Let’s Talk about Bosses

I’d like to take a moment to tell a tale of two bosses that I’ve had. I don’t really have a motive in telling this, no great feelings weighing on my heart or anything. Just wanna share and compare, and maybe someone somewhere will find something insightful.

I had a boss once who was the senior-most staff member on our team. He held his position due to this seniority and was expected to fulfill certain functions. For example, he was responsible for filling in for other staff if they were absent very suddenly, like on sick leave or something like that. He was a supervisor for the other staff and was expected to set the pace of the office, and he was responsible to the “director” of the office.

You might notice that I’m being a bit vague. This is intentional, since I want to maintain a veneer of professionalism for those I talk about. I also want to protect the privacy of those I talk about.

Anyway, despite the role that he was supposed to play, this head-staff member (quite honestly) tended to shirk his responsibilities wherever possible. The best example I can think of is when another staff member had to leave or was absent for the day, and when he was asked to fill their role for the day he quite violently argued with the Director and refused to do so. He had other, better things to do in his off-time — he was quite active with out of work activities like Jiu Jitsu and stuff. The altercations would last, maybe, five minutes, and then he would storm out of the office leaving the Director standing there flat footed with no one will fill the role that needed filling.

And, of course, she would end up turning to me to work extra hours in the day, and seeing that I’m just ever so compliant….


But I think probably the best example that I can think of is with regards to my vacation time. It was March, and I had plans to take an extended vacation later in the year in November. I had approached the Director asking for a very certain set of dates off, nice and early, and while I did say that it wasn’t a certain thing yet, she penciled me into the calendar with the understanding that I would later confirm my reservation of these days when I knew for sure whether I would take the vacation time.

Now let’s fast forward several months. I’ve just returned from an unrelated trip to Egypt to visit my dad, and I’ve already purchased my tickets for November. I have all the confidence in the world that I still retain my reservation of my requested time off in November, but on a whim I go in to check and see if I still have them. And, true to Murphy’s Law, guess who had reserved his name over mine? The head-staff member, my senior, my guide and team lead. No consultations to me at all.

Now, I contested this, but it wasn’t really any good. It turned out like this.

1) The head-staff member had seniority and a higher claim to what days off he wanted to have. He was attending a big jiu-jitsu conference in Brazil that couldn’t be postponed or anything like that. I was attending a convention that couldn’t be postponed either, but seniority ruled the day on that point.

2) I had made my intentions ambiguous and had not confirmed them with the Director, and since I had only been penciled onto the calendar those days were still free to grab by someone with much clearer plans, even if they were laid later than my own. He had requested his time off in June, when I had requested it in March.

3) Despite making clear that I was unhappy about the situation, my concerns were implicitly dismissed as a waste of time. “You can’t always get what you want, Jesse.” “I don’t have time for this.”

And that is what I remember most of this boss. Denying his duties, putting himself before his subordinates.


Now let’s talk about the second boss! She was officially a supervisor, and was primarily responsible for handling exceptional issues and pushing paper (time sheets, vacation time, discipline, and meetings). But, more than most bosses that I’ve had, she grew very relaxed and supportive of my work. And more than most bosses, she was fun to talk to and make laugh!

In my six month evaluation: “You don’t know how valuable you are.”

And when I was promoted: “I’m mad, because they’re taking one of my best agents.”

Any time I had a difficult task in front of me, she had my back. Had a special task, and she’d assign it to me to take care of. I wasn’t a senior agent by any stretch, but I would be given the perks of a senior agent anyway.

And whenever I had a particularly difficult situation, I could always turn to her and tell her what was going on and have her help me with getting it resolved. Any time that I needed something done, she would facilitate it for me and have it done in the end.


Now, I suppose that this doesn’t make for a very good direct comparison. I’m finding that it’s more difficult to talk about what I consider a good boss versus what I consider to have been a very bad boss. But I’ll say this much. Where I work right now, I have learned a lot about leadership and a lot about leading by example.

I think that I can safely say that I can see the value in that just looking at how my various bosses have deigned to treat me in the past. It is exceedingly important for bosses to support their staff, get their back when it’s tough, and be willing to take the lead in getting a task done. I feel really blessed to be in an institution where this is the leadership philosophy. It is such a wonderful environment to grow up in.