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Extra Extra

When confidence backfires


EXTRA EXTRA

A newsletter about early sales from The Extra Group

Who doesn’t want to be a bit more confident?

Confidence is, of course, a powerful and positive thing. It helps you silence your inner critics, beat back imposter syndrome, and be more resilient when things don’t work out.

But as I’ve worked with more and more founders, something’s been nagging at me. We’re missing nuance around confidence. Not all confidence is made equal.

I want every founder to feel confident in their ability to figure it out. I want you to feel confident that you have everything it takes to weather the extreme highs and lows of the entrepreneurial journey. I want you to be confident that you deserve a seat at the table.

But I’ve seen many founders become overly confident in their solution before they’ve got serious repeatable sales. I was that founder.

Being too confident too soon about your product creates real, existential risk to your startup.

Founders in this mindset tend to find themselves joining sales calls and pitching the value of their startup, hard. And when you push your product too hard, you might just push your buyer away.

So, at the beginning of each sales call, I don’t want you to be confident in your product. It will not create the conditions that help you accomplish the first purpose of your call: learning about what your customer needs.

Focus not on being confident, but instead, being curious.

Don’t join a sales call thinking too much about your solution. Join the call thinking about your hypothesis.

You have a hypothesis about what your target customer needs to get done, and why it’s so important for them to do so. In each sales call, you should be earnestly trying to learn and test where you’ve got it right, and where you’ve got it wrong.

By leading with curiosity, you create an environment where your buyers can tell you their honest experiences and needs.

We need to get your buyer's true needs on the table, even if it doesn't match up with what you thought.

I can say with confidence (😉) that customers honestly love this experience.

I regularly watch back founders' sales calls, and it’s clear that prospects thrive during a sales call where there's no pressure. When the call starts with an invitation to honestly share about their priorities and what’s most critical to fix, prospects are more at ease. They tend to create real, authentic connections with the founder.

Conversely, if you start a sales call with an air of confidence that your product is what they need without confirmation, you’ve accidentally created an environment that doesn’t welcome dissent or honest feedback.

This creates the perfect conditions for my least favorite outcome in sales: the buyer feels like they’re being pushed a solution that they don’t need or want. They feel awkward, but smile and nod to be polite. They don’t respond to your follow-ups. And the founder is left without ever uncovering what they do need.

When you start a sales call with humility and curiosity, your buyers will let you know what they need help with. Some will have a need that you don’t solve for. But some buyers might explain their circumstances and their needs, and your solution really can help!

🚦Green light!!! Once you've confirmed they have a need you can genuinely help with, it's the right time to switch gears. You've earned the right to confidently offer your help.

Pivoting from humility and curiosity to confidence in real time on a customer call is a tricky skill. I’m confident you can master it.


Can I get your help with something? I'm working on something new for founders. Check it out here. I would love your thoughts. Hit reply to tell me what you think.

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.

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Caroline Fay

67 West Street #GP24, Brooklyn, NY 11222
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Extra Extra

Extra Extra is a newsletter about the tactics and mindsets that drive early startup sales. I’ve helped dozens of startups get results like a 50x in repeatable revenue and a 400% lift in sales calls per week.

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