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A lot of business leaders are still hesitant to lean into AI. I get it. The hype, the unknowns, the fear of losing what makes work human. But resisting the shift is the real risk. Because when used well, AI doesn’t replace your thinking — it sharpens it.
I learned this firsthand a few years ago in an airport terminal. I’d been feeding ChatGPT a steady stream of my thoughts and frameworks for a few months when I decided to ask for help articulating a concept I’d been wrestling with while waiting for a flight. Within minutes, it returned a fully structured blog draft.
I laughed out loud. Not because it was perfect, but because it got so much right, so fast.
That moment sparked a conversation with a man sitting nearby. Turns out, he’d just given a keynote on AI and the future of work. We dove into a discussion on leadership, trust, and what it means to stay grounded when everything’s changing around you.
One moment of surprise turned into something bigger. The kind of connection you only make when something new, something powerful, is stirring.
AI isn’t just for brainstorming. It has the ability to expand your field-of-view, surface patterns, and connect ideas quickly. So even if you’re still a little apprehensive, let’s talk about how you can lean into AI in a deliberate, human-centered way so your company and your culture don’t get left behind.
Bringing AI In, One Step at a Time
When ChatGPT first landed in late 2022, it was mostly a curiosity that people (especially founders) experimented with. And for the majority of small and mid-sized businesses, it stayed outside the core workflows.
But since then, the landscape has changed — and fast.
At Ninety, we didn’t force AI into the company. We talked about it, and a lot of us chose to use it and build with it. But we let each department explore its capabilities on their own. Over time, the widespread adoption throughout the company became natural. People asked questions, ran tests, and started to see real improvements in both efficiency and consistency.
Now, we've developed an AI tool, Maz, that asks questions to prompt you to think more clearly about your Rocks and their milestones. It’s making ours more structured, aligned, and impactful. The same is happening with Org Charts, KPIs, and longer-term goals. AI is helping us to prompt better thinking and turn ideas into action. (As someone I deeply respect implores, learn to ask better questions and give better answers.)
And AI isn’t just helping our internal team at Ninety. It's helping our clients move faster with better results. The founders I coach are embracing AI and are genuinely more energized and excited about the future. They’re sending videos of team sessions using Maz to draft SMART Rocks together.
The point here isn’t to marvel at the possibilities. It’s to recognize the shift: AI isn’t something we’re experimenting with anymore. It’s becoming an essential tool for helping us think, grow, relate, and operate.
The future of AI is not about replacing humans, it's about augmenting human capabilities.
CEO of Google
Understanding Your Team
You can’t adopt new technology without accounting for the people who will use it. And every person brings their own pace, preferences, and ways of thinking. Some fit well into your culture. Some don't.
That’s why I’ve been spending more time diving into employee archetypes. James Root of Bain & Company surveyed more than 48,000 employees across 19 countries and surfaced six primary archetypes: Pioneers, Strivers, Operators, Givers, Artisans, and Explorers.
Why do employee archetypes matter? Because each archetype engages with AI through a different lens. Pioneers see possibility, always eager to explore what’s next. Strivers approach with caution, attuned to the risks and potential pitfalls. Operators seek clarity and routine, wanting to understand how AI fits into established workflows. Givers care about how it helps the team. Artisans look for quality and craftsmanship. And Explorers are energized by novelty and the chance to try something entirely new.
Same tool, but vastly different questions, frames, and needs.
This is where our leadership makes the difference. It’s about more than just deciding to adopt AI. We have to understand how to introduce it in a way that connects to our people.
Think about it: If you present AI as a way to move faster, the Artisan might resist. But if you show how it can help them refine their work, they’re more likely to lean in. For Operators, it’s about making the process clear and repeatable. Every archetype will see it differently.
If you treat everyone the same, you miss the opportunity to build real trust. The best founders understand who their people are, what they value, and how to speak their language, especially when things are shifting or stakes are high. And just as importantly, the most successful founders aren't naively thinking the game their playing is well suited for all.
The Founder’s Role
Whether we want to admit it or not, AI is changing work as we know it. It's not just affecting what we do, but how we do it, who does it, and even why certain kinds of work matter in the first place. And like every major shift, some will welcome the changes and others will resist.
If we look backward, this isn’t the first time work has evolved, and it surely won’t be the last. In Work 9.0, I explored how each new Age of Work brings its own mix of opportunity and disruption. What makes this moment different is the pace of change, the ambiguity surrounding it, and the pressure many of us feel to adapt.
Some companies will use AI to tweak the margins. Others will rethink entire workflows. A few will use it to reshape their entire industry. Where your company lands depends on two key factors: how ambitious your culture is, and how much uncertainty exists in your market.
If you’re operating in a high-stakes, fast-moving environment, AI will have to become a core part of how your team operates, or you'll go out of business (sorry). It has to if you’re trying to do complex things quickly. If your world is more stable and your culture is built for balance, AI might be embraced more cautiously, helping both you and your team improve processes or streamline repeatable tasks. The stakes are simply different. And that’s okay.
Not every company needs to be an AI company. But every founder should understand the landscape they’re navigating and what kind of change they want to lead.
This isn’t about going all in or holding back. Don’t default to extremes. You don’t need a mandate, and you don’t need to wait. What you do need is a deliberate path that aligns the nature of the opportunity your pursuing, your culture, and the level of your aspirations.
Make no mistake, this transition is happening. Some companies will evolve, some will no longer exist, and new ones will emerge. But that’s true of every major shift. The best leaders help their people find new ways to matter so they can continue to contribute, grow, and thrive.
Leading Through the Shift
We’re unquestionably in a defining moment in history, one where AI is reshaping work as we know it. It’s not just changing what gets done, but also how we approach it: what we value, how intensely we contribute, and whether our culture meets the moment or fails.
The best companies won’t treat AI as a shortcut. They’ll treat it as an invitation. A chance to build better habits, clearer systems, and stronger teams.
AI doesn’t replace the human side of leadership. It enhances it — if we’re thoughtful, if we stay grounded, and if we use it well.
If you're focused on building something enduring, this moment isn't just a challenge. It's your proving ground, your opportunity to shine. What you do next has the power to shape not just your legacy, but the legacy of everyone on your teams. Best wishes.
Want more on this topic? Check out this episode of the Founder's Framework Podcast.
