The Biggest Outbound Sales Mistakes Founders Make, Episode 4

Man, I see this one all too often as well. And it comes from a beautiful place for the most part. Founders have been gestating their products for 12 to 24 months and are now proud to show them off to the world. 

Just like joyful parents, they might exclaim, “Our app’s carefully crafted accounting module will allow you to spend 50% less time running numbers. You’ll be home for supper, even during the busy season.” While I love this pride – it’s one of the best parts of working with founders – it doesn’t bring home the bacon. 


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 10 weeks, 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 4th installment. Read on.

When putting outbound copy together, founders lead with their product or service.

Prospects are self-interested busy people (like most human beings). While they might be touched by your enthusiasm for your product from time to time, they’d like to know what’s in it for them at a very core level. There’s an old adage in outbound: you get a lot more from pain than you do from gain. Meaning, lead with the pain point your prospect is dealing with that you can help them eradicate with your solution. It will soften your prospects and allow them to listen to you – and, in many cases, read on. It will feel like you’ve empathically put your arm around them, and told them, “I feel your pain.” Instead of shoving your product down their throats right at the onset of your interaction.

We’ve found this adage to be so true over the years, that we’ve been able to develop or help our clients develop successful copy that is almost entirely pain point-based, with little else.

Something like this:




Have you been dealing with [PainPointA]? Has it been particularly stressful for you in the past couple of quarters?

If so, you’re not alone (many others we’ve spoken with have suffered from it) and we should chat. Over the past two years, we’ve developed a solution to [PainPointA].

What times work for you next week to see if we might be able to help?



Notice: all this copy does is mention the pain point, draw out the pain, state that we’ve been developing a product to eradicate it, and invite the reader to a call to see if we might be able to help. There’s no mention of how the solution works and what it actually does (apart from its impact/outcome).

Leading with pain will make your prospect feel respected. And not sold to. It makes them feel like you care about their suffering, as opposed to caring about selling your product. One makes it about you, while the other makes it about them. Now, which one do you think will get them to react more positively at the outset?



Next week, we’ll discuss a place founders err in because it’s been taught to them in school. Not making this mistake takes some unlearning – which as we all know – can be harder than actually learning.