How to Solve Million Dollar AI Problems

“AI is first and foremost a communication technology,” says Nobel laureate Daron Acemoglu.

He’s right – I started to introduce AI in my business 2 years ago, and it has completely transformed the way I work in two ways:

First, AI saves me a six-figure sum per year because tasks that used to take hours can now be done in seconds.

Second, I can focus more on the stuff I enjoy – like writing this newsletter and working with leaders 1:1 or in the Speak Like a CEO Academy.

To be clear, I do not use AI to create slop or generic content. That just breaks your brand. Besides, I enjoy writing and developing ideas.

Reaping the benefits of AI is the most important professional challenge of our time. Software may eat the world, but AI-powered businesses are devouring the competition.

Yet most companies see little or no return on their AI investment. According to a recent MIT study, 95% of corporate AI pilots are failing.

Here’s how you can unlock AI’s full value, whether you’re a solopreneur or part of a global enterprise.

What the Headlines Missed

A closer reading of the MIT report reveals something even more explosive than the 95% headline figure: the fastest mass adoption of workplace technology in history is already underway – and executives are behind.

It isn’t companies leading this shift. It’s employees, and leaders who ignore it do so at their peril.

While only 40% of companies have official AI subscriptions, 90% of employees are already using personal AI tools to get work done.

In other words: nearly everyone is powering ahead with AI, whether their company is ready or not.

Successful AI implementation depends on overcoming three challenges: business, technology, and communications.

The Business Challenge

To see a return on your investment in AI, you want clarity first: Which use cases should we focus on? How can we accelerate innovation with AI? What specific business outcome do we want to see?

(In transforming my company, I always start with a clear business outcome, like a time-consuming task I want AI to take over to realize a specific saving.)

Currently adoption of Generative AI is high, but disruption is low. In other words, companies are not ambitious enough, pick the wrong use cases, or stumble during the execution.

The Technological Challenge

Without getting the technology piece right, nothing else matters.

The 95% failure rate that has dominated headlines refers specifically to custom enterprise AI solutions – expensive systems companies commission from vendors or build themselves.

What the report found is that employees rather use $20 consumer apps instead of the bespoke $50,000 enterprise tool their company purchased.

The data is clear and rhymes with common sense: It is faster, cheaper and more promising to buy off-the-shelf than building your own tech.

The Communications Challenge

As I pointed out in my recent TEDx Talk, many AI implementation projects fail because people are scared that they will lose their jobs.

Leaders must therefore become the bridge between people and technology – making the case for change in a way that is honest, inspiring, and grounded in shared values.

Or as I put it, supercomputers need supercommunicators.

Companies must decide: Is AI part of their growth story or part of their efficiency story? I hope you chose the former, and use AI to empower not replace.

To make AI a success story in your organization and move from the dream stage to delivery, you need to overcome all three challenges. This is what my model looks like:

Despite the obvious challenges leaders face, I'm an AI optimist. An optimist isn't someone who believes positive results just show up magically. That's called delusional.

But as an AI optimist I believe that AI can be successfully implemented in every organization.

*** How to Solve Million-Dollar AI Problems in 30 Minutes is a series of fireside chats for leaders I co-host with my friend JD Meier, the former Head Innovation Coach for Microsoft CEO Satya Nadella.

If you are interested in joining these free but exclusive sessions, hit reply. No webinar, no sales pitch, no slides – just leaders making AI work for their business, not against it. ***

ON THE SHOW

Anti-Fragile Communication - How to Win Pitches

This week I'm a guest on Danny Fontaine’s podcast Pitch Masters (watch on Apple, Spotify, Amazon Music or YouTube). I unveil

What separates the world’s best communicators from everyone else
How Authenticity can be used to persuade, and present to your advantage
easyJet’s scrappy early days
My philosophy of anti-fragile communication
Practical insights on storytelling, structure, and confidence.

The good news: The bar is incredibly low as 99% of pitches rely on PowerPoint slides filled with jargon. And that means you can make an impression easily.

BOOK RECOMMENDATION

Become Powerfully Likeable

Kate Mason explodes the myth at the heart of many women’s communication struggles: that you must choose between being likable and being powerful. It’s a false choice – and a dangerous one.

Mason, a communication coach and former world-champion debater, names the double bind that traps so many women:

Speak up and risk being seen as “too much,” or stay agreeable and be overlooked. But she offers a radical reframe – the problem isn’t you, it’s the outdated rules of the game.

The solution? Stop modifying yourself to fit someone else’s standard of “likable.” Instead, redefine power in your own terms and align your communication style with who you are.

The book is packed with practical strategies for communicating while female: how to say no without guilt, how to take up space without apology, and how to stop obsessing over how you’re perceived.

As Mason puts it, the goal isn’t to be liked by everyone – it’s to be powerfully likeable by being fully yourself.

Kate will be a guest on the Speak Like a CEO show soon. I can’t wait to share our conversation with you.

Happy writing and an inspired weekend,

Oliver