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How To Play It Cool for More Productive Outreach

Ever met someone who’s trying way too hard to be liked? Someone who’s so desperate to fit in with the cool crowd that they end up more awkward than interesting? Then, worse, they eagerly invite themselves to join the group’s plans for the rest of the night?

That’s what most outreach emails read like to me.

People who hit me up with a guest post pitch try so hard to get everything exactly right in their very first email that I end up with exactly the wrong impression. The first problem? Too many words. Like the wannabe who babbles nervously through a conversation, the stranger who writes with too many words doesn’t seem confident enough to ask for a favor in a couple of sentences. The second problem is the “ask for a favor” part, which can be as presumptuous as inviting yourself to someone else’s party.

If you want to have more productive outreach, then you have to learn to play it cool. Here’s how to master a laid-back style for the best results.

1. Be intriguing.

Sophia Loren in 1959

Uncool: TMI

Too much information too early in any relationship takes away all of the mystery. Pare your outreach email down to the essentials.

Cool: Leave them wanting more

Brevity doesn’t mean boring. Sometimes, the less you say, the more that people want to hear. Leave room for curiosity.

What to try

  • Do you share links to your best six articles on a variety of topics? Too much. Try one outstanding one, on any topic. A discerning editor can see your ability or potential right away, and they’ll be compelled to ask for more.
  • Do you include your entire CV? Too much. Pick only the most relevant section about your experience to share. Even better, include only the most interesting tidbit, perhaps in a postscript that encourages them to reply. Something like… p.s. Ask me about the time that I [INTRIGUING THING HERE].
  • Do you drop names? Nothing sounds less cool. Wouldn’t you rather be the name to know? Lead your reader to believe that you are someone, instead of a person who just knows someone. Confidence is attractive.

2. Be laid back.

The Lennons

Uncool: Rushing into things

People who are in a hurry tend to focus on their own needs. Your goal is a mutually beneficial relationship, and that takes time.

Cool: Going with the flow

Cool people make things seem effortless. If you’re relaxed and patient, people will catch your vibe, and they’ll be happy to work with you.

What to try

  • Does your very first email to someone always contain a request? Try introducing yourself without asking for anything. Mention something you have in common — perhaps a shared interest you read on their Twitter bio that has nothing to do with business — to build rapport.
  • Do you expect a reply every single time? Don’t. People who are easygoing don’t stress about those who ignore them. Assume they got your note and simply aren’t interested at the moment. Try again much, much later with a different tactic. And never, ever write a subject line that contains the words “following up on my last email.”
  • When the time is right to ask for your first favor, do you make it easy for them to accept? Skip the rigid timelines and placement (“Could you share this link as soon as possible on Reddit and Inbound? I need to build momentum”). Instead, keep it simple and flexible, and it won’t even seem like you need a favor (“Sending this article your way — I think you and your fans will really like it”).

3. Be humble.

Mark Twain

Uncool: Complimenting yourself

Bragging is annoying. Humblebragging is more annoying. Being annoying is not going to help you build relationships. Modesty will.

Cool: Complimenting others

Genuine humility and modesty are such rare characteristics today that anyone who has them stands apart. People with those qualities assume and behave as if they have more to learn than teach. It’s a form of charisma. Who wouldn’t want to be around — or help out — someone like that?

What to try

  • Do your outreach emails come across as condescending? There’s a fine line between confidence and arrogance, and you might not even realize that you’ve crossed it. Ask someone independent to read your writing and make sure your tone is approachable.
  • What would happen if you sent a half-dozen emails a day containing sincere gratitude and appreciation? Short term, you’ve made someone feel valued (and chances are they’ll respond and remember). Long term, you’ve started a relationship with someone who you value.
  • Do you tend to write, “It would be great if you could…” far more often than “It’s great when you…”? The former is a request. The latter is a compliment. Make it a goal to write at least as many outreach emails with compliments than requests.

Playing it cool works

Intrigue people, and they’ll be curious enough to respond. Keep things laid back, and they’ll be more willing to help when you ask. Be humble and appreciative, and you’ll draw people to you.

When you approach your outreach this way, you’ll never come across as awkward or presumptuous. Instead of trying too hard to be liked, you’ll be liked for who you are.

That’s a great foundation for any relationship.



As Director of Marketing and Customer Experience at Raven, Arienne Holland divides her time between marketing, communications and understanding developers. Before Raven, Arienne spent more than a decade as an editor and graphic designer for Gannett. She’s a factoid junkie, typography aficionado and middle child who just wants everyone to get along.
  • Build Your Own Blog

    Cool article, Arienne.

    I’m noticing some folks are telling people to post more on SM about others and less about themselves, but then when you visit their pages 90% of their posts are self promotional.

    What’s your take on this?

    • RavenArienne

      Thanks 🙂

      Depends on the social media network.

      On Twitter, which is fast-paced and demand tends to build over time, value may come from a mix of your own content and someone else’s. You may not have the volume to keep up. On LinkedIn, it might not make any sense at all to post news from another company on your own company’s page. And on Facebook, I barely want to see all the status updates from people I know, never mind the people I don’t.

      If you keep the focus on what’s going to benefit your reader the most — and if you write your own articles and posts with that in mind — things tend to shake out on their own.

      For a fun experiment, though, search “bragging” on Google. Lots of articles out there talking about the benefits of self-promotion and bragging for marketers, including one from my friends over at Copyblogger: http://www.copyblogger.com/shameless-self-promotion/. Then search for “annoying social media” or some variation of those words to see how the other side thinks. It’s all food for thought.