‘Relief or regret’: The rule that guides Greg Brown’s biggest calls at Motorola Solutions

Greg Brown became chief executive of what was then Motorola in 2008. But it’s only in the last decade that he thinks he has become “a reasonably good CEO.” And he credits a series of career-threatening encounters with activist and private equity investors for getting him there.

Motorola invented the mobile phone, but by the time Brown was handed the reins, its cellphone business had been outpaced by Nokia and Samsung. Apple had introduced the iPhone just two months earlier, and Brown concluded that his company had no future in smartphones, which were losing hundreds of millions of dollars a quarter.

“We were a year and a half to two years away from bankruptcy, extrapolating out,” he recalls in an interview for The CEO Signal.

Brown resolved to spin off the mobility business for which his brand was best known, and says now that “there wouldn’t be a firm” if he had not done so in 2011. That let him start to build the new Motorola Solutions, an overlooked “jewel… buried in the bowels” of the parent company, as a leader in critical public-safety technologies. It now provides police forces, school districts, and hospitals with tools ranging from communications networks and AI-assisted video analysis to drones and defense equipment.

But the separation that set Brown’s company on a path to today’s $75 billion valuation nearly didn’t happen. As directors wobbled at the eleventh hour, debating whether to keep the company together and “get rid of Brown,” he confronted them with a back-me-or-sack-me ultimatum.

“I said, ‘I don’t care what you do with me, but you’re out of your minds if you don’t separate and exit cellphones. You want to shoot me? Shoot me. But you’re crazy if you do anything differently.’”

He prevailed, but it was not his last test. In 2014, under pressure from the activist investor ValueAct, Motorola Solutions board members debated whether to sell the whole company. Brown, who had already examined and rejected the idea, thought it would be “dumb” to distract the business with an auction process and risk selling at a depressed price.

“I said, ‘Bullsh*t, we’re not doing that,’” he recalls, “And if you want to fire me, go ahead and fire me.” He drafted a resignation letter, only for his wife to convince him late one night that quitting made no sense. He later apologized to the board for his “emotional” delivery, but not for the substance of his argument.

Those standoffs speak to the uncommon amount of pressure under which Brown has operated: For each of his 18 years as CEO, he has had an activist or a private equity investor on his board. Carl Icahn, ValueAct, and Silver Lake have each brought a level of extended scrutiny that few of his peers have faced.

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Motorola was already under siege from Icahn when Brown started. The veteran activist had launched a proxy battle and was calling for the company to split itself up. Brown admits to feeling intimidated by Icahn at first, but he decided to engage, even as his board objected to settling. “I also knew I had no choice,” he explains: “Carl was coming one way or the other.”

The two men reached a point of mutual respect, he says, where Icahn “knew I would do what I said I would do,” and Brown felt that the “endurance test” of answering Icahn’s frequent calls had made him a “tougher and stronger” CEO.

ValueAct’s 2014 challenge was scarring, but even as Brown rejected its push for a full-blown sale, he listened and ultimately agreed when it challenged him to unwind the largest acquisition he had made up to that point. “I am a believer in a meritocracy of ideas,” he explains. “Check your ego at the door [and ask], ‘What’s the right thing to do now?’ And that decision today might be different than what you would have decided three or four years ago.”

Despite his outburst to the board, he also agreed to test whether any buyer wanted the whole of Motorola Solutions. The process confirmed his belief that none did, but it caught the attention of Silver Lake. When the tech-focused private equity firm proposed investing $1 billion in exchange for two board seats, Brown saw a chance to bring in fresh capital and expertise. Bringing Silver Lake’s Egon Durbin and Greg Mondre onto his board was “one of the best decisions I ever made,” he says now.

Motorola Solutions bought out Silver Lake’s convertible notes in 2024, and Durbin and Mondre have since left its board, but Brown says his experience with them, ValueAct, and Icahn made him a better, more accountable leader.

“It made me transition as a CEO that thinks like a manager to thinking like an owner,” he says. The difference is that, now, when deploying capital, he asks himself: “Would you do that with your own money?”

There were “dark moments” in the process, Brown admits, but it taught him lessons that he now teaches to people who report to him, including on the importance of candor. “Share your mistakes. Share your indecision. Share your vulnerability. Just tell the truth,” he says. “Don’t bullsh*t around.”

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Brown describes himself as a consummate learner who is not embarrassed to ask “dumb questions.” But he realized several years ago that he was doing a poor job of prioritizing the information he consumed and managing his time.

“Early on, I was more doer than delegator,” he says. So he stepped back and asked what information he really needs to run the company, and how often he needs to see it. He now carries an iPad packed with financial, operational, and competitive data — and very detailed org charts.

He spends the largest share of his time playing the role of “chief people officer and leadership officer,” he says. That means that he’s constantly tracking people in the top four levels of the company, on his iPad and in one-on-one meetings, to assess their performance, potential, and “replaceability.”

It’s a practice informed by a moment when he asked his team to list the company’s four or five biggest challenges and its eight or 10 strongest executives, only to find that none of its best people were working on its biggest problems — or opportunities.

The ‘relief or regret’ rule for weighing up deals

Brown has reshaped Motorola Solutions through dozens of acquisitions, but the ones he decided not to pursue have been just as important.

He labored over one $5 billion acquisition target that would have opened up an interesting new market, but then asked his team at the last minute what they would feel if they decided not to do the deal and then found out that another company had bought it: “Relief or regret?”

Brown’s executives predicted they’d feel relieved, “and that’s exactly what happened.” It’s a rule of thumb he now uses for every major decision he makes, and he advises other executives to take a step back 90 days or six months after an important choice and ask whether they feel relief or regret. That, he says, will inform them whether they and their team members are making the right calls.

Why Brown doesn’t fear a RoboCop future for policing

The public-safety innovations that excite Brown, like drones that are dispatched to assess crime scenes before officers can reach them, remind some critics of dystopian sci-fi. Four decades after RoboCop came out, Brown has watched the film only once, and he believes technology will enhance human policing rather than supplant it.

There may one day be as many police drones in the sky as there are police cars on the street, he thinks, but “before dispatching a police officer, why wouldn’t you send a drone that can travel 60 miles an hour, that can get to the site on average in 45 seconds?”

Motorola Solutions’ contracts to supply US federal immigration agencies have generated pushback, but Brown says it does not sell “spying or surveilling” technologies. People, he says, “don’t want Big Brother surveillance. They don’t want to be watched and have information gained in an illegal way or monetized in an inappropriate way.”

As autonomous systems advance, he adds, his company’s offerings keep humans “in the loop,” making critical decisions such as whether weapons should be deployed.

“People worry about the advance of technology and making independent decisions autonomously or in a dangerous environment. I don’t,” Brown says. “In public safety, I just don’t think that will happen. And, quite frankly, I don’t think that’s going to happen in the military or US industrial defense technology segment either.”

Societies will need to monitor dangerous “corner cases,” he predicts. “But I am much more an optimist than a bear case person when it comes to RoboCop technology or AI.”