Teachable Moments (or not) W/ A Boss

Blaine Phelps
5 min readApr 23, 2024

Okay, here are my top 5 experiences with a boss over my career. Some were positive, most were negative — which taught me to never act like them.

  1. On an elevator, coming back from a dinner, with my boss (Manager) and his boss (Director). My boss, an alcoholic, drank heavily at dinner and afterwards (while meeting with clients). In the elevator, he was so drunk, he fell over and did a full facial. His boss looked at me, I looked at him. He got off on his floor, I got off on mine. Not sure if the boss got off on his floor (or if he passed out and woke up later). What would you have done?
  2. At an event that was being televised live on TV (Nickelodeon). The director of the product demanded more money one hour before it was to go live. We told him “No” (even though he was in a strong position of negotiation). I then stepped in and directed the live show — which was hugely successful. But, one month later, in December, Christmas eve, the company gave it out it’s annual bonuses. They ranged from average to outstanding. My boss, his boss, and the HR Director were all in a room.
    Here’s how it went:
    “You did an outstanding job on the Nickelodeon show last month. So much so, we are going to give you a bonus of Outstanding.” (This was 50% of what someone made over the past six months. For someone like me, that was a nice chunk of change. They continued.
    “But, we are terminating your employment with us. We will give you six months severance, plush cover insurance, …”. And so on. Seven years with the company and fired — don’t get me wrong, this was not a surprise (as much as one would think), since I had been on probation for over a year with renewals of that probation every three months. For a brief moment, I thought, after getting the outstanding bonus, that I would have the probation removed or put on another three month extension. Nope — my boss had fired everyone in the division over the past three years — I was the last one that he got rid of (took him long enough). My boss at the time was the same boss as written about in #1 above.
  3. In a meeting with my boss and co-workers. Four of us. In Israel. We were presenting our annual budget to the C-Suite. It was after our first year in business and had just passed $120M in sales (from $0). Every meeting I was in, up until then, had been done in English out of respect for my lack of knowledge of the language. We finished our presentation and my boss switched to Hebrew. Then everyone switched and started yelling at each other. Now, yelling is part of doing business when in Israel — a very passionate culture. I LOVED IT! It was always about being open, honest, and transparent. They were all yelling at each other and then the other three got up and walked out of the room. The CEO followed them out and the rest of the C-Suite got up and left a minute later, leaving me alone. About 30 minutes later, the CEO came back to the room and told me that the others had quit. Those three were the Business Unit Leader, the Sales Director, and the Product Director. Out of seven of us in the division, we were down to four, with me being the highest ranking left (I was the marketing director). The CEO told me that he did not want me to quit and whatever I needed or wanted, he would give me. Told him I wanted an immediate raise and another 10K shares in the company. He said “Done”, without batting an eye. (Wish I would have asked for more).
    Why did they leave? Because the C-Suite said no increase in our budget that we had asked for. We quadrupled the revenue of the company in a year and they were unwilling to give us more money to do more with.
    If I’m ever in the position again where a boss says “You can have anything you want”, I should have said “Give me 30 minutes and let me get back to you”.
  4. Had a boss who would put out weekly emails (some considered them edicts) a few hours before every weekly staff meeting. The emails usually said something like “This process is broken! You must do C, then E, then G, then A and B.” We would then go into the meeting, the boss would say, “Let’s discuss the process. First, you need to do A, then B, then G, then C, then E, then X, then M…” Usually someone who was new to the company would call the boss out and say something like “So, is the email correct or what you are telling us now correct? Both are different.” And then the boss would say something like “Don’t any of you listen! I want you to do it the way I just said. Disregard the email. Why don’t you guys get it?”
    But then, almost every time, by the end of that same day, the boss would “do” the process, and it was completely different than what the email stated or what was said in the staff meeting.
    This is the same company that I have written about that has over a 50% turnover rate of employee’s.
  5. Had a boss who was called out in a meeting by our future boss for saying and doing something that was never done. My boss simply stated that “He was incorrect, that that is not who I am, and why would I do that and jeopardize this acquisition?” (He and I were in an acquisition meeting to discuss the transfer of our marketing department to the company purchasing us). We then had to go out to dinner with our new boss and his staff. Throughout the meal, he continuously badgered and made digs at my boss about what he perceived to what had occurred. Again, it had not.
    My boss, besides the one statement above, kept his mouth shut throughout the rest of the day as well as at dinner. You could see the anger and disappointment rolling off of him, but he was the bigger person and did not raise to the baiting. (When we got on the plane, he went off (vented) on me — I learned how to be a better boss as well as a better person because of how he handled the wrong that had been dealt to him).

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Blaine Phelps

Lucky enough to have traveled the world and gained experiences that I like to share - and I do it now, through life coaching, mentoring, and teaching.