The 5 Most Common Mistakes You're Making With Your Cold Emails (and How to Fix Them)

[Authors note: The following is Part 2 of my “Writing Great Outreach Emails” series. If you’d like to master the art of email outreach and download all 3 parts (including a BONUS checklist to help you craft your next message), Click here to download ‘The Insider’s Guide to Writing Great Outreach Emails’.]

I get it.

Who’s not busy? I’m busy. We’re all busy. Everybody’s busy.

But other people being busy isn’t a valid excuse for you not getting any responses to your cold outreach messages. Most likely the lack of response has nothing to do with the recipient being busy and everything to do with making one (or more) of the most common mistakes I see people making when sending cold outreach emails.

Having both sent and received thousands of outreach emails in my career, I have a good sense of what works and what doesn’t. Early in my career as a trailer editor I was tasked with reviewing hundreds of cold submissions from other trailer editors so we could build our roster of freelancers (which included sifting through hundreds of résumés and multiple boxes of VHS & DVD demo reels...yes I just aged myself there).

Later in my career I started a boutique post-production marketing agency and hired multiple employees via cold job listings (after sifting through thousands of emails for each one).

And now having put myself out there very publicly with my website and podcast, I receive between 5-10 solicitation PER DAY from people who want to sell me their products, get on my podcast, put links on my website, have me pass along their résumé, or have coffee and “pick my brain.”

Needless to say, I know what outreach messages look like from the perspective of the person receiving them. And the vast majority are just plain bad.

Before identifying the most common mistakes and breaking down why most outreach emails fail to receive a response, however, it’s imperative that you put yourself in the seat of the person whos’ about to receive your message.

This is a process I like to call:

Crawling Into the Brain of Your Recipient

Picture in your mind right now a person you reached out to recently. Maybe it’s a famous editor, director, producer, bestselling author, or even a studio executive.

Imagine them in their daily work environment.

Imagine the amount of requests put upon them for their time, their opinions, and their expertise.

Imagine them being so busy they have to frantically eat lunch every day at their workstation.

Now imagine their email inbox.

While it may seem nearly impossible to compete for a busy person’s valuable attention given how little they have available, it is possible to stand out amongst the noise if you construct your outreach message correctly and you go out of your way to provide value to this person (more on providing value in my ‘Insider’s Guide to Writing Great Outreach Emails’). But because “providing value” is an elusive concept, and because outreach can be a tedious, time-consuming, and slow process, most people opt for the easy route instead as you’ll see below.

Here are the five most common mistakes I see people making with their cold outreach messages.

Mistake #1: Making it all about YOU

It’s common to think that the best way to get the attention of an expert, a potential mentor, or someone who can open that oh-so-elusive door to the next major stage of your career is to sell yourself and include every relevant piece of information that will set you apart from your competitors (and of course don’t forget to attach your resume and a link to your website!).

But you’ve lost the game immediately if you are making the message all about you and your own needs.

From your perspective you might be thinking “This is my one shot!” so you must share all of your credits, your experience, your education, and it’s imperative that you impress them with your uncanny ability to interpret the deeper meaning of their creative choices such that it reads like a graduate film school thesis.

But from their perspective?

A busy person will be just fine ignoring your email.

It is not their responsibility to respond to your message.

It is your responsibility to earn their response.

The fix: Stop thinking that this email is your only shot to sell yourself. The purpose of your first outreach message is not to land a job, or an interview, or a lunch meeting, or a phone call, or a shadowing opportunity. The purpose of your first outreach email is simply to get a response and start the conversation.

Mistake #2: Your message isn’t personal and reads like a template (or even worse is a group message)

I know how tempting it is to be as efficient as possible with the limited amount of time you have to network. We all love our Macro keyboard commands that get us from 8 keystrokes to 2 keystrokes...but outreach messages are NOT the place to focus on efficiency.

Sending 500 generic messages with a 1% response rate gets you 5 responses...and they’ll be tepid at best.

Sending 10 highly personalized, thoughtful, and hand-crafted messages to the right people with a 70% response rate gets you 7 responses...all of which have the potential to lead to a genuine relationship.

Stop hunting with a shotgun and start hunting with a sniper rifle.

Here’s an example of a common template message I’ll receive from acquaintances or former colleagues:

First of all...how do I know this is a template email? Because they used the wrong name! Yes they took the time to personalize the first sentence, but anyone with Google or IMDb can find out in 2 minutes or less what I’ve been working on.

For context, this is an acquaintance I know personally whom I’ve met at several past networking events, and he’s a great guy. I truly want him to succeed. But we’ve never worked together, so I don’t feel comfortable blankly forwarding his résumé for a job without knowing more about his job performance firsthand. And furthermore I only hear from him when he’s unemployed.

Had he instead watched an episode or two of Cobra Kai or listened to a recent episode of my podcast and commented on something that inspired him, I absolutely 100% would respond. But in this case it’s tough to make the time for coffee or lunch when this technically was written for someone else and not me.

Here’s an example of the type of group emails I get ALL. THE. TIME.

If I don’t know this person, or even if I’ve met them casually but not worked with them before, once again why would I refer them? Vouching for someone puts my reputation on the line.

And if I do know this person or I’ve worked with them in the past...why haven’t they made the effort to reach out to me directly?!?!?!

The fix: When you reach out to people, ditch the templates, stop worrying about the quantity of messages you can get out into the world and instead focus on the quality of your messages.

Demonstrate that you have clearly done your homework. Identify something unique about their work, quote something they said in an interview or panel, mention an obscure reference to a project they worked on twenty years ago that you love. Send them a link to an article that they’d find helpful and valuable. Make it clear that you’ve invested considerable time and energy into drafting a one-of-a-kind outreach message meant just for them. This will make them think, “This was nice of them. At the very least I should probably read the rest of their message.”

Mistake #3: You get too personal (and send your life story)

Yes yes, I realize I just told you NOT to send a template and instead take the time to craft a personal message. But please don’t send your life story. At best you have two minutes (or less) to get this person’s attention AND have them respond before they are onto other messages and urgent matters in their life. Your life story will have to wait for another conversation.

Here’s the perfect example of a very personal, heartfelt message that is clearly not a template composed just for me (that is still sitting in my inbox 3 months later).

I still have every intention of responding to this person...eventually. Their heart is in the right place and they’ve clearly done their homework on me, but alas because the email is incredibly long, detailed, and personal, and because crafting an equally thoughtful response will most likely take me 30 minutes or more, this will continue to sit on my pile of messages that deserve a response but just don’t fit on my calendar.

The fix: Be brief, but also be specific. In no more than two quick paragraphs you need to make the following two things clear:

Who are you?

And what do you want from this person?

Connect the dots for them so they understand where you are on your career path and what you have in common with this person. Share a few relevant details...then get to your ‘ask.’ If done right, you’ll have all the time in the world to share your life story when you meet for lunch.

Mistake #4: You haven’t made it abundantly clear how this person can help you (or why they should at all)

I can’t tell you how many times I’ve been told by someone desperately struggling in Hollywood, “Nobody in this business wants to help me.”

Think for a second about where you are right now in your career (I don’t care if you’re the head of Amazon post-production or an intern). Now imagine someone reaching out to you with a similar backstory, similar challenges, and facing the same obstacles that you perhaps overcame just a few years ago to get where you are today. If this person seems genuine and hard working with good intentions, wouldn’t you want to help them succeed?

I’ll bet you’d go out of your way to help them!

Why?

Because they remind you of yourself at that point in your life.

Now imagine receiving a message like this instead:

No doubt this person has good intentions, but there’s only one way I can help them: Giving them a job (or referring them). Except I don’t know anything about this person. At all. Why in the world would I consider them for an upcoming job opportunity or refer them if I know NOTHING about them or their past experience? I want to help people, but sorry. This is an instant ‘Delete.’

Had this person instead introduced themselves, briefly illustrated where they are now in their career journey and where they hope to be someday, and then made it clear where specifically they require assistance to take the next small step, I’d bend over backwards to help them.

It’s not that people don’t want to help you. It’s that you haven’t made it clear enough how they can help you.

The fix: Make it clear how you are similar to the person you’re reaching out to. Demonstrate you’ve done your homework so this person immediately understands why they are the right fit to receive your message and provide you some assistance. Find common ground. Increase familiarity so you don’t come off as another generic person hungry for a job. Then illustrate very specifically how this person can help you with a clear ‘ask.’ (more on that next)

Mistake #5: Your questions requires a lengthy response (or you’re asking too many)

At this point you’ve stopped selling yourself, you’ve ditched the templates, and your message is short and concise. And you’ve also made it clear who you are, what you want, and where you need help.

Now it’s time for the ‘ask.’

This is where most people blow it.

Once again, crawl into the brain of the recipient and review your questions:

Are they easy to respond to?

Can they respond quickly?

Have you asked too many questions?

Here’s a message that’s easy to respond to, doesn’t ask too many questions, and one can certainly respond to quickly, no?

If your first cold  ‘ask’ forces someone to open their calendar, you’ve already lost.

Yes this message is easy to respond to...but unfortunately the answer will probably be no - especially if it requires scheduling time in someone’s day they don’t even have for themselves. And instead of asking someone if you can “pick their brain” (i.e. extract years of their time and expertise for free) what if instead you simply “asked for their advice” to a very specific challenge?

Furthermore, no matter how brilliant your questions are (or how smart you think they make you look), if they aren’t easy to answer in 2 minutes or less, you’ll once again be filed to the “Someday” pile at best.

Here’s an example of how NOT to ask questions in your cold outreach:

Every single one of these is a great question...and each is a wonderful topic of conversation over lunch or a meet-and-greet phone call. And doing a good job of answering every single one of these questions would take FOR. EV. ER.

The fix: Make your ‘ask’ as simple as possible. Don’t ask more than one or two simple questions (you can always follow up and go into more detail later). Once again, the objective of your first cold outreach message is not to land a job or mentorship or lunch meeting. Your objective is to begin the conversation and earn a response.

It really is that simple.

Step Outside Your Networking Comfort Zone

I say this with zero hyperbole: Your career depends on your ability to write compelling and engaging cold emails.

I get that as an introvert putting yourself out there to people you admire and want to work with is terrifying. But if you’re tired of showing up to networking events and walking away empty-handed because you didn’t meet anyone new, or the people you did meet frankly can’t help you, then cold outreach is the most important soft skill you must master if you’re seeking advice about the next steps in your career, you’re looking for mentorship, or you’ve identified a potential dream project you’d love to be a part of.

Plus you can do it from home in your pajamas.

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