How AI might evolve Leadership & Organizational Culture in the next Decade

Twenty years ago, a friend proposed that our book club read an intriguing book called “Jennifer Government”. While science-fiction isn’t my typical jam but I couldn’t resist the premise. 

"Set in a dystopian alternate reality in which a United States-dominated global government is controlled by corporate entities, it focuses on the people working to maintain the capitalist system of the society. When Merchandising Officer Hack Nike, a low-ranking member of the sneaker corporation, is forced into committing a terrible crime to build awareness for a new brand, he attracts the attention of Jennifer Government, a legendary corporate watchdog working for what remains of the federal government. However, her interests may not entirely agree with those of the government she works for anymore."

The book ticked all the boxes. Particularly for a young Canadian marketer obsessed by the idea of working for Nike but who was on the fence about EKIN tattoos or changing my name as the book proposed. 

This young(-ish) marketer stopped thinking about joining Nike over a decade ago (their recent performance suggests I dodged that one) but now thinks deeply about the intersection of marketing, corporate culture, leadership…and everyone’s fresh buzzword AI. Not as some existential stroky-beard, Scotch-fuelled exercise but because the collision of those elements will have a profound societal impact. 

Leadership because those individuals, regardless of where they sit inside an organization, set the tone of what behaviours and decisions are acceptable and unacceptable…and what’s tolerated.

Culture because no corporate strategy gets effectively deployed without the full commitment of the culture

Marketing because it remains the true growth engine of any organization.

AI, because…well…you can’t draw a breath without AI being mentioned in breathless, and understandable, excitement.  

Recently, as I go through a series of courses on Futures Thinking and Scenario Planning, I’ve been thinking a lot about “Jennifer Government” specifically reflecting on what the future of work might potentially look like.

Here are a few that crisscross my brain like a ping pong ball in a wind tunnel. I welcome your feedback and opinions because Future Thinking and Scenario Planning is both a team sport and an exercise in emotion, not just imagination.

Autonomy becomes an Alpha activity

We’ve spent years trumpeting the need for organizations to give their employees more autonomy versus micro-managing their talents. Simultaneously the most progressive organizations have taken a mallet to hierarchies bashing org charts down to wafer-thin flatness while infusing self-managed team mechanisms (see Haier) as the ultimate expression of agility, responsiveness and competitiveness. A Team of Teams mentality has replaced divisions, geographies and conglomerations. 

Concurrently the rise of digital nomads and sovereign individuals, the backlash against RTO, the rise of work as a series of tasks versus a role and title (see most recent World Economic Future of Work Report) signals a world where individual contributor becomes a coveted badge of honor versus the glib definition of the lowliest person on the corporate ladder

This begs a series of questions for me.

How individualized will work become? If culture is borne from a set of shared experiences across a group, how does that sharing occur across truly individual contributors? Is there a role for leadership in this “alpha autonomous” modality? Who - or what form – takes ownership of that leadership?

Is my Agent a Cultural Fit?

The phrase “cultural fit” is one of those corporate terms that you either consider a mantra or an oxymoron like best practises. Whether you’re an advocate (not me) or a detractor its often seen as code for “people like you are going to have a hard time flourishing inside this company” 

As AI enables each of us to create a set of agents that act independently and make decisions on our behalf, will those agents become part of the experience set we list on our resumes or offer as our specialization, just as we ‘d merchandise bilingual skills or STEM certification? Will recruiters seek Hilton and his “agent army” to fill their next job role or just good ol’ Hilton sans agents?

Concurrently as organizations build their own agent army to act and make decisions across the enterprise, who determines if the company agent is truly superior to the agent a new wunderkind employee is bringing? Those “of an age” will remember the fun and games when mobile phones entered the workforce en-mass and IT Department were caught, like little Dutch boys, trying to plug legitimate concerns about cybersecurity amidst a flood of employee demands to get company email on their personal phones.

 Again, a few questions from me…

Can an organization have an AI agent “culture” where agent behaviours and decisions are codified like they are for human employees? If an agent helps me deliver my work product better than my employer’s existing systems, can they demand I not use it? Are agents the accountability of IT or HR if they’re “making decisions” on behalf of the company?

Maybe your agent and my agent can have a discussion and get back to us with their opinion?

Is Re-skilling a Right or an Externality?

The World Economic Forum recently released a deliciously, dense report on Future of Jobs 2025. It was jam packed with global surveys of employers and employees and highlighted a myriad of topics where a bifurcation of opinion and perspective was plainly evident.

One theme was the perennial recognition that there is a significant number of humans that are woefully equipped for the near-future skill demands of their employers. What the workforce has presently in terms of skills doesn’t measure up against where organizations are placing bets for their future commercial success. Houston, we have a massive problem.

Without getting into full scale scenarios like global mass unemployment, human obsolescence, Universal Basic Income and the impact of diminishing government tax bases, there is a more immediate challenge.

Core skills required by workers today according to survey respondents from WEF Future of Jobs 2025 report

So....Who is accountable for the urgent need for human reskilling?

Does it rest entirely on the individual? Surely if they want to remain competitive then that is on them.

Is it the company? It’s their success that a better skilled workforce will enable so shouldn’t they own this.

Is it, as many “socialist” countries might contend, the responsibility of the government to keep their countrymen and women globally competitive and productive?

Question two is a little tougher…who is responsible for paying for it?  

 Individuals? Seems fair, particularly in more self-directed markets like the United States

Companies? Does a portion of corporate taxes get dedicated to this investment? Ironically many readers will likely have experienced training or L&D being the first item cut at their company when times are tight.

Governments? Seems reasonable on many fronts but what happens if their citizens refuse to or are unable to be reskilled? We don’t penalize citizens for smoking, drinking, eating fried foods even when the implications of those actions have a negative impact on their countrymen.

The intent of asking these probing questions and “what if” scenarios is not to cause dismay and despondence.

Actually, it's intended to have exactly the opposite effect.

By asking these questions – and a myriad of others that YOU likely have bouncing around your cranium – we can proactively prepare for these situations.

Prepare in a way that ensures that we hold space for the incredible humans we have in our businesses.

AND do not miss the incredible unlock that these incredible - and largely untested - new technologies promise.

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More importantly, what scenarios are you contemplating as you look at how our organizations, our leaders and how our world is evolving?

What does business leadership look and act like in an increasingly digitized world?

What does organizational culture feel like for employees a decade in the future?

How is your leadership team preparing your business and your culture for this Brave New World?

Post-script

I re-read Jennifer Government recently and it has aged pretty well. Find it here on Amazon and get back to me with your thoughts.