The technology works. Employees are using it. What doesn’t work is that we’re asking leaders to drive massive change without equipping them to do it successfully. Until that gap closes, AI will remain stranded capital.

The math is brutal. MIT found that 95% of generative AI pilots at companies are failing. Bain reports organizations spent $30 to $40 billion on generative AI in the past year. And McKinsey found fewer than 1% of companies describe their AI adoption as “mature.” Massive investment, negligible return.

I spent nine years at Salesforce leading through major transformations. The technical side of change is never the hardest part. It’s always the human side that determines whether things succeed or fail.

What nobody’s saying out loud

I keep hearing the same pattern in conversations with executives. They have AI mandates from the top, with no clarity on how to get their people ready, on top of everything else they’re already managing. And there’s this thing they’ll only say in private, “I don’t know what I’m doing.” Nobody does.

In most organizations, leaders are still rewarded for looking certain, staying in control, running tight systems. Take a risk with AI and get it wrong? Most people believe they’ll be punished for failure. Those same behaviors crush the experimentation and trust AI depends on. 

Companies are essentially handing leaders technical training and telling them to figure it out. That’s hope, not strategy.

When Bret Taylor became Salesforce’s Chief Product Officer, I got 30 minutes with him as a rising product leader. I knew our approach wasn’t working and spoke from the heart about what I was seeing and how it needed to be better. He could have dismissed it, as I was several levels down. Instead, he listened. 

We created an Associate Product Manager program that taught not just technical skills but also critical leadership skills like how to challenge the status quo, navigate conflict, work across teams, and show up under pressure.

We didn’t just mandate change or add a training program. We changed the nature of the conversations teams were having by injecting new thinking and new ways of working at a grassroots level. Then we listened closely to what was working and what was standing in our way and iterated on our approach in real time. That’s how you build lasting change, not by announcing something and hoping everyone figures it out.

Most companies are doing exactly that with AI. Funding tools and training, while neglecting the systemic change needed to drive real transformation.

What the 5% actually do differently

Harvard Business Review analyzed what separates companies where AI pilots succeed from the 95% where they fail. The differentiator isn’t the technology. It’s leadership.

The winning companies do two things at once. They fund technical training and fund developing leadership capacity for transformation. Their leaders can navigate fear and resistance across teams. They create strategic clarity and alignment. They create safety for experimentation and failure. They model risk-taking in uncertainty and hold people accountable to entirely new standards.

That requires real support. Not just workshops, but individualized help for challenging situations. How to have conversations about readiness. How to create psychological safety when someone says they’re afraid of being replaced. How to navigate resistance when it inevitably shows up.

Most companies lack that leadership infrastructure. Gartner found 66% of CEOs say their executive teams lack AI confidence. The leaders who can create clarity and safety in chaos, their teams will become AI-first. The ones who can’t? Their teams will just be busy.

You can’t solve an adaptive challenge with a training program. Leaders need help applying AI to their actual work: their specific role, team, challenges. They need a place to work through fear and uncertainty without career risk. That’s fundamentally different from what most companies are funding, and the 95% failure rate proves it.

Companies are funding the wrong intervention

Companies are treating AI as a technical problem when it’s a leadership capacity problem. Your competitors are making the same calculation right now. Some of them are getting different answers.

AI is forcing us to confront something we should have fixed years ago. We’re asking leaders to navigate unprecedented complexity with the same development approach that hasn’t worked for decades.

The companies that get this right won’t just succeed with AI. They’ll build leadership capacity that outlasts whatever technology comes next.

The billions are already spent. The question is whether they turn into returns or stranded capital. That answer depends entirely on whether you’re willing to fund the leadership gap, not just the technology gap.

Sibling rivalry. Lying. Greed. Betrayal. A controlling, narcissistic father and a crumbling family empire with no one to hold it up.

Though we could be looking at any number of Shakespearean tragedies, the above is a loose plotline for the HBO show Succession. While the show is fictionalized, there are dysfunctional families and dysfunctional companies everywhere. Often, the two coalesce in a dystopian reality that makes for great entertainment but terrible business. It also gives the false impression that families that go into business together will only ever implode their relationships with their clients, their shareholders and each other.

In truth, well-educated leaders understand that the unpredictable and shocking final episode of Succession is what it looks like when you don’t have a succession plan—something that should be in place long before the head of the company passes away or Dr. Phil is called in for an intervention.

In real life, effective succession planning can save companies, not destroy them.

No one knows this better than Ivan Lansberg and Devin DeCiantis, who co-wrote The Enduring Enterprise as a tribute to the work they do together at Lansberg Gersick Advisors, an advisory company dedicated to serving the world’s leading family enterprises.

“One of the things that’s so unique about succession is just how predictable and inevitable it is,” DeCiantis says. “Not all risks are going to present themselves in such an obvious way to every single organization.”

“This is one of the reasons why we’re out there talking about this,” he adds. “We want more people to attend to this proactively rather than reactively.”

Yet reactively is how many companies—including family-run ones—respond.

Why do so few companies think about succession planning?

“Despite the fact that we’ve been at this now for 30 years, warning [people] that this is an important thing to do,” Lansberg says, “lots of very sophisticated companies globally don’t have good succession plans.”

Domestically, data from PWC’s 2023 US Family Business Survey reveals that in 2021, only 34% of family-run businesses had a robust, documented succession plan in place. So what’s preventing so many businesses from proactively creating succession plans if they’re so important?

The answer, Lansberg says, is layered—particularly when it comes to family businesses.

“Many entrepreneurs launch into building companies, and at some point in their development… limitations of their own biology come in and hits them in the face, and they start wondering, ‘How are we going to continue this enterprise? And how do I pass it on to my kids or not?’” he says. “Wrestling with that question becomes a very important feature, not just for the family’s continuity as an enterprising family but for all of the families that live off the enterprises that… [these] founders create.”

Still, broaching topics of death and hierarchy aren’t things that most families are naturally hard-wired to discuss.

“If you do the mental experiment of sitting with your parents to talk about what’s going to happen with the family when they’re no longer with you, it’s a scary proposition,” Lansberg continues. “It raises the question of how we’re going to deal with life without them, but it also erases all of the uncertainties of… my kids being greedy. Are they pursuing other objectives and not caring about us, and so forth and so on.”

Succession planning takes time

Another issue is one of obsolescence. According to Lansberg, reinvention is often necessary for a company to survive in the current marketplace. This can include bypassing blood lineage by bringing in non-family executives who may be able to offer fresh perspectives that can move the business forward. But most families may avoid these discussions out of fear.

“The sum total of all of these factors leads many companies to get caught flat-footed at the very moment when these issues need to be clarified and thought through,” Lansberg says. “And unfortunately, because of that, many end up failing.”

Scrambling can easily be avoided, DeCiantis adds, but disaster prevention takes concerted effort.

“It behooves any organization that desires long term success to… be more proactive and not just wait for the heart attack or the final episode of an HBO series to inspire them to attend to something that actually does take a considerable amount of time,” he says. “Succession planning isn’t something that you sit down to at 3 [p.m.] on a Friday afternoon and finish at 4 [p.m.] and call it a day, and you say, ‘Okay, I’ve got the plan, [so] let’s go and execute this now,’ and by Monday morning, there’s a new regime in charge.”

Which companies are doing it right?

In their book, DeCiantis and Lansberg show family business leaders across the world who they say have gotten succession planning right. In addition to highlighting notable family-run companies like Kikkoman, Samsung and the New York Times, the duo have profiled global companies that are still standing strong after surviving military coups, war, economic challenges, terrorist conflicts, technological shifts and political instability.

Here are just a few notable examples:

Toraya

One marker of success that DeCientis and Lansberg have seen replicated around the world in many cultures and industries—as well as in this company in particular—is submitting to the patronage of a powerful political entity. For instance, Toraya’s founding family has been making Japanese sweets (wagashi) for the Imperial House for over four centuries.

“Toraya was the preferred sweet maker to the Imperial House,” DeCiantis says. Because the family’s wagashi became desirable to the crown early in the first generation, he adds, they were given an imperial crest, which cemented their lifelong relationship to the now constitutional monarchy.

“[Toraya’s] success was so tied to the Imperial House that when [the capital] moved from Kyoto to Tokyo in the 1800s… Toraya [moved] with them,” he adds. “Their success is vested in the integrity that comes with the blessing of the Imperial House.”

CEMEX

Another enduring enterprise in the book is CEMEX, a pioneering Mexican family business founded by the Zambrano family in 1906. DeCiantis and Lansberg say that the family navigated economic upheavals and global market expansions to transform the company from a regional cement firm into a global leader in building materials.

IKEA

Founded by Ingvar Kamprad in 1943, the Swedish startup leveraged its early mail-order business to become a global leader in home furnishings. It also deployed modular strategies in business and ownership to overcome significant economic challenges and shifting market dynamics and maintain its commitment to affordable, high-quality, resilient designs.

Looking to the future

For companies that are hoping to weather the storms of unpredictability—whether they’re economic, political or familial—Lansberg and DeCiantis say that while being rooted in tradition has its merit, growing with the times is a more direct route to success.

“You have to think about the company… you want to build, not the one that exists today,” Lansberg says, “and then break down the skill sets you need to be able to succeed at that company.”

DeCiantis adds that success in succession is possible—“You just need to be intentional and patient and invest the time [and resources] necessary to get it right.”

This article originally appeared in the July 2025 issue of SUCCESS+ digital magazine.

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