The Art of reaching out to strangers

The Art of reaching out to strangers

Has there been a time when you thought to yourself – “I wish I know someone who…”? Maybe you were looking for someone who could give you a referral to your dream company. Or you were looking for a co-founder for your startup idea. Or when you were learning something new and looking for people who can show you the ropes.

Unless you’re well known, you’ll have to actively reach out in order to know these people. I’m going to tell you how you can initiate conversations and build a network of people who can help you in different situations. We will talk about how to send cold emails/messages to strangers but do this in a human way. In the process, you might make a few friends too!

Is it effective?

If you are wondering if this would work, IT DOES! Writing to people can be shockingly effective. A few emails or tweets to the right person has the potential to change your life. Especially if you can demonstrate that you have high potential and/or can be useful to somebody. If you’re thinking “well, I’m not impressive enough” you’re likely wrong.

A couple of things that are universally true for most successful/interesting people –

  • They read their own email.
  • Moreover, they’re good at responding to email.
  • They’re very, very curious people.

Not everyone would respond to you, but you’d be surprised by how many people actually do.

Who can you reach out to?

  • Is there someone you want to know. Find out their email or reach out to them on a social media platform like Twitter or Linkedin.
  • Hang out in places where such people are hanging out. Any platform that allows you to send private messages to people is a platform where you can make friends. Reddit, Goodreads, etc.
  • On someone’s personal site, when you enjoy the writing, shoot them an email and let them know about it.
  • I ask people I know for intros and suggestions for people I should meet. This point is severely underappreciated – one thing you can do right now is to message a couple of your friends asking them “do you know anybody I should meet and can you introduce me to them?”

At this point, I want you to pick one person and one person only. Follow along the rest of the article actually writing a mail for that person

Part 1. Preparation

Before you write, do your research

  • Before ever opening your email client, you need to research the people you’re talking to. Google their name, read their work online, bookmark some great pieces of work, scroll through their social profiles, learn about what makes them happy, angry or slightly annoyed.
  • Research will help you learn what they’re interested in and what they’re most likely to notice in a conversation. Use the information you collect wisely and in a timely manner.

Make yourself familiar

It’s called cold email for a reason, it’s your first contact with people who know little or nothing to you. Before sending an email, follow your contact on social media, try interacting with them and see how it goes. Another good way to do it is to contact them after a big change or success in their life, a quick “congrats” will go a long way. Try getting your contact to remember your name before you send an email.

Part 2. Composing the message


Keep it short and simple. The more you write, the less likely you are to get a response. 2-3 sentences max, with one of the sentences being a question or a call to action.

Think of what you want to say, stay focused on the main point of your email, and edit out all the unnecessary parts. While it may sound easier said than done, try this: assign a goal to your email and then to each sentence. Once you’ve done that, edit out the sentences that don’t support the main goal or point of your email. It gets easier with time.

Anything over a couple of paras and it gets sorted into the “later” bucket. The receiver isn’t rude, they just don’t have time for it when checking their email on the way to work. And “later” may never happen.

Subject line

You can keep it to-the-point, like – “NAME, BENEFIT”. For example, I’d be very interested if someone wrote, “Sankalp, let’s work on an article together”. Have an intriguing subject line. Use symbols. “?“ is a good one. Emojis also tend to work but might not always.

If you are sending a similar mail to multiple people, A/B test your subject lines and find something that works.

Make an intro

  • Be super clear on who you are. Why are you worth paying attention to? Don’t be afraid to self promote. There are two approaches to this.
  • You could either demonstrate credibility through your past institutions/roles. If someone gets a cold email from an exec at a large company, they’ll immediately pay attention. If you have a string of brand names on your resumé, excellent, mention that (in a non-trashy way).
  • Or, you could show off a body of work. Link to your Twitter/a paper you wrote/a Github repo/your blog which is interesting and shows why you’re worth paying attention to.
  • If you’ve already interacted with them on a social platform (in a positive way) then mention the interaction
  • You can also reference a mutual acquaintance or an event you attended together
  • I’m a fellow 500entrepreneur
  • We met at the GeoSocialMobileInnovation webinar last month
  • Suresh suggested I speak with you

Building rapport

  • Build Rapport in 1 Sentence. Example –
  • I’m a big fan of your blog
  • Congrats! – I read about your project in YourStory
  • Personalize the email. This should go without saying. Make sure you mention their name, the name of their company. Write about why they’re special to you and what made them stand out among many others. People can immediately spot a mass email so don’t even try sending one.
  • Research the person to understand what they’ve done in life, what they enjoy, what they stand for that you also believe in.
  • Find something you have in common. Never send an email before you find at least one thing. It more likely you’ll seem familiar and hence more likable to them. Telling someone you’re a part of their tribe in some way always helps. Just the fact that you’ve taken the time to research that person implies that their input matters significantly to you.
  • Similarly, if you’re selling software to an enterprise, take the time to speak with some industry/company insiders to understand what’s broken in their workflow that you can help fix.

What’s in it for them?

  • Make it about them, not you. When we get engaged in conversations with other people, we tend to focus on our own benefits and how what they’re saying relates to us vs. a whole other world of opportunities. Remember, your email won’t be relevant to a person unless it’s about them. Use this petty human characteristic against your reader and start with focusing on them and only them. Everyone appreciates a good listener.
  • Everyone wants to help with but it’s hard to respond to everyone. Easy ways to motivate them to respond to you: ideas for their companies or a thoughtful response to something they wrote or said.
  • Maybe you could also mention a relevant bit of info you found about their business online. It doesn’t have to be super intrusive, just something simple that’s easy to find, like their rating on Google places.
  • If you’re selling digital services, it’s best to focus more on the results you’ve brought other companies or can bring to the prospect. You can explain how it works later: the purpose of your email is to get them to respond with interest. Once they are curious about your business, it’ll be much easier to have a conversation with them. If you have case studies, use them!
  • Use a couple of sentences to cut to the chase on why my reaching out can be beneficial to them. Also, throw in social proof.
  • I think we can help you get new customers through our technology. We’ve helped a number of companies do this to date including BigCo, SmallCo, and InnovativeCo.

Make the ask

  • Use this to close your email.
  • Have a strong and clear ask. Don’t confuse them about what you’re asking for.
  • Have a single ask. The more you throw in there, the less likely are they to respond to you.
  • Add necessary details – they shouldn’t need to ask you clarifying questions.
  • Use a who/what/when/where/how/why question.
  • Be extremely direct and specific about what you want. Email people saying you’re looking for work versus asking for coffee and beating around the bush.
  • Examples
  • “I’m looking for customer-facing jobs in robotics that take advantage of my unique combination of technical skills and people skills. Who should I talk to?”
  • “Could you speak with 10 of our students about your journey on a Zoom call for half an hour this weekend or the next?”
  • “I want to speak with you about your experience with using Notion for writing and sharing articles, would you be available for 15 minutes on Thursday or Friday?”
  • “Let’s get coffee and exchange notes” kind of emails sometimes work only if both people are enthusiastic about networking and stand to gain equally, but not when there’s a more unilateral agenda.
  • Give them the context or material that can expedite ‘next steps’: If you’re asking an acquaintance for an introduction, append a note they can forward to the person in question. If you’re sending a cold LinkedIn request, add a couple of lines providing context so you stand out among the dozens of requests popular executives get on the platform today. If you’re asking for time to pitch your product, include a document that gives them a quick overview of the problem you’re solving, how you would be able to solve it, and why you’re better than what they’re currently using. If you’re looking for advice, share what you’re building, what you have learned so far, what parts of their experience might be most relevant to the questions you have. Offer to be directed to the right person in their team if they’re too occupied or not best qualified to answer. The meta guideline here is simple: empathize. Imagine yourself in the shoes of the recipient, what would I want to see or know to be able to quickly respond to a request for time? The lower the friction or cognitive load in providing support, the more likely it is that you’ll hear back.

How to schedule time

  • Anchor the conversation with 2-3 options around both time and place. Windows of time are totally fine. “Would you like to meet over coffee at Stable Cafe between 2-4pm on Thursday or Friday?”. Don’t Ask “when is best for you?” or say “we should grab coffee!” without an anchor time. It seems nice because you give them all the choice, but you’re also putting all the work on their desk and gives them no information about your preferences.
  • Say what you want to talk about during the meeting in the email. It makes it easy for them to say yes and it gives you both a little reminder when you go back and check the email right before the meeting. Don’t use the term “I’d like to pick your brain about …” It screams “I’m not willing to do the legwork to come up with specific questions and topics.”
  • Give as much information as possible – “I’m based in the Indiranagar and I’m in HSR on Thursday afternoons.”. Don’t be vague or pretend to be busy when you’re not.

Part 3. Sending the message

When should you send it?

  • Check the clock before sending the mail. Mornings are best, but not too early, I tend to aim at 11 am delivery. Because, everyone needs a couple of hours at work to get some focus, think about the big picture and plan out their day before they dive into an endless pile of notifications. Be respectful of their time if you want them to notice you.
  • Make sure your email is still relevant, i.e. don’t share old news that’s already been covered and hope to score another point. Don’t go through a random contact list and blast off emails before checking they still have the same interest/work at the same place. Before sending, double-check their timezone and schedule the email to reach them while they’re at work and still focused enough.

What if you don’t receive a reply

  • There’s no shame in following up.
  • Unless you send a follow-up, you’re not even trying. And they know it, so unless you follow up, they will probably just ignore you, correctly believing that you do not even want to talk to them so much. This is true even for people you know personally!
  • Sometimes people are just going through a super busy phase at work / personal life, but don’t assume that people aren’t interested in helping you. You’re just not going to be a priority most of the time.
  • Send 2-3 follow-ups. Consistent follow-up is key, but don’t be too aggressive! Sending someone 16 emails isn’t necessary.
  • Send a follow up in 2 days, then 7 days, then 21 days. Don’t send 3 follow-ups in 3 days,
  • Now, if they didn’t reply to you after having 4 chances to do so, that’s a pretty good indication that they don’t want to talk to you.
  • “Bumping this back up”, “It seems like this isn’t the best time for you, when should I write back?”, “What would you like to see for this to be more interesting for you / your company?” And well, you’ll never be at a 100% response rate with cold outreach, but it’s always useful to know your funnel and the levers you can pull to optimize it.

Sources and additional reading

This post is compiled from various sources (noted here). It started when I stumbled upon this compilation. While going through all these articles, I started seeing common patterns and advice. I organized these notes into one mega-article so I could reference it easily. I put it out in the hope it also helps someone else.

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