‘I Feel Like a Better Manager’: Execs Share How AI Transforms How They Lead

It hasn’t taken long for business leaders to discover that AI can help them manage people, and they are using it in ways that executives likely couldn’t have dreamed of several years ago—from reimagining how an org chart works to using AI to help them write a tricky email. We spoke to five CEOs—and one chief human resources officer—to learn how they are harnessing AI to help get the most out of their people. They are: Arvind Jain, CEO, Glean, an AI enterprise search platform that has 1,000 employees and was most recently valued at $7.2 billion, according to PitchBook Stacy Spikes, CEO, MoviePass, a subscription-based movie ticketing service, which recently announced a $100 million capital investment Aakash Shah, CEO, Wyndly, a startup focusing on personalized and modern allergy treatments, which ranked No. 333 on the Inc. 5000 this year Renata Black, CEO, EBY, a membership-based women’s intimate apparel company that has raised more than $18 million, according to PitchBook Ashley Kirkwood, CEO, Speak Your Way to Cash, a sales and speaking training organization Ali Bebo, chief human resources officer, Pearson, a U.K.-based education and testing services company Throughout this process, these leaders are finding that AI is pushing their employees to reach beyond what they thought they were capable of—like setting benchmarks, preparing for one-on-ones, and improving reports before they reach their managers. And it’s giving CEOs a lot to consider when it comes to how they run their workplace. The technology, says Spikes, is “going to create more than it will take away.” 1. Supercharge the org chart Jain, who started Glean in 2019, sees himself as a facilitator. That means he has to make sure every task gets assigned to the right person or group—and for him, an old-fashioned org chart just isn’t good enough. “It gets obsolete quickly, because the world is changing so fast,” he says. That’s why his company, which makes AI tools designed to help businesses find answers and automate workflows, has created a kind of living org chart with AI. Jain says that when he has an idea, he doesn’t have time to waste working out which person or team has capacity to take it on. Instead, he wants to get straight to the person or people who can best work on it with him. Glean’s AI examines employees’ work and contributions in real time, mapping core competencies in a way a traditional org chart can’t. The AI is “constantly observing on any given subject matter who are the top voices, who are the ones who are answering the most questions in Slack or in Teams, who are the ones who are writing authoritative documents on that,” Jain says. He adds that he uses this tool every day to help Glean move fast on new ideas and keep projects on track. Pearson’s Bebo says that employees use an in-house AI agent called CARA that can answer questions about their role and ways that they can excel or get promoted: “She is what I would describe as our people’s friend as they think about navigating their career here,” Bebo says. CARA is designed to act as an enabler, helping both employees and managers be more effective and understand where they are in relation to their job expectations and goals. “We don’t want to have AI replace managers, but we really want to think about how it helps our managers even perform better,” she says. One way Spikes sees AI transforming his workforce at MoviePass is by creating more opportunities for the people he has—and for tomorrow’s hires. “I’m finding that it is overall increasing how you’re going to use people, not decreasing how you’re going to use them,” he says. “I think that’s the beauty of this emerging technology.” 2. Transform meetings from status updates into deep conversations Shah, Wyndly co-founder and CEO, uses AI to better prepare for his one-on-ones, especially with his executive team and co-founder, Manan Shah, his cousin. He sees it as akin to the culinary technique of “mise en place,” where chefs prep everything they need before they turn on the heat. “If we can get everything prepped before we’re ready to jump into the work, it makes the work both more fulfilling but also just more effective,” he says, adding that it also creates room for more interpersonal connections between him and his direct reports. “I think that’s what the difference maker is between a good and a bad leader, at least for me, is whenever I’ve been able to spend more time on the interpersonal stuff, I found that I feel like a better manager,” Shah says. At intimate apparel retailer EBY, CEO Black says the entire company is mandated to use AI to help optimize reports and analysis before presenting anything to her. Black makes them show her their original plan and how they optimized it using AI. As a result, her people have more clarity into what they are doing and how to achieve their full potential, she says. “AI allows them to present information in a much clearer way that allows them to be more confident in what they’re presenting,” she says. In turn, she is able to give them better feedback. 3. Power up performance reviews and employee evaluations Bebo, who joined Pearson in 2021 to assist in its culture and business transformation, says that AI agents are embedded in the performance reviews at the company. But while managers are still doing the employee evaluations, the AI can help both employees and leaders craft sharper and more articulate reviews and self-assessments so that every single one “sounds like Pearson.” The agents aren’t mandatory, but for managers who do use them, Bebo reports that they have sped up the performance review process and helped them deliver meaningful feedback to their employees. Glean takes this approach one step further in its performance reviews, says CEO Jain. While managers and employees use AI prompts to help them write their assessments like at Pearson, Glean also uses AI to collect and analyze each employee’s contribution to the company, enabling managers to have a complete, clear, and—crucially—objective record of everything the employee did during the review period. That combats biases and favoritism, Jain says, but it also means he doesn’t forget or overlook any of his employees’ achievements or sticking points. “The conversation shifts from getting on the same page to, actually, we are already on the same page, and this is now a time to solve problems that you run into so that you can become better, you can grow as an employee,” he says. 4. Use AI prompts to get the best responses from your people Spikes, who co-founded MoviePass in 2011, left in 2018, and then returned to save the company in 2021, says he started using AI prompts with his teams to challenge them to think differently about how they are tackling business challenges or new projects. “That curiosity helps speed up the team,” he says, mentioning that some projects that used to take weeks now take as little as a couple of hours. What that gives him as a manager is not just a faster outcome, but also more opportunities for iterations and feedback, leading to a better outcome. “You get much more of a response loop that you just didn’t have before,” Spikes says. Jain also uses AI prompts with his Glean executive team, asking them to set business goals each week. Then he uses a custom-built AI that helps him track progress and gather insights on each of those goals. He says that gives him a “deep understanding” of precisely where there was forward momentum and where there were slowdowns or blocks. And Wyndly CEO Shah says his business is moving to a similar model. When people do their daily check-in, they are prompted to think about how what they are doing is aligning with the business’s goals and to preempt what questions Shah might have for them based on what they report. That way, he says, “everyone’s speaking the same language.” 5. Let AI be a thought partner Knowing what to say and how to say it is crucial to getting a CEO’s message and vision across to their employees, and AI can act like the ultimate comms specialist and thought partner to do just that. “Anytime I have to write a very complicated email, I just press play. I tell it exactly what I want to say, and then I say, polish this up, and then make it super short and punchy. And it gives me a really strong response,” EBY’s Black says. Speak Your Way to Cash CEO Kirkwood, who published a book with the same name as her company in 2021, agrees that AI can help take the edge off otherwise potentially tense interactions with staff. “If I have to have a difficult conversation, it’s helpful for me to have a script,” she says. “That way I can have it quickly, succinctly, get in and out, and not open up any legal liabilities.” AI can also help temper hard-to-hear feedback so that your employees get the message without getting over-anxious, Black says, adding that because she has a very direct style of communication, AI can help soften her tone without losing impact. “That’s like the AI coaching me on my leadership skills,” she says. Wyndly’s Shah puts it another way: When he wants to send out a company-wide message at Wyndly, AI is a strategy for getting over “blank-page syndrome.” And at Pearson, some of the company’s executives have created digital twins that act as “thought partners,” helping them role-play different conversations and strengthen their arguments, Bebo says. “Think of AI as your friend and a partner,” she says. “It doesn’t replace your owning and delivering and making sure you’re sending the right message. It’s just sharpening the conversation.” BY CLAIRE CAMERON, FREELANCE WRITER