A senior financial services executive, Ryan Sparks, shared something unexpected with us in a discussion: He had built a “Jamie Dimon.” Earlier in his career, he had access to the JPMorgan Chase CEO, regularly engaging with his operating committee and occasionally with him directly. That proximity had a real impact on Sparks’s career and thinking.
What struck Sparks most was Dimon’s leadership style and how it shaped the thinking of everyone around him. Dimon challenged assumptions, pushed for bigger thinking, and asked questions that made people pause.
As Sparks’s career progressed, he changed roles and organizations, and that access disappeared. He had other mentors and advisors, but he no longer had someone embodying that caliber of thinking discipline.
Using generative artificial intelligence, he created a version of that lost thinking dynamic to codify the relentless questioning and rigor that Dimon embodied, and embed it in an agent he could call on to challenge his assumptions and expose his blind spots. That got us thinking. What if senior leaders stopped treating Gen AI primarily as a tool for producing work and started using it to improve how they think?
Your board isn’t always built for this
Senior leaders already have people around them: boards, executive teams, mentors, coaches, and advisors. But each relationship has constraints. Corporate boards have governance responsibilities. Executive teams have organizational responsibilities and personal agendas. Mentors have limited time. And the more senior you become, the harder it can be to find people willing to tell you what they really think about your strategies and recommendations.
At the same time, senior leaders are facing greater challenges and uncertainty. Gen AI impact is changing business models and jobs. Geopolitical risk is rising. Executive tenures are shifting.
Having the right minds around you when you’re trying to make sense of it all is a game changer. This is where Gen AI gets interesting. You can use it to create a personal board of directors built around the kinds of thinking you need most.
Build for the thinking you are missing
As professors and organizational change practitioners, we draw on Albert Bandura’s work on human agency to examine AI and leadership thinking. Bandura proposed that there are four qualities that help people take agency over their own behavior:
- Intentionality: You decide what you intend to accomplish and make a plan to act.
- Forethought: You anticipate possible outcomes and let those expectations guide your actions.
- Self-reactiveness: You manage your behavior to carry out your intentions, monitor progress, and adjust your actions.
- Self-reflectiveness: You examine your thinking, capabilities, and actions.
Doing all four well is difficult, especially when you are operating under pressure. That’s why the composition of your board matters. You need different kinds of thinkers who expose different weaknesses in your reasoning. Here are five recommended personas you should include on your board, even if your board meets in your kitchen.
The Provocateur: Jamie Dimon
The provocateur questions what everyone else has accepted. They challenge sacred cows. They are suspicious of consensus and ask the questions everyone may be thinking but won’t say out loud.
Everybody needs a Jamie Dimon. Dimon has never been particularly interested in making his opinions comfortable for the room. Describing the prospect of AI displacing a multitude of truck drivers, he warned, “you can’t lay off 2 million truckers tomorrow.” He called for phasing in automation alongside retraining. He has pushed executives to confront what happens to workers and society when companies move too quickly. That’s the value of the provocateur.
When everyone around you agrees, this board member asks incisive questions. Fold them in when you’re making a big bet, facing uncertainty, or making a strategic pivot.
Ask this agent: “What are we all accepting as true that deserves to be challenged? Where might we be agreeing because it’s easier than questioning the plan?”
The Systems Architect: Satya Nadella
Big ideas are easy to admire. Making them work inside an organization is much harder. When you say, “Here’s where we’re going,” the systems architect asks, “What has to change on Monday morning for that to happen?”
Everybody needs a Satya Nadella. To prepare Microsoft for the AI era, Nadella reorganized its leadership to help the company move faster on AI. He replaced its long-standing senior leadership team with groups focused on governance, engineering, and Copilot. He began reviewing AI metrics weekly, bringing product and engineering decisions closer to him.
Ask this agent: “What must change in how my organization operates for this strategy to work? Where is the friction?”
The Pattern Spotter: Reed Hastings
Some leaders see change after it happens. Others notice the signals earlier. The pattern spotter has lived through enough cycles to recognize when something familiar is happening in a new form. They can parse out and distinguish a meaningful signal from the hype of whatever happens to be dominating this week’s conversation.
Everybody needs a Reed Hastings. Netflix moved from DVDs to streaming, then from distributing other people’s content to producing its own. Each shift required acting before the next model was completely obvious. Hastings doesn’t have a crystal ball that can predict the future. Instead, he has repeatedly been willing to question whether the business that succeeded yesterday should still be the business tomorrow. Your pattern spotter should do the same for you.
Ask this agent: “Where have we seen something like this before? What happened next? And what’s different enough this time that the old pattern might mislead me?”
The Outside-In Voice: Mira Murati
Every industry develops assumptions: “That’s not how our customers buy,” “Regulation would never allow it,” “Our business is different.” The outside-in voice isn’t impressed. This person brings ideas from other industries, markets, technologies, and geographies and asks why something that works elsewhere couldn’t work for you.
Everybody needs a Mira Murati. Her career has crossed automotive technology, product development, and frontier AI. That mix matters because some of the most useful questions come from people who aren’t trapped inside one industry’s definition of what is possible. Your outside-in board member should make your industry’s rules feel less permanent.
Ask this agent: “Where can we find inspiration? Has someone faced a similar problem? What assumption are we treating as a constraint simply because we’ve always operated that way?”
The Humanist: Jacinda Ardern
Every transformation impacts a human being, whether it’s job losses, a change in the hierarchy, or team members worrying about their new role. The humanist makes sure to think through these consequences before the rollout, not after.
Everybody needs a Jacinda Ardern. As New Zealand’s prime minister, she led the country through several moments of crisis. After the mass shootings in 2019, she helped turn public grief and outcry into gun control legislation. When facing unfamiliar problems, she brought experts and community members into the discussion. She communicated uncertainty directly and considered people’s lived experiences in her decision-making. Your humanist should force you to examine how your strategy will impact people.
Ask this agent: “What am I asking people to believe, unlearn, and become? What will this change cost them? And am I giving them what they need to make that transition?”
Now put the board to work
You don’t need access to Jamie Dimon, Satya Nadella, Reed Hastings, Mira Murati, or Jacinda Ardern to start. To identify who you need to access to complement your thinking, start with one decision you’re wrestling with. Then choose the board members, actual leaders, whose perspectives would be most useful. Feed an AI system (such as ChatGPT, Claude, Perplexity, or Gemini) the source material that captures how those leaders think: shareholder letters, interviews, speeches, books, podcasts, public testimony, or other first-person material. This makes your board different from others and unique to you. While some leaders may have a “Jamie Dimon,” others may have a “Mark Cuban.”
Then give your board the decision. Consider asking each board member to share their perspective on the decision. What does the provocateur attack? Where does the systems architect predict failure? What pattern does the pattern spotter see? What does the outside-in voice say that your industry is missing? What human consequence is the humanist forcing you to confront?
Then, once you have insights from your board, make the decision yourself. That’s the point. The best use of a Gen AI board is creating more friction before you make the final judgment.
