What Not To Do in Cold Outreach

Cold outreach has been one of my favorite parts of sales for a very long time. I think it is in large part because I enjoy writing. I majored in English and Creative Writing in college and my friends used to joke that I would never find a job. Joke’s on them (I guess) because writing is still a pretty large focus of my day job in tech sales. 

For a very long time, I have been preaching the idea of “shared values” in cold outreach. The idea behind shared values is that you need to link something personal you share in common with your potential buyer. It could be a shared appreciation for a specific mentorship program or even something as simple as attending the same alma mater. My argument behind this was that evolutionary biology suggests that human beings are tribal and feel safer amongst people who are similar to them in some way.

When I wrote my book “Authentic Selling: How to Use the Principles of Sales in Everyday Life” nearly five years ago, I dedicated an entire chapter to my cold outreach philosophy. This chapter was called “Weirder Than Waldo,” because it preached the idea of standing out from the crowd in order to capture peoples’ attention. A cold e-mail course by the same title followed, and I was routinely asked by major sales programs and communities to give talks about this outreach philosophy.

As AI has infiltrated the sales world, the need for shared values in cold outreach has only deepened. That is because personalization has become commoditized by AI. It is now very simple for AI to find something specific about a person as a means of making them feel that the outreach was tailored to them. I very consistently receive emails saying something like, “I saw you went to Princeton. I hear their reunions are really fun. Now let me tell you about this product I am selling you.” Never mind that the opening sequence about me has absolutely nothing to do with the segue and ensuing introduction of the product, but when dozens of sellers are using the same hook, all that is really happening is that what I consider to be “spam” just looks different than it used to.

What AI cannot do is liken itself to the other person. And that is because AI does not have a soul (or shared experiences with the buyer). And so the influx of AI SDRs has only done one thing: it has proven me right and it has made authentic, human connection even more valuable in cold outreach.

This leads me to what you should not do in your cold outreach. First and foremost, don’t do what I mentioned above – lead off with a corny observation about the buyer only to ditch it and segue into your sales pitch. If you are going to use a corny opener, at least make it relevant to your sales pitch. Failure to do so just feels gimmicky. Why mention something about someone for the hell of it? Buyers are smart enough to know most emails are automated now, so the personalization is no longer useful. The personalization now needs to be relevant. I once received a cold e-mail where the observation was that I knew how to speak French. Of course, my knowing the French language had absolutely nothing to do with why I should consider the product being sold to me. All this does is leave the buyer thinking that your outreach is at worst distasteful and at best not very thoughtful. 

Here is another thing you should not do: don’t lie. A client of mine recently forwarded me cold e-mails that one of our competitors has been sending them. I was appalled to see how bad the outreach was because this particular competitor is backed by some of the biggest investors in Silicon Valley. So, what is it that they are doing?

They are having the CEO pretend to email the SDRs on the team asking them to reach out to XYZ person at a company because they are a very appealing target for a very special partnership. Never mind that the CEO should reach out himself if XYZ target is actually very interesting and worth his time. The SDR forwards the “email” from the CEO to the prospect saying that the CEO asked them to reach out to such a special prospective client. The entire scheme is contrived. What’s more is that a used car salesman tactic is applied: “Let us know if you want to be one of the first partners for this program, otherwise we will offer your spot to a competitor.” I am not making this up. I think it goes without saying why people should not do this, but in case it is not clear, when you are obviously lying to people as your first impression, you are centering your interactions around deception. The prospect immediately feels that doing business with you will lead to sneakiness and uncomfortable interactions. People still do this stuff, and yes, they somehow receive large injections of capital to do more of it. 

To that end, anything that feels sneaky in nature is unlikely to yield a positive response. If you forward a thread to make it appear like it was an internal email the person should read or use some gimmicky subject line like “emergency” that forces someone to open a message, they will generally not be too happy to figure out what is really going on once they put two and two together. The same is true of spoofing someone’s local area code when attempting to call them. Not to sound like a curmudgeon, but on principle, I will never agree to a meeting with anyone who spoofs my local area code, which is referred to as “neighbor spoofing.” For one thing, I literally worked for 7.5 years at a software company that prevented this illegal behavior for top tier banks. It is deceptive and it is illegal – just not enforced to the degree where salespeople will actually stop doing it. If on principle you need to start your relationship with someone by tricking them, then you should think again about the nature in which you are conducting yourself. There have been times where I have been dealing with sensitive personal situations and received a call from a local area code only to find out that it is yet another recruiter in the UK trying to see whether or not I have staffing needs. 

I think there is also a certain level of basic thoughtfulness that should go behind outreach. For example, when we run sequences, we try to be mindful that there might be overlap between personas in different campaigns. This means we need to spend manual time and effort ensuring we are not spamming the same people over and over again with different campaigns. The same is true for people who are doing automated outreach over LinkedIn. There is nothing more annoying than receiving a connection request followed by an immediate sales pitch, where the cadence is something like every few hours or every day, including weekends and holidays. When it is Christmas morning and you open your phone to a bunch of sales pitches, you know immediately that the other person is not actually writing the message. It does not take a lot of time and effort to clean up these campaigns and sequences. If you are on the receiving end of laziness, chances are you will feel that you are not so inclined to want to do business with someone who is lazy. 

There is one last thing I would say, and it kind of goes against the grain of what many thought leaders would teach. I think lacking self-awareness can be detrimental in cold outreach. You would never walk down the street and interrupt a stranger’s day to ask them something you needed help with without apologizing first or acknowledging that you were interrupting their day. Why is cold outreach any different? You are still interrupting someone’s day, albeit digitally. I’m not suggesting you lead off with an apology – that would be weird. But I do believe it is OK to neg yourself and let them know you understand if they are not interested. I actually think this shows them that this is not life or death for you and that they do not need to feel threatened by saying “yes” to you. I realize many sales gurus would say you need to assume the sale and not apologize for asking for someone’s time, but I think being presumptuous about an outcome – like literally ending the email by asking about meeting at a specific time – subconsciously makes the other person feel a certain way about you that may not ultimately be fair.

If I were to synthesize all the feedback, it would be pretty straightforward: be an honest version of yourself. Too many times I see people resorting to tricks and gimmicks that I doubt they would pull with friends or family members at home in their personal lives. When in doubt, ask yourself a simple question: would I treat my closest friends this way? If the answer is “yes,” you might be in business.