If you’re a CEO, you’re likely already thinking about AI. You may be experimenting with a few tools, or you’ve tasked someone on your team with staying current. For many leaders, the conversation has moved past whether to engage and onto how to move forward in a way that’s practical, thoughtful, and aligned with company strategy.

All the big research firms are predicting significant use of AI now and in the future. According to Accenture, 40% of all working hours could soon be impacted by large language models. Gartner projects that by 2030, AI will automate up to 80% of routine project management tasks. And Bloomberg Intelligence forecasts that generative AI is poised to become a $1.3 trillion market by 2032, signaling the scale of transformation already underway. Whether or not these predictions are accurate, the progression from Web 1.0 to 3.0 reminds us that major shifts do happen, and there’s little doubt AI will be a force in business going forward.

With all the noise around AI, the path forward can be overwhelming. In working with CEOs across industries, I’ve seen a few practical approaches that help cut through the uncertainty and turn curiosity into action.

1. Begin with a business problem, not a tool
Rather than starting with “What can AI do?”, begin by asking, “What problem are we trying to solve?” Whether you’re looking to reduce churn, improve forecasting, streamline onboarding, or increase customer retention, anchoring AI exploration in real business needs to drive productivity leads to more relevant and effective applications.

2. Stay curious and grounded
You don’t need to become a technologist, but it helps to understand the fundamentals. The goal isn’t technical mastery, it’s being informed enough to ask better questions and guide your team wisely. Learn the difference between automation and generative AI, keep up with evolving capabilities and limitations, and engage with other leaders who are curious about AI.

3. Lead through uncertainty
Resistance is normal. People may feel unsure, skeptical, and probably feel threatened. As CEO, your job is to set the tone. Position AI not as a way to eliminate jobs, but as a tool that enables people to focus on higher-value work. Encourage a culture of experimentation where small wins and smart failures are both seen as progress. I will always remember a sales leader of mine who had worked before and after spreadsheets. He decided to lean in and learn how Excel could help him, but some of his colleagues resisted. The colleagues became irrelevant within a decade, whereas my friend was able to work for 30 years in an elevated role.  

4. Select the right internal owner
AI ownership matters a lot, but it doesn’t need to live with your CTO or engineering lead. The most effective AI lead is often someone creative and cross-functional who can spot opportunities across departments and operate at both the strategic and tactical levels. They don’t need deep technical skills, but they do need to be respected in the organization. Look for a strong problem solver to spearhead the effort across teams, helping connect the work to broader business goals while building buy-in as they go.

5. Start narrow, but start now
Choose one focused use case to test small enough to implement quickly, but meaningful enough to learn from. It could be summarizing internal meetings, improving outbound sales emails, or tagging support tickets. Run a pilot, measure the outcome, and build from there. This kind of targeted experimentation builds confidence and insight without draining resources.

6. Make it part of strategic planning
AI isn’t just a tech initiative—it belongs in your broader planning conversations. In our Strategic Ascent engagements, we’re now routinely asking: What capabilities does your leadership team need to build in the next 12 months—and how might AI help or hinder that progress? Treat AI as an enabler of strategic priorities, not a separate side project.

7. Dedicate cross-functional time to uncover new ideas
There are hundreds of ways AI could be useful in your organization. But unlocking those ideas requires input from different perspectives. Set aside time for cross-functional sessions where people share what they’ve tried, what’s worked, and what they’re curious about. We’ve seen CEOs host short roundtables where team members answer one simple prompt: “Here’s one way I’ve used AI this week.” Insights emerge quickly when ideas are surfaced collectively. Making it part of the leadership team and department head agendas ensures it gains traction.

8. Train and scale what works
Once you’ve validated a few useful applications, don’t stop at experimentation. Roll it out thoughtfully. Offer training. Set guardrails. Give your teams a clear invitation to build on what’s already working. Often, the most creative and high-impact use cases come from those closest to the work. Make sure they’re equipped and encouraged to explore.

At Katahdin, we’re taking this same approach. We’ve dedicated an internal team member to focus on how AI can support our own operations and enhance the value we deliver to members. She’s experimenting, documenting what we’re learning, and helping us stay ahead of the curve. We’re also collaborating with one of our member companies to design a tool that supports CEOs in our peer groups—one that we believe will help them build stronger cases, receive more focused feedback, and get more out of the Collective experience.

AI isn’t just about tools—it’s about leadership, culture, and capability. The companies that thrive in this next chapter will be those that move deliberately, stay curious, and bring their people with them.

You don’t need to take it all on at once. But this is the moment to get moving. Start small. Learn fast. Stay engaged.

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