Reporting to two bosses can be one of the most difficult managerial situations to master. But with a little patience and exemplary communication skills, the experience doesn’t necessarily have to be a negative one. If approached with a positive attitude, and if you can provide consistent work documentation, there can be career payoffs to answering to two masters.

The first step: Get to know them
Early in the relationship, IT managers should get to know their new bosses and learn how each works. For example, do they want you to check in each day, once a week, or just send an e-mail? Is one a micromanager and the other more laid back? Will one boss serve as the primary contact and provide info to the other or do you need to provide both the same info and data all the time? IT managers need to work with the two bosses to set priorities and expectations at the start.

How you manage and balance your time, your bosses’ expectations, and your available resources will determine your success.

“I have had this [two boss scenario] happen on numerous occasions and the best advice that I can give is to communicate,” said Darrell Bilbrey, an IT professional with BlueCross BlueShield of Alabama. “I made sure that both bosses had a clear understanding of my projects and priorities. We would negotiate priorities if there was a conflict.”

Communicating early and clearly is necessary to avoid hurdles and get off to a good start.

“It’s important to know how they managed previously and what outcomes they will expect of you,” said Jason Schweizer, of Right Management Consultants, a career transition and organizational consulting firm in Philadelphia, PA. “The management styles of the two will undoubtedly be different. How different will determine how difficult your position will be.”

“Make your decisions and evaluate how well they worked. Then go ask them how you did—regularly, routinely, and openly. You have to make a practice of managing your bosses as you manage your business,” Schweizer added.

You, and you alone, are ultimately responsible for your own workload and it’s well worth the time to document everything and become your own project manager in managing two bosses.

“Business objectives that reduce cost, increase revenue, and are highly visible cannot be delayed. If you simply say that you don’t have time for everything assigned, you’re a poor performer. [But] if you give the ineffective manager a way out of the issue, you’re a hero,” said TechRepublic member WRLang, who, with 23 years of IT experience, has found himself reporting to multiple bosses on several occasions.

When the bosses are at odds
The biggest issue in having two bosses is when the two bosses don’t communicate, share information, or work well together. As there is little an IT manager can do to change this, the work documentation effort can be incredibly valuable to not getting caught in the bosses’ crossfire.

Stay alert for any conflicting messages you receive and be careful not to put yourself—or let them put you—in the middle of a managerial disagreement.

“Trying to broker a compromise without the input from either [manager], or only from one, is deadly. You can approach such a situation by asking them for resolution…[and] some direction,” said John Reddish, founder and president of Advent Management International, Ltd. “Where there are clearly conflicting messages coming from the two managers, it is [your] job to kick the problem back upstairs to them to resolve it.”

Avoiding the middle of a management conflict is a common theme among those who have survived this experience.

The two bosses “may try and force you to resolve their conflicts,” said WRLang. “Make the managers resolve their own conflicts by scheduling meetings with them both together with you. Make every effort to be diplomatic and stay out of the middle, or they will both blame you for any problems.”

And, if you think two bosses are tough to handle, TechRepublic member Randall Smith has actually had to report to three bosses at one time. “Communication was key” to his survival.

“Let both bosses know the tasks you are currently working on. This will help to prevent them from ’over-tasking‘ you,” said Smith.

Getting on common ground
Mapping out specific project and work priorities is double the work when you have two bosses to please. Getting them to agree to set priorities is often an IT manager’s most difficult challenge.

When you hit the first hurdle with this issue, it’s up to you to diplomatically and professionally bring all parties together in one room and make it clear what you can and can’t do.

“Don’t jeopardize your job by trying to handle too many tasks at the same time. And don’t try to prioritize the tasks by yourself,” said Smith. “From experience, I have found that this can end up in a conflict between you and the bosses. This may give you a bad mark on your record, or it could end up getting you terminated.”

And when you’re just about to start banging your head against the wall, due to conflicting directions and expectations, just remember it could be much, much worse.

Bjorn Olson, a business development consultant with BlueRock Technologies, had four bosses when he worked for CGI, one of North America’s largest technology companies. Documenting everything he was working on was a necessity, he said. Documentation of this kind provides several functions:

  • It enables others to support what you have done if you are traveling, sick, or on vacation.
  • It provides a paper trail to clearly demonstrate what occurred if anyone starts to point fingers at something either done or not done on a particular project.
  • It helps maintain an up-to-date “to do” list to ensure you are meeting deadlines and expectations.
  • It allows your bosses to see on a regular basis what the “other boss” has requested you to do.

Though the additional hours required to document work was challenging, Olson said the unique management experience was a positive one. It presented opportunities to learn and grow, and his accomplishments received four times the attention.

“Because of my hard work and dedication, it was not just one higher level person who noticed, but it was four higher level people who saw my accountability and work ethics, so I had much more leverage than if just one had ‘noticed’ me,” Olson said,

“If you are fortunate enough to be heavily challenged, take advantage of a tight situation and prove your worth. It can only benefit you,” Olson added.