We ask 5 smart voices for their 100-word take on 1 provocative brand challenge. Today’s question is . . .

What do you tell yourself right before sending that scary email?

Laura Simms

“The scary emails I send usually fall under one of three categories: 1. Saying no,  2. Holding a boundary, and 3. Asking for something that feels really big to ask for. Once I’ve written the email, I scan it with two things in mind: ‘How would I feel if I was on the receiving end of this email?’ and ‘Would I stand by this if it was reprinted somewhere public and my heroes read it?’ Makes for a great integrity check before I press send.”

 Laura Simms is a career coach who helps people find work that feeds their purse and their pulse. Find her at Create As Folk.

Srinivas Rao

“One of my favorite phrases is ‘World War III is not going to erupt in your inbox.’ I send emails to influential people on a daily basis because I run a show where I interview them. I always make it a point to remind myself that if they say no or turn me down,  it’s not a reflection on me or my work. The other kind of email is one in which you try to resolve a conflict. I generally will try to avoid doing that via email. But when I have to, I remind myself that at least the weight of all that uncertainty will be off my shoulders and I’ve let the other person know how I feel.”

Srinivas Rao is the host-cofounder of BlogcastFM where he has interviewed over 300 bloggers, authors, and entrepreneurs.

Jamie Wallace

“Step #1: Avoid sticky-wicket situations by making sure communications are consistent, clear, and complete. By keeping everyone in-the-loop every step of the way, you can usually eliminate the need for scary emails.

“Step #2: When life gets messy, and you find yourself – with fingers poised over the keyboard – unsure of how to say what needs to be said, aim to write something that is direct, honest, brief, and offers solutions. If possible, start with a phone call instead of an email.

“Step #3: Remember that even the scariest email is not the end of the world. Life will go on.”

At Suddenly Marketing, Jamie Wallace helps clients create resonant brands, standout content, and loyalty-inspiring customer experiences. And she makes sure they have fun doing it.

Kylie Bellard

“My tactic is to reread, reread, and then reread again, each time making sure my missive says what I want to say, how I want to say it. If I’m really nervous about an email, I sleep on it before sending it. Often after a night of sleep, I see typos that I would have missed otherwise. Then I press send, step away, and take a nice, deep breath.”

Kylie Bellard is an uber-compassionate coach and photographer who teaches people how to like themselves so they can bring all their wonderfulness to the world.

Emma Alvarez Gibson

“Risky emails are really frightening for me, I’ll admit. There’s always a stomachache, and often a shortness of breath. So I start by slowing my breath down. Then I think about how whatever issue is contained in the email exists outside of the email — meaning that communicating a problem is different from creating a problem. Then I imagine the worst possible outcome, and get good and comfortable with it. I know odds are good that that won’t be what happens, but am relatively prepared if it does.

“And then, finally, I hit send. And breathe some more.”

Emma Alvarez Gibson is made of words and branding. She’s working on her first novel.

In the comments, we’d love to hear:

What do you tell yourself to make sending those scary emails a little easier?  Add your perspective, then share this piece with your audience so they can see what you have to say, and weigh in, too.