How To Humanize Your Outreach Messages And (Actually) Connect With Prospects.

There are no silver bullets or magic techniques in business—but this comes close. One of the primary reasons most cold outreach fails is because the sender never forms a relationship with the recipient. They do everything except optimize for connectivity. They might spend hours researching a company, but when they send their message it lands in such a way that it feels totally hollow and contrived. Rather than speaking with a prospect they speak at a prospect. This might sound incredibly obvious when it’s written out this way, but 99% of businesses fall for this trap. Instead of actually connecting with people using emotions and communication, they try to connect using logic and a de-personalized business case.

As I’ve stated in other essays on this site, people buy with their heart and their head. Even the most detached, cold-blooded executives still make decisions on emotion. This is especially true in a direct outreach situation. Nothing kills more deals than failing to connect with your prospect.

Some salespeople and solopreneurs have intuitively grasped this, and tried to solve it. But what usually happens is that they end up trying to connect instead of actually connecting. They might personalize their cold emails or direct messages but it always ends up sounding trite and contrived because despite their good intentions they somehow still failed to connect.

Have you ever received a cold message or an email like that? The person has done their homework on you but it still falls completely flat? It’s because they have pretended to connect with you instead of actually connecting with you.

Here’s an example:

Hey James, love what you’re doing with MXW Group. I see that you’ve posted some essays on your website. Those are really well written by the way.

Why does this fail? Because the person looks like they’ve done their homework but all they’ve done is checked a personalization box. There is no emotion or connective tissue underneath this message and therefore it doesn’t resonate.

Here’s a more common example:

Hey James, love what you’re doing with MXW Group. I saw the essays you’ve written. I really liked the one about how to humanize your outreach messaging.

This is slightly better, but it fails for the same reason as the first message. There is no connective resonance or magnetism to the message. It’s just checking a box.

Now let’s make a subtle shift:

Hey James, we haven’t met yet. Loved your essays—especially the one on messaging. That’s something my company struggled with for a long time. Your writing reminds me of Alex Hormozi, has he influenced your work at all? Also, saw you’re in Montreal. One of my favorite cities, I lived near Frontenac metro, whereabouts are you?

Feel the difference? What changed? I shared things about myself and asked questions. I spoke like an actual person and therefore I became an actual person in the mind of the prospect. I call this The Riff Technique. Find something you can talk about (i.e. riff on) and then just start talking about it. The key is to make at least one heartfelt observation and then riff on it in (i.e talk about it) in a way that humanizes you. You might have also noticed that I stacked a few different observations together. This is Riff Stacking and allows you to further humanize yourself and lets the prospect take the conversation in a bunch of different way. You might worry that this approach is overwhelming, but I’ve found that usually prospects reply to the questions they found interesting and ignore the ones they found less relevant.

That’s literally all you have to.

Stop trying to connect with a person and actually give them handholds to connect onto. Think of yours message like the face of a cliff. At the top of the cliff is a summit with the desired action you want them to take. But If there’s nothing for your prospect to hold onto, they will never be able to grab the wall and they will bounce off.

Your goal is to open the message by giving them footholds and then naturally connecting your messaging back to the product your offer. Ideally your riffs are product related, but you can mix and match depending on the vibe.

One common question is: What do I do when a prospect doesn’t have anything worth commenting on? The more you practice, the more you will get a sense of what you can comment on, but in the absence of anything obvious, you can look them up on social media or LinkedIn and check out their background until you find something. Don’t be creepy or inappropriate, but keep searching until you find something.

To summarize this entire technique in one sentence: instead of trying to connect, you can actually connect with your prospect by sharing more about yourself in a way that connects with their business or something you observed about them. That’s the power of The Riff Technique. Once you master it, your reply rates will soar and you’ll stand out in a sea of same.