Win the Boss Over–5 Points

bigstock-Boss-threatening-employee-38536018I recently had coffee with a friend, reminiscing about his previous company and one of the co-CEO’s there who has since moved on.

   “Smart guy,” my friend said, “although we never got along very well.”


   “You were either with him or against him, not a lot of grey. I wasn’t part of his inner circle.”

   “I got that already, but any reason why not?”

   “Oh sure, I know exactly why.”


   “There was one time he wanted to get into on of the [Asian] markets and was making a big push to do so. For a number of reasons, both Legal Counsel and myself [Gov’t Relations] both said no, sorry, not the way to go.”

   “I know General Counsel almost always says ‘no’ a thousand different ways, but Gov’t Relations is usually a bit more circumspect.”

   “True, although at the time I felt pretty strongly about it.”

   “You were, what, a couple of levels below him?”

   “Two at least.”

   “So what happened?”

   “He cut me off after that, didn’t want to have anything to do with me. And you know, the thing was that there was really no reason for me to have been so adamant–Gen Counsel could have gone to the mat on that one without any of my help or input. It really didn’t matter.”

* * * * *

My friend was most likely right in his assessment of the situation, and also saw (years later) that he was completely wrong for getting into a no-win argument with the co-CEO, and for something that did not significantly matter; the wrong fight to fight.

He wouldn’t win, and saying “no” was political suicide. He now knows that, and hopefully will learn from that in his current job. Sometimes having the wind knocked out of you is a sure cure to not do it again..

So here are 5 points, short and sweet, when dealing with the boss, or the boss’s boss:

  1. Always be calm, cool and collected. Doesn’t matter what you feel on the inside, but never look or sound quavery.
  2. If you’re going to offer advice, be polite, measured, and to the point.
  3. Do not withhold info, good or bad. Never ever catch your boss off guard with the unexpected.
  4. ‘Know your turf, and know your boss’. Don’t stray where you don’t belong.
  5. When the boss succeeds from your efforts, you succeed. It is a win-win, not winner-take-all.

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