As a nonprofit CEO leading Big Brothers Big Sisters of Puget Sound, I’ve spent a lot of time thinking about how technology like AI intersects with real-world leadership challenges. Recently, I chatted with a fellow CEO who confessed she’d been using AI for eight months, but when her board asked about its benefits, all she could say was that it saved time on writing tasks. Turns out, she’s not alone. Surveys show that while many organizations have dipped their toes into AI, only a handful truly view it as a strategic asset. This isn’t about the tech failing us or a lack of training—it’s a leadership gap, plain and simple. Most of us are stuck using AI to churn out answers faster, chasing that elusive “time back” in our packed schedules so we can handle more meetings or emails. But what if we flipped the script? What if AI wasn’t just a productivity crutch, but a catalyst for better questioning? In my experience, that’s where the real magic happens, turning a tool into a genuine edge for leaders. I’ve seen this play out time and again: the bottleneck isn’t the AI itself, but the quality of the questions we bring to it. And trust me, that’s a skill we can learn.
My perspective on this isn’t purely from the nonprofit world. I cut my teeth in big tech at companies like Microsoft, Verizon, and Qualcomm before shifting to mission-driven roles. Watching both sides embrace AI has been eye-opening—they pour resources into the tools but barely touch the human sidepant, the curiosity that makes it all click. It’s about asking the question underneath the surface question, peeling back layers to uncover what’s truly driving decisions. Before AI entered the picture, many vital questions felt too risky or expensive to explore. Say you’re a leader wondering if you’re really the right fit to steer your organization through a tough crisis—that’s a tough, vulnerable question. In the old days, you’d need a trusted advisor with all the context, available at your beck and call, or you’d have to expose that vulnerability, risking your reputation or relationships. Most of us just avoided asking, not because we didn’t care, but because the price tag was too steep.
Enter AI, which has dismantled three key barriers that kept those deep questions locked away. First, the social cost: You can whisper your darkest doubts to AI without fraying a single relationship or hurting anyone’s feelings. Second, the time cost: No need to schedule a meeting or wait for someone to free up—it’s always there, instantly responsive. And third, the judgment cost: That nagging inner critic that filters out embarrassing or uncomfortable thoughts? AI doesn’t judge; it just listens and responds to what you actually say. This is a game-changer for intellectual honesty. Imagine feeling free to probe into things like imposter syndrome, ethical dilemmas, or even doubts about your team’s direction without the fear of fallout. It’s like unlocking a door that’s been bolted shut for years. But here’s the catch—most leaders aren’t leveraging this yet. They’re busy automating the easy stuff, missing how AI could fundamentally change how we think and lead.
Of course, with great power comes great risk, and AI isn’t immune to that. If we’re not careful, it can silently erode our own thinking muscles. Think about it: AI can draft emails, summarize reports, and spit out decision options like it’s nothing. A leader could zoom through a week of tasks, churning out outputs without ever pausing to form their own opinions, wrestle with uncertainty, or make a genuinely tough call. MIT Media Lab researchers call this “cognitive debt,” a term they coined after a study where students using ChatGPT for essays showed weaker brain activity. When the AI users later tried writing on their own, their brains stayed under-engaged, as if they’d gotten addicted to outsourcing. It’s like taking on financial debt—quick gains now, but long-term costs later. This maps straight to leadership: without practicing those mental reps, our ability to discern and decide atrophies. I’ve seen this in my own talks with nonprofit leaders. I ask them to list AI tasks from the past two weeks and rate what required their personal judgment versus pure processing. The ratio often shocks them—not because they’re lazy, but because AI’s frictionless nature blurs the line between true thinking and autopilot mode. Leaders who audit this early gain an advantage, avoiding the trap of letting AI replace their brains.
So, how do we channel AI toward better questions instead of falling into that debt pit? I always start with simple prompts that force introspection before diving into action. One gem is: Before asking AI for options or frameworks on a big decision, try this: “I’m going to describe the most important decision I’m facing right now. Don’t give me options or a framework. Tell me: what is the question I haven’t asked yet that would change how I’m thinking about this?” People who’ve tried it come back floored—the question AI surfaces is usually one they’ve dodged for months, like questioning core assumptions or worst-case scenarios. Another prompt flips it to reveal the risks: “Here are the tasks I’ve used AI for in the last two weeks: [list them]. Which of these required my judgment and values, and which ones were processing work? What does the ratio tell me about how I’ve been using my own thinking?” Just making that list can be revealing; if you can’t name five tasks, or if you rattle off 20, it signals something about your habits. These aren’t tricks to use AI better—they’re tools to use yourself better, reminding you that AI’s value hinges on the thought you bring. It’s empowering, like having a patient coach that never tires.
Yet, let’s be real: AI has limits, especially for the heart of leadership. McKinsey nails it when they say only human leaders can define why we work and what we’re achieving. AI can unearth those big-picture questions, challenge us on them, and hold space without bias—but it can’t answer them for us. That requires curiosity, honesty, and the courage to face whatever bubbles up. Skills like AI literacy or governance are important, sure, but the bedrock is that willingness to ask your rawest questions to a tool that doesn’t blink an eye. And here’s something rarely discussed in all the productivity hype: AI democratizes access in a way history never has. For generations, probing deep questions with expert guidance meant having the right connections—advisors, networks, insider access that was rarely fair. Now, a nonprofit leader without fancy consultants, a first-gen exec lacking mentors, or the head of a tiny org without a research team gets the same high-level thinking partnership as anyone else. Questions that once cost a fortune are free. It’s a seismic shift, the biggest leveling of intellectual access in our lifetime. Leaders who seize this first will innovate in ways others can’t even imagine. No matter your sector, size, or role, there’s a massive opportunity right now to level up—by asking smarter questions, not just faster answers, we can amplify AI’s power and deepen our own leadership depth in ways that truly matter.
