What’s the craziest thing you have said to your boss?

Craziest Thing you have ever said to your boss - StartupStorey.com

Some of us do not like our bosses, which tends to bring about crazy things you should never say to your boss. This is part of our series of articles on job hunting and funny stories at the workplace.

It can happen to anyone: you slip and forget who you are talking to, and suddenly you’ve shared way too much information with the boss.

Or the boss overhears you saying something that’s NSFW (not safe for work.) Employees have told me about their taxes, gastro problems, and even affairs.

That’s just TMI (too much information).

When you spend 40 hours a week with your coworkers, it’s easy to become a little too familiar and blurt out things that cross the line.

It’s particularly dangerous when you are talking to your boss.

You may think it’s not a big deal. After all, they’re just words.

However, what you say to your boss says a lot about you. It reveals pieces of your overall character, your attitude about your job, and your judgment.

When you speak without thinking first, you have the potential to do more harm to your career than you first realise, and it can be difficult to make up that lost ground with your employer.

Don’t get me wrong, work is life and bosses should be human, it’s just that you do not need to share it all.

Here are a few things you should never say to your boss.

Thomas, Manager

I started as the only person in the tech department of a consulting and training company. The company had just spent about $30K (if I recall accurately) on a nice looking, but not at all user friendly new website design.

It had been languishing for months due to the company they’d contracted dragging their feet on implementing it. I redesigned the site to be more user friendly and got it up in a month.

From there, the tech department grew and more folks were added to the department.

One guy, who was an applications developer and a real programmer (I was more of a UI guy, though I could program if I really put all my brain power and concentration into it) was brought on board.

In the back of my mind, I knew he’d probably end up as my boss, but at the time, our mutual boss, the VP, swore up and down that was not the case.

I didn’t care if he was… in fact, he probably should be I thought because he’s more knowledgeable about the entire development process than I was and that’s what the company needed at the time.

The problems started when this new guy was telling me to do things that I didn’t have time to do with my own work load.

That’s what had prompted me to get clarification about our roles in the first place. The other problem was that I had a hard time respecting this guy.

He was obviously a very good programmer and knew his stuff, but he didn’t seem to have a good handle on when to or when not to fool around, or how to carry himself in an office.

This wasn’t a startup; this was a consulting and training firm that dealt with government agencies.

I’m all for having fun at the office, but there seemed to be a self-awareness that was missing from him (or maybe he just had a rebellious attitude).

For example, he’d bring a fart noise maker into the office, which was pretty damned funny in our tech department.

The problem was that he’d use it in other parts of the company as well, which wasn’t so funny. There was other similar things like this that made me question his judgement.

So when this guy would ask me to do things I didn’t have time to do, I’d wonder if he just didn’t want to do them himself, or if he really needed the help. I was never sure and all of us had full work loads.

Certainly one of the weirder things that you should never say to your boss – why don’t you do it yourself?

We butted heads a few times as this came up, and we finally had a sit down where I told him how I felt. I said I respected his programming skills and he was obviously very talented in this area, but I had a hard time respecting his decision-making and judgement because of various things I saw and mentioned.

I told him I had no problem working with him and we didn’t have to necessarily like each other to work together.

He was flabbergasted. No one had ever told him anything like this before. I reiterated that he brought a lot to the table and that I respected his talents.

I finished by saying I’d be happy to help him if I had time and if he really needed the help, and it wasn’t because he just didn’t want to do it.

This conversation was on the heels of yet another visit to the VP asking if things had changed and if he was now, or would soon be my boss. I got the usual emphatic “No”.

Well, as you may have guessed, this guy became my boss several weeks later. I should have trusted my instincts and surmised that the VP was just a chickenshit and afraid to tell me the truth all along, but I was young and naive.

This guy was brought on to head up the department all along. And should have been.

While I didn’t get fired right away, probably because I was a very hard and effective worker, and regularly stayed until 7 or 8 at night to get my work done. I’d really enjoyed that job up until I was under the thumb of this guy.

Several months later, I ended up being fired for being 2 minutes late.

By that time, I loathed the job and it was a huge relief. I ended up opening my own business and went on to bigger and much better things.

Epilogue: A few years after this went down, I found out that this guy ended up getting fired a few months after me for his behavior and apparent office misconduct.

Related: How To Handle A Bad Boss: 7 Strategies For ‘Managing Up’

Getrude, Office Executive

I was a mid-level manager in a leading Insurance company. We used to go for annual strategic retreats with senior management.

Being a private business, management did not usually have access to company financials.

However, at the strategy retreats, the CEO would provide us with highlight numbers without analysis or a plan of how to improve performance.

At one of the sessions, the CEO gave us highlight numbers that showed that we had made a loss for the third year in a row and as usual, I didn’t hear any plan or clear strategy on how to reverse the trend.

I still don’t know what made me raise my hand up and interrupted the CEO and said ‘A CEO who stands in front of his staff announcing a loss 3 years in a row should be holding a resignation letter in his hand’.

One of the craziest things you should never say to a boss – or to anyone at all.

The room went quite and icy. My direct boss who was the Commercial Director called for a tea break. The retreat was cancelled and we went back to headquarters.

A hastily called board meeting discussed my conduct and I learnt later that there was push to fire me with words like ‘prima donna’ bandied around my name.

I eventually left that company and found a business that competes with my former employer.

I keep asking myself today how I would handle a junior employee who said the same words to me. It also pushes me never to be in that situation.

Another funny story: Funniest Excuses by Employees who are Late for Work

Read the Strawberry Startup ebook

James M, Office Executive

Straight out of grad school I worked for a consulting firm for a few months before I landed my current job.

Anyway my horrible boss went to an Ivy League school and didn’t leave a chance to remind me of that.

Oh, you know in Harvard we did things differently.

Oh, in Harvard we referenced so and so textbooks.

And bla bla bla . You get the point.

So one day he leans back in his chair, his arrogance spilling out.

What do you think is the one thing that Ivy League students have that other schools don’t?

I was tired of him reminding me for the past six months that I didn’t study at an Ivy League, and his condescending tone, treating me like shit.

Hmm, let me think? A mammoth loan?

I watched his face turn an angry shade of red.

I floated back to my cubicle. Happy and content.

Nope, I didn’t get fired. But I did have another job offer waiting. A plump good one!

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