Email Like a Bosslady

By: Chelsea Sonksen
Founding Editor, Bossladies Mag


The other day I was listening to a podcast where the interviewer reminisced on the movie You Got Mail and the e-mail culture of the 90s. “Back then, you waited so long for the computer to retrieve your messages that you were really disappointed if there was nothing there,” he said.

In ‘98 when the film was released, I was in the 3rd grade, which means I was still passing notes written in crayon, not worried about email. By the time I was in high school, the iPhone had come out, and email had become the instantaneous, in-your-palm, relentless method of communication it is today. And for this I feel like I got the short end of the stick.

So today, I’m breaking down some thoughts about email to spark a conversation about the new landscape of communication—what is most effective, what is most healthy, and what allows us to have the most impactful connections with our colleagues, friends, and customers.


Bosslady Best Practices

When to Follow Up

Most people check their email more than 10 times a day, so when we don’t hear back from someone within 12 hours, it can seem like an eternity. But it’s important to remember that each bosslady operates on her own schedule. Some can’t answer emails from 9-6 because they work a day job and some have a no-email-on-the-weekend policy.

TIP: Unless you need a response immediately, don’t “circle back” until at least 4 business days have passed. And when you do reach out again, provide the person you are emailing with more information. That way, you’re not just awkwardly reminding them that they haven’t responded, you’re furthering the conversation and giving them more context on which they can base their response.

Appropriate Times to Send Email

So many of us work atypical hours. Even so, sending email in the middle of the night can create a feeling of anxious urgency that you pass along to your recipient—especially if you’re writing to someone who works for you.

TIP: A lot of bossladies use Boomerang, a Gmail add-on that allows you to schedule your messages. That way you can still compose emails in the wee hours, but they won’t send until a more appropriate hour the following day.

The Rainy Day Plan

In the course of running a business, we are all going to get emails that frustrate us. Unfortunately, these are inevitable. But how we answer them is totally in our control.

TIP: Never respond to an upsetting email until you’ve sat on it for at least a day. That way, you’ll have time to process why it is upsetting you and how you want to respond to the situation. Then, when you DO write back, don’t include any hints of your disappointment or anger. They won’t serve you. Instead, make your boundaries clear and respond with honest, compassionate integrity.

The Exclamation Point Abundance

Email can be so emotionally unrevealing, so to counter that, many of us add extra exclamation points. (Me included. No judgment here.) But I can’t help but think something is lost when a simply constructed sentence with a period at the end connotes anger or apathy. Could we rewire our thought processes to assume friendliness even when the sentence ends with a mere period? But until then...

TIP: Allow yourself one or two exclamation points per email, but cap it there. That way you leave your fellow bosslady with good vibes, but all the important information in your message isn’t obscured by unnecessary enthusiasm.

The Sign-Off Conundrum


Each of these carries assumptions: a friendliness or lack thereof, a familiarity or coldness. But really, no matter how I close my email, I mean the same thing: Thanks for your time. Talk to you soon. This is the end of my message. It’s that simple. Yet I always feel conflicted about how I ought to say goodbye. For a time I tried ‘xx,’ but that felt insincere. Did I really mean I was sending hugs to everyone I was writing? I worried I only felt I had to sign off in such a cute, light-hearted way because I’m a woman.

On the other hand, there is a reason I chose not to work in a corporate setting. I like having fewer restrictions about how I communicate. I like treating people as I would a friend instead of just a business contact.

I have no tip on this one because I’m still not sure of the best way to signoff. Most of the time I type ‘Warmly,’ hit Send, and call it a day.