It is SHOCKING how many cold outbound sales emails I get that are just… bad!

I have no doubt it’s the same for you.

Now, I’m not talking about the hundreds of sales emails that hit the Promotions or Social tabs or even all those emails that hit the spam folder. I’m talking about those one-off cold outbound emails that sneak their way through all the defenses and make it into the inbox.

If you write and send out outbound emails, you’re most likely struggling to get very many responses. It’s not an easy thing to do.

I can’t promise you any quick fixes, but what I can do is tell you exactly what to avoid… at least if you’re emailing me.

Why is outbound so easy to get wrong!

Outbound isn’t easy, but it also doesn’t have to be hard. It’s pretty basic stuff, and it all revolves around one core principle: Patience!

Outbound email is at the very top of the sales funnel. You’re not going to go from an unknown to a closed contract in one email exchange. It’s just not going to happen, at least, not with any regularity.

You wouldn’t expect to see a pretty girl/boy across the way, walk up to them, introduce yourself, and before they say a word, you ask them to go home with you.

Or, maybe you would, but in that case… yuck.

Ewww... go away with your outbound email

If you wouldn’t do it in person, why do it through email?

No reasonable person would expect to build a meaningful exchange by starting off that obtuse and aggressive.

Unfortunately, it seems most of us lose a grasp on reality with our emails and we go for the close with our first hello. It’s no wonder that only 16% of marketers say outbound practices provide any quality leads for sales (Source:

Most of us are doing it completely wrong.

Here is EVERYTHING you should stop doing, immediately!

1.) It’s not about you

Oh, the number of emails that start of with the word “I” is painful. With the very first letter, you’ve made the email about you and not me.

Granted, “I” isn’t bad by itself. It can actually be very valuable.

“I” can give context on who you are, why you’re emailing me, and how you got my email address, such as:

“I really like your post on Linkedin…”
“I was recently shopping in your store…”
“I came across your name through…”

The vast majority of the time though, “I” is used more like this:

“I wanted to…”
“I would like…”
“I was hoping…”

I don’t know you. I don’t care about you. I sure as heck could care less about what you want.

In your first three words, you’ve made it clear your email is about you and what you want. You’re trying to sell me something for your bottom line and any value to me is secondary.

Your outbound email is not about you

This is how you come across. I promise.

It doesn’t matter what’s in the rest of your email. It’s about you, not me. With your first word you’re an instant


What to do instead:

Provide context. Why are you emailing me? And no, your need is not the reason. If that’s the best you can come up with, then stop wasting your and my time.

There has to be real value for me, if there’s not, then all you’re really trying to do is trick me and rip me off.

Who are you? Why are you emailing me (what’s in it for me)? How did you get into my inbox?

2.) Don’t be wishy washy, don’t waste my time

“I hope this email finds you well…”
“I hope I’m not bothering you…”
“I’m sorry to trouble you…”
“I know you’re busy…”

Ugh. There’s being polite, and then there’s being weak.

be confident in your outbound email

When you apologize for introducing yourself, what else am I to think?

First off, yes, matter of fact, you are a trouble and unsolicited sales emails do bother me.

Second, If you’re going to sell me something, if you’re going to be of any value to me, you need to be confident in what you’re doing.

“I hope” and “I’m sorry” is starting off your email with an apology. It’s like a limp handshake. It’s a huge turnoff.

Besides, is what you have to offer me so weak that you need to apologize? Are you not going to be making my life better? Why would you apologize for that?

What to do instead:

Be confident. Don’t “hope.” KNOW that I need you and what you have to offer. If you’re not sure or confident in your value, then why on earth would I ever be?

3.) Who the heck are you and why are you emailing me?

Get to the point. I know this isn’t a personal love letter, it’s a business call, so let’s do it.

Again, I don’t know who you are, nor do I care about you, not yet. Give me a reason to and be quick about it.

Obviously, this one makes it a little tricky. You need to relate to me, not bore me by talking about yourself, get me interested, and make an ask before I quit reading.

What to do:

Be patient. You’re not going to close me in one email, so don’t go for the gold right away.

outbound emailing requires patience

Don’t give into the dark-side, have patience. Do the work!

A good trick to keep in mind – don’t try to sell me your product, your business, or even your overall value proposition on your first email. Sell me on having a conversation. Get me talking about myself.

You do that, you get a reply from me, then you have a conversation to work with.

Let’s put it this way. If you can’t get a simple conversation going, you’re definitely not going to get my trust enough to close me.

4.) Don’t BS me.

You might think you’re slick, but it doesn’t matter what box you put it in, BS smells and it’s easy to sniff out.

Flattery, unless it’s genuine, is the quickest way to get on my BS list.

your outbound email stinks

Regardless of how it’s packaged, you can smell it a mile away.

Complimenting when done right is great. These are not:

“Your company’s reputation precedes you…”
“It’s clear your team is talented….”
“Your business is ________ “
“Our clients rave about you…”

Best case scenario, I’ll ignore it. Worst case scenario, I’ll call you out on it and you’ll either have to fess up or double-down. Either way, you just killed any chance of credibility with me.

Unless you have an honest compliment, don’t do it. No one likes a suck up.

5.) Seriously, stop the BS

Of course, you’re going to make me money, increase my revenue and save me time. That’s a no-brainer.

“I’d like to connect with you to increase your profits…”
“We can help your business…”
“…save you and your business time…”

Honestly, I’m not receiving emails from the other guys saying they’ll lower my profits, lose me sales, and waste my time.

It’s the same as recounting your day. You don’t need to tell me that you woke up. It’s a given. Stop wasting my time with dribble.

Your stating the obvious in your outbound sales email

Glad you’re not emailing me to waste my time and lose me money.

It’s not a selling point. All it communicates to me is you either have no value, or you don’t understand the value you have to offer me.

Either way, you made it clear you’re a waste of my time.

What to do instead:

If you’ve going to offer a value, make it specific to me and the unique obstacles I face. Unless you’re a pro at your research and know exactly how to hit me with your first hello, it’s best to ask discovery questions before pitching me your value.

Get to know me so you know how to help me.

6.) Stop asking stupid questions

Asking questions is ABSOLUTELY what you should be doing in your initial outreach.

However, asking leading questions is a dangerous game that almost everyone seems to fail at when attempting.

“Would you agree that…”
“Are you happy with______, or would you like more ________…”

When you ask leading questions, you’re at risk of annoying and offending your reader.

One, if they’re rhetorical questions, then the answer should be obvious. If the answer is obvious, then I get the distinct impression you’re treating me like an “idiot.” Not really your best approach.

Your outbound email has stupid questions

^ what this says ^

Give me some respect.

Two, if the questions are obviously leading to your pitch, I’m not going to be happy with being lead into a corner. When you’re lazy and obviously trying to trick me, I’m going to zig and zag around your attempt.

You won’t corner me.

That’s not to say rhetorical and leading questions don’t have a place. They do, when done tactfully.

This method that takes a considerable amount of skill to pull off effectively. If you’re struggling with your outbound emails, it’s best to stay away from these and ask simple, honest discovery questions.

Why waste your time with leading questions when there are so many valuable and helpful questions you could be asking?

7.) YOU are emailing me, not your business. Drop the we stuff.

You’re not an automated system. You’re not a collective. There isn’t a group of you sitting at the keyboard typing out your email.

You’re a person. So am I. Be personable.

If it’s hard enough to get me to engage with just you. You can bet I definitely don’t want to talk to a we or us.

Try this:

Read your email out loud to another person in a public setting before sending it to me. Did you sound like a representative fool?

Re-write and try again.

8.) Stop assuming you know better than me

It really irks me when you send me an email telling me about my business and my needs.

“… businesses just like yours…”
“… as you know, you need…”
“…we can help your business…”

Even if you know, you should know, you don’t. You don’t because you don’t know me. Get to know me first, then you can apply your knowledge and pitch me your solution.

Never assume to know someone’s problem without asking them. It’s unbelievably rude, and I’m easily offended.

your outbound email is assuming too much

If we’ve never talked, how could you possibly know how to help me?

It’s also not a trust building factor if you’re right, it’s an intimidation. When you tell me my problem without getting to know me, I get the distinct impression that you either are, or you think you are, smarter than me.

I don’t like that. It puts me on the defensive, you know-it-all!

What to do instead:

Ask questions that will lead me to my own discovery. When you ask insightful questions, you become helpful. When you become helpful, you become trustworthy.

If you’re really that smart, you don’t need to throw it in my face, I’ll recognize it on my own.

9.) Leave your laundry list to yourself

Don’t list out your services. Not now. It’s too soon.

I didn’t ask you to email me. I’ve expressed no interest. I have no clue who you are. Now is not the time to vomit your product or service listings.

Sending me a long list of your company’s services scream that you don’t know the first thing about me.

How so? Because you just sent me a laundry list of items that do not apply to me. Sure, maybe one or two do. But, that makes my point. You just threw a bunch of spaghetti at the wall hoping that something stuck.

It’s lazy on your part and work on mine.

What to do instead:

At this point, you should know more about me than I do you, so make your content relevant to me. Forget the list and hit on the one or two things you know matter to me.

10.) Don’t make me do the work.

No, I don’t want to read your case studies, download a pdf, or follow a link to some long article.

Why not? Again… I DON’T KNOW YOU! I’m not going to spend my precious time learning about you to discover if I should let you sell to me.

“I would like to send few of our…”
“You can download…”
“Click here to see our…”

Wait to develop a context before you “suggest” a resource I may be interested in. I don’t accept fliers from strangers when walking down the street and I won’t do so online either.

What to do instead:

Your goal with the first email is engagement. Once I’ve replied and there is a context for it, then you can offer a resource that will be helpful and progress our interaction closer to our mutually beneficial end goal.

11.) Stop trying to “get”

The laziest of them all.

If your outbound email has the word “get” you’re doing everything wrong.

“I was hoping to get…”
“… can I get…”
“…I would like to get…”

Why on earth would I give you anything? You haven’t earned it.

What to do instead:

Give to me, stop trying to get. If what you give me is valuable, I promise, I will reciprocate. It’s a law that I do.

12.) The phone is just as valuable as my time and I don’t spend it on fools

I don’t think I’ve ever received an outbound email that didn’t ask me to schedule a meeting or call. It comes through in a variety of ways, but the ask is ALWAYS there.

“Are you available for a quick call?”

This is WAY too soon to go for the close.

Despite being the completely wrong CTA for this stage of the buyer’s journey, there are three major red flags about getting this ask in email one.

If you don’t know what that the buyer’s journey is, then stop emailing now and don’t start again until you do.

Learn what a buyer’s journey is all about.

One, you know absolutely NOTHING about me. You’re outbounding someone that can very well be 100% a waste of your time, and you have the availability to be on a call?

How desperate are you? Who has the time for that unless you’re scraping the bottom of the barrel?

I get the point of outbound, but don’t you have better things to do than spend hours on the phone with a never going to happen “lead.”

Two, you KNOW NOTHING ABOUT ME. Honestly, I don’t care about your time, even though it raises a red flag.

What really turns me off is, why are you trying to waste my time? Can’t you slow down and try to qualify me to see if it’s even worth my time to call you?

I get it, maybe a call is more efficient for you, but it’s not for me. I wasn’t even looking for you, so how are you all the sudden worth my time on top of my already busy schedule?

Third, realize, my time is more valuable than my money. When you ask me to give you a call, you’re asking me to GIVE YOU $50, $100, $200 just because you emailed me.

I promise you, this is my response EVERY SINGLE TIME!

No no no bad outbound email

This. I promise. This is my response.

What to do instead:

Respect your time and mine. Ask questions to qualify me. Discover if I’m even in your market and could benefit or afford your solution. Find out what my specific needs are so the call, if we have one, can be more beneficial and efficient.

Without any exploration before a call, I know all you’re going to do is go through a script, which will be long-winded, or you’re going to “wing it.” Either way, both are a waste of my time.

Do some prep work. Warm me up before going for it.

Also, make it easy for me. Don’t ask questions that will require me to write an essay response.

No Time For That Outbound Email

Give me a reason, and do the work on your end. I’m busy and disinterested.

13.) You’re giving up too soon

I’m a little sadistic with outbounders. The really bad ones, I’ll try to “educate” by playing along. I’ll give them buying indicators that position them to make the right moves. They never do.

you're giving up to soon with your outbound emails

Yes, I will mess with you if you make these rookie mistakes.

Other times, I’ll ignore their first attempt and see how persistent they are. Not surprisingly, they all give up way too soon. Most of them only email me once. Some only twice.

Not one of them has emailed me past 5x’s. That’s still too soon. On average, 30% of leads come from email 6 – 8!

Just by the numbers, if you’re calling it quits before email 6, you’re losing 30% of your sales simply because you gave up too soon.

14.) Your breakup email is insulting

It doesn’t matter if it’s your 3rd email or your 12th. Telling me that you’ll no longer be emailing me because I haven’t responded oozes desperation.

You won't guilt me into responding to your outbound email

Did it work with your high school boy/girlfriend? No? Then why do you think it will work on me?

What’s insulting about desperation? It’s a guilt trick.

You’re not really closing the door on me. I know you’re not because you’ve still included your CTA. All you’re really doing is letting me know you’ve done your part. You’re shining a light on how hard you’ve worked trying to get my attention, and dirty old me couldn’t take the time to reply.

Seriously, did you break-up with your girl/boyfriend, who never even actually knew your name, in highschool the same way? How’d that go over?

15.) Always assume I’m not interested.

It’s your job to get me interested. That’s the entire point of your email, is it not?

If you’ve done your job, and you’re not shotgunning your outbound emails in a “spray and pray” approach, then you should have a high expectation of getting me interested.

16.) Always assume I’m too busy.

It’s your job to show me the value – it’s called selling. You need to get me interested so that I want to spend my time.

Your outbound email should get me interested

I start off not caring. If you waste my time, I will continue not to care.

Get to the point. Make it easy for me. Clearly define the next step and take control. Don’t leave anything open-ended.

17.) Don’t remind me I’ve ignored you

Always assume I’ve seen your emails, but never acknowledge that you’ve sent me an email until I respond.

If by chance, I do open email #4 and the first thing you do is mention you’ve emailed me before, I’m no longer paying attention to what you said.

I’m now thinking:

  • “When did you email me? I don’t remember that.”
  • “Oh yeah, I remember… I also remember why I ignored you.”
  • “You did. Was there something important in that email? What am I missing? I don’t have time for this.”

There is no benefit in drawing my attention to the fact I’ve already made a decision in the past that you were not worth my time. All you’ll do is predispose me to arrive at the same decision again.

18.) Do your homework.

This is in the top three! Man, I hate it when you email me expecting me to do your work for you.

“I’d like to speak with someone from [company] who is responsible for…”
“Could you please refer me to the person in charge of…”
“Would you be so kind as to tell me who is responsible for…”

This one actually gets a visceral response from me every time.

Outbound emails are infuriating

If I could destroy your communication device, I would.

If you’re too lazy to find out who you should be talking to, don’t ask me to pawn you off on my co-worker or boss. Your crappy email will reflect on me, and so far, I don’t like you myself – I almost already hate you.

If my company and all the employees are easily identifiable on my website, linkedin or any other easily accessible public tool, then there is no reason you should be making this request.

If you really need to ask me to pass you on, you need to try to win me to your side and become an advocate. You do that, then I’ll HELP you sell!

What to do instead:

If there is honestly no way to know and all signs point to me being your best point of contact, then assume I’m the correct person. I’ll let you know if you’re wrong, in which case you can politely ask for a referral.

Chances are, I’ll point you in the right direction or forward your email to the right person without you even having to ask.

19.) Don’t be lazy.

Re-read your email a few times before sending it. Fix the typos. Fix the grammar. Remove the fluff.

Don't be lazy when outbounding

I will match and exceed your laziness.

My time is precious. Sending me an email full of errors tells me you didn’t take the time to proofread. If you’re too lazy to read your own email, you can bet I’ll match and exceed your laziness.

21.) Stop referring to your offer as a relationship or partnership.

Those both require work, neither of which I’m inclined to do for you. I’m not your friend. I’m not your partner. You are nobody to me.

If you really feel the need to “define” our relationship, then consider yourself my waiter. You’re here to help me and make my life easier, no? Then don’t approach me with a de facto quid pro quo obligation.

relationships are work stop emailing me to start one

Relationship? I have enough. I don’t need more. Needy, clingy much?

21.) Never copy & paste

If I didn’t respond to your first email, don’t you dare copy and paste then resend the exact same email.

Always assume that I’ve seen your previous emails and they weren’t good enough. Try again.

Even if I haven’t seen your previous emails, if your next email does get an open, I’ll most likely see your previous emails stacked above them – if they’re all the same, I’ll just get annoyed. You instantly lose face and all I see is a lazy person trying to get my attention.

I’ll probably never get rid of you if I respond now, so there’s no way you’re going get a reply from me.

22.) And please, show some passion.

Not a big one, but it is annoying and weak. If you’re going to be of any value to me, take charge

“Feel free to email me…”
“If you would like…”
“I’m here if you need…”

If you’re not excited about what you can do for me if you don’t care that I’m going to do worse without you, then how will I ever get to those conclusions on my own.

When you put the ball in my court to continue or kill this interaction, I’m going to squash it. You’re making me work and I’m already busy enough.

If you don’t care, then neither will I.

Lead, lead well, and I’ll follow.

What to do instead:

Tell me what you’re going to do or what I’m able to do next. Make it clear what is going to happen next and why.

Tell me what you’re going to do next, or construct your email in a manner that my next steps are obvious. Such as, ask a direct and specific question that I can easily answer – prompting an interaction.

What you should be doing with your outbound emails instead

Be a human being

I know you have a job to do. So do I. But why does that mean either of us has to put on a charade? Talk to me like we just met outside.

Be honest

It’s okay to make your intentions clear. It’s actually refreshing and it makes you more trustworthy. I hate being sold, and I hate being tricked. However, I do like knowing what I’m getting myself into.

Be inquisitive

Get to know me. Ask me questions. Get to know me. I like talking about myself, and I like it when people want to get to know me – even if it throws me off for a minute – that’s why being honest and letting your intentions be known is so important.

Act as if

Act as if you wanted to be with me. Act as if you were trying to get to know me because you were interested in me.

Act as if you were making your first approach after I caught your eye. Don’t try to sell me, try to date me.