Tom Wilson is not sure that he would have hired the Tom Wilson who took the helm of Allstate in January 2007. As a new CEO, he recalls, “I was a typical individual performer.” But he thinks he has become a more inclusive leader since then, learning to trust his team to handle “the stuff that isn’t going to bring the ship down,” so he can focus on what matters most.

He has also become more comfortable with taking risks, having concluded that few executives lose their jobs or destroy their companies over just one bad decision. “The big challenge for CEOs is, they get risk-averse,” because once they have landed the top job, they don’t want to lose it, Wilson observes. But he would like to see more of his peers stick their necks out.

“These are hard jobs to get; they are hard jobs to keep, but they come with an obligation to do hard things,” he explains.

That belief has encouraged him to wade into politicized waters that most CEOs try to avoid. Back in 2019, he told his peers they should “save capitalism by paying people more.” The response was “crickets,” he recalled in an interview for The CEO Signal show. Then, last year, he urged Americans to overcome “an addiction to divisiveness,” and launched an initiative to address people’s growing mistrust of each other — only to encounter abuse from online activists who accused him of lecturing.

Despite the blowback, Wilson is undeterred about putting his company at the center of fractious public debates. “Businesses understand we have an obligation to society, and most of us try to lean into it every day. I think it’s at discontinuous points like today that we have to sort of ask ourselves: Are we doing enough?”

Turning the debate about AI and jobs on its head

Polls that capture workers’ anxiety about AI suggest that the technology is fast becoming the next great threat to public trust in business. That is more than an abstract risk to a company like Allstate, Wilson believes.

“We sell trust,” he says: “You give us your money, and then you trust that when something happens, we’re going to be there.” Customers who don’t have faith in their insurance company will shop around, he notes, so if people are gripped by a broader sense of distrust, “it’s bad for communities, bad for our team, [and] bad for our business proposition.”

Allstate had already pledged $7 million to an Aspen Institute initiative on building trust at a moment of polarization, but Wilson is now focusing on the question of whether companies can address the fear that AI advancements will come at the expense of people’s livelihoods.

“The computer is going to do a whole bunch of work for us, and so we could just cut costs and move on. But that’s not what people want … from business,” he says. What they want are good, meaningful jobs, Wilson says, and he thinks he still has an opportunity to create more of them.

So Allstate has tasked individuals on each of its AI teams with looking into how the technology might change its business model, allowing it to do things that were once too hard or too expensive, in ways that would also employ more humans. Rather than just sending an auto insurance customer the money to fix their car after a crash, Allstate could arrange to pick up the vehicle, get it repaired, and return it, he has suggested as an example.

“You can use artificial intelligence in your existing business model,” Wilson says, “but the question is, how do you change your business model using AI to do it cheaper, better, and faster for customers?”

Wilson is aware that CEOs are typically incentivized to cut headcount, not add to it. “I’ve never been in a boardroom where somebody [asked], ‘How many good jobs did you create?’” he says, “and I think this is a problem.” Shareholders don’t measure businesses by their hiring or reward them for it, he notes.

It may feel like “working against the winds of commerce,” but CEOs can still “hold ourselves accountable” to this goal. “You just have to be resilient and say, ‘Yep, I know you’re one of the stakeholders, but I have an obligation to our employees, and so I’m going to try to do it,’” he says, adding that “shareholders will give you the space if you perform.” Allstate’s stock market performance has been uneven in recent years, but its latest earnings beat estimates and showed it gaining market share.

Wilson says his board has long endorsed the idea that Allstate should serve its employees, customers, and communities, rather than shareholders alone. “So when I say, ‘Look, I might hire 500 extra people just to try something out,’ they’re like, ‘Yeah, OK, do it.’”

Knowing when to speak up when others fall silent

Wilson’s conviction that businesses should use AI to expand the workforce rather than shrink it comes from his approach to analyzing “longer-arc” questions. He studies the trends shaping his business, he says, as he tries “to look for patterns” and determine the correct approach to them.

“But then once I decide, then I go all-in, and don’t waver from what I’m trying to do,” he says. “If you get this construct around you, then you can [take] action quickly.” He has brought the same approach to his thinking about when he should participate in debates on societal questions.

Wilson says he is “disappointed” so few of his fellow executives will touch topics that look vaguely political. “There should be more voices,” he says, even as he acknowledges the fatigue CEOs feel, with activists constantly asking them to add their name to public letters.

His advice is to be selective. “CEOs need to stand up and decide what’s important to them, [and] what’s important to their customers,” he argues. But they also need a structure to guide their responses, he adds.

At Allstate, Wilson developed a “societal engagement framework,” through which it has assessed roughly 100 different topics against three criteria: “Does it help us do a better job for our customers? Do we know anything about it? Can we actually effectuate any change?”

If an issue ticks those three boxes, then the next step is to explain to shareholders and other relevant stakeholders what they can expect Allstate to speak publicly about — and when they shouldn’t bother Wilson.

“A good defense is a good offense,” he explains: “As long as you tell people, they’ll be fine with the change.”

Earning trust by helping people find their purpose

The challenge of getting a company like Allstate to adapt fast enough to shifts in technology and social expectations also comes down to trust, Wilson believes. If you want employees to change, he says, they need to believe that you’re on their side.

So when he talks to Allstate agents about AI, for example, he tries to describe specifically how it will change their daily work. “Everybody just wants to know, ‘What am I going to do today?’” he reasons. “Greater clarity leads to greater empowerment.”

He has applied the same principle to Allstate’s corporate purpose, which it defines as protecting customers from life’s uncertainties. The definition is broad enough that “you could drive a Mack truck through [it],” Wilson admits, so his challenge is to make such a sweeping statement mean something in practice. That has meant taking “all the fluffy corporate speak words out of it,” and then developing the “strategic middleware” that translates its overarching goals into the specific behaviors and day-to-day operating standards that Allstate wants to encourage among its employees.

Unusually, Allstate has also taken a bottom-up approach, putting more than 75,000 employees through workshops designed to help them “articulate and pursue their individual purpose.”

There is a direct return on that investment, Wilson says: “We give to get. If we give you that opportunity, then you will give us back with engagement, extra effort and bringing your whole self to work.” But it also builds towards Allstate’s broader corporate ambition. “If you want to be a purpose-driven company, you have to be powered by purpose-driven people.”