The Two-Boss Dilemma: Dealing With the Challenges of Having Multiple Bosses

   By SheSpeaksTeam  Aug 08, 2012

If you thought putting up with your demanding boss was hard, imagine having multiple bosses all with varying expectations of your work. Many of us go to work every day and must answer to more than one boss often making the daily grind that much more difficult to navigate.

A recent report from NBC News discusses the challenges of having two bosses and how employees must be extra careful in this type of a workplace situation. Everyone wants to be on their employer’s good side, but when there is more than one to answer to the daily demands can become confusing and even contradictory in some situations with one boss asking for a job done one way and the other another way.

Career expert, Connie Thanasoulis-Cerrachio, offers some tips on how to please all of your bosses at once. She says, “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. 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.”

Those with more than one boss often run into the deadline dilemma where each boss considers their assignments urgent leaving the worker juggling too many tasks at once. Career and executive coach, Anita Attridge, has some tips on how to deal with this very situation. Attridge advises, “If you have multiple 8 a.m. deadlines, consider asking each boss if he or she could accept the work later in the day. 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.”

Do you answer to more than one boss at work?

How do you deal with the challenges of having more than one boss?

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DredelsPlace by DredelsPlace | SAN DIEGO, CA
Aug 20, 2012

I had a job with two bosses and it drove me nuts. The problem was their lack of.communication with each other. One liked things one way and one liked them another. It was like I had to choose who I liked best and go with that one. In the end, I was going so crazy I eventually found a new job and quit that one.

AnAmericanHousewife by AnAmericanHousewife | Unsubscribe, AL
Aug 09, 2012

I had this at a previous job. It was a 'new' position they were trying and I was the new hire. One was great with sharing... the other - not so much. She made snarky comments, was snide with both me and the other director she had to share me with and was like a petulant child. I loved working for the one Director but the other one just brought down morale with everyone! I resigned and during my exit interview I let them know these two directors didn't play well together. They did away with the position and didn't rehire another 'two boss" position. The Director I really loved working for never got an assistant at all after that. We stayed in touch through emails and met for coffee once in a while. The other, snarky Director did get her own assistant after complaining long enough, but then she soon retired anyway! LOL.

momsaidthatsit by momsaidthatsit | LIMERICK, PA
Aug 08, 2012

I totally have this at work! Great article!