Emailing Strangers (“Message in a Bottle”)

For my research, I emailed more than 500 small business owners.

INDIVIDUAL emails, mind you, not a mass email. Out of this, 78 bounced back, 32 replied, and 14 concluded in an interview.

The percentage is low and worthy of hurt feelings, but I thought it was worthy of a victorious air-punch. Referrals gained me another 6 contacts leading to 20 solid interviews. Responses also came in from smaller batches. Two weeks ago, I emailed 30 start-ups and heard from 6 of them. The response rate had improved! Almost 25+%.

I haven’t mastered the art of emailing strangers, but this much is clear:

  • Keep the message short. Don’t force the reader to tease through thick paragraphs. According to Guy Kawasaki: “The ideal length for an email is five sentences. If you’re asking something reasonable of a reasonable recipient, simply explain who you are in one or two sentences and get to the ask.”
  • Experiment with your style. Sometimes, the magical expression isn’t evident until you send a few emails to see what works, and what doesn’t. So send a few emails, see how it works, and tweak the message until it feels just right (save your best contacts for the last). I dabbled a lot with my message until it struck a precise chord:

I am writing my PhD on small businesses in Singapore and plan to write a chapter on the start-up scene in Singapore. For this research, I have been interviewing business owners, as well as industry leaders and govt officials. I would really like the chance to interview you about your experience running a start-up in Singapore. 

  • Be personal. If you want personal attention, give personal attention. How did I do that with so many emails? The message was (usually) similar except for the subject header and company name. If the business sincerely impressed me, I would mention it, even simple things such as “enjoyed your website.”
  • Call to action. There’s a higher chance that the email will be ignored unless we specify the exact outcome we desire. Guy Kawasaki suggests answering 5 questions:

Who are you? What do you want? Why are you asking me? Why should I do what you’re asking? What is the next step?

I learned to be clear about when to meet, where to meet, and how to connect. Have a concrete plan, but note your willingness to be flexible.

Please let me know if there is a time that works for us to meet. I’m happy to chat at your office or at a cafe nearby this week or next. You can text me directly at 8765 4321 or email — it would be great to hear from you. Looking forward!

  • Follow-up. Emails get buried or forgotten. Don’t feel like you are spamming when you send a second email. It’s just a message! You can also make a phonecall. I followed-up with 88 trade associations and won a few more replies in the second round. (Thanks, Mike!)

It’s easy to send emails. The trick is to send effective emails that lead to action. Keep it short and purposeful, be direct and personal, and you will probably see better results. Let it be more than just a message in a bottle!

Get a reply with short, focused, and action-oriented email messages.

Get a reply with short, focused, and action-oriented email messages.

Do you have any other suggestions? It seems like the most important step is to identify a convergence of interests, and frame it in a way that feels irresistible. There is no silver bullet, just an art of words adapted to different contexts.

On the flip side, many of us are overwhelmed with emails, so how do we deal with it? Since emails are easy to send, I’d say that even a one-liner – or a very short reply – is a humanly decent way to acknowledge someone who took the trouble to write to you. Consider it a flow of karma!


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