When is it a good idea to go after your boss?

Never. Not unless you're sure he won't be in a position to exact revenge. Or unless there is some reward (I have trouble imagining what it might be) that outweighs the continuation of your career.

The same logic exists for peers and even some subordinates, certainly those with ample political power to wield.

The fact of the matter is, no one likes to be embarrassed, "disrespected," ridiculed, or made to look small. No one wants their dirty laundry aired. Doing so almost always engenders animosity, and can produce long-term, motivated enemies.

These were the exact thoughts that were running through my mind after I caught my boss in a well-crafted attempt to cover-up...something.

He had signed off on a particularly ugly distribution deal when in a mid-level job several years earlier, one giving powerful rights to a distributor in virtual perpetuity without any checks and balances to protect the company. When I first heard about this, it made me idly wonder what kind of pictures the distributor might have....

Interestingly, the company didn't seem to have a copy of the agreement anywhere -- I suspect for obvious reasons. The distributor, however, kept one. When we tried to squeeze him on a performance related issue, he was only too eager to show it to my VP of Sales. The VP saw the signature on behalf of the company at the bottom of the contract. His name proved my now current boss had been behind the agreement, or had at least approved it. My VP of Sales kept a copy "just in case."

I knew I had some pretty embarrassing stuff in my hands -- the trouble was, what to do with it?

I could use it to embarrass the boss, cutting him down in front of my peers, or perhaps even board members. But to what end? His annoying sense of superiority made the idea somewhat tempting, but then what would I do? He wasn't likely to be fired over the incident -- it was a good dozen years old, and there was no guarantee there was anything behind it beyond stupidity on his part. If he kept his job, that would leave him in a position to exact revenge. I could only shudder at the possibilities.

I could attempt to blackmail him with the information in a high-risk game of Russian Roulette. Of course, I had no idea what had motivated him to sign the agreement in the first place. As a result, I was unsure exactly what I "had." Besides, blackmail was not my style, a tactic I strongly felt was hitting well below the belt.

I could leak the information, although in this case it would have been pretty obvious where it had come from, leading directly back to the retaliation problem.

I even considered giving it to the corporate ethics officer and letting him sort things out. He did work for the same guy I did (yeah, the one behind this terrible contract), making the risk of my name coming up far from negligible. I had confidence in the ethics officer's integrity, and felt there was a good chance he would handle the situation properly, but again, to what end? The incident, as I mentioned before, was old and likely would have led nowhere. And while my identity might remain unknown by my boss, that would certainly not be true with respect to certain board members. That could easily kill my chances for future advancement.

Ultimately, as the incident didn't have any obvious moral or legal violations to it (although there was plenty of smoke), I decided to simply leave things alone. Sometimes the high probability of something going wrong can make even the juiciest piece of political ammunition too risky to touch. Sometimes it is best just to let sleeping dogs lie. 16.4

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If you are intrigued by the ideas presented in my blog posts, check out some of my other writing. Novels: LEVERAGE, INCENTIVIZE, DELIVERABLES and now HEIR APPARENT (published 3/2/2013) -- note, the Kindle version of DELIVERABLES (a prequel to HEIR APPARENT) is on sale for a limited time for $2.99.

To the right is the cover for HEIR APPARENT. In this tale, some is killing corporate leaders in Kansas City. But who? The police and FBI pursue a "serial killer" theory, leaving Joel Smith and Evangelina Sikes to examine other motives for the killer. As the pair zero in on the perpetrator, they put their own lives at risk. There are multiple suspects and enough clues for the reader to identify the killer in this classic whodunnit set in a corporate crucible.

My novels are based on extensions of 27 years of personal experience as a senior manager in public corporations.

Non-Fiction: NAVIGATING CORPORATE POLITICS