It’s hard to appreciate just how horrible most prospecting emails are until they start pouring into your own inbox.

For many years, as a professional copywriter, I’ve been writing emails by the truck load. And I was also using outbound email as a way to prospect for new clients.

But it’s only more recently that I’ve been developing my own business to the point where I am now on the receiving end of prospecting emails from other people.

Oh, the horror!

Before we get into finding the right voice for these emails, let’s see just how easy it is to get them wrong.

Too long!

Hey, we’re strangers. Don’t send me a 500-word prospecting emails. No way I have time to read it.

Why would I? I don’t know you, and I have trouble enough finding the time to read and answer emails from people I already know and work with.

Too familiar!

I’m not your buddy. I’m not your friend. I might be, one day. But not at first contact. So don’t write to me like I am.

Be real. You’re a stranger trying to connect with me for the first time. Write accordingly.

I’m not saying you have to be super-serious, or that you can’t be a little playful or lighthearted. Just don’t assume a level of friendship that doesn’t exist yet. That can be really off-putting.

Too generic!

Been using that pack of handy templates again?

I’m not against using a quality template to get the ball rolling. But I’d always recommend you make some edits, so your email feels fresh and unique.

Think about. If your email uses the exact same structure and language as two other emails I received this week… guess what… I’m not going to be impressed.

OK… now let’s look at those three ways to be a little more conversational in your writing tone.

It can really help if you picture your email as being the first step in an ongoing conversation.

Why? Because it is. At least, you hope it is.

You write that first email. She writes back, showing a tentative level of interest. You then follow up. And so on.

At some point, if you don’t drop the ball, your email exchange will escalate into a phone call and then, perhaps, a face-to-face meeting.

So yes, your email is the start of a conversation.

Here are three ways to make that a BETTER conversation.

1: Open by showing interest and genuine empathy.

Again, think of the conversation analogy.

Imagine you’re at a party, and someone comes up and just talks AT you, as if they’re the most interesting person in the world.

They clearly aren’t interested in you, they’re just interested in themselves.

Don’t be that guy.

Make it clear from the first line that it’s the reader you’re interested in.

That means holding your tongue and not talking about yourself or how wonderful you are.

It also means doing a little homework.

You have to do your own math and figure out the potential value of that prospect, and how much time you should put into researching that individual and her business.

A high potential value means you really should put in the time to find out about her as an individual. Start with LinkedIn.

If it’s going to be more of a bulk email, at least research the industry.

And maybe open with a reference to a recent item in the news or business press that might impact their business.

Do that and you’re opening in a way that is empathetic to their situation. It’s about them and not about you.

You can send this same email out to an unlimited number of people in the same industry, and they’ll feel you are writing to them personally.

2: Ask an open-ended question that isn’t self serving

There is a huge temptation to use a first contact email as a way to broadcast the value of the services you offer. Immediately.

I get that. Yes, it’s tempting. But again, it’s a terrible way to open a conversation with a stranger.

Instead, ask a question.

With tip #1 I suggested opening with an observation about something in the news.

If you do that, or something like it, you could follow up with a question like, “Have you given any thought as to how this might impact your business?”

And there lies the engine of your email.

Ask the question, show that you have a shared interest, and give her a reason to write back with an answer to that question.

No, you haven’t closed the sale or set a meeting. But you have started a conversation that could, in time, take you all the way.

3: Be different.

This is the main reason I stop reading prospecting emails.

As soon as I recognize the language or structure of “yet another pitch email”, I stop reading and delete the email.

Your challenge is to make sure you write something that never triggers that kind of response.

Find a way to make your opening sentence and paragraph different. (Again, see #1 above.)

And look for other ways to make your email jump out from the crowd. (And yes, that could include a personalized image!)

4: Read your email out loud before you send it.

I know, I promised three ways. But I couldn’t not include this one.

Once you’re done, take the text of the email you plan to send and read it out loud. Preferably to someone in your office, or even at home.

Look them in the eyes as you read it.

This can be totally embarrassing.

You might even think, “Ouch, I sound like a total sleaze!”

Well, it’s better to come to that realization before you hit the send button.

If it doesn’t feel right while you’re reading it, or if the other person laughs, snorts or just walks away… go back and try again.

The best way I can think of to encapsulate everything I’m sharing in this post is to say…

Always imagine that first email is the start of a conversation with a real person. And it’s a conversation you really, really want to last for a very long time.

Nick Usborne has been working as a copywriter and trainer for over 35 years. His book, Net Words, published by McGraw-Hill in 2001, paved the way for a new generation of online writers and copywriters. Nick is the founder of Conversational Copywriting.