4 Critical Keys To Manage Multiple Bosses


When Eric Chen, MBA JD, Associate Professor of Business Administration at Saint Joseph College, got his first job, he had two bosses—Harry and John. Harry was a small, squirrely fellow in his thirties who had small glasses and squinted all the time. He was so high-strung that if he had too much coffee, he’d start shaking uncontrollably. John was about the same height as Harry, had six kids at home, and was always quick with a smile and a laugh. Harry’s management style was borne of a tough culture. John’s management style was more nurturing.

“Harry micromanaged my work, John would tell me, ‘Just do it. I trust your work.’” Chen said. “If something went wrong, Harry would start shrieking royal epithets. John would make light of it, because, in his words, ‘if you can’t laugh at yourself, something’s wrong with you.’ They were two different bosses. There’s no right and wrong here. They were just different. Different is fine.”

Face it: managing multiple bosses is tough. And in this environment, reporting to more than one supervisor is becoming more and more prevalent, particularly as companies look to capture perceived cost savings and avoid layoffs. But as Chen learned not all bosses come with the same personality, work styles, or expectations.

According to Vivian Scott, Certified Workplace Mediator and author of Conflict Resolution at Work for Dummies, when an administrative assistant has one boss it takes some time to settle into a routine that works for both people. Then, add in another manager and now you have to create a routine that includes not only your one-on-one working relationship with the first boss but takes into account the other relationship and the dotted line that exists between the two bosses.

“It’s difficult for managers to see an administrative assistant’s resource as something other than “theirs” so it could be quite easy for the two supervisors to start their own turf war with you in the middle,” Scott said. “That dotted line I referenced is often invisible to them, but certainly not to you as their support staff.”

When an administrative assistant is serving the needs of multiple bosses, it is imperative for the administrative assistant to:

1. Learn how to talk to the bosses

Part and parcel of this is for the administrative assistant to communicate well with both bosses. You must understand what each boss means and pick up verbal and non-verbal cues to help the communication along. People are different and they communicate differently, sometimes in a brutally direct manner.

“One of my bosses, Jean, hailed from a military background and had achieved the rank of Captain. She expected to be obeyed. Her orders were usually clear, concise, and logical. There were no niceties here – only do it, or die. So long as you did it, you were fine. If you didn’t do it, you had problems with Jean. But that’s just how she communicated.”

Other bosses are indirect. Another one of Chen’s bosses, Rhonda, was so concerned over hurting feelings that she didn’t ever want to come out and say things directly. Instead of telling someone to get more coffee, Rhonda would announce, “Is there enough coffee for everyone?” Someone would then go check.

“Bosses come with their own little red wagons full of their own history, experiences, expectations and the like. If you’re trying to make your work relationships ‘one size fits all’ you risk not getting the most out of your manager in terms of what she’s willing to do for you,” Scott said. “If you have a boss who likes people to start with the bottom line and you’re meandering your way around the topic you become an irritant rather than an ally.”

2. Finish assigned projects as soon as possible

Much of this is about time management because the most important commodity an administrative assistant has is his or her time. By completing tasks quickly and efficiently, so as not to have tasks pile up needlessly, the administrative assistant can buy time to deal with unforeseen emergencies.

“Emergency situations have a tendency to blow away the best-laid plans,” Chen said. “So, the administrative assistant must ‘stash away’ or ‘bank’ time. In order to do this, the administrative assistant must complete tasks efficiently in order to prepare for the inevitable emergency. You might not know when the emergency will occur, but you do know that it will occur.”

As an administrative assistant, you are vital and necessary to the production of your bosses. If you do not support your boss, then he or she cannot do his or her job effectively. Scott believes an administrative assistant’s work is the currency that others are judging your bosses on.

“At the end of the day, if your bosses don’t make their sales quotas or are late with reports, they get dinged for it. And, you don’t want to be the one responsible for that. I’ve seen bosses hang on to administrative assistants who have rough personalities but get the work done more than I’ve seen bosses retain administrative assistants who have great people skills but don’t accomplish anything.”

3. Have the bosses communicate with each other to decide priority

Working for two bosses is like being involved in a love triangle. However, to avoid the inevitable blow-up, there should be transparent communication between all parties, according to Chen. To facilitate this, Scott recommends calling a meeting with the three of you.

“Set it up by saying, ‘I have something I’d like to discuss that’s very important to me’ and put it on their calendars. Run the meeting without whining or complaining or pointing fingers. Start by letting them know you’re interested in all three of you looking your best and then point out what everyone is doing well. Then, be specific about items that have fallen through the crack or times when you’ve felt awkward about knowing what to work on when. Have at least three solutions ready and let the conversation go from there.”

Chen admits it’s often tough to get everyone together for a face-to-face meeting, but in the end, face-to-face meetings do work best. By having a sit-down meeting with everyone involved, the administrative assistant can facilitate an open discussion about expectations and ground rules. If everyone is on board, it’s difficult for people to cry foul after the fact.

“If there’s a conflict between bosses, make it clear that you’re not choosing sides and you want your bosses to duke it out over what gets done first instead of putting you in the middle,” Chen said. “Ultimately, bosses should realize that there is the good of the company to consider, and work things out between them.”

4. Be professional and don’t show favoritism

Chen believes it’s not unusual to like one boss more than the other. This is dangerous because sometimes, the administrative assistant might subconsciously do the work of one boss better, or faster, than the work for the other boss. The best thing is to remain impartial and professional.

“When an administrative assistant is professional and executes tasks efficiently, favoritism doesn’t rear its ugly head,” Chen said. “Do your job well. Address the support needs of your bosses efficiently. Then, there will be no hint of favoritism.”

However, Scott cautions administrative assistants not to worry about trying to fair in the sense of “split down the middle” fair. “I would concentrate on needs and expectations. If one boss requires less, so be it. If they’re pretty equal in terms of workload, then talk with them about your ideas on how you will prioritize and get their buy-in.”

Overall Scott encourages administrative assistants with multiple bosses to keep in mind that individuals are never against you. “When you support another person, look for ways to let them know you have their back no matter how many people you’re working for. They, in turn, will have yours.”

(This post originally appeared as an article in the August/September 2012 issue of OfficePro magazine.Terah Shelton Harris is a freelance writer based in Alabama. Her work has been published in Women’s Health, Hallmark, Natural Solutions, and more.)