When Damola Adamolekun, 36, accepted the CEO role at Red Lobster, the nation’s largest casual dining seafood chain was in bankruptcy and weighed down by years of operational missteps. On paper, it was the kind of job most executives might politely decline: high risk, thin margin for error, and limited time to stabilize. For Adamolekun, though, it was an irresistible equation.
“I think this can be the greatest comeback in the history of the restaurant industry,” he told me in a wide-ranging interview for Fortune‘s newly-launched CEO Playbook vodcast. “To lead that would be a once-in-a-lifetime opportunity.”
For corner office aspirants, the decision framework Adamolekun describes offers a blueprint for assessing when to take on a transformational role. At the heart of it is risk-versus-return, akin to the calculus in investing, where Adamolekun began his career in finance before shifting to restaurant leadership: first as CEO of P.F. Changs, followed by Red Lobster. “Investing is the business of risk assessment, and I think you should manage your career the same way,” he says. “Risk on its own isn’t something to avoid. You just need adequate return.”
That “return” isn’t only financial. In Adamolekun’s case, it was the chance to make history by leading a legendary turnaround, backed by owners and a team he trusted. The potential downside, he says, was clear: the company could fail despite his efforts. But the upside—a revitalized Red Lobster and a career-defining achievement—was worth the gamble.
This kind of decision requires more than rational calculation. It also demands self-knowledge. “Some people don’t want to take any risk because they’re not comfortable in that environment,” he notes. “You need to know yourself as well, and the risk-reward tolerance is going to be different for every person.”
Ambition plays a role, too. Adamolekun says he has never shied away from setting daunting goals, even at the risk of publicly flopping. “Some people refuse to set ambitious goals because they’re terrified of failure,” he says. “I’m not afraid of that. I don’t mind setting really high goals, and I don’t mind going after difficult things. You do your best and try to win.”
When weighing whether to take on the helm of a company in crisis, aspiring CEOs should step back and interrogate three essential dimensions of the role:
- What’s the actual upside? Look beyond financial incentives. Is the role a chance to redefine an industry, leave a legacy, or develop capabilities you can’t elsewhere?
- Do you trust the backers? Turnarounds live or die on aligned stakeholders. Without supportive ownership, capital, and a resilient team, the odds of success diminish sharply.
- What’s your risk appetite? Not every leader thrives in crisis. Assess honestly whether you’re comfortable betting your reputation—and perhaps your career—on a comeback.
For Adamolekun, his current ambition distills down to a single, audacious mandate: “To save Red Lobster. That’s enough.”
Have a CEO with must-hear views on leadership? Pitch them to ruth.umoh@fortune.com for Fortune’s CEO Playbook.
Ruth Umoh
ruth.umoh@fortune.com
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