Why You Might Do Your Best Work When You Don’t Have A Boss

When unexpected changes leave employees without a boss, they are often given room to grow.

Why You Might Do Your Best Work When You Don’t Have A Boss
[Photo: Paul Sutherland/Getty Images] [Photo: Paul Sutherland/Getty Images]

The distress over employee retention has reached a fever pitch. The data couldn’t be clearer that knowledge workers really are on the move en masse. By one recent reckoning, 41% of U.S. employees are considering leaving their current positions within the next 12 months. The time it takes to fill an open position after a departure is lengthening pretty much across the board, with some of the most in-demand fields suffering the most drawn-out hiring processes.


One consequence of all this shuffle doesn’t get a lot of airtime: The considerable (and very likely growing) share of employees who abruptly find themselves getting by without a boss for longer stretches. What’s less clear is whether this is a net positive or negative, and surely the answer varies from one person to the next.

But suddenly losing your direct supervisor and being forced to figure things out can have its upsides. According to some people who’ve dealt with that, losing a layer of managerial oversight can sometimes clear the way for more productive work, and even offer an unexpected career boost.

Learning To Experiment

In 2014, Jacob Warwick was about two months into a marketing job at pricing analytics startup ShoppingScout when both of the people senior to him in the department were let go. It was a mixed blessing at first, Warwick says: “Good because I had an opportunity to take more of a leadership role, and bad because I was expected to take all those leadership jobs without getting paid to do them.”

During the four months that followed, Warwick got to hire in some fresh talent in order to “build out what we were trying to accomplish, with new goals and very little experience in how to accomplish them.” Without getting directives handed down from a department head, Warwick’s team had to answer directly to the company’s top brass for their wins and failures during that period. But they were trusted to experiment, if only by default.

“In a way, that lack of experience was a good thing,” Warwick reflects, “because in a startup you need to evolve very quickly. The willingness to test and hire new people after leadership was gone actually opened up some possibilities.” To pursue them, though, he needed to deepen his knowledge base quickly, an experience that left Warwick with a lasting habit. These days, he says, “I spend more time preparing than doing. I know that sounds counterintuitive at a startup, but I study the ins and outs as much as possible.”


Facing an unfamiliar concept, he says, “I would read 15 articles, find three or four people in the industry that understood it, and do that [brushing up] before I came to a meeting.” Working without a boss, he jokes, “taught me to be more full-assed and [less] half-assed.”

Following Your Interests

One reason people job hop is to do something new and see how it compares to what they’ve been doing. But other people’s career changes can unintentionally give their direct reports at the companies they leave behind similar room to explore.

When your boss leaves, it’s not uncommon to have to pick up the slack, like Warwick did. But you may be just as likely able to rewrite your own job description. Erica Hirsh is a writer in Boston Medical Center’s communications department, and she’s had two bosses leave within a year of each other.

Because her team is small, both of those departures forced the remaining members “to figure out what we actually needed to be doing” after having taken on a handful of new projects. Suddenly finding themselves short-staffed, they could then recalibrate in a way that played to their own strengths. Hirsh says she was given considerable “flexibility in terms of what types of things I wanted to take on” from her boss’s role. “On a personal level,” she says, “I got to do more, [including] co-lead a project that had been in the works for almost three years.”

Both bossless gaps lasted around three months, but even after a new supervisor was appointed, Hirsh says, “for the most part people were pretty great about me continuing to do the things I wanted to continue to do.”


When The Unsupervised Becomes The Supervisor

Eric Trott was on a two-week vacation in Bangkok when his boss hit him up on WhatsApp to say she needed to talk. When Trott contacted her, the message was essentially, “By the time you get back I’ll be gone.” Trott had worked with his boss for a little over two years, both early members of the design team at the business news site Quartz.

“The idea of not actually having anyone to oversee me, or check in on anything, or set new goals for me was kind of confusing in the beginning,” Trott recalls, a period that lasted for four to six months. “It took a while for them to find someone.”

But within a few weeks, Trott says he’d hit his stride. “It forced me to lay the groundwork to grow my team to the five designers I have now,” he says. Having one designer reporting to him at the time whipped Trott into boss mode on the fly. “That was the most crucial–I had to flip a switch. You’ve got to pull your team together and dig in and set future goals.”

Just as Hirsh and Warwick found, the experience made gave Trott “the freedom to dictate and navigate and create my own path,” despite the fact that there was “no real confirmation or validation in that path” close at hand, “like I was blindly stumbling along and somehow making it work.”

Ultimately, all three of them made it work. Warwick parlayed his experience into a higher-level job at a new startup where he’s now in a director role. Hirsh was promoted from a staff writer to a senior staff writer position, a role that hadn’t previously existed. And Trott credits his outgoing boss for advocating for him just before she left; he was promoted to associate director of design amid the transition, a role into which he quickly grew.


And as Hirsh also found, the new boss that Trott eventually reported to respected that. “It took maybe about four months to really feel like I had a boss again,” he says. Far from being stripped of the new responsibilities he’d had to pick up, Trott’s incoming supervisor leaned on him in order to settle in, making his deepening expertise even more of an asset.

“You don’t usually expect to have to teach your boss something,” Hirsh concedes. But if you’ve figured out how to work without one for a while, then you’re probably shaping up to be somebody else’s boss in the process.

Update: An earlier version of this story misstated the name of Jacob Warwick’s previous employer.

About the author

Rich Bellis was previously the Associate Editor of Fast Company's Leadership section.