And, the less than great bosses…

One of my more frequented posts is a “Tribute to a Great Boss” which I believe many folks check out as they want to see the attributes of someone who does the job well, as so many do not. This boss is also very humorous, so his many sayings are worth the read.* Yet, even though he was the best boss I ever had, he was not perfect. Nor are the many other bosses I have had the pleasure of working for. Some of their imperfections stood out more than others, but I have been blessed not to work for any screamers or tantrum throwers, which unfortunately exist.

My second favorite boss was a terrific story-teller and was supportive of me and others. His stories were so riveting, we would end up correcting them as he retold them again and again to new audiences. Our office flourished under him and the three years we worked together were memorable. Yet, his Achilles Heel was impulsive decisions and he left his role out of frustration, a decision he later regretted and put a strain on his marriage which ended in divorce. We missed him greatly after he left.

My favorite story of his is when he arrived at a meeting with someone he had not met before the administrative assistant had arrived. He was waved in and the guy proceeded to tell him about a legal problem. My boss is a great listener, so he is taking notes and is rapt with attention. When he finished his story, the guy said “What do you think I should do?” My boss said, “I think you should hire an attorney.” The guy looked at him and said “Who are you?” The guy had mistaken my boss for an attorney he had a meeting with next.

On the flip side, my first boss out of college was a great salesmen who was promoted to management, a very common mistake. Great salespeople do not necessarily make good managers. He was not an exception to this rule. He went out and bought 23 management books and read them all. One of his rules was to have a “quiet hour” from 9 am to 10 am, so no client calls or internal meetings could be had. Now, mind you, our business was to consult with clients, so not taking a call from them during that hour was not good for business. Eventually, the other senior folks in the office suggested he cease this practice. Unfortunately, he was asked to leave about six months after I got there, so the company lost a great salesman. We missed his excitement and passion to go see people.

I also had a boss that was a very good subject matter expert, but whose people’s skills left something to be desired. I learned a great deal from him both good and bad. I learned the subject matter in a practical way and he taught me how to dive into new things. Yet, I also learned how not to act as some of his mannerisms would make you feel awkward. He was like our Sheldon from “The Big Bang Theory.” He is very smart and we remember him fondly in spite of his mannerisms. One of his shortcomings was small talk at client meetings. You wanted to make sure the meeting stayed focus on the issues. He was excellent with the issues. One of my favorite stories about him was in a client meeting when a key contact of our client was arguing over a legal issue with someone in the client’s general counsel office. My boss used both hands to inch the legal plan document over to the attorney and said what was written here says otherwise winning the argument for our contact. To see him push the document slowly over to the attorney was priceless.

One of my least favorite bosses was on the arrogant side, but he also was cheap. He would spend the company’s money on himself, but he would be quite frugal with his own money. An easy example is we would have year-end holiday parties at his house, with a secondary purpose to stock his liquor cabinet, as he would over order supplies. In spite of these traits, he had a congenial side and he contributed to our success, so we tolerated his behavior. We had a great run under his guidance, but it was more due to the caliber of people we had working under him. Yet, he would tell others in the firm how he harnessed these horses underneath him to achieve the success we had. That was a stretch.

Through my earlier years, I worked with a mentor who was one of the best consultants I ever worked with. He was never my boss, which is good, because he would have been horrible at it. He was a great consultant because he did not tolerate anything less than perfection. Unfortunately, no one is perfect, so he would have had issues with lesser talented people. I had to redo a lot of work at his suggestion. Yet, not being my boss, we could tease him about some of his habits to work very well with him. He was not my boss, but he had a great influence on my life and career. He is a lot like the final person I worked for at a small firm. He also pursued perfection on client issues and had a great reputation, but he was not a very good business person around time and expense management.

Each of these bosses I remember fondly to varying extents. I learned a lot from each, but none could be construed as perfect. Of course, neither could I.  I guess one piece of advice I would give to someone starting out is recognize the strengths and weaknesses of your boss and manage up. If you need face time to ask questions, schedule it. If your boss does not take the time to communicate well, help him or her using words comfortable to you. Also, where you can, discuss possible solutions and not just the problem.**  If you help this navigation process, then you can survive and flourish. And, don’t ever work for a screamer. If you do, keep your resume up to date and begin searching for a new job in case nothing is done about it.

* You can check out this post with the attached link:

** There is a great article called “Who’s Got the Monkey?” which will help you in managing up through offering possible solutions rather than passing the problem back to your boss.


7 thoughts on “And, the less than great bosses…

  1. That story about the mistaken attorney is a classic, I hope they both laughed it off. There is great wisdom in this post, I wish I had this sort of advice when I was first starting out. Managing up is fine as long as that doesn’t mean treating your peers or subordinates as lesser or lower priority. I have seen that happen all too frequently and is a real obstacle to a strong team.

    • Thanks Judy. Your point is well taken on treating your peers well. By managing up I am referring it helping your boss manage your efforts. An interviewee told me once that he would schedule a weekly meeting with his boss to ask all of his questions. We hired him. Thanks again. BTG

  2. Note to Readers: I wanted to let you know I purposefully did not include several other bosses. For the most part they were supportive, but were more vanilla and did not stand out as much. I had good relationships with each which matters a great deal. I did have one favorite story of one of these bosses who smoked unfiltered Camels back in the day when you could smoke in your office. As we met late in his office, he realized he was out of cigarettes and patted every pocket to make sure. When unsuccessful, he reached into his ash tray and picked the largest stub and lit it up. That is a person who wanted a smoke.

  3. How sad that the great salesman got promoted to boss where he was doomed to failure and fail he did, thus the company suffered the loss of his true skills.

    Lordy, I worked for a lot of bosses, both good and bad, in my career. There were a few that I felt sorry for: nice guys but inadequate in one way or another; there were a few that I would have turned myself inside out for, would have marched through hell and back for; and there a few whose utter ineptness or good-ol-boy attitude made me chuckle when they stumbled.

    • Linda, I like how you categorized your bosses. The promotion of a good salesman to leader is not uncommon and fails more than it succeeds in my view. It usually requires the person to do more of what they don’t like doing and less of what they do. Thanks for your thoughts and anecdotes. BTG

  4. Your analysis of good and bad bosses remind me so much of school principals. I had a few excellent principals as bosses in my career and had a huge load of bad ones… In fact, I would’ve had more principals to work for than years of service if it had not been for the last seven years of my career under just two sets of principals. Stability is a key to good education, but we are not in a very stable time in the education business. Of course, it could get a lot worse with a Republican President again in 2016.

    • Agreed on all counts. My mother taught second grade and she said the principal set the bar. She respected this one who sought excellence from all but was fair and supportive.

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