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Be doubly careful when working for 2 bosses

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Working for two bosses requires an employee to balance the demands of both with intelligence and sensitivity.

 My colleague is an anomaly among the writers at Forbes. She splits her time reporting to two different editors. She jokes that Editor A owns her right side and Editor B her left, and some days she feels like she is being stretched both ways. But she says it all works out, because they all communicate well and share the same goals. Editor A thinks that has a lot to do with the culture of the Forbes workplace. “We work in an environment where people always pitch in and want to help out,” he told her. “We know that everyone is working their hardest, and people just don’t act resentful or put-upon here. That makes trust and cooperation much easier.”

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As companies dismantle their old internal walls — as marketing talks more to finance, for instance — more and more people find themselves reporting to multiple bosses. Ideally, everyone involved has the same basic mission, neither boss is trying to outrank the other, and the person being bossed knows exactly what his or her tasks are and how the individual is being measured. In tougher cases, bosses may have conflicting agendas or views of the company’s direction.

“Communication is the most important part of it,” said Anita Attridge, a career and executive coach with the Five O’Clock Club, a career coaching organization. “If your bosses don’t work well together, you have to negotiate with them to arrive at a win-win situation.” In that situation, said Attridge, explain to them both that Boss A wants one thing and Boss B another, and offer a solution that can meet both of their needs.

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“The best way to please any manager or any two or three managers is to communicate clearly, leaving very little to chance. For example, be clear about deadlines and deliverables,” said Connie Thanasoulis-Cerrachio, a career expert and co-founder of SixFigureStart, a career coaching firm. “The people who have the most trouble with these types of situations are those that don’t communicate well, take things personally, gossip and/or get overly emotional. You need thick skin and a confident demeanor to survive and thrive in business. Remember, you are there to do a job, so focus on the results.

The younger and more junior you are, the harder it may be to push back. It’s the age-old dilemma of the person on the bottom rung: seemingly endless requests from seemingly countless people. “You don’t have to be an order taker,” Thanasoulis-Cerrachio said. “Give them feedback so they know what is involved and what you’ll be doing.”

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At the other end of the spectrum, more seasoned employees should have more skills under their belt that can help in potentially difficult situations, like juggling multiple bosses, Thanasoulis-Cerrachio said. If you are more experienced, learn how each boss likes to communicate and, more importantly, know what their goals are.  “Help each achieve their goals and you will always be employed,” she added.

Workers with two or more bosses often juggle multiple assignments that each boss considers urgent. It can be difficult to manage the heavy workload and the bosses’ conflicting demands. Attridge says that in such a situation you should negotiate your deadlines. “If you have multiple 8 a.m. deadlines, consider asking each boss if he or she could accept the work later in the day,” she said. “The answer might be no, but at least you’ll have tried. You’ll very quickly learn which bosses are willing to work with you, and who is more resistant.” Attridge advised to always give bosses an alternative, rather than a flat-out “I can’t do this.”

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Learn your bosses’ styles, and keep them at ease by making sure they know what you’re doing and for whom. My colleague says Editor B wants her to check in every 48 hours with an update on what she’s doing and any problems she might be having. Editor A is more hands-off, just wanting the work they agree on done on deadline. Neither knows what she is doing for the other unless she tells him. Most of the time she does so casually, by dropping by their offices with an update, but when she is feeling particularly busy and unsure how to prioritize, she’ll email them both with a list of her tasks and ask them for their advice.

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My colleague says her type-A organizing works to their collective advantage. “An electronic calendar is a must, and so is keeping it updated,” said Thanasoulis-Cerrachio. “Ask what is important to your bosses regarding scheduling so there are no misunderstandings. It also shows you are a mature professional that manages your time and your relationships with ease.”

Serving multiple masters can have definite advantages, too. It can get you more allies and exposure within the organization, and you can benefit from experiencing the management styles and knowledge of two different people.

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“Successful employees think strategically about their careers and where they want their careers to go,” said Thanasoulis-Cerrachio. “If marketing is your focus, and one manager clearly has more of a marketing role, you may want to gravitate towards that person. But don’t forget about your other boss. Make them feel like you care as well. Remember that you can learn so much from anyone, so don’t let two managers throw you. Make sure you profit from every experience.”