The Biggest Outbound Sales Mistakes Founders Make, Episode 1

“I never respond to spam. People that cold email me are lame. It’s just terrible. I would never respond to that. I don’t believe it’ll work for us.”

I can’t tell you how many times founders have said this to me when I suggest doing outbound email as a go-to-market tactic. The founder puts up his defenses and isn’t willing to try something because it hasn’t worked on them before. This might be the most flagrant of all mistakes founders make when devising their outbound sales strategy.

“I’m going to take the unique circumstances of my little world, and extrapolate that they would not work on the entire universe of all possible leads.”

That’s how ridiculous the thinking is if we’re to articulate it out loud. And despite that, I see it happen all the time.

In the last 8 years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. I’ve done my best to help. And in doing so, I’ve spotted patterns: those costly outbound sales mistakes that keep occurring, and that prevent startups from growing to their full potential. Over the next 10 episodes, we’ll examine each of these very closely: at the pace of one per week. Consider this your mini-series on the biggest outbound sales follies founders make. And here’s your first installment.

Founders think the only outbound techniques that will work are those that would be effective on them. 

This is the worst reasoning possible. The sample size is one. And you as a founder might be very different from your target persona. For example, a technical founder might not quite understand what it’s like to sell to Heads of Customer Support. In my experience, getting Customer Support folks – even after becoming leaders – to respond to emails is a slam dunk. Much like good salespeople, they are service-oriented and have been trained throughout their careers that being responsive over email is a crucial part of their job. A technical co-founder who has been an IC the rest of their career is more than likely going to display disdain towards email piling up in their inbox. Their motivations previous to being a cofounder have been about the famed “Maker’s Schedule” where deep coding is prioritized above all else. No interruptions or distractions should come between an engineer and their work.

Another example: a technical cofounder who is selling to a neighboring persona — VPEs/CTOs — might not fully grasp that the person who has managed people is not an IC engineer, like they were previous to founding a startup. Instead of prioritizing this “Maker’s Schedule”, with no email interruptions, the VPE has had to manage people and thus embraces a healthy relationship with his inbox.

The point is: there’s no reason to generalize from your specific little world into what might work for your go-to-market strategy. It prevents you from setting up experiments and seeing if those work out.

Usually, there’s fear behind the excuse of not trying something. But that’s for another day; you’re not looking for a shrink session in this piece. What ends up happening pragmatically is: founders don’t outbound email, they don’t even try cold calling, and they don’t take prospects out to dinner. These and other viable tactics to get in front of prospects end up tossed aside before they’re given a fair shake.

Next week, we’ll cover one of the biggest mental blockers I’ve seen with founders. A piece of resistance that costs them millions in revenue, every year.