Scott Dunlap

In the late 90′s Internet heyday, I was a product/marketing executive working for a brilliant but crazy man who had a tendency for selling solutions well ahead of our ability to deliver. We had the following exchange once:

Boss: Make it happen.

Me: What you’re asking us to do is physically impossible given the constraints of today’s technology.

Boss: Maybe you didn’t hear me…I told you to make it happen.

Me: I get that you are holding the bar high for us, but this is crazy. In fact, you are crazy. You are narcissistic, juvenile, crude, conniving, sexist, and lacking any ethical boundaries whatsoever. You are crazy! Yet somehow you consider that combination of attributes to be your leadership style. You are seriously fucked up, like, in a need-a-strait-jacket sort of way.

Boss: [pause] You forgot “rich”.

He went on to the next meeting with a smile. ;-)

Deepika Kalra

Boss: So, you’re from LSR?

Me: Yes!

Boss: You girls study so much! Back in college, every time I would ask my LSR friends out they would say, “Oh no, we’re studying. Assignments on way.”

Me(giggling): Oh no, we don’t! We don’t study for assignments. I guess they didn’t like you much.

PS LSR= Lady Shri Ram College for Women

Adrián Lamo

The crux of this story is an action, but it was how I handled it with my boss that probably saved my job.

I was 18 or so and working as a network admin at a nonprofit law firm. There were a pair of creepy toy pigs that sat around the office (we dealt with a lot of minors, and I can only assume someone thought they’d make them feel at ease). They seriously looked like horror movie fodder, and the executive director dreaded them.

One night, upon learning of her fear of them, I picked the lock of her office and left them sitting, in separate chairs, staring at the door. I re-locked the door and went home.

The next day the office was in something of an uproar. Lacking common sense at that age even more so than I do now, I copped to it immediately, explaining “I thought you could use the company – it’s lonely at the top,”

The executive director – a very nice, slightly older lady – was actually vastly amused by the explanation (and partly by learning it had been me who did it), and just asked me not to pick any more locks.

Over the course of the day I overheard at least twice co-workers discussing how anyone else would have been fired, on the spot, for breaking into her office (I guess I never looked at it that way?). But my boss took it for what it was – a prank – and I think my reaction (I showed no sign of guilt or attempt to deflect blame, since 18 year-old me didn’t see it as having done anything wrong) sold her on the innocence of it.

Needless to say, now when I break into executive offices, I’m billing by the quarter-hour. =P

Heather Wilde

Me: “I need a letter to get out of jury duty – they want me to sit on a trial that will last a minimum of 3 weeks.”

Boss (joking): “Oh, I’m sure I can hire a replacement for you tomorrow. It is Silicon Valley after all.”

Me: (ignoring him) “Plus, they want to sequester me, and my husband gets back from China tomorrow – he would be super pissed if he was gone for a month and didn’t get to see me for another month and it was all your fault.”

Boss (considering): “He knows where I live.”

Me: “He DOES know where you live.”

Boss: “I’ll write the letter.”

via Quora