How I Built a Personal Board of Directors With GenAI

Want a group of advisers who are always available — and challenge you in wise and unexpected ways? Consider composing a personal board using virtual personas modeled after current and historic figures and executives.

Vipin Gupta Reading Time: 9 min 

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Summary:

Using GenAI tools, leaders can construct a virtual, personal board of directors made of personas modeled after current and historic thinkers and strategists. Author Vipin Gupta has made an MVP Board based on leaders including Steve Jobs, Indra Nooyi, and Nelson Mandela. Each virtual adviser offers distinct perspectives on strategy, innovation, ethics, and operations questions. Combined with your human relationships, your own virtual board would form a hybrid team of advisers.

Leadership experts have long championed the concept of a personal board of directors as a way for executives to surround themselves with a circle of trusted mentors, sponsors, and advisers. I’ve advocated for and practiced this model myself during the past several years. But here’s the twist: What if your board members didn’t have to be real people? With the rise of generative AI (GenAI), every leader can build a personal board of directors composed of virtual personas modeled after some of the greatest thinkers, strategists, creators, and operators in history. This isn’t science fiction. It’s a modern, scalable way to access world-class insight and clarity on demand. And I’ve built one.

Traditionally, a personal board includes former managers, trusted peers, and friends — people who offer honest feedback and diverse perspectives. These relationships differ from mentorships and sponsorships: Mentors guide, and sponsors advocate, while boards challenge and provide advice.

But real-world personal boards are hard to maintain. They require time, energy, and availability — luxuries not always in abundance. I found myself yearning for a broader, more flexible perspective. That’s when I turned to AI. Generative AI provides the ability to simulate, customize, and scale advisory insight through persona modeling and prompts.

My virtual advisers don’t replace real people in my life, but they’re always available, always sharp, and never afraid to challenge conventional thinking. Combined with my real-life advisers, this virtual board of directors forms a powerful, hybrid brain trust.

Meet My Virtual Personal Board of Directors

One aspect of virtual boards is that they are not limited by geography, networks, or schedules. I built a team of AI-powered advisers, each modeled after an iconic leader — real or archetypal — with a distinct leadership lens and personality. I refer to this collective as My Virtual Personal Board of Directors (MVP Board).

To build my MVP Board, I first identified where I needed a consistent perspective across the core leadership domains: strategy, innovation, ethics, systems, and storytelling.

I selected iconic figures who embodied excellence and diverse thinking styles among those disciplines. Using ChatGPT, I created virtual identities with defined roles, mindsets, and challenge prompts to simulate dialogue through structured reflection. The MVP Board is not static. I’ve added new voices and rotated out others. This adaptability is part of its long-term power.

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About the Author

Vipin Gupta is president, CTO, and chief product officer at FliptRx, a software-as-a-service company focused on the pharmacy benefits management industry. He also advises Fortune 500 companies, coaches senior executives, and serves on both corporate and nonprofit boards. He is the former chief innovation and digital officer at Toyota Financial Services.

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Comments (5)
Oleksii Badika
I add one more voice with the question of how exactly this was implemented by the author. Because it is obvious that the ability to effectively use such a useful tool will greatly depend on the convenience of the interface.
Sonali Shetty
This was not a use case that had previously even thought about. So thank you for a new perspective and expansion of how I could benefit from Gen AI. I love to breadth of your personal board.
Andy Dahl
@Martin Williams – I like @Walter Adamson's Projects idea. I’m also experimenting with creating as a Custom GPT and testing a few different approaches with swappable personas and built‑in actions trained around specific deliverables and formats.
Walter Adamson
@Martin Williams - how you implemented this in ChatGPT? A quick start is to use Projects - add files relevant to the role and the overall company strategy etc. Then in the "Instructions" define the role and expertise of your Board member. You can see the examples in the article you add "You are ...." in the instructions. You can also give them some traits such as a "typical COO of a mid-market industrial family owned firm" and also such things as "you enjoy playing the devil's advocate" etc etc

Go to the next level by researching your most respected experts in the field and add them to your Board (each as a new Project) and power-up by reminding them something like "you are to apply your XYZ Framework to boost the power of our thinking and leverage our outcomes" or such. 

Then operationally you have as many Projects as Board members. You would start a conversation with one and then share with others, perhaps building on it perhaps just getting everyone's initial opinion. As things evolve create documents and add them to all the Board Members files which are literally the files you load up.

Some important tools of trade: 1. There is no sharing of context between each conversation in a ChatGPT Project, which has downsides and upsides. 2. However, if you allows it, ChatGPT collects memories which you direct it to remember, and snippets from across all your conversation which it deems important. 

Therefore, if you are "single purpose" e.g. you have a pure ChatGPT account for one job with one employer and you allow both memories then your Board Members will magically recall conversations about the business from all across the business. This is very useful. On the other hand, if you advise several different businesses in several different roles and go deep in several different domains then the shared memories dilute your ability to nudge your Board Members in the right direction. I turn all memories off not because of any privacy reason but because they distract the AI from what I want.

I trust this helps, Walter Adamson Linkedin /adamson
Martin Williams
Great  idea! And an insightful article. I’m intrigued to know more about how you implemented this in ChatGPT. Can you sketch out what you did to create the board?