The Chicago Journal

The Rise of Generative AI in Corporate Leadership

A quiet shift has been happening in executive suites across the Fortune 500. Generative AI, the technology that started as a consumer curiosity in late 2022, has moved from the IT department to the boardroom in less than four years. Chief executives who once described AI as something their CIOs were “exploring” now describe it as central to their operating model. The transition has not been smooth, evenly distributed, or universally productive — but it is real, and the implications for how companies are run are bigger than the technology press tends to acknowledge.

The story is no longer whether large companies are using generative AI. The story is what they are using it for, what they are not, and what kind of leadership the tool is reshaping.

From Pilot Projects to Operating Reality

The arc of corporate AI adoption has moved through three distinct phases in roughly three years. The first was experimentation — small pilots inside finance, marketing, or HR teams, often run by curious managers without formal executive sponsorship. The second phase brought formal AI strategies, dedicated chief AI officer roles at firms including Mastercard, S&P Global, and Eli Lilly, and large enterprise contracts with the model providers.

The third phase, which is where most large companies now sit, looks different. AI tools are no longer concentrated in dedicated teams. They are embedded in legal review, financial planning, code generation, customer support, supply chain optimization, and increasingly in the executive workflow itself. CEOs are using internal models to draft board memos, summarize earnings call transcripts from competitors, and pressure-test strategic decisions before sharing them with senior staff. The technology has become infrastructure rather than initiative.

This shift carries an important implication. When AI is a project, leadership decides about it. When AI is infrastructure, leadership decides with it. That second relationship is the one reshaping how decisions actually get made.

The New Skill Set at the Top

The capabilities that defined corporate leadership for a generation — strategic vision, capital allocation discipline, talent development, board management — have not disappeared. What has changed is the supporting skill set sitting underneath them. Executives now need a working understanding of model capabilities, limitations, and failure modes that did not exist five years ago.

The competence is not technical. CEOs are not expected to fine-tune models or read research papers. They are expected to understand, at a conversational level, what generative AI does well, where it hallucinates, what kinds of decisions it can usefully support, and what kinds it cannot. That understanding is becoming a basic literacy requirement at the senior level, similar to how a working grasp of digital advertising became table stakes in the 2010s.

The leaders who have adapted fastest tend to share a few characteristics. They use the tools personally rather than delegating that work to staff. They have direct relationships with their vendor counterparts at OpenAI, Anthropic, Google, or Microsoft. And they have built internal evaluation frameworks that let them measure whether AI deployments are actually producing the ROI claimed in the original business case.

The leaders who have struggled tend to have outsourced their understanding of the technology to consultants, which has produced expensive strategy decks and limited operational change.

The Productivity Question Nobody Has Fully Answered

The economic case for generative AI in corporate settings still rests on contested ground. Vendor-published studies show productivity gains of 20% to 40% in coding, customer service, and marketing copy production. Independent studies show more modest results, with significant variation by task type and worker skill level. Some functions — junior-level legal review, code refactoring, first-draft content production — show clear, repeatable gains. Others — strategic analysis, novel problem-solving, complex negotiation — show benefits that are harder to measure and easier to overstate.

What is unambiguous is that companies have committed real capital to the technology. Enterprise spending on generative AI is projected to exceed $300 billion in 2026, according to IDC tracking data, up from roughly $40 billion in 2023. Whether that spending is producing commensurate value remains an active board-level debate at most large companies. The CFO conversation has shifted from “we should be investing” to “show me the returns,” and the executives who can defend their AI spend with concrete metrics are gaining influence over those who cannot.

The Workforce Question Leadership Cannot Avoid

Generative AI’s most consequential leadership challenge is not technological. It is workforce-related. Large companies including IBM, Klarna, Salesforce, and most of the major consulting firms have publicly announced AI-driven changes to hiring patterns, particularly for entry-level knowledge work. The pattern is consistent: junior roles are being absorbed by AI tools, while senior roles are being augmented by them.

That pattern creates a structural problem that executives are still working through. Senior knowledge workers were once junior knowledge workers who learned the trade by doing the work that AI is now doing. Removing the entry rung from the career ladder produces short-term productivity gains and a long-term talent pipeline problem. The most thoughtful CEOs are now talking publicly about how to preserve apprenticeship pathways in an environment where the apprentice-level tasks have been automated. The less thoughtful ones are simply cutting headcount and assuming the talent pipeline will sort itself out.

What This Means for the Next Decade of Leadership

The leaders who will define the next decade of corporate management are likely the ones currently in mid-career — senior managers and rising executives who have grown up using these tools and who understand them at the level of intuition rather than abstraction. That cohort will move into C-suite roles over the next five to seven years, and when they do, the questions executives ask of generative AI will get sharper.

The questions today still tend to be strategic: what should we do with this technology? The questions a decade from now will be operational and competitive: what specific advantage are we extracting from this technology that our competitors are not? That second framing is the one that will separate the companies that genuinely benefit from AI from the ones that simply spent a lot of money on it.

Corporate leadership has always been about translating capability into outcome. Generative AI has expanded the capability layer in ways that are still being understood. The leaders who win the next phase will be the ones who treat the technology as a tool inside a larger judgment process — not as a substitute for the judgment itself.

Kate McKay on Age Out Loud and Living With Confidence

By: Daniella Stewart

There is a version of midlife that gets sold quietly.

Be grateful. Be calm. Do not push too hard. Accept what is.

Kate is not buying that version of the story.

Through Age Out Loud, she is pushing in the opposite direction. Not recklessly, not blindly, but intentionally. She is asking a different question altogether. What if this stage of life is not about managing decline, but about stepping into something more honest?

Not louder for attention.

Louder for truth.

Consistency Is Not About Feeling Ready

Kate does not pretend that motivation is reliable. She is blunt about it.

Motivation gets you moving. It does not keep you there.

What actually carries people forward is something deeper. A clear vision of who they are becoming. Without that, it is too easy to quit when the second thing feels uncomfortable.

And they always do.

She talks about consistency as a practical matter. Doing the workout when you do not feel like it. Showing up anyway. Repeating the habits that keep you steady.

Not perfectly.

Repeatedly.

There is also an honesty in how she frames discomfort. She does not see it as something to avoid. She sees it as part of the deal. If you want to build anything meaningful, you are going to have days when you do not feel like it.

The difference is what you do anyway.

Because for her, skipping is not just skipping. It is a moment where you quietly decide to let yourself down.

And she is not interested in building a life that feels like that.

The Shift Away From External Approval

There is another layer to what holds people back, and Kate does not tiptoe around it.

We are living in a constant performance loop. Approval, comparison, attention. It is everywhere, and it is exhausting.

She has noticed something interesting, especially in midlife. The tolerance for all of that starts to fade. People begin to see through it. What once felt important starts to feel empty.

That is where the shift begins.

Instead of asking how I look or how I am perceived, the question becomes more personal.

What actually feels right for me.

What kind of life do I want when no one is watching?

That shift is not dramatic, but it is powerful. It moves people from performance to ownership.

Kate ties this back to something deeper. Being grounded internally, spiritually, emotionally, in a way that is not constantly pulled by outside opinions.

From that place, self-trust begins to build.

And once that starts, the need for validation fades.

Living Out Loud Is Not a Performance

There is a misconception around bold living. It is about being the loudest person in the room or constantly pushing limits for attention.

Kate’s version looks different.

It is quieter in some ways, but far more demanding.

It is about not shrinking.

Not adjusting yourself to make other people comfortable. Not filtering your life down to something easier to explain or easier to accept.

That does not mean it comes without friction.

She has faced criticism. A lot of it.

Too emotional. Too much. Too different.

And what stands out is not that she avoided it. It is what she felt. She is very aware of how she is perceived. She notices judgment. It affects her.

But she made a decision anyway.

Not to dim herself to make other people more comfortable.

That decision did not happen overnight. It is something she is still working through. But it sits at the core of how she lives now.

Because when you hold yourself back long enough, you do not just limit your life.

You limit your impact.

Confidence Gets Misread All the Time

One of the more interesting things Kate points out is how often confidence gets misunderstood.

People see someone grounded, clear, and direct, and they label it as arrogance.

That disconnect can make people hesitate. It makes them want to soften themselves, tone things down, and stay more neutral.

Kate knows that pattern well; she tried it, and it did not work.

Because when you start shaping yourself around how others might interpret you, you lose something essential.

Her shift has been toward accepting that not everyone will understand her. Not everyone will see her clearly.

And that is fine.

Because the alternative is living in a way that feels smaller than it should.

The Real Work Happens in the Small Decisions

There is nothing complicated about the way she talks about change.

It is not about massive overhauls or dramatic reinventions.

It is about small decisions made consistently.

Setting up your environment to support you. Having a plan so you are not negotiating with yourself all day. Removing friction where you can.

And when you fall off, which she fully expects people to do, the response matters.

No spiraling. No waiting for the perfect restart.

You just get back to it. That is what consistency actually looks like.

Not perfection, repetition.

A Life That Feels Like Your Own

What Kate keeps coming back to is this idea of ownership.

Not living based on expectations you never chose. Not chasing approval that never satisfies. Not waiting for confidence to show up before you act.

Instead, build a life that feels aligned from the inside out.

That means paying attention to what actually fulfills you, not just what gets attention.

It means being honest about what no longer fits, even when letting go is uncomfortable.

It means choosing how you show up, intentionally, even when it would be easier to drift.

The Message She Wants to Leave Behind

If there is one thing she wants people to take with them, it is not complicated.

You are not too late, you are not behind, you are not done.

If anything, you are standing at a point where things can finally become more real.

Less performance. More truth.

Less pressure. More clarity.

Less waiting. More living.

Kate is not offering a perfect path. She is offering a different lens.

One where strength is built, not assumed.

Where confidence is created, not found.

Where this stage of life is not something to survive, but something to step into fully.

And if you follow that through, it leads somewhere most people do not expect.

Not to a completely new version of yourself.

But to one that feels a lot more honest than anything that came before.