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Tips for Working with Multiple Bosses

by Vivian Scott
December 2013

Conflicts of Interest Blog by Vivian Scott

Vivian Scott

When companies consolidate departments or lay-off employees, the action often results in administrative support staff working with multiple bosses. Though the strategic goal is to save money, the act can backfire if the new normal doesn’t quickly fall into place. Assistants play a critical role in how swiftly that happens. Here are a few tips to help:

1) Acknowledge that bosses are unique individuals. Managers don’t all come with the same personality, or work style, or expectations. It’s difficult enough to create a smooth routine with a single manager, let alone two or three. 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. Spend some time getting to know what makes a particular boss tick and you’re well on your way to success.

2) Openly discuss sharing your time and talents. One-on-one working relationships can be tricky on their own but when you add in another boss the solid and dotted lines on the org chart can feel more like a twisted path to Satan’s playground than the reporting structure they’re meant to describe. Relax. Meet with the managers in the same room at the same time with the intention of creating a plan that makes sense for all parties. Conduct the meeting without whining or complaining or pointing fingers. Start by letting them know you’re interested in everyone looking their best and then be specific about items that may fall through the crack or any awkwardness you anticipate regarding what to work on when. Have at least three solutions ready and let the conversation go from there.

3) Throw favoritism out the window. Don’t worry about trying to be fair in the sense of “split down the middle” fair. Instead, concentrate on needs and expectations. If one boss requires less, so be it. If your managers are pretty equal in terms of workload, then talk with them about your ideas on how you’ll prioritize and then get their buy-in on the plan so that you can refer to it later if needed.

4) Be flexible. Everyone knows there’s a certain amount of shifting, adjusting, and modifying that takes place with any change at work. Accept that. If Plan A isn’t working, be okay with going back to the drawing board and reworking, rediscovering, and revising.

5) Stay focused on the work. What you produce is the currency that others are judging your bosses on. Sure, they’re graded on their leadership or people skills, but if at the end of the day they don’t make their sales quotas or are late with reports, they’re penalized. And, you don’t want to be the one responsible for that! Managers have been known to hang on to administrative assistants who have rough personalities but get the work done more than they retain assistants who have great people skills but don’t accomplish anything. (Disclaimer, this is not permission for you to behave poorly, it’s simply an example of how important the work is.)

Lastly, a good thing to remember about managers (or any individual coworker for that matter) is that people are never against you, they’re simply for themselves. Regardless of the reporting structure, look for ways to let people know you have their back. They, in turn, will have yours.


Vivian Scott is a Professional Certified Mediator and the author of Conflict Resolution at Work For Dummies.  She spent many years in the competitive and often stress-filled world of high tech marketing where she realized resolving conflict within the confines of office politics was paramount to success.  Through creative solutions to common conflicts she was able to bring various entities together, both internally and externally, for the betterment of projects and a productive working environment.     

Prior to retiring from Microsoft in 1999 she developed the “America at Work” video series, a six-part program featuring small businesses employing technology in attention-grabbing ways.  “America at Work” aired on the USA Network and received the Silver Screen Award from the International Film and Video Festival for outstanding creativity.   Using discerning negotiation, mediation, and problem-solving skills, she successfully worked with others to co-create “How-to Guides”, “Seminar in a Box”, and even one of the first on-line Guerrilla Marketing books.   

Since her retirement, Ms. Scott has gone on to earn a B.A. in Interdisciplinary Arts & Sciences with a concentration in American Studies from the University of Washington.  She completed an extensive practicum with the Dispute Resolution Center of Snohomish & Island Counties where she has mediated numerous cases, helping parties resolve conflict in workplace, family, and other disputes.  Her private mediation practice has handled cases ranging from assisting business partners in ending their relationship to creating a new working environment within a law firm.  Ms. Scott is a member of the Washington Mediation Association and spends a majority of her time advocating embracing peace in a volatile world.   

Her book, Conflict Resolution at Work For Dummies, can be found in bookstores, on,, or any number of on-line bookseller sites.    

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