April 17, 2025 at 12:15 pm

Boss Didn’t Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

by Mila Cardozo

Older man using a laptop

Unsplash/Reddit

It’s unfortunate when someone is living in an echo chamber.

In this man’s case, he tried telling his boss that using Outlook would make their lives easier, but he didn’t want to listen.

He had no choice but to drop the subject and let the ship sink.

Let’s read the story.

Boss doesn’t understand Outlook

Happened over a decade ago, before workplace chats were a regular thing.

My boss at the time was an old-timer, I’m pretty sure he was past his retirement age.

No grudge against that.

He was very good at most aspects of his job, just set in his older ways.

This created a few technical challenges.

Often, I would have to call a meeting with our colleagues in Japan with him included.

For various reasons, he would get upset if I scheduled these without talking to him first about his schedule, even though his calendar showed him as free.

He insisted that I have this checked in directly with him in his office.

The problem is, he wasn’t always there.

There was one simple way to reach him.

So what I would do was just send him an Outlook meeting invite to just him and him alone for the time I proposed to have this meeting.

It was convenient because I was already looking at his availability in Outlook.

He could accept if he works, and then I could update the meeting with everyone else needed.

But it wasn’t convenient enough for his boss.

He sees this and hollers at me to go to his office. He’s a pretty big loud dude, so everyone in my vicinity hears.

He proceeded to ream me out for not doing what he asked.

I’m sure he didn’t understand that he was the only one on the invite and he wasn’t appearing to decline the meeting in “front” of anyone.

He wouldn’t listen.

I tried to explain but then proceeded to say that under no circumstance should I book a meeting with him without chatting with him in person.

Sure enough, a day or two later, a very important meeting request comes through for that afternoon with some higher ups, and he’s not around for me to talk to as it was later in the day.

There was only one way not to upset his boss that day, apparently.

My manager’s number two, who heard the minor fiasco above, takes me aside and says “I know what he just yelled at you about, but I think you should just book that meeting”.

He didn’t even need to be there, it was just proper for him to attend.

Needless to say, I didn’t, quoting what boss man said and that meeting never happened that day.

I vaguely remember him losing a few points for not being able to have this meeting, but nothing nuclear.

Bosses usually benefit from listening to their employees; too bad his boss didn’t want to.

Let’s see how Reddit reacted to this story.

A reader shares their thoughts.

Screenshot 1 95e921 Boss Didnt Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

Yup.

Screenshot 2 1ecd14 Boss Didnt Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

Someone shares a similar story.

Screenshot 3 44e801 Boss Didnt Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

Another story.

Screenshot 4 c0bdfa Boss Didnt Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

Another commenter chimes in.

Screenshot 5 6720fe Boss Didnt Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

Oh my.

Screenshot 6 66fff8 Boss Didnt Understand How Microsoft Outlook Worked And Refused To Listen To An Employee, So He Let Him Miss An Important Meeting To Teach Him A Lesson

This is why learning new things is so important.

If you liked that story, check out this post about an oblivious CEO who tells a web developer to “act his wage”… and it results in 30% of the workforce being laid off.