The Biggest Outbound Sales Mistakes Founders Make, Episode 5


You’ve been there. 

You’re making one last push to get through your email before shutting down for the day. A subject line catches your attention, “quick question?”. “Catchy, enough…I’ll bite,” you think. 

You peer into the email. The long blocky text overwhelms you. The first line reads, “Hey Jim, I hope this email finds you well. I am reaching out to you because you seemed like the perfect industry expert for me to interact with…” The stench of formality and lazy flattery waft out of your inbox. And you can’t possibly go on.

You rush to close your email client and your MacBook in one fell swoop. Work. Day. Over.

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 5th installment. Read on.

Founders write outbound copy that is too lengthy and formal.

This may be the most frequent mistake I see from founders as they start writing outbound copy. Their copy is far too long. And it’s mired in formality. You have to realize a few things that are simple, yet not applied nearly enough. Your recipients are usually highly busy people whose lives you just interrupted with a message. They don’t know you at all. And they’d like to get back to the things they were doing before you barged in on them. Use that inbox interruption wisely. Write crisp copy that leaves them intrigued. Leaving them wanting to have a quick conversation with you. Nobody reads your long emails (well, maybe your mom does). 

As a quick thought exercise, visualize your prospect. Susan is a high-profile CTO at a Series B startup in San Francisco. She was plucked out of her last gig by Andreessen Horowitz, who both recruited her hard and also led the Series A. Her frenetic workdays have her juggling hiring at lightning speed – her VCs have just dropped $45M on the management team’s lap to scale the team – and managing her direct reports. She has an equally ambitious husband – who runs a cleantech startup – two children, and a Labrador at home in Noe Valley. Despite her sturdy support staff, she has very little time for herself while working. When she does go into her downtown SF office three times a week, she steals a glance at her phone on a 20mins break as she waits for her favorite lunch: fish tacos at the food truck downstairs. 

That’s the opening you’ve got, for your outbound email.

When working from home, free time is a rarer occurrence. Her family takes up most of the interstitial time between Zoom meetings or deep work. Only when she’s walking Charlie, the family’s 2-year-old pup, does she sneak in a look at her smartphone. 

Those are the few times you can reach her via email. And her phone – despite being a recent iPhone – has limited visual real estate. 

With those time and space constraints, the point is: you’ve got to make your email count. Keep the email body copy to 4-8 sentences. 

You can easily build that muscle with an exercise our Head of Outbound & Ops Rob has developed over the past couple of years. He initially used it as a forcing function on himself. He then revealed it to me and had me use it for my email copywriting. Now, we’re using it with all of our coaching clients. We’ve dubbed it the “60-Second Torture Exercise”. And it’s dead simple. Set up a timer for 60 seconds, and allow yourself just that one minute to write a first pass at your email body copy. What this will force you to do is be punchy and concise. You’ll get in. Make your point. And get out. 

You can then use more time to revise your copy and make it better through edits and the like. But that first pass in 60 seconds will set you up for success. It’s a bit like forcing yourself to splatter paint on a blank canvas. You’ll be on your way to a masterpiece in no time.

The second thing you need to realize is that our retinas and brains have become incredibly well-trained to recognize automated copy. Within half a second, we’re able to look at an email and know if it was written for an email blast versus something more personalized. Your job is to beat that system. Even if you’re doing email automation. 

You might ask, “Well, how do I do that?” By writing like you would to a friend. An email that looks like you wrote it to a friend won’t reek of formality and is much less likely to trigger our automation detectors. Now, this might not be an easy habit to build. Most of us have to unlearn all the proper business English we were taught in school. You have to unload excessive formality and inject your personality into your writing. Do all of that, and you’ve got a much better shot at grabbing your prospect’s attention and engaging them.


Next week, we’ll talk about – what feels like small potatoes to most founders – but should be treated with the utmost care and importance. Ignoring its significance – ironically enough – translates to founders getting ignored by their prospects.