Worst Boss = Great Lessons

If you’ve worked for any length of time, chances are that you thought of someone when you read “worst boss” in this post’s title. Bad managers seem to be everywhere and you cannot help but wonder how they keep their jobs. Still, I’ve found that my worst bosses have actually taught me some of the best lessons of being a manager… if only by illustrating what not to do.

Consider. We often learn far more from our failures than we do our successes. With success, you have discovered a way forward and you tend to reinforce the same behavior since it works. That’s fine but it’s in failure that we learn humility to acknowledge what has happened, perseverance to keep going and creativity to think of another approach. We are tempered by all our experiences and failure can sometime teach us far more about how to succeed than success does.

In that same vein, bad managers can help illustrate what not to do if-and-when we take on a leadership role ourselves. Yes, this harkens back to my recent hyper-optimism post about finding the good in any situation, but it is true. Let me illustrate with my own worst boss. (Obviously, names are changed to protect the guilty so I’ll just call him “Sam” here.)

First, some good. Sam had about 10 more years of experience than me and had started at least two successful businesses by the time I’d met him. He was fairly intelligent, worked hard and was a pretty good salesman. Those were all great skills. But Sam had an overriding need to come out on top which permeated pretty much everything else about the guy and made him very difficult to work for.

I went to work for him wide-eyed and trusting. While he was recruiting me, he painted a bright future with significant earnings potential for me… which would more than offset my very, very low base salary. I’d make it up easily.

So I worked hard for months, regularly working weekend and putting in 80 – 100 hours a week. When my review time came, I was expecting a sizable bonus. That’s when I learned that he’d held certain facts back as we were negotiating my compensation. What’s worse… Sam had forgotten what he’d originally told me and said that everything was on track with the business plan which called for us not to break even for three years. (In fairness, I should have thought to ask about their projections but I was young and trusting… so, first lesson learned.) All my hard word did garner me a small raise… enough to keep me there but I now knew I could not trust Sam.

Eventually, we learned I had a talent for speaking “lawyer” so Sam would have me review all our contracts. In doing so, I started to see how he’d include seemingly innocent clauses that, if things didn’t go his way, he could then invoke severe penalties on our partners. So my next lesson from Sam was to read contract language very carefully and to look at it from multiple points of view. It’s rare but this particular lesson has helped me catch a few nasty surprises over the years.

While in the office, Sam could be a bully and it was not uncommon to find him yelling at someone… often bringing them to the point of tears. While I recognized that we sometimes need to tough, I also realized that it could be done in a way that is professional and that doesn’t demean the person. Sam ruled by fear and anger. I swore I never would do that and I think I have lived up to that standard.

Finally, after I had moved on, I heard about how Sam physically threw his business partner out of the building after a particularly heated argument they had had. He then dissolved their partnership while somehow retaining all the rights to the technology and assets that the other founder had brought to the company (see the part above about contracts). Ironically, Sam became a millionaire a few months later when he sold the company while his former partner continues working to this day. I’m sure he congratulated himself on being a shrewd business person but, for me, it seemed like Sam intercepted someone else’s success. To this day, I try and recognize the efforts of those around me and to ensure that credit goes to the right people.

So, to recap the above, my worst boss ever taught me:

• The importance of negotiating in good faith and looking for the “win-win” for all parties
• The need to actively listen to others and to understand their point of view
• That showing strong emotions can be very effective and even appropriate in situations… but that it should be done sparingly
• To constantly look for ways to give credit – where it is deserved – and not try to claim it myself
• And to always, always read the fine print

None of the above excuses poor management and if you ever find yourself in such a situation, your primary motivation should probably be to get out of there as quickly as possible. But, while you’re there, try and treat it as a learning opportunity as well. Your future employees may thank you for it.

I’m pulling for you!