Cold Email Exposure Therapy

I sent unsolicited emails to 100 complete strangers. Here’s what I learned.

Photo by Aaron Burden on Unsplash

It’s the late afternoon and the email quota I’ve set for the day remains untouched. I got on board with the idea that I should be cold emailing about six months ago when I joined an online course that exclusively focused on outbound marketing tactics — something that still terrifies me to my core, hence why I’m writing this instead of my daily emails. Six months 100 emails later, hitting “send” is still just as uncomfortable as the first time.

When I first started freelancing, I had no idea what I was doing, but I knew exactly what I wasn’t going to be doing: Cold calling and sending people my info who never asked for it. Unsolicited sales techniques were out of the question.

The idea of sending an email to someone who is a) in a position of power, like a CEO or something, b) having them actually read that mail, and c) having them respond to that email, was something that made me more nauseous than the budget meals I was eating because I had no clients. 
But hey, I was young and naive (six months ago). And even though cold emailing is still so far outside of my comfort zone that I’m filled with dread every time I open Gmail, most days I can actually hit send and feel good about what I’m doing.

It took a lot of mindset work, tackling limiting beliefs, and hurdling over mental barriers of being too pushy and annoying, but here I am. 100 cold emails later and here are a few things I’ve learned.

Inbound vs. Outbound strategy

I thought I could pick one and stick to it, but that falls under the category of putting all of your eggs in one basket. Something entrepreneurs are warned to avoid. You need a good combination of both. As a writer, I need to show the world what I’m capable of and back up what I’m selling. In addition to writing my own content here on Medium, I try to contribute to other publications on and off of Medium to attract people to my site. I thought creating content was enough, but I was missing out on an entire segment of my audience.

I assumed that my audience was people who are actively looking for someone who knows about writing and marketing. But that was completely alienating the people who don’t know a thing about writing or marketing. These are the people I can actually help in a real and significant way. I needed to create the content to back up my claims of being good at what I do, but I also need to show people what their missing and why they didn’t even know they needed content marketing or good copy to improve their business.

Emailing leadership is a must

CEO’s and other leaders look at the big picture. They’re big idea people and out of the box thinkers, most of the time. Emailing a CEO was one of the most intimidating feelings when I began cold emailing because I put them on a much higher pedestal than I put myself. Talking to CEO’s, most of the time, is just talking to people who have huge ideas that they’ve put into action and that’s exactly what I’m trying to do with my business/services. I always have to keep that in mind when I start to feel intimidated by a CEO. They had to do things that made them uncomfortable in order to stand out and prove that they deserve their spot. And that’s exactly what I tell CEOs who ask me why I’m emailing them instead of their content manager or blog coordinator. 
Another thing; The managers and other team members who work in-house, will very rarely understand why you’re reaching out. They have their jobs, and they don’t like someone else coming in and shaking things up for them. It’s a threat and an annoyance. I get that, I’ve been there. But I also know that when you work on an in-house team, your focus is usually split a million ways, and sometimes hiring an expert to take a look at how you’re doing things and offer solutions, can make your job way easier. That’s where I come in and add value.

Warm up your tone

When I worked in an office and did marketing, I got tons of emails from contractors telling me how they could do my job better than me. What I was doing wrong, and how they could help the company. I ignored every single one of them. Now, I make my emails as personal as possible. I take the time to check the person out on social media, read things they’ve written, learn more about their values…anything that will break the ice and let them know that I’m a lovely (real) person who admires what the company is doing and wants to help. Not a business with an agenda to sell. Write the email the way you would approach them in person. Pretend you’re writing an email to an old colleague or a friend (with some discretion). I’m not saying pretend you’re best friends with this person, but when I began to show my personality in my emails, add humor, maybe even some snark and sarcasm, the responses I got were warmer. But do the research first and see what the tone of the company is before dropping a LOL or meme reference.

Don’t make it about you

My first drafts of my cold email pitches read like the most desperate classified ad. I went on about my experience and how hardworking I am and all of the skills that I have. I read them now and want to shout “WOW WHO CARES, they don’t even know you!” The thing about cold pitching is that you’re not applying for a job. Don’t show up uninvited to someone’s party and spend the entire time talking about yourself. No one knows who you are and no one cares. Add value. Make reading the email worth their time. They want to know first and foremost how you can help them rise above beyond what they’re doing. This doesn’t mean attack their current strategies either. It means find gaps that they’re unaware of and offer suggestions. Then show them why YOU are the person that’s going to help them close those gaps and meet their goals. You don’t have to give anything away for free, but you need to show them what you have to offer and how it’s worth their time to hear what you have to say.

Use a scheduling tool to alleviate the anxiety of hitting “send.”

The biggest pain point I experienced during cold outreach was actually getting to a place in my email where I felt confident hitting send. But the longer I spent on the writing, the more times I read it and edited it, the less confident I was in sending it. My new strategy is to write, edit once, and schedule. And never spend more than an hour on a pitch. At that point, it becomes counterproductive. Someone is going to spend 30 seconds or less reading the email and deciding if they want to move forward. It doesn’t have to be perfect. It just has to be genuine and get their attention. Scheduling the email helps me forget about it and do something else. By the time I think about it again, it’s already gone, and there’s no going back.

Following up is just as important as the initial email

If you’re not following up, you might as well not even send the email, to begin with. Following up on a regular basis increases the conversion rate, it’s simple math. One thing to remember about following up is not to be passive aggressive. Don’t ask if they got the email. Bring it back to the value. Give them some FOMO. Keep it short but sweet. Don’t repeat what you said in the initial email, but give a quick hey “If you have some time, I’d love to hop on the phone and talk about how X can help you achieve Y.”

The biggest takeaway is just to do it. It’s going to be uncomfortable. You might encounter some people with an attitude or ask you to stop emailing them or flat out say no, but it’s all part of the process. Once you accept the inevitable rejection, it’s so much sweeter to accept the wins that will happen from consistency and passion for what you do.


Sarah Aboulhosn is a writer and content strategist who loves murder podcasts, flying over oceans, and stand-up comedy. Learn more about how her and how she helps businesses grow at www.sarahaboulhosn.com.


This story is published in The Startup, Medium’s largest entrepreneurship publication followed by 313,216+ people.

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