I believe the following are true:
- You know yourself very well.
- You trust yourself.
- You hopefully trust your choices.
- And you probably go about your day trying to avoid bad decisions.
Do you agree? If so, you’re the perfect test subject to determine whether the cold outreach via email, phone, or direct message you’re about to send will land with your subject.
Now that you know that about yourself, here’s my request for 2026:
Before you send that message, ask yourself, “Would I respond to this?”
But before you ask that question, put yourself in the message recipient’s position:
- You do not know who this email is from.
- Your attention is elsewhere, and your mind is probably not on the subject of this outreach.
- You are likely programmed not to trust emails from people you do not know.
Please review the message you just wrote. Would you respond to it? If the answer is no, or you’re not sure (another version of no), then I don’t need to tell you what to do. That’s because you go about your day trying to avoid bad decisions (see fourth bullet point at top).
Products are still sold and purchased, and babies are still being born
Have you ever approached someone you were interested in and provided a bulleted list of why they should go out with you?
No, you haven’t (again, see bullet #4). But the real reason is you know that tactic would fail. And if someone did it to you, you’d run away.
That “too much too soon” style of outreach is something we see every day. We’ve shown it doesn’t work for dating, and it rarely works in business. But it keeps happening in business because most are OK with a 0.2% response rate. It might annoy thousands, but it’s worth reaching the handful who will accept.
So if we don’t use a spray-and-pray approach in dating, how are people still meeting, going out, getting married, and having babies?
They start with “Hello” or a similar greeting to elicit a response. And that’s what should be happening in sales. What’s the minimum needed to get a response? If you get a response, then build on it. Start asking questions. Show genuine interest in the other person. No false flattery. We do this in dating. Why can’t we do this in our professional lives? In dating, we try to make the other person feel physically attractive. In business relationships, why not make your sales target feel professionally attractive?
This is the philosophy behind a program I run for SKOs (sales kickoffs) called “Business Networking Pickup Lines.” It’s a fun in-person workshop where participants stand up and practice 30-60-second exercises in “business flirting.” Take a look at this video (and read the reviews).
Business Networking Pickup Lines
CISOs are people just like you
Why should sales be any different than how we engage in real life? Security professionals are people just like you. Just because you reach the title of CISO doesn’t mean you all of a sudden have a rigorous by-the-book style of decision-making. They’re humans, and they respond positively and negatively to outreach in the same way that you do.
Before you send that long, cold email or send that awkward, very involved DM, ask yourself, “What would I respond positively to and would I like the message I’m about to send?”