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How to Email in this Crazy Town

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Samara Bay“Samara, you have to change the way you email Hollywood people.”

It hit me weirdly hard. Maybe because I’m a writer, and an English major, and I pride myself (yup, pride was definitely involved) in being a good communicator. But here was my good friend, who worked at one of the top talent agencies in Hollywood, calling me for a full-blown email intervention. I had just cc’d her on a note to an agent she was graciously hooking me up with for a meeting. And though I had written what I thought was a perfectly charming, delectably compelling introduction note, the fact was: I had not.

“Your natural enthusiasm comes off as forced on the screen and you’re providing way too much info up front. That just scares people. This is Hollywood. No one cares if you’re bubbly – they care if you’re worth their time. And long emails are not worth their time.”

I actually cried, I remember, on the phone, because it felt like what she was saying ran contrary to my instincts and my own taste – and if I can’t trust myself who can I trust? But more than that, it also felt like all the worst stereotypes about Hollywood’s soullessness and shallowness that I try valiantly to dissuade myself from believing in were suddenly, with one innocent suggestion about email style (for god’s sake), crashing down upon me in torrents of existential hopelessness. I was kind of a mess.

And then I got over it. And saw, of course, that she was right and that we can adopt attitudes in email that are no less authentic than the attitudes we put on when ordering a latte or speaking to a heartbroken friend. We can choose to be clear, concise, and emotionally uninvolved. And I’m here to say: detached emailing can be fun, liberating really. And we must do it from time to time if we want to get what we want in this town.

Email is just communication. And the point of communication is usually to land on the other person. If we’re hustling, following up, emailing about a job prospect or a representation prospect, it can feel like it’s about us – we have the need and we’re hoping it gets fulfilled and there may be a wee bit of desperation there – but paradoxically, we’re much more likely to see said need fulfilled by making that communication about them.

And their time is valuable. And that’s not personal. This town is crazy.

So I share with you what I learned the hard way – 10 guidelines for writing a work email that will get a response:

1) Keep it short. If it takes more than 2-3 sentences, it may be something that should happen in a follow-up in real life or on the phone. Think about what you really want to say. Of course, brainstorm away if that’s your style – write it however long you want just to get your thoughts out, but then edit dramatically. Ask yourself: am I apologizing unnecessarily? Am I saying the same thing twice? Am I stripping when what I should be doing is the tease? THAT’S WHAT GETS CUT.

2) Don’t bury the lead. I understand deeply the impulse to give two paragraphs of context before dropping your ask. DO NOT LET YOURSELF DO IT. Write it like that if you wish, and then cut-n-paste the ask to the top and pair down the rest. If it really feels too abrupt at the top, start with “I’m thinking of you because…” or “I’m sure you’re busy but I wonder if…” and then ASK YOUR ASK. Be bold. State your intentions. If you’re convinced context is really essential, and indeed sometimes it is, consider saying “more info below” and then paste it below your sign-off, above your signature, at the end of the email.

3) If you haven’t gotten a response and it’s been a week or two (especially if you’ve downloaded one of those devious plugins that lets you see if your email’s been opened and it hasn’t) send a try #2. You can even make the subject heading “Try #2.” Never get pissy in the email – remember that they’re busy and remember, too, that following up with them is the polite thing to do not the naggy thing to do. “I’m sure you’re extremely busy, so just a reminder that…” Unless they are actually avoiding you, they will be grateful for this.

4) A little humanity, a little humor, but a lot of professionalism. “I heard your show got picked up – congrats!” or “I hope you survived the polar vortex back east.” Because, again, this is about them. But then dive into your reason for writing, RIGHT THEN. And yes, that one exclamation point I used above? That should be the only one allowed in the whole email. Enthusiasm in the room = good. Enthusiasm in email = feels like shmacting. Don’t push.

5) If you have six reasons for writing, only mention one. Two if they’re connected. But more than that and you risk glazed eyes and nothing getting done ever.

6) If it’s a really tough ask, it may be freeing to ‘make the problem the solution.’ Instead of hedging or pushing the exclamation-pointed compliments, try something along the lines of “I have to admit, this is hard to ask.” Use this one judiciously, of course, but if it frees you to ask your ask concisely, and in a way that will elicit a response, then it’s worth it.

7) If it’s a regular follow-up with someone you’re courting as a mentor or future rep, who’s loosely suggested you stay in touch, I pass along this advice from a wise higher-up in the biz: use a SUPER simple format. The subject heading should reference something shared and funny (if possible); the main body should entail two items, literally numbered 1 and 2. 1 should be something you’re up to that you’d like to share with them (a link, perhaps, or a one-line anecdote that shows off something you’ve recently accomplished), and 2 should be something you curate off the web that you think would interest them, with a line to the effect of “In case you missed it, this is pretty great.” Wrap with “hope you’re well” or a more specific request if that’s your goal, and CALL IT A DAY.

8) Speaking of, if there’s a specific action you want the reader of the email to take, put it in statement form, not question. “If this works for you, please write back to confirm,” rather than “What do you think?” If you want to try to get them on the phone, “I’m available between noon and 3pm Wed, Thurs, Fri. Let me know if there’s a time in there when you can hop on the phone for a quick chat,” rather than “would you be available for a phone call this week?” The fewer back-and-forths required to pin down specifics the more likely you’ll actually get your desired action acted upon.

9) If it’s a thank you letter, make it only a thank you letter. It’s dangerously easy to turn a note that’s meant to be entirely generous into something that’s more about us than them. RESIST.

10) Finally, read it from their point of view before hitting send. If you’re an actor, genuinely think about their moment before, their headspace, their motivation. GO THERE. If you’re not, you can still do this of course. The secret is to let go – if just for a moment – of whatever baggage we may have about their status, their company’s reputation, our own fears or impostor syndrome or anger, and truly empathize.

Then, at least in our little corner of Hollywood, it won’t be soulless and shallow at all. Good luck and let’s GET WHAT WE WANT in 2015, y’all!

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About Samara Bay

Samara's all about collaborating to tell stories that are good for the world or good for a laugh or both. She edits books, copy, and scripts in Hollywood and contributes culture and tech/innovation content to various publications, including Wired: Insider and the Huffington Post. She's a frequent moderator at Silicon Beach conferences and was recently on the leadership council for the United Nations’ first ever summit on the role of media in promoting social causes. She's an Ambassador of coworking space WeWork, an Advocate for artworxLA, an Al Gore-trained Climate Reality Leader, and a member of the Alan Alda Center for Communicating Science. As a speech and communication gal, she dialect coaches on TV and film sets (most recently Captain America: The Winter Soldier, X-men: Days of Future Past, The Lone Ranger, pilots) and works one-on-one with professionals in the creative, science, and business arenas to improve their ability to convey their message and connect. Follow her on Twitter and IG @samarabay and check out her website, www.samara-bay.com, for more.