The Questions That Matter Most About AI and Leadership

sconway04
Sep 11
4 min read

*The hardest part of AI isn’t the tool......it’s the conversations in rooms like this, where leaders balance trust, purpose, and progress.*

AI has exploded in both scale and speed. In just a few years, billions of dollars have been invested globally, thousands of new startups have launched, and estimates suggest there are now well over 10,000 AI tools, likely tens of thousands worldwide, spanning everything from workplace productivity apps to advanced research platforms. Universities across the U.S. are responding with hundreds of new AI courses, certificates, and training programs to help leaders, employees, and students keep up with what’s possible.

The pace is staggering. And yet, when I meet with leadership teams, the most urgent questions are not about the latest model or the number of tools. They are about where to begin, how to make sense of it all, and how to move forward with clarity.

That is why I keep returning to a simple idea: the right questions matter more than the right answers. Clarity does not come from trying to master everything. It comes from asking what truly matters.

“The right questions matter more than the right answers.”

1. Where did this begin?

The story of AI did not start with today’s headlines. Decades ago, researchers and engineers were building algorithms, training models, and exploring automation in labs. What has changed is not just speed or scale, it is who has access and how deeply AI is now tied to everyday decisions.

But the real beginning of our moment is not technical. It happens when AI stops being a topic for specialists and becomes a leadership priority. Suddenly it is not just about IT. It is about trust, jobs, competitive strategy, compliance, and how people serve purpose.

In leadership roles I have held, I have seen how quickly a technology shifts from abstract to urgent. AI has crossed the line from “someday” to “now.” And that shift forces leaders to ask different questions, not just what or how, but why.

2. What’s the biggest misconception about AI?

One misconception I hear too often is that AI will replace human ingenuity. It is easy to see the fear: many stories are about automation, displacement, and disruption. But that view misses the richer truth. AI is a tool, and like any tool, its value comes from how people use it.

The organizations that are adapting best are not chasing automation for its own sake. They are asking how AI can amplify what people do best. They are creating space for creativity, judgment, relationships, and purpose. These are the questions that spark transformative work.

Leaders who thrive will be those who do not treat AI as the destination. They will treat it as a catalyst for human strength, for innovation, and for clarity in purpose.

3. What’s the hardest part for leaders?

The hardest part is not the technical complexity. Most leaders do not need to build models themselves. The challenge is in the rooms where fear, expectation, risk, and regulatory exposure collide. It is in leading teams across silos when some people want to move fast and others want to move carefully.

Leaders feel pressure from investors, boards, and employees to deliver, to prove ROI, and to stay ethical. Navigating that tension is exhausting. What helps is focusing less on perfection and more on clarity and momentum. It starts with one decision, one area, one team.

“The hardest part of AI isn’t the tools — it’s the conversations in the room.”

That shift from feeling stuck to making a first move is often more important than any technical milestone.

4. Why does this matter?

AI is not just about cost or efficiency. It is about trust. It is about how people feel about work, how communities are affected, and how industries change. Every choice made in the boardroom echoes beyond profit margins to culture, inclusion, and the meaning of work.

Transformation that lasts is built not just on tools but on values. The strongest organizations will be those that hold purpose, ethics, and human wellbeing alongside innovation. Competitive advantage will still matter, but so will resilience, responsibility, and identity.

This moment is bigger than technology. It is about leadership defined by clarity, compassion, and courage.

5. What’s the first step?

When everything feels overwhelming, the best move is usually the smallest one. Identify one question that feels stuck, one decision you have postponed, or one team area you want to experiment in. Move that forward.

Progress compounds. One step leads to learning. Learning builds confidence. Once people see change, they want more of it. You do not need all the answers at the start. You need the courage to begin.

AI will continue to grow with more tools, more programs, and more urgency. But success will not come from mastering every new product or chasing every hype cycle. It will come from asking the right questions, even when the answers are uncertain.