Early in my career, I had the opportunity to listen to a talk by Bill Howell on “managing your manager”.  I don’t recall much about the talk, but one item that stuck with me was his advice, “Never argue with your boss, because even if you ‘win’, you lose.”

At the time, I was young and cocksure and tended towards confrontation in my interactions with co-workers.  If I disagreed with somebody, we each threw down our best technical arguments, wrangled over the problem, and may the biggest geek win.  Being “right” was the most important thing.  So Bill’s advice seemed outright wrong to me at the time.  Of course one should argue with their boss!  If they were “wrong”, then let’s mix it up and get to the “correct” solution.

Flash forward a few years later and I was working as a Senior Sys Admin at a company in the San Francisco Bay Area.  We were trying to roll out a new architecture for supporting our developer workstations, and I was clashing with my boss over the direction we should go in.  Worse still, the rest of the technical team was in favor of the architecture that I was championing.  True to form, I insisted on going for the no-holds-barred public discussion.  This, of course, transformed the situation from a simple technical disagreement into my completely undercutting my boss’ authority and basically engineering a mutiny in his group.

Matters came to a head at our weekly IT all-hands meeting.  Because of the problems our group was having, both my boss and his boss were in attendance.  Discussion of our new architecture got pretty heated, but I had an answer for every single one of my boss’ objections to my plan.  In short, on a technical level at least, I utterly crushed him.  In fact, in the middle of the meeting he announced, “I don’t need this s—“, and walked out of the meeting.  I had “won”, and boy was I feeling good about it.

Then I looked around the table at the rest of my co-workers, all of whom were staring at me with looks of open-mouthed horror.  I don’t think they could have been more shocked if I had bludgeoned my boss to death with a baseball bat.  And frankly I couldn’t blame them.  If I was willing to engineer a scene like had just transpired in our all-hands meeting, how could they trust me as a member of their team?  I might turn on them next.  Suddenly I didn’t feel so great.

I went home that night and did a great deal of soul-searching.  Bill Howell’s words came back to me, and I realized that he’d been right.  Admittedly, my case was an extreme situation, but if I had followed Bill’s advice from the beginning, things need never have escalated to the pitch that they finally reached.  The next morning, I went in and apologized to my boss and agreed to toe the line in the future, though it certainly felt like a case of too little too late.  I also started looking for a new job, because I realized nobody there really wanted to work with me after that.  I was gone a month later, and my boss lasted several more years.

My situation in this case was preventable.  As I look back on it now, I realize that my boss and I could have probably worked out some face-saving compromise behind closed doors before having any sort of public discussions.  Of course, sometimes you find yourself in an impossible situation: whether because of incompetence, malice, or venality on the part of your management.  In these cases you can sit there and take it (hoping that things will get better), fight the good fight, or “vote with your feet” and seek alternate employment.  The problem is that fighting the good fight often ends with you seeking alternate employment anyway, so be sure to start putting out feelers for a new job before entering the ring.  Sitting there and taking it should be avoided if at all possible– I’ve seen too many of my friends’ self-esteem totally crippled by psycho managers.

Bottom line is that one of the most important aspects of any job is making your boss look good whenever possible.  This doesn’t mean you can’t disagree with your boss.  Just make sure that you don’t have those disagreements publicly and make it clear at all times that you’re not attempting to pre-empt your manager’s authority.  “Managing up” is a delicate skill that needs to be honed with experience, but as a first step at  least try to avoid direct, public disagreements with those above you in the management chain.

And thanks for the advice, Bill.  Even if I didn’t listen to you the first time.