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

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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.”

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 who is your boss – it’s no longer quite as easy to answer.” –Rick Lash

In fact, people often have more control than they think, says Lash. “Mostly what you are doing is being very proactive and actively managing multiple bosses by really leaning on your indirect influence,” says Lash. “If a boss says to you he needs this tomorrow, be aware of what’s coming down the pike so you can manage upstream. Some practical advice would be things as simple as creating one master priority list of everything on your plate and making sure all your bosses have a copy, so when a boss says you need to do this tomorrow, the boss will have an understanding of how this fits in with the other things on your list. Related to that is people being able to get good at self confidence to a degree – to ask your boss, ‘If you want me to so this, what is it you want me to take off the list, because I also have three other deliverables due in the next few days.’”

It is also useful to know how to leverage your network to influence people who have influence over a boss who tends not to listen, says Lash. “Who within your network does your boss tend to listen to? That’s another powerful way of getting control.”

Of course, there are times when managers actually don’t want cooperation. “When one manager has no particular respect for the other or their line of business or its contribution to the bottom line, they are going to think whatever work you do for me is more important,” says Yost. “If they can’t see the ROI of that other manager’s function, it’s never going to be justified in their mind that the work for the other manager should take any sort of priority. And it is possible, depending on the environment, the two managers may be competing for that next level up, so if they see that person as direct competition, it’s not unheard of for them to do things to damage the other person’s performance.”

That’s when it’s time to involve HR. “You are not in position of demanding that they play nice,” notes Yost, “so you need to engage HR who hopefully then goes to their report to help manage that relationship.”

When Two Bosses Are Better Than One

But even in that scenario, an employee can eventually come out on top. “It’s a learning opportunity,” says Yost. “You can learn from both good and bad — and hopefully if I want to become a manager someday I can learn something from bad managers about what not to do.”

“To get your managers together and have this Kumbaya moment – I’ve never actually seen that happen where it works.” –Edward Yost

The larger organizational benefits of reporting to multiple bosses are both numerous and long proven, says Kevan Hall in Making the Matrix Work: How Matrix Managers Engage People and Cut Through Complexity. In the book, Hall identifies four key advantages to the organization: to break silos and free up talent otherwise inaccessible to the rest of the organization; to manage supply chains and integrate business regions, functions and processes; to respond more quickly to changing priorities; and to develop talent with broader perspective and greater skills. But Hall also argues that structure solves nothing all by itself. “Much more important are the networks, communities, teams and groups that form within a matrix to get things done,” he writes.

Having the multiple bosses that come with a matrix structure makes life harder, but it also brings great benefits. “Employee engagement comes when individuals feel a sense of ownership for meaningful goals — not from rigid job descriptions and goals set by others. By giving people more freedom to shape their goals and role and higher levels of capability for dealing with ambiguity, we can build even higher levels of ownership, commitment and employee engagement.”

There is also, many have noted, a value in working for two or more bosses that, for workers who play their cards right, can open up a bigger view of the organization and a path toward career advancement. Many recent college graduates entering the workforce are expecting to land with a boss who will help them with their career, says Priscilla H. Claman, president of Career Strategies, Inc. in Boston, but given the demands on managers today, that’s not realistic. “You used to hitch your wagon to a rising star, and that whole concept is gone,” Claman says. To expect a manager to function as a mentor in a matrix environment “is actually not a reasonable expectation.” What the enterprising worker can do, however, is piece together support from multiple bosses within an organization. What it takes, Claman says, is an entrepreneurial mindset – anticipating what bosses will need and taking the initiative to act on it. “If you are literally doing just what is requested of you and you have two bosses, sooner or later it’s not going to work. You can’t just be obedient – you have to be asking, ‘what do you want me to do and why?’ You have to be able to walk across internal boundaries, speak to different types of people.”

“The term I would use is you have to be careful not to become a corporate peasant,” says Lash. “What that means is if you stay in your little village you are at a huge disadvantage because you lose the wider perspective on the world. What happens if your boss gets fired? You have a close relationship with your boss, but then you are starting all over again from a career development standpoint.”

The wise worker might even stop thinking in terms of having a boss – or even bosses. Says Lash: “You have multiple people who serve different roles. You have to deliberately cultivate a wide network of influential people you can draw on to get a broader perspective on the organization. The more contacts you have, the more ears you have to get a sense of where people are, and the more proactively you can position yourself to manage things that will come your way.”

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