6 Cold Email Tips I Use to Turn Strangers into Paying Clients

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I spent the first 8 years of my entrepreneurial journey growing my business on the side of my day job.

Working every day during my hour-long commute by train, I quickly learned that running a full-time business on a part-time schedule was no easy task. 

I knew that if I ever wanted to quit my job and start working for myself full-time, I would need to learn how to reliably generate new business over and over again.

And while there are lots of different ways you can get freelance jobs on a regular basis, for me, cold emailing became a reliable, relatively easy way to generate enough revenue to grow my business.

Does Cold Emailing Still Work?

Cold emailing (the art of emailing a complete stranger in order to drum up business) has gotten a bad reputation over the years.

And with good reason.

Don’t you just hate it when you get a phone call during dinner to let you know that “you’ve been selected to win a 2-night stay” at some hotel you’ve never heard of?

Sleazy, unsolicited salesmanship can be just terrible.

When it comes to email, it’s even worse. Bad enough that, almost from the beginning, email providers have included a “Junk,” “Trash,” or “Spam” folder with every account.

Gmail has even gone so far as to separate out your “promotional” emails from the emails you actually want to read.

Knowing all this, it’s completely understandable you might ask: Does cold emailing even work these days?

But I’ve spoken with literally hundreds of freelancers and small business owners who swear by using cold email to attract their ideal client.

I’ve had the same experience.

Here’s some recent data from my company.

The green bars represent my company’s revenue:

You can see the months where I was actively sending cold emails to potential clients (the high points) and then you can see the months when I was busy working on projects and didn’t make time for cold outreach (low points).

What a stark contrast!

6 Tips for sending cold emails that convert

In the last few years alone, I’ve personally booked hundreds of thousands of dollars in new business all by figuring out how to send cold emails that convert strangers into clients.

So today, I want to share a few pro-level tricks I’ve learned along the way for sending cold emails that actually convert.

Have I ever sent a bad cold email? Boy have I. Undoubtedly. But over the years, I’ve learned what makes for a good email and a bad email. I’ve learned what makes people open and respond to cold emails and why they get ignored.

By using these tips and a lot of trial and error in your own market, you can see some really great results.

Here’s my range of open rates on recent cold email campaigns.

That means over half (and sometimes nearly 3/4) strangers I email are actually opening my message.

Without any further lead-in, here’s how you can send better cold emails too:

1. Figure out the right cadence for cold emailing

Often-times, success in cold email outreach depends entirely on just how many emails you’re willing to send in a day or week.

My friend Jorden took her remote writing business to $5k/mo in a matter of months.

She explains:

“You can’t just send 10 cold emails every week and expect amazing results. You need to cold email at least 20 people per day if you really want to build a clientele fast.”

I agree with her and I’d even up the ante. If you can send more than 20 cold emails a day, do it. The more scale you can achieve early on, the more results you’ll see quickly.

If sending 20 emails a day sounds overwhelming, remember: automation is your friend.

Try using tools like TextExpander, Boomerang for Gmail, or Reply to help you scale quickly.

The more emails you can send, the quicker you can learn and improve. And the sooner you’ll learn what it takes to convert clients in your industry.

2. Find the right person to contact (or get close)

Getting high open rates (and more importantly, high response rates) depends a lot on who you’re actually sending an email to.

There was a time early in my career where I thought I could just send an email to [email protected][companyname.com] and ask them to connect me with the right person to talk to.

That was stupid. It was a waste of time.

Instead, what I do now, works infinitely better and it doesn’t take that much longer. Of course, this is primarily for business-to-business outreach. Finding personal email addresses of clients can be much more difficult (but targeting them with Facebook ads may pay off).

Once you’ve found a company you’d like to work with, free tools like Linkedin Company Pages (click “see all employees” and then filter by job role) and the Hunter.io (which helps you guess a person’s email address) make this whole process much simpler and more effective.

When trying to determine who the right person is stay away from the extremes of the totem pole. 

People “at the top” are very busy and are less likely to respond to your cold email. But people “at the bottom” often have zero power to make a decision to hire you. 

Instead, aim for middle management (Managers & Directors) who usually have some autonomy and budget, but also have time to check and respond to email.

3. Include more than one person on your cold email (one superior if possible)

I’ve only recently started doing this, but it has yielded tremendous results for my cold outreach efforts.

When sending a cold email, try to find two contacts at the same company (maybe in the same department) that you can email together.

You can make your best guess at this using Linkedin Company pages and filtering employees by their title or role.

You’ll have even more success if you can find two people with a boss/employee relationship.

You can always start your email by saying something like: “Sorry for CCing you both here, but I wasn’t sure which one of you I should email my question to.” That way, they both realize someone else is copied on the email.

Why does this work so well?

Consider what you might do if you received an email and your coworker was copied on it. At a minimum, you’d talk together and decide who should respond.

Now imagine what happens if your employee is on the email. Or, better yet, if it’s your boss.

All of a sudden, the email is a topic of conversation or maybe even an action-item. And it’s about as far from “tossed in the trash” as you can get.

4. Personalize every single cold email you send

If you thought my friend Jorden’s advice to send 20+ emails per day sounded overwhelming, then you may not like this next trick. 

But you’ll soon change your mind when you see just how much of a difference it can make in your response rate.

That advice? Personalize every single cold email you send.

What you simply have to realize is you’re not the only one sending cold pitches via email. That means you have to stand out. 

The more robotic and templated your email feels, the less guilty the recipient will feel for deleting it.

Above all of that, business development and sales are just way more fun when you’re yourself about it—instead of some faceless bot.

Here are a few simple ways to personalize each email you send:

Always use names to open and close your email.

Use a tool like TextExpander to set up customizable text templates instead of starting completely from scratch every time. Then fill in custom fields with something personalized to the recipient.

Use conversational language or at least “email conversational.” Avoid phrases like “to whom it may concern” or other things you’d never say in real life.

Be friendly and remember that people like to do business with people they like. Your pitch might be awesome, but if they can’t see themselves being work-friends, your odds go way down.

The advice from my friend, David (who grew two successful creative agencies) sums it up well:

“When you get an email that feels like it’s talking ‘at’ you and not ‘to’ you, it’s easy to feel offended and aggravated. And that quickly leads to the trash can.”

5. Keep it short and easy to respond to

Here’s one of the biggest mistakes I see people make when sending cold emails (I get dozens of cold pitches every week):

They try to close the deal with the first email.

The thinking probably goes something like: “I’ve only got one shot to do this right, so I better just give them all the information and then ask for the sale.”

Instead, go easy on the poor stranger. 

Remember, they’ve never met you. They’ve never heard of you.

You wouldn’t go up to a stranger you’re interested in at a bar and start sharing your entire life story followed by a marriage proposal.

This scenario is similar. Keep your email to less than 5-6 sentences that are easy-to-read and simple to answer “yes” or “no” to. Here’s an example:

Hi, Sarah. 

My name is Preston and I’m a fellow blogger. After 10 years of struggling to learn WordPress (I’m sure you know what that’s like) I finally started HandyWP.com to help bloggers who hate the tech side of blogging.

I know you work in the blogging space and I would love to see if there’s some synergy to be had between our brands.

Mind if I send a few collab ideas your way?

Preston

It’s pretty straightforward: 4 sentences with a really simple ask at the end.

I’m not asking for a major commitment, just that the doors of conversation be opened.

The second I get an affirmative response from this email, this is a “warm” lead and I can make progress toward booking a new client.

6. Follow up like a crazy person

Let me make myself very clear here: if you fail to build a solid follow-up process into your outreach strategy, you will most likely fail.

I don’t even need to crunch the data to tell you that most people who eventually become clients don’t respond to the first email I send them.

It takes some reminding, some prodding, and some gentle nudging to get people to respond to a complete stranger. 

There are two basic types of follow-up that I recommend you use (and one you should stay away from!). Here they are:

DO send a simple reminder with the original email threaded below and a statement like: “Hey, Sarah. I just wanted to check in and see if you got my original email. No rush, but I’d love to chat more about how we can collaborate. Thanks! Preston”

DO ask a question & refer back to your first email with something like: “Hey, Sarah. Just checking again if it would be okay for me to send a few collaboration ideas your way. What do you think?”

DON’T send a templated follow up without threading your previous email. I’ve literally had people send me an email that just says “I’m checking to see if you received my last email.” No previous message included. No context. Nothing. Plus, it’s terribly rude to expect me to dig back through my email to find their first one. Not happening.

Start where you can and build on it

Some of you are probably doing the math here and freaking out a little bit:

20 emails per day

+

15-20 follow-ups every few days for weeks.
=
A LOT of emails.

I totally get that. The nice thing is, you can start as small as you want. Of course, results will also come more slowly, but there’s nothing wrong with sending one cold email per day when you’re starting out.

What I personally love about cold emailing is you can literally turn it up or down, on or off, like a water faucet every time you need more freelance jobs (or have too many).

It’s mostly free, very easy, and super-effective. Paired with more traditional freelancing methods like finding new jobs on freelancing sites or using your online portfolio to get clients, it can be a major boost to your freelance business.

If cold-emailing is something you haven’t tried before (or you’ve tried with little success) now’s the time to give it another shot. You might be surprised at your results.


Preston is the founder of Millo and the author of Cold Emails that Convert—an easy-to-follow course and workbook to help you craft a cold email that transforms complete strangers into paying clients.

Preston Lee

Preston Lee is the founder of Millo where, for over a decade, he and his team have been helping people escape their desk jobs by starting a blog, becoming a freelancer or building a side-hustle.

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