#83: The One Question That Can Make Or Break A Deal

Read Time: 3 min



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I will keep this issue short and sweet in light of the holiday weekend in the States. Today, I will discuss the most common question you will hear as you begin pitching your product. If you do not know how to reframe and answer this question with poise and conviction, it can make or break a deal.

You can own the room as a founder who oozes confidence or be portrayed as someone who isn’t ready to lead. It all depends on how you answer the question.

Don’t fake till you make it. Fake it till you become it.

~ Amy Cuddy

The prospect question I’m referring to is this.

“How long have you been around, and how many customers do you have?”

This is the one you have to crush. Why? There are multiple reasons.

1. Credibility
   Prospects want to know if other companies have validated your product. If you don’t have the answer dialed in, it makes you look weak and unpolished. This is why we present a risk-free offer to get them onto a paid POC.
   
   

2. Risk Perception
   Early-stage startups already feel risky to companies, but they’re very tempting because of the idea of building in-house or outsourcing. Startups are agile and nimble and can move fast. This question is their way of assessing whether partnering with you is a gamble worth taking—or a strategic opportunity.
   
   

3. Builds Trust
   The way you answer this reveals not just the data but your confidence, clarity, and command of your business. It’s your chance to make them believe in you as much as you believe in your product.
   
   

4. Shapes First Impressions
   You risk being seen as inexperienced if your answer feels defensive or hesitant. If it’s bold and reframed to highlight your unique strengths, you’ll set the tone for the entire conversation. Remember what I always say: you must control the conversation by conveying authority. People buy because they believe you’re competent, an expert, and you can deliver on expectations. Every word that comes out of your mouth either moves you closer to or further away from the finish line.
   
   

5. Differentiation:
   They’re not just asking for numbers and social proof—they’re asking why you are the right solution. Use your response to spotlight your vision, traction, and why being "early" is actually an advantage.

Now, let’s discuss how you responded to this rebuttal.

“That’s a great question (name). I’m glad you asked it. We’ve been around for a (number of years) and have spent a tremendous amount of time understanding the problems in the space and becoming true experts in the areas of (whatever it is that you solve). Because of our deep experience and the time we’ve invested, we made a conscious choice to only work with a handful of clients by design. We decided only to partner up with customers for whom we feel we can absolutely knock the cover off the ball. Unfortunately, because we’ve adhered to this decision internally, we’ve had to turn down quite a bit of revenue from many customers who wanted to partner with us. We optimized our process to partner with companies to which we can show the best results for, not just capturing logos. Based on our conversation, I think you might fit well within the caliber of customers we’d partner up with. Let’s talk about the next steps. How does that sound?”

Memorize this. Master it. Write it down on a post-it note and stick it to your laptop when pitching. If a prospect asks you this question, it should become like second nature, delivered with conviction and confidence. If you deliver this right, the prospect will be thinking, “Holy shit, these guys have lighting in a bottle,” and it’ll pull on their FOMO strings. They’ll forget that you are a new, unproven startup and will try to find a way to make it work.

One last thing. It doesn’t matter how well you deliver this if they have not been qualified as an opportunity, the deal is not going to go anywhere. The idea of delivering this response is to convey conviction and confidence in your ability to crush it for them after they been vetted as an opportunity at revenue.

That’s it for today!

Happy Thanksgiving!! 🦃 🇺🇸

Darren

P.S. If you’re a venture-backed SaaS company interested in coaching, book a call here.

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