How to write a cold email

Making meaningful connections in an age of inbox infinity

Oct 25, 2024

The cold email. Just typing those words probably made some of you cringe. I get it. As someone who has both sent and received an ungodly number of these digital missives, I have thoughts. Today, we’re talking about what makes them work, what makes them fail, and how to write ones that actually get responses.

Setting the stage

Before we get into the how, let’s talk about the why. In an age of LinkedIn automation, AI-generated outreach, and the endless barrage of “quick questions,” you might wonder if cold emails are dead. If anything, they’re more valuable than ever—precisely because they’re harder to do well.

Perhaps it’s nostalgia for a time when an email in my inbox signaled infinite possibilities—a new connection, an opportunity, kind words, a party (!!)—but I love a cold email. I got my first job from a cold email, many clients, and even a few friends. As for the emails that landed flat: I don’t remember them. Like they say, you miss 100% of the shots you don’t take, same goes for the emails you don’t send.

The anatomy of a good cold email

If you’ve been following along, you know I spend a lot of time thinking about how we communicate online. After teaching countless students, reviewing thousands of emails, and yes, sending quite a few cringe-worthy ones myself, here’s what I’ve learned about crafting cold emails that work in 2024:

Subject lines that actually work

Think of your subject line as the cover of your book—it needs to intrigue without trying too hard. Skip the generics. Be specific, be genuine, and please, for the love of all things holy, proofread twice.

☻ Superb: Specific, genuine, actionable

“Loved your piece on AI hallucinations—thoughts on a follow-up?”
“Quick question about your talk at Config 2024”
“Fellow RISD alum interested in your approach to systems design”

☹︎ Not great: False urgency, creepiness, generalities

“URGENT”
“Note from an admirer”
“Quick question!” / “Coffee request” / “Following up”

Opening lines that hook

You’ve got about 2.7 seconds before someone decides whether to keep reading. Here’s how to make them count:

✔ Do:

Start with their name (spelled correctly!)
Reference something specific about their work
Show you’ve done your homework
Make it clear why you picked them

𝙓 Don’t:

Use vague greetings like “Dear Sir/Madam” / “To whom it may concern”
Include cringey/creepy/generic words like: synergy, stalking, brain-pick, obsessed

The ask: Be specific, be reasonable

Your request should be clear, concrete, and considerate. Think small wins:

Good asks:

“Would you be open to a 15-minute chat about your experience transitioning from agency to in-house?”
“I’d love to get your feedback on a specific project—particularly how we handled the typography system.”
“Could you share any insights about leading design teams at early-stage startups?”

Bad asks:

“Can I pick your brain?”
“Would love to connect”
“Looking for mentorship”

I’m on the fence about portfolio reviews. While it is an extremely legitimate ask, I often find that folks requesting them or other website feedback generally do not want feedback—rather, they usually want a job. These are two different things.

Don’t accidentally bury your ask either. Consider bolding it for emphasis. I always like this advice from Simon Sinek: To get what you want, ask for it first and save the pleasantries for later. When an email is front-loaded with too much flattery or miscellanea, there’s a danger that the ask might get lost or worse—make your entire note feel insincere. (As if you are only saying kind things because you want something, even if not the case!)

“If you want a meeting, ask for a meeting. Provide some time options and ask for a specified length. If you want an introduction, ask for an introduction ... Make the process ridiculously easy by just asking for what you want.” —Jason Freedman on how to email busy people

Keep it short

People are busy. Think of writing like UI—your email should be clean, intuitive, and functional. The best ones balance brevity with detail, personality with professionalism. You’re not just asking for attention; you’re designing an interaction. It’s not enough to toss words into an email and hope they’ll stick. Intention and execution are key.

From: Be mindful and get the job you want by Sebastian Speier

“Do not write novellas to art directors—if you’re going to write an art director, keep it short and sweet. Don’t attach massive pdfs of your work, don’t pressure them to write back to you with criticisms. Chances are, they are very busy, and if you make them “work” for you, it will annoy them and most likely tarnish future working relationships.” —Jessica Hische, on getting freelance work

Give before you get

Before hitting send, ask yourself: What are you offering? Sometimes it’s just genuine enthusiasm about someone else’s work. Other times it’s a relevant insight or connection. We each bring something to the table. Keep that in mind in your outreach.

Close: Make it easy to say yes

Give your recipient clear next steps and painless logistics. I like to include:

If the ask is to meet, offer 2–3 specific time slots (I like Calendly, but if you’re asking for their time—this can put the onus on the recipient which is not ideal)
If the ask is for an intro, include a self-contained, east-to-forward email
A genuine thank you
A great sign-off
“If a closing line can be so meaningful, so important, why are emailers squandering the opportunity, putting no thought in the closing? Time, perhaps, iPhone-finger exhaustion, multi-tasking—they’re all possible excuses. And many times, acceptable ones. We can’t be expected to neatly tie up every email every time. But once in a while, it would be delightful if people applied the same sincerity to the last impressions that we do to first ones.” —Liz Danzico on email closing lines

Include a link to your work, your social channels—somewhere in your email. It gives them a chance to vet ya or refresh their memory if they forget ya. Don’t include images in your signature, as they usually break or show up as attachments.

The follow-up dance

Here’s where most people mess up: the follow-up. Too soon feels desperate, too late feels forgotten. My rule of thumb? One week for a gentle bump, then let it go.

No response is a response. Some of my best professional relationships started months or years after an initial cold email, when the timing was finally right. Don’t be offended if someone doesn’t get back to you. Life happens.

The template trap

While templates can be helpful starting points, they’re just that—starting points. Each email should feel custom to its recipient. Yes, this takes more time. Yes, it’s worth it.

Subject: Specific reference to their work + clear intent
Hi [Name],
[Personal connection or specific reference to their work]
[Why this matters to you/Brief context]
[Clear, specific ask]
[Make it easy to say yes with concrete next steps]
[Sign off],
[Your name]

Ask for an introduction

I know we’re talking about cold emails, but if you can get a lukewarm introduction, go for it. And when making introductions yourself? Consider an opt-in from both parties before making the connection.

When AI enters the chat

It’s 2024. ChatGPT is writing emails, fielding customer service questions, and drafting marketing copy. So what’s left for us humans to do? Well, when it comes to cold emails, authenticity matters more than ever. People can tell when an email is churned out by a bot—it feels off, like an uncanny valley of communication.

Yes, AI can help craft emails. No, you shouldn’t let it write them entirely. The research, personal connection, and genuine interest? That’s all you. The goal is to sound like a real person who has done their homework and has something genuine to say. (You do, right?) But AI can help. Here’s how:

Brainstorming different approaches
Polishing grammar and tone
Finding better word choices

While tools can help with outreach at scale, the magic comes from the human touch. It’s in the nuances—the specific reference to someone’s work, the witty aside, or the clear connection between your interests and theirs. You can automate follow-ups, but you can’t automate sincerity. As more of our interactions get outsourced to algorithms, the cold email becomes a space to prove we’re still human.

Be yourself (but really)

Perhaps this is the most generic, cross-stitched-on-a-pillow advice: Be yourself. Your email should feel like a person wrote it, specifically you, and definitely not an AI (looking at you, LinkedIn automated messages). Show personality while staying professional. Your point of view, authenticity, is your differentiator.

Be Yourself - Cross Stitch Pattern — They’re not wrong.

Tip: When in doubt, try saying it out loud. Ask yourself, would I say this?

A thoughtful, well-researched email that shows you actually care about the person’s work will always stand out in a sea of automated or otherwise thoughtless outreach. Maybe that’s why personal emails still work in 2024—they’re one of the few spaces left for slow, considered communication. I’d argue that the cold email remains one of our most powerful tools for building relationships and opening doors—when done well. In choosing to craft a personal message, we signal our willingness to invest time in building real connections.

Cold emailing is fundamentally about making human connections in a digital world. Treat each email as a conversation starter, not a transaction. In a world of constant notifications and fleeting connections, it offers something valuable: a moment of quiet, deliberate outreach. The next time you’re tempted to fire off a quick Slack message or LinkedIn DM, consider the slow email approach. Who knows? You might just get a response that changes everything.

And remember: everyone you admire started somewhere, probably with a cold email of their own.

Best regards,
Carly

P.S. What’s your favorite—perhaps unhinged—email sign-off? Sound off in the comments.