Weirdest boss you have had and why? (Bit of fun - let's see how times have changed)

Hi everyone

Thought it would be a bit of fun to see if any of you have been unfortunate enough to have a weird/bad boss in the past.

One of mine (yeah, I've had a few) was in the early 90s.  Just after getting the job, I was speaking to the accountant who said to me (and I quote) "You know why he took you on over the others he interviewed?  He said last time he took on the girl with the biggest t**s and it didn't work out so this time he said he picked the one with the biggest smile".

I have to say, I couldn't wait to get out of there.  Thankfully, the decision was taken out of my hands after he had a major scuffle in reception with a director from another company and the following day we went into administration and were made redundant.

Let's hear your bad boss stories


  • In one of my very early HR roles, back in the late 80's (can't believe I am old enough to have worked in the 80's!!!) I was an HR Administrator. The HR Manager had a big, important office with a big important desk. I used to knock and wait to be called in and then he would ignore me and carry on with what he was doing for maybe 10- 15 minutes while I stood there waiting for his attention. What a @%^&*!
  • In reply to Deborah:

    I, too worked in the 80s.....I remember knocking and waiting for the oh so important ones....
  • Working an after-school and Saturday job in a bakery (with cockroaches). The store was family-owned, and when my first shift finished I got changed (out of my brown nylon dress and apron uniform) and prepared to go. Shock from the rest of the team - the unwritten-but-rigidly-enforced rule was that no one was allowed to go home until we had all escorted the owner-boss to her car and waved her off. This meant about 4 or 5 people stood around for 15-20 minutes at the end of each day, to do a most bizarre Downton-esque departure ceremony. Every day.

    Owner-boss was also extremely patronising, apologising for my inability to add up quickly enough in my head to a customer I was serving - again the 1980s, but tills from the 1950s that didn't add up. Customer was mortified, and I lost count.

    Suffice it to say that with the cockroaches and the management style, not to mention the chic outfits, my tenure there was relatively brief.
  • In reply to Nina Waters:


    - his brother was once long ago our boss: he'd 'only' been a Colonel not a General but shared many of the family traits - fortunately not quite so startling though!!
  • My first jobs were dishwashing stints in local restaurants. In one of the restaurants I worked in (when I was about 20), I progressed to "sous-chef". I had boiled, peeled and cut up a big washing up bowl lot of potatoes for sauteeing in preparation for the evening service. Taking them out of the cellar and carrying the bowl up the stairs, the chef/proprietor pinched my bum. (He had a habit of doing this to everyone who worked for him, his wife explained to me and all other staff members). On this occasion, for some reason I was so startled that the bowl (and contents) went flying absolutely everywhere. He, his wife and the rest of the team thought it was hilarious. I did see the funny side eventually. Thankfully, that evening most people ordered chips.

    My very first interview for a "proper" job two years later required a translator - bizarrely, even though we were both speaking the same language, I simply could not make sense of my interviewer's questions, the HR person (also in the room) had to summarise them for me ("what he means is xyz.."). It was slightly off putting and I did not get the job, but I considered it a lucky escape.
  • I've just done a straw poll of all my direct reports and funnily enough they were unanimous in answering the question!
  • When I was a ladieswear manager, a senior manager used to conduct my 1-2-1 meetings in front of our lingerie department and ask me to pick out items that would make his wife more attractive to him in the bedroom.... his wife also worked for the same company in a very senior position!
  • In reply to Chelsea:

    In legal terminology, maybe a bit of vicarious liability going on there.......?
  • In my early 20's I was instructed by my manager to wear a low cut top with a short skirt to a meeting with a potential client. I'll never forget it.

    He'd be eating his teeth if he said that to me now.
  • I once had a manager who acted more like a mother; and I mean things like would brush fluff off clothes, smooth down flyaway hair, and one tried to wipe what they thought was a smudge off a colleagues face. Everyone had to follow their rules, and their time lines - regardless of whether it makes sense or not.

    It was just odd and inappropriate - plus their management style was very 'because I said so'.

    I ended up moving teams as there was zero autonomy.
  • This happened to a colleague...

    We worked at an accountancy firm as PAs. Her boss was one of the partners. He used to get her to do all his private stuff too e.g. collect his dry cleaning, etc. She went in his office one day and he asked her to go and buy something (I can't remember what) and he then proceeded very casually to take out of his wallet his platinum bank card. He then threw it across the desk at her and said "Use my platinum card. That's the closest you will get to ever having one".

    She was a really sweet and clever girl but was in floods of tears.
  • In reply to Lisa:

    Reminds me, Lisa, many decades ago before 'equal opps' were invented, even then being taken aback by a Secretary / PA's official job description presented to me as a member of the Works Job Evaluation Committee which under ' Other Duties' read

    "Attend to her (sic) boss's personal needs"
  • In reply to David:

    The sad thing is, David, that was the 'norm' back then.
  • A long time ago I had a boss who called me every morning at 9:00 a.m. sharp to see if I was in the office on time. If I was only 5 minutes late it was a major issue.

    He however called from home or his car and was usually in the office at least 1 hour late.
  • In reply to David:

    I once had a colleague whose job description had a line in it saying "xyz's PA needs to be pretty".