EXTRA EXTRA

A newsletter about early sales from The Extra Group

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I find it helpful to reflect on things I wish I’d done differently when I was selling at my startup, Skillist. And there are oh so many to choose from. 🥴

One mistake that haunts me I think a lot about is that I put far too much stock into any given deal.

I would cherry-pick only the positive indicators: the prospect was friendly, they paid our platform compliments, they were open to chatting again.

I would be excited to close the prospect, only to find myself crushed and confused when they passed.

Part of what I wish I’d done differently is obvious: I needed to lose the “happy ears.”

• I heard the prospect expressing interest in the software, but I know now they were just being polite, and that I’d ignored their gentle indications that they weren’t going to buy.
• I heard a prospect’s clear intention to buy, but didn’t factor in that the person I was talking to had zero purchasing power, and that the deal would die on their boss's desk.
• I heard “I’m not sure,” but believed if we just kept talking, I could convince them to change their mind – but almost always, that “I’m not sure” meant their mind was made up.

So yeah, you could say employing a healthy dose of realism to our pipeline analysis would have been wise!

But there’s an additional layer here that gets talked about less.

You are very likely to overindex on the deals in your pipeline if you do not have enough deals.

The ultimate solution is not just to temper your expectations. It’s to increase the number of deals in your pipeline so that you have room for error.

The reality is that you will never close all your deals. It is frankly unlikely to close the majority of deals (though, if you get really good at defining your buyer narrowly, it’s absolutely possible).

So really, if I could turn back the clock, I would lose the happy ears, but more importantly, I would have gone harder on pipeline and spent way more time booking sales calls.

The benefits of increasing your pipeline’s denominator are significant. When you have a healthy number of sales calls on the calendar per month (ideally fifteen per month):

• It takes the pressure off any given deal. You will become less thrown off by losses. When you’re having multiple sales calls per week, you’ll get comfortable with the fact that some people just don’t have demand for your supply.
• You’ll waste less effort and time on deals that won’t close. Because you have lots of calls per month, you’ll get better at identifying the buyers who actually are interested. You can spend time strategizing on and nurturing those deals – and you’ll feel confident putting low-intent buyers on the back burner. (They know where to find you if they change their mind!)
• You’ll get concentrated data on your outreach strategy. If you’re struggling to book fifteen sales calls per month, it means you aren’t doing enough outreach, or your outreach strategy isn’t converting. It’s usually a little bit of both. When you set a big goal to book 15+ calls per month and run at it, you’ll glean lots of insights on what your buyers respond to in a concentrated period of time. With all that data, you can now iterate on your outreach approach faster, which of course speeds up your time to a repeatable sales process.
• You’ll become better at sales calls, faster. No amount of prep, deck-building or script-writing can prepare you for running real, live sales calls with real, live prospects. If you’re not having many calls, it’ll be that much harder to improve (and I’ll be honest with you – every single founder out there can improve how they run sales calls).

I know outbounding and building pipeline isn’t a sexy or fun part of the founder experience. That’s probably why I didn’t prioritize it when I was building my startup! But hindsight is 20/20, and I now see all too clearly that it’s one of the most important (and underestimated) activities that will take you to product-market fit.

This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, an exited social impact founder who’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.

Caroline Fay

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