Probably the most awkward feeling call happened to me just recently.

I was to interview a guy that's like 10 years older from me with 10y more experience in mostly unrelated tech. I was prepared to have some respect for the guy, and was a bit anxious, but that changed quickly.

The first fucking thing he says, on the fucking job Interview is essentially "I've worked in tech for 20 or so years, and I don't appreciate being tested" great start .. needless to say, I tried to reformulate all my prepared Interview questions so they sound as casual as I could while still trying to get him to tell me *anything*. Most of the time I just felt like "why are we even here dude, you clearly don't care about any of this"...

About 12 or so questions later It was finally clear that none of his experience is useful, and even the exp he has sounds like past companies kept him around as a number...

I want to try a few more edge cases, hoping to find anything we could work with, when he calls me out on it and says "Well now you're testing me, I don't like being tested" at which point I pretty much gave up on the dude and let my HR colleague talk.

Then out of nowhere the guy brings up his mortgage, and how he needs money, and how no one wants to give him a job, and that if we don't want him, we should just tell him now.

Then he starts asking how many people we're interviewing, which is obviously stuff we can't answer, I just said "normal amount" to dodge the question at first, but that just made him more closed off and he just silently remarked "so you can be picky..."

That was one of the most painful interviews I had so far. Me and ny colleague pretty much instantly agreed that he's not a good culture fit for us. Probably not a fit for any company really, not with that attitude.

PS: it was a video call, though he had his camera turned off at first, so it was only me with a camera for half the call. He turned it on just about as I had enough of him.

Sort of a meeting, sort of an informal interview, I've dialled in from the home office and my audio setup includes a standalone mic and some noise cancelling headphones. It's going really really well when all of a sudden I see something in the preview window of my webcam feed.
Behind me, looking very concerned and confused is my 73 year old Nanna who'd decided to pop in and see me as she was passing by.
It's common for me to keep the front door locked, but my Nanna has an emergency key and knows I don't always hear a knock at the door, so let herself in.
So she's now in the house, calling out to me and she can hear me talking, so follows the sound of my voice thinking maybe I'm on the phone. Walks right into the office, where the door is behind me, eventually puts two and two together to work out that I can't hear her and finally sees herself on my monitor. She panics and goes to hide in the corner of my office, almost underneath my workbench because she's old and doesn't know where she would or wouldn't be visible from.
The rest of the meeting went really well, but overran by at least half an hour. Meanwhile I can see my poor Nanna hiding away in my peripheral vision.

It’s perfect that this week’s topic is “Most awkward video meeting” because I just had two.

The first one was to demonstrate a software process. I had everything lined up and perfectly (or so I thought) ready to demo, kind of like a cooking show. Except the deployment totally failed. I’m still struggling to figure out why several hours later. Luckily I’m getting a second shot at it soon and they weren’t mad.

Then I went and took a shower. Checking out my eyebrows in the mirror, I decided they were getting overgrown, so I took out a trimmer with a guard on it to thin them out a little. Except for some STUPID and INEXPLICABLE reason I TOOK THE GUARD OFF right before I shaved off the right eyebrow almost to the skin! I couldn’t believe it. It was like my brain sabotaged me knowing I had an important video call coming up where I might be making a ton of money if all went well.

What the hell was wrong with me?! What could I do?! I stood there cursing my existence and making plans to become a hermit in the desert. Well, I couldn’t do that. And I still had a video call in a few minutes. I couldn’t just leave one eyebrow unshaven. So, I did the only thing I could do. I cropped the left one and tried to make it match as much as possible.

It wasn’t terrible, but it was definitely noticeable on HD video and certainly up close and in person when my wife and kids returned home soon. I started panicking and wondering just how I could literally save face after idiotically mutilating my face for all to see.

Then, I got an idea.

Now, I’m a manly man. At least, I consider myself to be. I don’t shave my eyebrows for any kind of metrosexual caché. I do it because if I don’t the grease from my face that gets into my brows eventually transfers to my glasses and then I get annoyed by all the smudges. As a dad who was never comfortable when my girls wanted to put makeup on me, I suddenly became aware that their massive trove of makeup “stuff” might just save my bacon!

So, I snuck into their bathroom and, lo and behold, the exact right shade of color for my missing brow brooms was sitting right on the counter. I dabbed a little on each finger tip and carefully (oh so carefully) tinted the area mangled by my apparent dementia.

It was actually pretty amazing how it all turned out. Even on HD video it was undetectable. And when the true test occurred…i.e. my wife and kids returned home and I had to talk to them face-to-face, absolutely NO ONE was any the wiser!

Now I gotta figure out how to keep up this charade for at least a week, maybe two. I hope they don’t put that makeup tray away somewhere where I can’t…oh, wait, they never put anything away. I’m good.

The videoconference started and I had no shirt on, fortunately there was only one guy and he laughed but understood haha

Most awkward video meeting?

Can a conference call count? This happened several years ago.

Diving into international markets that could potentially make us millions of $$ (no pressure), while the phone was ringing the CEO's number (in Norway), my manager leans over and whispers
DevMgr: "This project will be managed using *proper* software development methodologies, none of this agile shit you want to use."
<CEO picks up>

I had already been in talks with their dev team to get a feel for their tech stack and we had discussed project milestones, potential release cycles (laying the ground work for using agile methodologies) before getting upper mgmt involved.

The partner dev team was listening and kept throwing out agile buzzwords and I could tell my manager was getting pissed. He would blurt out "Those specifications will need to be fully documented before PaperTrail writes one line of code!". No one said anything, but I could tell the other mgrs/VPs in the room were uncomfortable with the hostility towards discussing features.

"Wait, wait, waiiiittt. Let me put my shirt on."