Horrible bosses and Great leaders - A real life story - part one

This is the first in a series of stories about some Great Leaders and Horrible Bosses I have run into during my time out on the world.

I see a lot of memes with pictures of horrible bosses whipping their staff and great leaders harkening down the angels and rays of sunshine glowing from their jeweled crowns.  While those are fun to look at, they lack context.

In this series I am going to give some real world examples to provide a greater level of context to those memes.  Some of these examples you may cringe as you read because it is just like your boss or someone you worked with.  Some of them you will smile as it is like the leader you follow and you can appreciate all the more how great they really are.

All of the stories are true, albeit the names have been changed to protect me, because face it, people don't like the truth unless it makes them look better.

Horrible boss number one.

We shall call her Dairy Queen, or DQ for short.

DQ was one of those bosses that was probably a likable person in her private life, but I never knew her in that capacity.  She took on the role of the wise matronly figure at work.  This usually meant she talked down to you like a child.  It was simply something you got used to.  Kind of like tetanus shots.

The style of management of DQ was simple, you were either liked because you were one of her hand chosen teacher's pets or you were disposable.

As it turned out, I was the latter.

DQ probably knew her job, but she held that knowledge to herself like it was the winning lottery numbers.  Only sharing the results with you after you found out your ticket didn't win.  Even then if she pulled the actual winning numbers, she wouldn't tell you what the truth was.

She was always too busy to help, but never to busy to find some criticism under the guise of being helpful.

She spoke in infinite catch phrases that never amounted to anything other than lots of words and virtually no direction. 

To say it was frustrating would be an understatement.  You could have played buzzword bingo on her conference calls she spoke with so many inane colloquialisms.

All I could ever figure out from her was no matter what I did she had a problem with it, but I only knew this because she would tell my co-workers there was a problem and never actually tell me anything.  She did this under the ruse of helping others understand their job by basically gossiping about people.

She would say these phrases that we have all grown accustomed to, and that would be it.  It was like she was trying to cure cancer by forcing you to drink Diet Coke all day, because that's what she did.

Example One:

I would get on a semi monthly call with her that was supposed to be weekly, but she was too busy, and it would go something like this:

DQ - you need to make sure you are being a team player…

Me - ok, thanks for the feedback, what does that actually mean?

DQ - you know, motivate the team, and do more things with them so they feel like they are part of the team.

Me - I get the reference, but can you give me an example of what specifically I have done right or wrong in this regard?

DQ - well I heard you weren't being a team player and your job description is all about making sure the team works as a unit.  You know, be a team player.

Me - ok, well that isn't entirely an example, I am just trying to get something in mind that helps me know how you measure me being a team player or not.  It kind of makes a difference if I know as opposed to guessing.  Since you brought it up, I had assumed you had a definition or examples.

DQ - well when I hear you aren't being a team player I tell you.  That should be good enough. Part of being a team player is not arguing with me, is that a good enough example?

Me - well, it isn't really an example, it's more like getting a speeding ticket when you don't know what the actual speed limit is and all you are told is you are going too slow or too fast.  It just lacks reference…

DQ - it sounds to me like you need some more training on your job.  Perhaps we made a mistake in promoting you.

Me - {sigh}, yea, ok, I will work on being a team player

DQ - glad you understand me, I don't know why you make things so difficult.

So, that was how pretty much any conversation with DQ went.  Which was nowhere fast and usually in circular fashion and with some passive aggressive and negative reminder I was beneath things like facts or explanations.

A horrible boss provides no examples, no reference point, nothing to actually measure their request with.

A great leader has examples and tangible explanations. A great leader can answer questions without a circular reference. A great leader has anticipated what your needs are in regard to helping you understand an issue.

A horrible boss relies on mind reading and veiled threats. This was DQ.

Example Two:

Another thing about DQ that I struggled with was her perception of reality.

She just didn't want to accept reality as being real. 

She would say late on a Friday that I needed to be in some obscure city Monday morning for a meeting by 8:00 am.

My job involved travel, so I accepted that.  The issue was once I pointed out the logistical reality of meeting her request, she would get all indignant as though I was refusing to do my job.

The conversation went like this:

DQ - I need you in {nowhere Wisconsin} Monday morning.  We have a meeting and you are required to be there no later than 8:00 am.

Me - ok, I do live on the west coast, and the only way I can make it with both the time zone  difference and literal time it takes to travel is to leave Sunday.  I have to take three flights to get to {nowhere Wisconsin} and there will be a few hours of various layovers based on the multiple flights I need to catch.  (She actually knew this, I don't know why I had to say it.)

DQ - well, then you need to do that then.

Me - ok, so to clarify, then I am flying with pretty much less than two days notice and on a Sunday to be there Monday morning.  That means the flights are going to be expensive and I am traveling on a weekend and staying somewhere Sunday night which goes against our actual company policy.  Are you saying that is approved?

DQ - if you can't adhere to your core job functions and my direct requests, maybe we need to reevaluate your responsibilities.

Me - ok, I'm not sure where you got that assumption from what I said.  I am just asking for approval, in writing for travel outside of the company policy.  I really don't want to pay for work travel out of my own pocket.

DQ - it sounds to me you aren't being a team player

Me - I am being a team player, I am cutting into my weekend to travel for work, to be somewhere on a Monday morning, I just want to make sure that the trip is approved because it is outside of the company policy and is going to be much more expensive because of the short notice to book the flights and related expenses.

DQ - let's just go ahead and cancel this trip and talk next week.  I really thought you would understand how your job works and be more reliable when asked simple tasks.

Me - {sigh} ok…

A great leader understands what it takes to comply with a request outside of your normal work routine and responds to that in a dynamic way.  A great leader has thought about these things before the request was made.  A great leader understands exceptions to company policies will need to be approved on occasion.

A horrible boss just says words and phrases without explanation and context hoping that it is just complied with without any follow up to obvious gaps in the request.  A horrible boss will use passive aggressive phrases as a form of fear to motivate people.

Example Three:

DQ would also frequently send out these emails to all of the people that reported to her with some update on a process or staffing.  We knew the email was to all of us because it would say in the subject line something about being to all of us.

What she didn't do was check to make sure everyone was on the email chain or distribution list.  She just would re-forward an old email and remove the content from the prior email.

A great leader has a current and up to date email distribution list of their staff.  A horrible boss doesn't.  It's just that simple.

Inevitably DQ would forget someone that reported to her on an email.  We got used to this so we would forward the chain to the person that didn't get it and copy DQ and say something like “it looks like Dave was accidentally omitted from this chain so I sent it to him”.

That seemed to work until people started replying back and forth to prior emails and DQ never bothered to read the email where  she was told Dave had been omitted.  So we had to do this a few times every week.

This created confusion as people would seem to come and go on the email chain and it make the communication more protracted.

Which resulted in getting an unpleasant email from DQ that would say something along the lines of “…please do not forward any of my emails without my approval…”. Which we would reply and try to say, all we did was notify her and Dave that he was omitted.

Since DQ was outside of ever doing any wrong, she wouldn't admit it was an oversight, let alone an oversight on her part.  If we were lucky she would reply with some veiled threat to add this communication issue to our personnel file so we wouldn't forget the proper chain of command.

A great leader admits mistakes, even small ones.  A great leader takes ownership of the communication process and appreciates when things are corrected before they become worse.

A horrible boss shoots the messenger and then usually burns down the messenger's village to send a clear signal that no one should ever point out mistakes or omissions ever again.

Example Four:

Another trait of DQ we struggled with was the good news / bad news communication style.

DQ would tell us bad news as though we were responsible for it, even if it was not related to us or our area.  She would also only share good news with her hand picked chosen few as though they were blessed enough to be given the honor of hearing the sounds of doves being released and the angels singing.

This meant all I ever got was bad news.

A great leader has a open and honest communication style sharing both good news and bad news as it is relevant to the entire group or individual.

A horrible boss takes the role of the ministry of Truth from Orwell’s 1984.  Sharing a version of the news, as they see fit, and always with spin, and usually lacking all context.

Example Five:

DQ was about throwing you under the bus or taking credit for your work as a management style.  

If a given process didn't go as planned, regardless of why, DQ would say to the group “…the TPS reports didn't process according to plan, so I will work with Michael to make sure they go correctly next time…”.

This would happen even if I only had a really small part of a project and the lions share of responsibility fell on her.

Conversely, if the TPS reports went flawlessly she would take credit for it when her part was minor and someone else had the lions share of the credit due to them.

We would get some public statement like “…I'm so proud to be able to guide all of you to such great results, I'm glad my training has paid off…”. Which was tantamount to her taking credit.

It honestly just became part of who she was.  We would cringe with any news she released because of this.

A great leader gives the credit to their team, period and every time.

A horrible boss takes the credit for all positives and spreads the blame as far and as fast as they can across their team and to anyone else possible for any negative or failure to meet expectations.

Example Six:

If you have traveled, specifically flown on larger airplanes you are aware that they have wifi available for purchase. This isn't usually a great connection, but it's enough to send and receive emails.  So it has some value for the average business trip, especially on longer flights.

DQ would require that we work on flights, which really meant checking email.  Since I didn't have to pay for the service and it did make sense I never had any problem with it.

I was working out of an office in the Midwest for a few months which meant I was flying twice a week and each flight was four hours.  I also got enough emails about random questions and time sensitive stuff that made having access that much better for me to respond as I got them.

On the airline I flew the internet was $15 per flight, which was $30 per week or $120 per month.    Or if you paid $49 you got a slightly better internet connection for the entire month, regardless of the number of flights you took. 

I suspect you can guess where this is going already…

I think I am making a wise and mindful decision when I do the math and determine it is a better usage of my time and the companies money to get a higher connection and pay less than half of the cost by getting the monthly rate as opposed to pay for each segment.

I was wrong.

I submit my expensive report with the single charge of $49 and not the eight charges of $15 (aka $120).  My reimbursement request is denied.  I contact DQ and ask why:

Me - I noticed my internet charge for the airline travel was declined, I'm not sure why..

DQ - The company policy is that we don't pay for monthly internet service for flights.  You submitted a charge for a monthly service.  I declined it. What don't you understand?

Me - I understand that, but if I pay for $15 for each of the eight segments it's $120 and it made more sense to pay less, so I got the $49 rate, and it's faster.

DQ - Well it isn't covered by the policy so I am declining the charge and since you didn't adhere to the policy you are going to have to pay for the internet on your own.

Me - Well, I was actually doing work, as you can see by my email time stamps.  And honestly, it really does make more sense than paying more than double.  So I really don't understand the logic here.

DQ - It’s the policy.  I won't approve any variation to this.  You have to pay.

Me - So if I had purchased all eight segments at $120 you would have paid, but since I got the monthly rate at $49 you aren't, even though I was working; that's the take away message I am receiving.

DQ - Yes.  Please follow the policy.

I was waiting to be told I wasn't a team player.  I simply ended the call because it wasn't worth my time to debate her.

Great leaders think outside of the proverbial box.  Horrible bosses follow a mindless routine because they can't or won't make a decision that involves even the hint of risk.

Great leaders are looking for creative innovation to existing challenges that allow for cost savings and improvements to efficiencies.  Horrible bosses have to win because their fragile ego demands it.

Great leaders find a way to praise an employee that used common sense to overcome a broken process. Horrible bosses don't.


I don't miss DQ. But I do value the time I worked for her for one reason.

Don't do what she did and your chances of success are simply better than if you did.  She based her decisions on being right for the wrong reasons because of her ego.

Take a deeper look at your interactions with your co-workers and staff.  Ask honest questions about how you are perceived and how you come across.  Be open to actual constructive criticism as opposed to saying you are open to it.

Drop your ego and face the fact that you are wrong on occasion and your strength is in owning your failures as often as you make them.

Give credit to your team publicly whenever they have a success and never publicly broadcast negative news about someone on your team.  You take that responsibility and work with them in private.

Explain yourself to others in a succinct manner to be understood without the need to inflict your position or title on them as a negative fear based motivator.

The next chapter is is a great leader “William the conquerer”