How AI Can Help Founders Truly Level Up

Most of us wake up already focused on our to-do list for the day: the meeting we need to run, the decision we need to make, or the tough conversation we need to have. As our companies scale, they ask more of us than they used to. We need more range, more perspective, more patience. But for many of us, our own development as leaders keeps getting pushed further out as more urgent needs fill the day-to-day.

That creates a real paradox. Leadership capacity has never mattered more, yet the space to intentionally work on ourselves feels harder to protect than ever. Our teams are bigger, our systems are more complex, and there never seems to be enough time to tackle everything. The leaders who don't make time for growth end up relying on the same thinking patterns that worked when the company was smaller, even though those patterns no longer match the reality they’re leading in.

Our tendency to put our personal growth on the back burner isn't because we don’t care deeply about our companies. It’s simply how human development works. We all operate from a center of gravity shaped by experience, success, failure, and how we’ve learned to make sense of the world. Until something stretches that center, we repeat what's worked before, even when our environment is clearly asking for something more, something different.

Most leadership development tends to happen outside the flow of real work, which means it’s often the first thing to get postponed when pressure or tight deadlines show up. What’s missing isn’t desire or discipline. It’s a way to support our own growth while our business keeps moving.

This is where AI has the ability to meet us inside the reality of our day and support growth while the work is happening. When used well, AI doesn’t replace reflection, wisdom, or responsibility. What it does do is make leadership development more accessible, more consistent, and more embedded in our everyday. So let’s talk about how we can use AI to support our growth and help us genuinely level up as leaders.

When Growth Asks More of Us

As our company grows, there’s a point where effort alone stops being enough. There are more meetings, more people involved, and more decisions that carry real weight. The business is still moving forward, but keeping everyone and everything aligned starts to demand more energy than it did before.

This isn’t about our own skill or competence. Most of us are excellent operators with strong instincts and a history of making good calls (that’s how we landed here in the first place). What’s changing is the nature of the work itself. The pace and complexity begin to outgrow the way we’re used to handling it. What once worked well no longer provides the same traction.

For years, most of us have relied on books, workshops, coaching, and offsites to support our development as leaders, especially those of us who have been in the game a while. A lot of that has been genuinely helpful. The limitation is that most of it lives outside the day-to-day, separate from the situations where leadership is actually tested.

Real growth happens while the business is moving. It shows up in a hard conversation that doesn’t go as planned, when we feel pulled in conflicting directions, or in a week where everything feels compressed and there’s not a clear path forward. Those experiences shape how we lead, yet development support rarely shows up there.

And that’s the gap we keep running into. Most of us truly want to grow and deeply believe in becoming better leaders. What’s been missing isn’t motivation or discipline. It’s sustained exposure to questions and perspectives that stretch how we think without pulling us out of the day-to-day of running the company.

That’s where the power of AI comes in. It allows development to happen continuously rather than occasionally, and inside everyday work rather than from the sidelines.

A Different Kind of Support, Inside the Work

What makes this moment different isn’t just the technology itself. It’s where that support can now live. For the first time, development doesn’t require us to step out of the business. It can happen in real time as we’re thinking through decisions, preparing for hard conversations, or reflecting at the end of the day.

Most of the developmental support leaders have relied on in the past required context switching. We had to step out of our work to reflect, learn, or recalibrate, and then try to carry those insights back into the messiness of real life. Sometimes that worked. Other times, the distance between insight and application was simply too great.

AI changes that dynamic. Not by telling us what to do, but by helping us think more clearly in the situations we’re already facing. It can sit alongside us as patterns begin to show up across weeks and months of work.

A lot of people assume AI is just a way to get quick answers, a glorified search engine at best. But for those of us who use it with intention, AI becomes less about answers and more about awareness. It helps us surface how we’re framing an issue, what assumptions we’re bringing into a conversation, or where we might be defaulting to habits that once served us well but now deserve a second look. That kind of support matters because it meets us where leadership is actually happening.

AI isn’t a replacement for our judgment, experience, or human connection. It doesn’t absolve us of responsibility, and it shouldn’t be used to outsource thinking. What it can do is strengthen our ability to see more, consider more, and choose more deliberately in real time.

That’s the real opportunity. Not automating leadership, but supporting the kind of thinking that allows us to grow alongside our companies instead of slowing them down.

Some people call this artificial intelligence, but the reality is that this technology will enhance us. So instead of artificial intelligence, I think we'll augment our intelligence.

Ginny Rometty

Former President and CEO of IBM

Growth Comes From the Right Kind of Stretch

As humans, growth happens at the edge of our current capacity. We don’t grow by revisiting ideas that already fit comfortably inside our worldview. We grow when we’re asked to hold perspectives that stretch how we understand people, systems, and ourselves.

The challenge is that most of us can’t see the edges of our own thinking very clearly. We’re operating inside a worldview shaped by past success, hard-earned experience, and what’s worked before. While that can help us to move fast, it also limits what feels relevant or even possible as complexity increases.

This is where AI can help in a very specific way. Not by pushing answers at us, but by offering the right kind of challenge at the right time. When a system begins to understand how we tend to frame issues or respond under pressure, it can introduce questions, scenarios, or perspectives that stretch us without overwhelming us.

That stretch might show up as a different way of looking at a stakeholder decision, an invitation to consider a viewpoint we dismissed too quickly, or a prompt to actually explain the reasoning behind our thought process. And as we engage, the challenge can adjust.

Over time, this kind of support helps us to become more comfortable holding nuance and competing truths at once. That ability matters more and more as our organizations grow because the work itself demands broader perspective and better judgment, not just faster execution.

At Ninety, this belief sits at the core of what we call a Developmental Operating System, or DOS. We’ve been working on this idea for over a decade, grounded in the belief that leaders don’t just need better tools to run the business, but better support to grow themselves. The goal isn’t to push leaders toward a fixed ideal. It’s to meet them where they are and help them expand how they think, decide, and lead over time.

This is also why we’ve been so intentional about how AI, including Maz, shows up in our platform. The aim isn’t to automate leadership or tell people what to do. It’s to offer thoughtful guidance that takes into account who a leader is, where they are in their development, and what they’re trying to build. That might mean highlighting patterns in how someone sets goals or runs meetings, then offering a small, practical challenge that encourages a different way of showing up next time.

When done well, this kind of support makes development more accessible than it’s ever been. What was once available only through elite coaching or years of trial and error can now show up in the flow of everyday work, reinforced through practice and reflection over time. That allows more founders to grow alongside their companies instead of falling behind them.

This isn’t about technology replacing humanity. It’s about technology helping us do the deeply human work of seeing more clearly and showing up with greater intention.

How You Can Start Using AI Today

At this point, the question isn’t whether AI can support leadership growth. It’s how we can use it in a way that actually helps, without turning it into another distraction or shortcut. The difference comes down to intention and where we invite it into our day.

Here are a few ways to start using AI developmentally, right inside the work you’re already doing:

1. Use AI before important conversations: When you’re preparing for a 1-on-1, a difficult conversation, or a decision that affects multiple people, describe the situation and ask for help thinking it through. Not for the right answer, but for better questions. What assumptions might you be making? What perspectives might you be overlooking? What outcome are you optimizing for, and what might you be trading off in the process?
2. Reflect while the work is still fresh: After a meeting that didn’t land the way you expected, or a decision that left you uneasy, take a few minutes to unpack what happened. Ask where you may have reacted out of habit rather than choice, or how the situation might have looked from someone else’s Seat. Done consistently, this kind of reflection builds awareness.
3. Look for patterns over time: Every few weeks, share themes from recent decisions, conversations, or frustrations and ask what tendencies might be showing up. Leaders grow faster when they can see how they consistently respond under pressure, rather than treating every situation as unique. Pattern recognition is one of the most powerful inputs to development, and it’s hard to do alone.
4. Turn insight into one small behavior to practice: When something meaningful surfaces, resist the urge to overhaul how you lead. Choose one observable change and try it for a week. That might mean speaking later in meetings, asking one more question before offering an opinion, or summarizing what you heard before responding. Growth becomes real when insight turns into action, even in small ways.

Used this way, AI doesn’t replace coaches, peers, or lived experience. It strengthens all three by keeping development active inside your everyday work. Instead of saving growth for spare time that often gets pushed to the side or forgotten, it becomes something we practice alongside running the business.

Building AI With Care and Responsibility

As you think about how you can use AI for your own development, there’s an important boundary worth holding. Every AI system reflects the values and assumptions behind how it's designed. If it's built to prioritize speed, output, or narrow definitions, it will reinforce shallow leadership rather than expand real capacity.

That’s why context and care matter. Tools meant to support leadership growth should invite reflection, strengthen judgment, and respect human agency. They should help leaders see more clearly, not tell them what to think or do.

At Ninety, we’ve approached this work deliberately. The aim isn’t to push leaders toward a fixed ideal, but to support them in growing alongside what they’re building with greater awareness and intention.

This work isn’t about technology replacing humanity. It’s about using technology thoughtfully to support the deeply human work of leadership. That’s how we can not only build organizations that endure, but how we can leave a lasting legacy worth being proud of.