The Meeting

An email from Annie pops up on Jessica’s screen as she returns to her office from her second long-winded meeting of the day. Annie doesn’t usually email her unless it’s important, since she’s right down the hall and does a great job of working independently the majority of the time.

Again, unless it’s important. Or there’s a problem.

Jessica opens the email immediately.

Hi Jessica,

Would you be available for a 20- to 30-minute meeting this week? I have some great ideas and an actionable, well-researched strategy to improve productivity and morale around here.

I’d love to have a short discussion when it’s convenient for you. Please let me know what would be best for you once you have a chance to check your calendar.


What the…?!?

Jessica intuitively attempts to guess what Annie is thinking. As Annie’s manager, a focused leader (and an empathetic woman), she looks deeper into the email than many others would.

This isn’t like Annie. She likes to focus on her work and stay out of everyone else’s projects. She never brings up things like morale or productivity. She’s my most productive employee and has never needed to improve upon her output. What’s going on with her?

Hi Annie,

Of course we can. Let’s meet first thing tomorrow morning. How early can you get here? I have a ton of meetings but would like to make time for you beforehand.


Annie sees Jessica’s response and lets out a big sigh.

Doesn’t she realize how long my commute is?

Case in point.


I’m usually here before 8am, which is really the earliest I can arrive. I have a long commute to the office. How’s 8am?


Jessica arrives very early the next morning to be sure she’s had enough coffee and is on alert in case Annie throws a curve ball at her. Annie walks in at 7:55 with a Venti cup of Starbucks and bags under her eyes. She was a bit of a nervous wreck overnight and barely slept. She considered canceling her meeting but instead took a 5am bath and hit up Starbucks at 6am so she could also be prepared and awake. She quickly reviews her research notes on her way into Jessica’s office and the two cordially bid one another good morning as they try to hide their nerves.

Annie has rehearsed this conversation more times than she can count.

She has gone back and forth between bringing up the request to work remotely right off the bat…or slowly introducing the question by describing how much more productive she would be if it weren’t for the many hurdles she had to clear to perform her work in the office.

“So, I was wondering if you’d consider letting me work remotely any time soon…”

Oh boy. Here it goes.

“You mean work from home? And not in the office?”

Jessica is so good at hiding emotion. Is she upset? Surprised? Relieved?

Annie goes on to explain how distracting and frustrating all the distractions and gossip from people in the kitchen and down the hall are to her (and how they hurt her focus and productivity) and how she feels limited by the office environment (and the disgusting fridge!).

Jessica nods in agreement with a smiley eye roll, showing Annie that she understands completely.

“And I don’t mean to complain. I love my job. Some people thrive in physical offices and around colleagues – some people are naturally very social, even at work – but I have a position that requires intense, uninterrupted focus.”

She then goes on to discuss her proven ability to thrive in silence and how she’s so much more productive when working independently. She reminds Jessica that she’s paid for her work and not her time, and that she’s never needed direct supervision or observation in any way unless it was by her own request.

Wow, this is much easier than I expected. She gets it.

“And I understand the value of working in the same place with others on your team, as well as your supervisor, of course, but I would be able to come in if there’s ever a need for hands-on collaboration or face time with colleagues or clients.”

They both know this has never happened and likely never will in Annie’s case. She’s in a behind-the-scenes kind of role.

“And I know this isn’t your problem at all, but the commute is a killer.”

Then Annie moves on to what she thought would be the hardest part to discuss with Jessica, who still keeps a paper planner by her side at all times and often turns her cell phone off when she’s deep in research or review.

Annie pulls out her research notes on all the options in today’s digital world for remote workers. She explains how amazing and seamless the communications and collaboration options are these days, and as she pulls out her list of the most profitable companies that employ almost entirely remote workforces, Jessica stops her.

“Annie, I think this is a great idea and would clearly benefit both your career and your personal life. My only concern is how to present this to the other owners and the rest of the company, as there are surely a ton of people who would love to work from home. We don’t want it to seem like you are getting special treatment, and we can’t easily say that it’s because you have proven yourself to us and require less supervision than most of them.”

Annie is overjoyed and motivated to make this work.

“Why not, Jessica? Isn’t that what you should say to show them what you expect from your employees? If they don’t fit that description, yet they would also love to be able to work remotely, maybe you would be setting a bar for those willing to reach it and be rewarded with the trust and privilege to go virtual.”

“Good point, Annie. Can you give me a day or two to work out the details before we announce this? As long as the other owners agree and IT is all set you could probably plan to start next week. Let’s just keep it quiet for another couple days before we move forward. Sound good?”

Wow. Does it ever. Woo hoo!!!

Annie tries to keep her calm, reserved demeanor as she shakes Jessica’s hand. But inside she’s smiling huge and jumping for joy and can’t wait to call Tom.

She did it.