January 3, 2026 at 5:45 am

An Executive Keeps Saying She Isn’t Getting Emails, But This IT Worker Realizes She Wasn’t Following His Instructions

by Ashley Ashbee

Man typing on laptop

Pexels/Reddit

Sifting through an email thread is akin to trying to find a pin among needles. It’s needlessly difficult and then people make it worse.

See how this worker figured out the “problem” an executive was having.

Why don’t people listen.

I’ve been in Systems roughly ten years at this point. If I miss one syllable someone says, I’m evil jerk. There is no winning.

Someone sends a 13 thread email chain and wants me to piece together what they need.

Now I can try and piece it together and miss something and they get mad. Or I can flat out say, “Could you please summarize what it is you need from me? I feel if I try to piece it together I will miss key information.”

But it’s still a huge hassle.

Both approaches are going to get someone mad at me, but I’d rather they be mad at me and I have all of the information.

Meanwhile, no one listens to me. I was in a meeting Friday and said, “I have addressed both the functionality and config item.”

This woman spoke after me, “See, West is only talking about the config item, we need to address both.”

This was a recent interaction with an exec.

A C-level executive asked me to send credentials for a new hire. I sent them in an encrypted internal email. She replies, verbatim: “I did not receive the email.”

This was odd—she was receiving all my other messages and this is an internal email. Still, I gave her the benefit of the doubt and sent it again. Her reply: “I did not receive the email.”

Then it started making sense.

I ran a trace. It showed as delivered.

I followed up: “It shows delivered. Please check your junk or deleted items.” Her response: “I did not receive the email.”

So I checked her mailbox from my end. Sure enough, the emails were sitting in her deleted items. I let her know. Again, she said: “I did not receive the email.”

At this point, I called her. She shared her screen, opened her deleted items, and there they were. I asked her to open one. She said, “But they’re blank.” I explained: “Encrypted emails don’t display in the reading pane. You have to double-click to view them.”

Yet the exec won’t own her mistake.

I also politely pointed out the text in the reading pane that explained this.

Here’s the wild part: she was getting the emails, was deleting them, and never once said, “They’re coming in blank.” She insisted she wasn’t receiving them at all—even after being told they were in her deleted folder.

Not once did she mention, “Oh, I deleted them.”

Here is what folks are saying.

Sounds aggravating.

Screenshot 2025 12 16 at 2.34.31 AM An Executive Keeps Saying She Isnt Getting Emails, But This IT Worker Realizes She Wasnt Following His Instructions

Take deep breaths!

Screenshot 2025 12 16 at 2.34.52 AM An Executive Keeps Saying She Isnt Getting Emails, But This IT Worker Realizes She Wasnt Following His Instructions

I despise this.

Screenshot 2025 12 16 at 2.35.21 AM An Executive Keeps Saying She Isnt Getting Emails, But This IT Worker Realizes She Wasnt Following His Instructions

So frustrating, I’m sure.

Screenshot 2025 12 16 at 2.35.34 AM An Executive Keeps Saying She Isnt Getting Emails, But This IT Worker Realizes She Wasnt Following His Instructions

Wow. That’s just sad.

Screenshot 2025 12 16 at 2.35.34 AM 1 An Executive Keeps Saying She Isnt Getting Emails, But This IT Worker Realizes She Wasnt Following His Instructions

(Pulling hair out.)

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.