How to Start a Conversation Online

By Andy Crestodina

Every digital marketer does it. Some do it well. Others …not so much. But it’s a critical part of social media, online networking, and public relations. Let’s talk about starting conversations.

There’s an art to writing that first message. And there’s science behind that art. Dating websites have tons of data on what works in first messages. Let’s see what marketers can learn from the hopeful boys and girls on dating websites.

Ready? Ok, Romeo. Let’s go.

1. Mention Their Interests

In a study by OkCupid, they show that the member would get a higher response rate for first messages that mention the specific interests of the person they’re talking to.

A bar graph illustrating the success of various interests, including literature, grad school, video games, movies, and bands. The interests increase in success rate from literature at 32% and bands at 44%.

This may be personal interests (such as zombies and metal bands) but in marketing, it’s more likely to be a reference to something professional, such as:

  • A comment on a topic that they’ve mentioned recently: “I saw your post/tweet/article about pinball…”
  • A prediction they’ve made: “I see you predicted that arcade games are making a comeback…”
  • An opinion you share: “I totally agree with you that 80’s games are underrated…”
  • A compliment on something they created or accomplished: “You’ve got the high score on the pinball machine at SuperDawg. Congrats!”
  • A thank you for something useful they shared: “Thanks for sharing that article from Flipper Quarterly. I found that really useful…”

Mentioning an interest is your chance to show that you have something in common, and to do it in a positive way. 

2. Show That You Did Your Homework

How’d you find that interest? You read their profiles, you’ve read their content, you’ve researched their company. You’re listening and paying attention.

Everyone likes to be noticed.

A bar graph of successful phrases in opening messages including: curious what, your name, noticed that, good taste, and you mention. All fall between 40% and 50%.

If you’re starting a conversation with a high-value potential contact, like a prospect, job candidate, journalist, or influencer, dig deep into the research. Indicating that you’re deeply engaged makes a huge difference.

  • I read your book, and I agree that…

  • I’m subscribed to your podcast and I noticed that…

  • I’ve been reading your blog for the last few months and…

3. Be Humble and Self-Effacing

For guys on dating websites, this is life and death. The ladies can smell arrogance a mile away. Self-effacing language shows humility. But it also acknowledges the obvious: it’s awkward to contact someone out of the blue.

A bar graph of phrases including: sorry, apologize, awkward, pretty, probably, kinda. The words decrease in success from 38% to 27%.

Tip: A first message should be direct and concise. But if there’s a place for softened language, it’s in the one sentence that admits you’re coming at them out of nowhere.

4. Be Personal and Original

Another finding from the OkCupid study found that the most generic salutations get the worst results. “Hi” “Hey” and “Hello” were the most common openings, but also the least effective.

A bar graph showing the success and failure of specific phrases. The phrases that fail include: hi, hey, hello, holla. The phrases that succeed are: how's it going, what's up, yo, howdy, hola.

I’m not suggesting you start a message to a New York Times editor with “Yo!” The lesson here is this: don’t start by sounding like everyone else.

5. You can’t win if you don’t play …patiently

Any pickup artist will tell you that you’ve got to put yourself out there. Have the guts to reach out. No guts, no glory. But don’t rush it. It may be worth it to slowly put yourself on their radar in the days and weeks leading up to the first conversation.

Social media gives you all kinds of ways to do it. Here’s a sample of the 35 steps in the complete online networking guide

  1. Follow them on Twitter or Google+ (which don’t require their approval)

  2. Share their content on Twitter or Google+ (and mention them)

  3. Comment on something they wrote (show that you thought about it)

  4. Share content on Facebook or LinkedIn (and mention them)

  5. Write something that refers to them (and quote, link, or credit them)

  6. Start a conversation (possibly mentioning what you wrote)

Once the conversation has begun, ask a follow up question. Open-ended questions work best. Avoid asking questions that can be answered with a single word.

Once a good connection is make, you’re ready to politely ask for something. I find that an offer to collaborate is a great way to start.

Go for it, player! Ask her out!


Our friends at Bluewire Media created an excellent blogger outreach template. Enjoy!

There is more where this came from…

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