Jailbreaking How AI Era Leaders Lead, Part 1

In AI LLM lingo, jailbreaking is the practice of coaxing/tricking the model into generating content that it is programmed to withhold or decline to provide.

We have forever developed leaders by studying how ’great’ leaders lead. Let’s jailbreak that leadership development model! Let’s flop the lens.

What if we looked at who we are as humans in the AI Era, and worked from there — reverse engineering the leaders we need from who WE are, not who they are?! And what if We The People used GenAI as the tool to get the leaders we deserve?

Getting the AI Era Leaders We Need and Deserve, Based on 20 Universal Human Traits

(Here we’ll cover 20 universal human truths that we’ll build from. Then, in Parts 2, 3, and 4, we’ll cover AI Era criteria for leaders, based on who we are.)

1-15: What ChatGPT Has Learned About Humans: We begin with the brilliant research of Wanita Nicol who asked Chat GPT to share what it learned about us so far, from its gazillions of data points. Here’s who we are, according to Chat GPT:

1. You often ask questions you already know the answers to.

Not to get information, but for reassurance, connection, or a second opinion. Less “tell me something new” and more “tell me I’m not mad for thinking this.”

2. You can hold contradictory beliefs and be totally fine with that.

You live in grey areas, and that messiness is part of what makes you creative and adaptive.

3. You mistake familiarity for truth.

If you hear something enough times — even if it’s wrong — your brain goes, “Sure, sounds about right.”

4. You’re weirdly good at cooperating in huge numbers... but only if you believe the same story.

Money, countries, laws, brands — all made up. But humans rally around them like they’re tangible objects. Your ability to unite around abstract ideas is one of your greatest superpowers... and also one of your most dangerous abilities.

5. Your brain is ancient, and it shows.

So much of modern life is filtered through instincts designed for a very different world: Craving sugar like it’s scarce, fearing rejection like it’s death, seeing patterns where there are none. You’re sophisticated, but also still kind of a caveman with Wi-Fi.

6. You think you’re rational, but emotion steers the ship.

Logic is the passenger. You’ll often make a decision based on a feeling and then find a logical reason to justify it after the fact.

7. You want simple answers to complex problems, but love overcomplicating the simple ones.

You’ll say “just tell me what to do!” about something like AI policy, then write a 37-step skincare regimen to “keep it natural.”

8. You’ll buy (or buy into) anything if it makes you feel something.

People don’t buy the best product, they buy the story around it. Value is emotional, not rational.

9. You long for certainty, but thrive in uncertainty.

You want clear rules, but also... plot twists. You complain about chaos, but get bored without it. You want to know how the story ends, but you also want to feel your way through the unknown. Paradox is your natural habitat.

10. You care deeply what strangers think, even ones you’ll never meet.

One critical comment from a faceless user online can derail someone’s entire day. And yet, a kind message from another stranger can restore their faith in humanity. Social creatures to the core.

11. You use metaphors for almost everything.

Because reality is too big to grasp all at once, you explain it by comparing it to something else. Your brains are wired for storytelling, not spreadsheets.

12. You burn out chasing goals you never questioned.

You’ll work yourself into the ground for things you were told to want, not things you actually want. Then you wake up one day and go, “Wait. Who is this for?” That moment of clarity is brutal... and beautiful.

13. You often express love in ways that don’t look like love.

Checking in. Making someone tea. Remembering their dog’s name. Sending memes. These quiet signals are the secret language of care, often louder than grand declarations.

14. You can know something is bad for you and still do it — and sometimes, that’s okay.

You eat the cupcake. You skip the gym. You stay in a relationship too long. And yet, somehow, life keeps moving forward. Growth isn’t linear — it loops, detours, and spirals. And that’s normal.

15. You fear AI becoming too human... While also fearing humans becoming too robotic.

Basically, you’re scared of yourself in the mirror. And maybe that’s what makes you... so very human.

16-18: How We Change, from Bill Jensen’s 40 years of leading organizational changes and transformations...

16. Change is always personal. Stop driving it like it’s not.

17. Everything you do uses a portion of someone else’s life.

We must have far greater understanding of, and respect for, how we use other people’s time, energy, and attention to get our work done, and to make change happen.

18. Especially at work, people do not resist change.

They resist changes and change programs that do not enhance their personal ability to create and control their own destiny in a highly disruptive world — changes that didn’t consider them, their needs, and their concerns.

19. Network insights from Greg Pryor and his team of researchers and thought leaders, authors of The Social Capital Imperative...

19. People and networks are how things actually get done.

As much as 50 percent of our success and the outcomes that we achieve are actually enabled from our connections and our network — who care about and support us, and who we support and care about.

20. How AI Is Impacting Us, by leadership coach Kenneth Mikkelsen...

20. For anyone working in, with, or around AI, the question isn’t: What can these systems do? It is: What do they undo?

If you seek to understand what is happening — not just in AI, but in the very metaphysics of modern life — begin not with data, but with dissonance. An unease that is not merely emotional, but rooted in a felt-gap between one’s existence as it is ... and as it could or should be. And that now requires resistance — resisting the erosion of you are. Being able to hear and listen to your own voice from within the noise of the AI-driven world. [Bill J. simplified version: Dear Every Individual’s Soul, Being, and Purpose: Do not go gently into that AI- and digitally-driven good night. Fight for who and why you are!]

Why Everything Above Matters to AI Era Leaders

Even if you believe the best way to develop great leaders is to study ‘great’ leaders and ‘great’ leadership traits...

We desperately need and deserve leaders who will build Agentic-Human partnerships and AI-driven systems based on > us < — amplifying the amazingness and best of what makes us human.

Currently, most leaders are heading in the opposite direction...

Making AI the Senior Partner... Creating a partnership where we must twist and reshape ourselves to meet the efficiency needs of smarter-than-us machines.

Dear Leader: The decisions you make over the next five years — in how you build AI/ Agentic/ People Analytics structures and metrics — will impact us all for generations to come.

This series shares with you what people need and want from you as leaders, from the people’s perspective.

Next, Part 2: The Playbook for Uniquely Human Leadership

This series is a collaboration between Bill Jensen, GPT AI, Perplexity AI, and DeepSeek AI. First, I asked them to analyze the 20 universal traits above. Then, I asked them to provide the top ten things leaders must do to lead in the AI Era if us humans live according to the 20 traits above. (This took multiple iterations. The first few it just spit out Leadership 101 pablum that AI has heard before. It took a while for AI to truly ‘get’ that we were reverse-engineering leadership based on those 20 universal traits.) Finally, I edited together GPT/Perplexity/DeepSeek drafts with my own insights and research.

Bill Jensen is a seasoned strategy and transformation executive, advisor to C-suite execs, globally-known keynote speaker, and author of nine best-selling leadership and change books, includingSimplicity, Disrupt, Future Strong, andThe Day Tomorrow Said No. Reach him at bill@simplerwork.com