All Things Sales

As automation technology advances, our ability to scale ourselves also improves. The innovations in email, SMS, and even chatbot automation have made it way easier to do with a small team what used to require a very large team to accomplish.

I’ve put together a list of 5 things that will help you start to scale yourself more effectively into automation technology. This is by no means an exhaustive list, and some of these will be familiar to you already in some form or another, but I suspect a few of these will excite your creativity a bit.


1. One-To-Many (One-To-One)

One of the biggest mistakes you can make when automating your sales messages is buying too much into the concept of “one-to-many” selling. One-to-many sales is often misconstrued to seem like one person standing in front of a group of people shouting a message to all of them. All that does is water down the message and encourage people to ignore you.

One-to-many sales is supposed to be more like that one person being cloned and having individual conversations with everyone in the room. That’s where the technology comes in (since we haven’t figured out human cloning…yet).

So when you’re crafting your sales message, approach it less like crafting a speech and more like writing a text to a friend. Sales is just a conversation between two people, and the more that other person feels like you’re talking to them and them only, the more likely they are to trust you (and buy from you).

2. Email Formatting

When was the last time you used a section header when you sent an email to your mother? (Maybe the question should be, “When was the last time you sent an email to your mom?”)

How about numbering? Bullet points? A background color? Logo?

When was the last time you formatted a link to a friend so it read “click here”?

Some of us are prone to using certain formatting very often. I, for example, am a prolific italics and bold user. I write the way that I speak, and I’m very particular about the words that get emphasis. In some situations, I’ll even use numbering or bullet points to drive my point home. These are much less common than bold or italics.

When crafting sales messages, you can go a long way to making everything seem more real by removing most of the extraneous formatting. Get rid of header images and logos, make the whole email left-justified with a completely white background. And in some cases, forget the fancy link formatting and just drop the whole, ugly link right into the email.

If you really want to master true one-to-many selling, you have to construct everything as though you were writing to your mother.

Now we get into some more tactical stuff. Some of these things you may have seen before, some of them probably not. Remember, these ideas are meant to enhance your sales messages, not necessarily replace them. Use these sparingly.

3. Fake Forward

This works every time. And the people that it doesn’t work on nearly always appreciate what you’ve done and comment on it.

The concept is fairly simple. When you send an email to someone, and then they don’t respond after a couple of days, what do you do? Normally, you’ll open up Gmail, go to the original thread, and compose a message to the original recipient that looks something like this:

Hey Bill,

Did you see my message below? There’s a great deal on widgets going and I don’t want you to miss it!


Gmail then takes that message and attaches it to the same thread in the recipient’s inbox. The cool thing is how easy it is to trick Gmail into doing the same thing with an automated set of emails:

All that Gmail is looking for is a matching subject line. So if you send an automated sales message, and then 3 days later send the exact same message, but add “FWD:” to the beginning of the subject line, Gmail will attach the second message to the same thread as the first one.

Now for the fun part:

Any modifications to the original text of the message will show up in the new message. So if you take your original message and add the “FWD:” to the subject line, you can add a message to the top of the original one that will look like you were “just checking in”. You can even add personal signature lines that will make it even more convincing, like:

“Sent from my iPhone.”


“Blame Siri for any typos.”

Pretty fancy, no?

4. Double Fake Forward

My favorite way to take the fake forward one step further, is to create the implication of an internal conversation that the prospect is then “brought in on”. The way you do that is by constructing a whole conversation between yourself and another staff member (who should be a real person but technically doesn’t have to be).

So it goes like this (this is a fitness business example):

  1. Prospect opts in for free workout video series, and is then given a call to action to come in for a free PT session (the CTA can be anything).
  2. Prospect doesn’t schedule PT for a certain number of days.
  3. Prospect is sent the following “bribe” email.


Subject: FWD: RE: FWD: Notification: Bill Withers requested the video series

Hey Bill,

Check out what I was able to score for you!

———- Forwarded message ———-
From: Joe Johnson <>
Subject: RE: FWD: Notification: Bill Withers requested the video series
To: <>

Sure man, we just got a brand new shipment of the new protein bars, he can have a box if he comes in for the PT.


From: John Robertson <>
Subject: FWD: Notification: Bill Withers requested the video series
To: <>

Hey JJ,

I’ve been back and forth with this guy. He’d be a great fit for the gym, is there anything I can offer him to get him down here?


———- Forwarded message ———-
From: No Reply <>
Subject: Notification: Bill Withers requested the video series
To: <>

Hey John!

Bill Withers requested the video series.



It works like a charm, but you can’t overdo it. It needs to be natural and real, like you’ve actually had that conversation internally and then you have to actually fulfill on it.

5. Manychat “Mistake”

The ability to automate messages through social chat media is an incredible innovation. I personally believe it will soon lose its luster and become not unlike email is now, but that’s a conversation for another day.

For now, it’s an incredible tool that allows you to engage your customers a bit more directly. It also gives you a uniquely amazing opportunity. Let me explain:

Sometimes you don’t need to design grand schemes to convince your prospects to trust you (see #4 above). Sometimes you just need to employ simple techniques that will gently nudge the subconscious mind into accepting that it’s a real person they are speaking to.

All you have to do to accomplish this is convince the prospect that they aren’t interacting with a bot. In their mind, it’s either a bot or it’s a real person. So if you can convince them that it’s not a bot, you’ve done your job.

So how do you convince someone that they’re not communicating with a bot?

You just have to do what they don’t think a bot would ever do, like make a spelling mistake, for example.

You’ll want to call attention to the spelling mistake, however, so I like to do what I would do if I was actually the one writing, which is immediately fix the mistake. So it looks a bit like this:

Building the “typing” notification just seals the deal.

Remember, we’re not trying to beat a Turing test, we just need the prospect to think they’re talking to a real person, because they’re much more likely to open up and make a buying decision if they believe that’s the case.

EPILOGUE: There are a lot of ways you can scale your personality to make your sales more effective. The key is to create an experience that is both believable and beneficial to the prospect. If you go overboard with any of these things, it will come back to haunt you. If you try to use all of these techniques on all of your prospects, it will come back to haunt you.

These things are like salt – you don’t have to use them at all, but if you use them right, it really enhances the food you’re cooking. Use it too much, and it kills everything you’re trying to accomplish.

At the end of the day, sales is simply a conversation between two people, and everything we do to scale it needs to protect the integrity of that one on one conversation.