team one-on-one, and within weeks, usage was taking off across the company. What changed? When leaders started sharing their own use cases, their support shifted from theoretical to personal. They leant in. They encouraged progress and found solutions.

And when employees saw their CEO talking about how they use ChatGPT, when other leaders saw the benefits and encouraged staff to use AI, it gave everyone permission to try it themselves and created the atmosphere for usage to flourish.

"We had all the pieces," their AI programme lead said. Except, we argued, the most important one: leading by example.

After hundreds of sessions with everyone from global CEOs to individual business owners, here's what we've learned: companies don't transform because of AI strategies. They transform when their leaders start utilising AI themselves.

Leaders assume that AI can’t help them, and that it’s just for their teams. But there's always a simple way AI can amplify their expertise. And these small wins add up.

Leaders think AI is about efficiency. But often it's about getting help with the boring stuff so you can focus on what you're good at. AI, used well, is about amplification of what makes you irreplaceable.

The jeweller can now share their expertise without dreading having to write about it. The CEO who felt behind is now leading from experience. They all started sceptical or nervous but after trying it in a coaching session, they wondered why they'd waited so long.

AI transformation doesn't happen when you make AI someone else's job. It happens when you make it part of your job.

That's it. That's the blindspot. And fixing it is simpler than most leaders think. Just ask the jeweller.

If anything you've read here piques your interest, we'd love to hear from you at hello@poppins.agency