Alicia Diamond

Actionable advice for passionate business builders

Actionable advice, tips, and musings from a 2x Chief of Staff & passionate business builder

The Reluctant Boss

As someone with aspirations for the corner office (hi!), I’m immensely interested in the day-to-day life of CEOs. I’m passionate about working on the business, which I’ve come to appreciate is a rare skill. Yet, the more I learn, the more I worry that I don’t have everything required to be the very public face of a company. According to the WSJ, I might not be alone in my hesitation:

A 2014 study by London’s Cass Business School found that reluctant bosses are better at navigating office politics and maintaining control while also promoting autonomy. Because they came to power by doing hard work in the trenches, their leadership is often viewed as more legitimate.

Other studies have found that ambitious professional women often have a difficult time imagining themselves as leaders—but as CEOs, they tend to earn high marks for traits like humility and collaboration.

I posit that a reluctant boss is likely in the role for all the right reasons. They’ve been encouraged (pushed) to take the job based on their performance, rather than their personal relationships or personality. Charisma only gets a CEO so far, as he or she needs to be focused on the business, rather than in external facing roles. 

Being an enthusiastic, charismatic, highly visible public figure with a lively Twitter account may add value, but those duties won’t coax a hesitant leader out of hiding. Some executives […] would rather shut the office door and apply their vast experience to solving problems. Ideally, a leader excels at both, but let’s be honest. These proclivities rarely flower in the same pot.

I’ve worked very closed with CEOs since the beginning of my career and one consistent trait is that they do their best work when they get to focus on what they enjoy. Not earth-shattering, but important to keep in mind when considering a high performing individual from a discrete functional area for the top job. It’s important to look under the hood to see what made that marketing exec so successful: did she get the best out of her team? Or was she driving the day-to-day operations with gusto? Did she drive collaboration or steam-roll her way to implementing her great ideas? 

The job of CEO is extraordinarily difficult. The WSJ goes on: 

Maybe we should start paying COOs like CEOs and invite the vice president to live in the White House, too. Or split the toughest jobs between people with complementary skills, as Salesforce’s Marc Benioff recently did by elevating his trusted operational chief, Keith Block, to the role of co-CEO.

In any case, something has to give. The best way to protect the leadership pipeline is to stop clogging the valves.

I might add: let’s also shine a spotlight on the non-charismatic leaders among us, the quiet heroes who shun all capes. The just might coax a few more wallflowers into the too-empty pipeline.

Alicia Diamond