Hi everyone, David here.
Over the last few months, I’ve been trying to reconcile two competing narratives I keep hearing about AI in the enterprise. On one hand, you have the stories of companies built by a single human and a dozen AI agents; startups racing to $100M in ARR faster than ever before; and billions of dollars pouring into new AI ventures. On the other hand, there’s an MIT report saying only 5% of AI projects are actually successful.
At a recent Not Another CEO dinner, every founder at the table said they wanted to build an AI-first mindset inside their company. But when we got into the details, it was clear that adoption was much slower than anyone expected. Engineering teams were souring on coding assistants because of low-quality code. Product teams weren’t sure how to apply the technology meaningfully. And most CEOs admitted that while they talked about AI at every all-hands, the actual usage across their organizations was limited or uneven.
So I started asking more tactical questions: What are the companies that are getting this right doing differently?
Across dozens of conversations, I’ve heard three consistent patterns. And based on what I’ve seen work, here’s the order I’d recommend tackling them:
Get your team to start using AI
Get business traction through small, focused projects
Appoint an AI champion, or czar, at your company
Step 1: get your team to start using AI
Getting your team to start using AI in their day to day sounds simple, but it is often the most difficult challenge to overcome.
When I talk to CEOs and their teams, I hear a surprising amount of hesitation. Even at fast-growing, tech-forward companies, people are scared to experiment with AI. People are naturally resistant to change; and while they might use ChatGPT, they assume adopting it for mission critical work is too complicated, technically complex, or not even relevant.
That’s why I love this example from a recent CEO I met with: he offered a $100,000 bonus to the first employee who could fully automate their job using AI. Yes, this is a huge incentive. But the result was equally huge: his entire company started playing with tools and sharing discoveries. Previously hesitant employees started experimenting.
Here is another, more distributed approach: a company gave every employee a mandatory $1,000 AI budget to spend before the end of the year. People could spend the money on any AI product, whether related to work or personal life, but they had to spend it on something new. That one policy created a ripple effect across the organization, and it transformed AI from an intimidating buzzword into something tangible and approachable.
We experienced a microcosm of this at Not Another CEO. Earlier this year, Nick and I wanted a custom GPT to help with podcast production. A consultant quoted us $10,000 to build it. We honestly did consider that for a moment, but ultimately Nick said, “Let me just try to see if I can do this myself.” That was at literally 5PM on a Thursday. The next morning, he sent me a working prototype that did everything we needed.
That experience was eye opening for me: even people like Nick and myself, who live and breathe technology and are always testing new products, can be hesitant “because its AI” and it “sounds scary.”
So if you’re leading a team, just get people playing with AI. Don’t overthink it. Make it approachable and overcome people’s fear by providing incentives that will build momentum.
Step 2: get business traction through small, focused projects
Once your team is experimenting, the next step is to get broader traction across teams and functions.
Your goal isn’t to overhaul every workflow at the company overnight. It’s to find a small group of motivated people, give them a clear mandate, and let them run fast.
One CEO I spoke with had an idea for an AI-powered feature that could change his product. He messaged his team: I’ll be in the office next weekend building this. Who’s in? About 20% of his product and engineering team volunteered. By Sunday night, they had a working prototype. The feature went live shortly after and now saves customers countless hours. He gave the team an unannounced bonus; and seeing the impact on the business, his team began asking him when they could do it again. (Nearly everyone showed up the second time).
Another founder of a larger company had a similar realization. Her team was already stretched thin on the core roadmap, and she wanted to get momentum on AI. So she and her co-founder started building a new AI product nights and weekends. They demoed early versions to customers, got feedback, and secured commitments from the first few buyers before looping in the broader team. Only after that validation did they merge it into the main product and make it a supported feature.
While these examples are about building AI features (versus adopting a new AI tool internally), the same pattern applies: empower a small team to work “outside the machine” on a project, prove the project’s impact, and then celebrate the win across the company.
When you carve out small, independent teams to build something with AI, they can move faster and think differently without worrying about legacy processes or systems. And once they begin to show success, it will naturally begin to build momentum across the rest of the organization.
Step 3: appoint an AI champion, or czar, at your company
Once you have early wins, it’s time to put someone in charge of AI adoption.
Whether you call this person Chief AI Officer, AI champion, or AI czar, what matters most is the responsibility. You need someone who is passionate about driving AI adoption, can push forward projects across the company and serve as an effective internal marketer. Their responsibility is to keep the momentum going, make sure people know what’s working, highlight wins at the leadership level, and coordinate projects across teams.
One company I know appointed their head of HR as their AI champion. She was naturally curious, great at internal communications, and passionate about driving change. Another company’s chief of staff organized an internal AI Summit; they invited twelve employees to present how they were using AI in their daily work, from automating meeting notes to building new customer workflows. I sat in on a similar event at another company, and it was incredible to see the creativity on display. People left inspired and full of new ideas.
A central champion of AI is critical. No matter how much you build early excitement and traction through incentives and small wins, like with anything, momentum will fade without oversight and ownership.
At first, your AI champion might be part-time. But as usage grows, or if you are a larger organization, the role will naturally evolve into something full-time.
Start small & reinforce consistently
AI is already changing the way we work. But building an AI-first mindset across a company won’t happen through top-down mandates. It happens through curiosity, experimentation, and consistent reinforcement.
So start small: give your team permission to play. Move fast on one or two high-impact projects. Then appoint a champion to keep the momentum alive. The companies that master this sequence will be the ones that truly harness the power of AI in not just in their products, but in how they operate.
If you’ve found creative ways to get your team experimenting with AI, I’d love to hear from you. Please reply to this newsletter, or email me at david@notanotherceo.com.