So, a unique situation at work just developed – now I have two bosses. I’d like to think it’s because I’m such a whopping success in my job that it takes two managers to corral my activities but nope – it’s an organization change that led me to this situation. I still report to my current boss for some of my accounts  but now report to his peer from the standpoint that the numbers and deals I project that I’ll close on other accounts impact both guys.

Not a big deal.  Except it’s a really big deal because serving two masters means I now have double the opportunity to screw things up royally!  If all goes well over the next several months this should iron itself out so I won’t have to lead a dual life forever.  But today I am well aware that this current situation I’ve found myself in could be a total minefield.

Here are Be Better Guys' tips for how I’m planning to manage having a dotted-line report to a second boss…and if you find yourself in this situation maybe you can use these tips too.

Talk Talk: I am committed to over-communicating to both bosses several days a week.  Here’s why – if I force myself to get in the habit of regularly firing off emails and communiques to both guys with updates on my deal status – good and bad – I won’t be accused of withholding information should a major deal fall through…which happens to the best of us.  So I have regular one-on-ones set up with the two of them together so I give them both the information they need to keep their bosses happy.  Which leads to…

Give ‘Em What They Want: Think about your job from your boss’ point of view:  he or she oversees several people just like you.  You and your team work to meet deadlines and bring in deals and produce outcomes that YOUR boss signed him/herself up to.  Your job is to make your boss look good. With that in mind when serving two masters recognize what each needs to look good in the eyes of their boss and give it to ‘em.

Just Like With Children--No Favoritism: I report to one boss directly who signs my paycheck.  Worked for him for over a year. Drank with him. Even jammed on some music with the guy. Like him a lot. The other guy I’ve “worked for” for about two weeks. It’s real easy to consistently deliver to the boss I’ve known for a while and sort of blow-off Boss II. That would be a big mistake. Both are peers; both are equally important. Both can support my career or torpedo it.  Time has to be spent fairly with both and I’ll (and you’ll) need to watch out showing any favoritism. It’s natural. It’s also dangerous.

Doing Double-Duty: Now I have to double my efforts on the job when it comes to reporting my forecasts and attending team calls.  Hell – I’m literally on two completely different teams with different dynamics and cultures.  One’s like the good ol’ boy fraternity crowd and the other’s like competitive-as-hell boy scouts.  Deal with the fact that you have to do much of your efforts twice for each group and don’t complain.

This is An Opportunity: My exposure to leadership just doubled.  Now the head folks will have two teams crowing about the business I bring in.  That’s a double-edged sword in the event I suck royally the rest of the year.  But if I’m good I’ll have two guys in positions of leadership and respect telling their management chain about my performance.  Now’s the time to put pedal to metal and not whimper about additional workload.

Maybe you’ve never had a situation like this develop where you report to one person but dotted-line report to another.  But I’ll bet you have.  Almost everyone I’ve ever known in a professional setting has at one point.  Again – it’s an opportunity.  But you have to know you’ve got double the sets of eyeballs watching you.  It’s a chance to catapult yourself into real visibility…or right into the dumpster.  I’m planning on the former.  Let’s see how it goes….