The Email (Annie Takes It to the Remote Work Cloud)

Annie is armed with remote work research as she walks into the office today.

She was up all night gathering facts, case studies, and proof that the remote work concept is a practical solution to her many struggles, and she’s ready to discuss it with her boss.

But then she second guesses herself during her (long) commute.

She apparently has too much time to think on the drive.

Annie concludes that approaching her boss with the request to make her position remote may be too forward, especially since she is filled with all that confidence she built up last night – the confidence in the concept, not the approaching her supervisor part – and she becomes hesitant.

Annie can’t just show up and insist that letting her work from home is the right decision. Clearly anyone and everyone, including her boss, would love to work from home.


Why is Annie special? Why does she deserve to eliminate the commute and daily showers and office wardrobe while everyone else sits pretty in the office?

Annie decides to send an email requesting a meeting.

Ten minutes go by as she stares at a blank screen.

How do you start a conversation like this?

She’s always been a great writer and is rarely at a loss for words. She takes a stab at it after several more minutes of thought:

“Hi Jessica,

I was hoping we could plan a meeting for tomorrow to discuss a few things. I’ve been struggling with some things at work and wanted to discuss them with you…”

Nope. She’ll think I’m quitting.

“I wanted to discuss the possibility of making some changes to my position…”

That sounds like I’m planning to ask for a promotion.

“I have some great ideas and an actionable, well-researched strategy to improve productivity and morale around here.

Bingo. She hits send.

Oh boy. What did I just do?!?