The Biggest Outbound Sales Mistakes Founders Make, Episode 9


It might seem like a tiny faux pas. Benedict Evans certainly doesn’t think so, in the tweet above.

Why would anyone care if I sent them a Calendly link in an outbound email?

First of all, I don’t make the rules. Human beings have gotten offended by much smaller things. You can hold your fork a certain way in some social settings and some folks will think you’re a peasant. The fact of the matter is sending over a Calendly link to schedule an initial call when doing outbound can feel like a power move to some people (usually the old guard, I’ve found).

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 9th installment. Read on.

Founders use calendaring software exclusively to schedule the initial call.


When you’re getting an inbound request, it’s very different. The prospect is coming to you, and expressing interest in your product or service. Asking them to schedule through Calendly is much less abrasive. When you’re reaching out to folks unannounced, and you’re putting the burden of scheduling the call on them, you’re bound to get some negative reactions.

Some people – usually the younger, more tech-savvy crowd, I’ve noticed – won’t mind and even welcome the opportunity to use a Calendly link to reduce the email back and forth. In my experience, technical and product folks fit in that group. But you’re going to get folks that find it off-putting that you reached out cold, and then had the audacity to seek their help in scheduling.

The bottom line is, as a salesperson, it’s your responsibility to cater to your prospect/customer; in this case, shouldering the scheduling work.

My simple suggestion here? Ask the prospect what times work best for them and offer a calendaring software link as an alternative they can use as well. That way, you’ve got all of your bases covered.


Next week, we’ll dissect something founders could do to help themselves achieve success. Unfortunately – more often than not – it’s ignored, or relegated to the land of inaction.