The Multiple Boss Dilemma: Is It Possible To Please More Than One?

Nearly everyone finds it tough keeping the boss happy sometimes. But what if you had a steady stream of conflicting requests and competing deadlines coming simultaneously from two bosses or more? An increasing number of workers are finding themselves reporting to multiple bosses, experts say, and figuring out how to manage those who manage you comes with its own special set of demands – and opportunities.

“You are seeing now a lot more project- and team-based organization, which in some ways is a variance on the matrix organization,” says Wharton associate management professor Matthew Bidwell. “You might have a boss in one department, but you get stationed on these teams that each have their own goal…. I think we have a lot of lightweight matrices, where there is a clear line of authority along one dimension but strong coordination along the way. You know one person is your boss, and you know you will get a lot of requests from another person. And you have to do your best to accommodate them.”

Multiple Boss

Multiple Boss

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For some, the distinction between the direct line and the dotted line is fading. “People have to struggle to ask the question of who is your boss – it’s no longer quite as easy to answer,” says Rick Lash, a Toronto-based senior client partner at Korn Ferry. “You will have different bosses — the one concerned with a particular project, but that individual may not be [the one] who does your performance review, so you have different bosses you are trying to please.” Knowing whom to keep happy, making clear where loyalties lie, facilitating communication – all these hurdles multiply exponentially with two or more bosses, says Lash. “Not only that, but often you are managing expectations of bosses who aren’t speaking to each other, so there is a lot of ambiguity, a lot of people assuming you are their primary priority,” he says. “Everyone wants a piece of you, so managing conflict becomes a major challenge. Part of this is about how you manage boundaries. Because if you are not careful you can become totally overwhelmed.”

More Matrices

Finding yourself reporting to multiple bosses can happen as a result of design or default. Sometimes it occurs when a workplace adopts a matrix organization model – in which employees have multiple reporting lines, often across functions – or merges operations with a corporation on the other side of the globe. The use of teams has increased, and promises to accelerate. “Workers will do more project-based work, forming and re-forming into teams rather than having a static role,” concluded “Global firms in 2020: The next decade of change for organisations and workers,” a 2010 report by The Economist. “Problem-solving and project-management skills will be critical, according to survey respondents. Successful managers will assemble and oversee cross-functional teams rather than an unchanging set of direct reports.”

“You know one person is your boss, and you know you will get a lot of requests from another person. And you have to do your best to accommodate them.” –Matthew Bidwell

In a 2015 Gallup survey of 4,000 U.S. workers, 84% of respondents said they were matrixed to some extent; 49% reported serving on multiple teams some days; 18% on multiple teams every day with different people while reporting to the same manager; and 17% reporting to different managers in their work with different teams.

Knowing how many bosses you’ll be working for is sometimes unclear before the job candidate and manager shake hands over a new post. It was only after several months into a new job that social worker Mary Davis (a pseudonym) discovered that she would be reporting to two different clinical supervisors. “When people work together for a period of time they develop rhythms and shortcuts,” says Davis. When you find yourself reporting to someone else, “even if the quality of the client experience and other outcomes are the same, the process feels inefficient when each supervisor has different management styles and expectations for how the work should be completed.”

Coordination, too, became a surprise part of the job. “Sometimes, for instance, there are emails that go out, and I end up communicating with one and not the other. A lot of it is about the learning curve, trying to figure out what each individual relationship is like, with me and each of them, and also them with each other, and making sure I appropriately adapt to that piece.”

Peter Cappelli, director of Wharton’s Center for Human Resources, has this bit of advice for prospective employees interviewing for a new job: ask to speak to someone in the organization who is reporting to two bosses about how it’s working out. “It’s about execution rather than structure,” says Cappelli, “so it’s not about looking at a chart.”

Indeed, says Bidwell, when two bosses are in the picture, it’s important to know how disputes are handled. “Every five to 10 years you bring the consultant in and come up with this brilliant Platonic model for the structure of the organization that is very crystalline, and in the intervening years life happens and you discover you really need to coordinate better and certain people get a dotted line. And then there is politics and some groups get more power than others, so the organizational structure ends up looking messier all the time. I think there is a logic to teamwork that requires more complicated relationships, and if we’re going to be an effective organization we cannot operate in our little silos. But this can also be a recipe for conflict and delay.”

Sometimes it’s clear that a workplace could benefit from a less highly structured hierarchy. Social worker Davis and her co-workers in another job at a large health care institution were instructed to never go to anyone but a single supervisor with problems, and when that supervisor’s behavior became erratic, they felt hemmed in. “We were in a very untenable situation, because there was a lot of work falling between the cracks and tons of personnel challenges because of her personality changes. We didn’t know where to go, so we went to HR, and they kept saying we couldn’t go to anyone but the supervisor.” Eventually, the supervisor’s behavior was recognized as the onset of mental illness and the situation was resolved, but Davis feels a lot of grief might have been avoided if employees had had a more permeable reporting line. “It’s a problem when the structure is too rigid,” she says.

Any number of experts offer words of wisdom on how to deal with two bosses – it’s important to schedule frequent meetings, for instance. But do most workers really have the political capital to convene meetings? “To get your managers together and have this Kumbaya moment – I’ve never actually seen that happen where it works,” says Edward Yost, human resources business partner with the Society for Human Resource Management. The best plan is to become familiar with the management styles of each boss, and to be proactive about communicating your workload to each, he says.

“People have to struggle to ask the question of

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