Where most AI deals die

Title: Where Most AI Deals Die


Read time: 3 min

Today I want to talk about something that can change not only the trajectory of your company but how you carry yourself as you grow into the role of an entrepreneur.

I've worked with hundreds of salespeople and hundreds of founders. And the ones at the top of the food chain—the ones who really win, they're wolves. Fierce competitors. Dogs. What drives them isn't a paycheck or a pat on the back. It's something internal. A will to win; to prove something. To themselves, to doubters, to everyone who counted them out.

I'll be vulnerable for a second because I think this matters.

I didn't have the best childhood growing up. I’m not going to go into details, but I often felt like my voice didn’t matter. Powerless in a way that I never forgot. And as I got older I made myself a promise, when I was in a position where my voice could be heard, I was going to make sure it was.

Sales was a perfect fit for me because that's exactly what sales is. It's about being heard. It's about understanding people, listening deeply, and moving them to take action. That's my why. And that why, is a big reason why I was successful then and continue to be successful now.

Your why matters more than your pitch or your process. More than any framework I could ever give you. Because when shit get hard, and they will get hard, your why is the thing that keeps you in the fight.

Let's talk about the three things you have to develop to win in sales consistently

1. Command the Room

I can tell you that within the first sixty seconds the person across from you has already decided whether you're worth listening to. Not based on what you've said yet. Based on how you showed up. Your voice, tone, energy, the posture you carry into the conversation. All of that is communicating something before a single word about your product comes out of your mouth.

Speaking with conviction isn't about being loud or dominating the conversation. It's about sounding like someone who knows exactly what they're talking about and isn't afraid to say it. That quality, that calm confidence is what conveys competence. And competence is what makes someone lean in and trust you enough to keep listening.

Founders and salespeople spend all their time working on what they say and almost no time working on how they say it. That's a mistake. Your delivery is doing more work than your words. The prospect is deciding whether to trust you based on how you sound, how you carry yourself, and whether you feel like someone operating at a high level. Get that right and everything else gets easier. Get it wrong and it doesn't matter how good your pitch is.

Record your calls. Listen back with fresh ears. Find where you go flat, where you rush, where the energy drops. Then work on it like it's a skill because it is.

2. The Art of The Question

This is what separates good salespeople from great ones and most people never fully develop it because it requires something many struggle with, the ability to go where the conversation gets uncomfortable.

The best salespeople aren't afraid. Not afraid to ask the tough question, to challenge when something doesn't add up, not afraid to sit in silence after something lands and just let it breathe. That quietness alone signals confidence in a way that words can't.

If you accept the surface level answer and move on because going deeper feels risky. The ones who win follow the thread. They hear something in an answer that most people would let slide and they go right at it. They ask the follow up nobody else asked. That's where the real information lives, not in the prepared answer but in what comes out when someone feels genuinely heard and pushed at the same time.

Being a great listener is a massive part of this. Not listening while waiting for your turn to talk but actually absorbing what's being said and using it to shape the next question. When you do that well the prospect feels it. They stop feeling sold to and start feeling understood. That rises the price of your stock.

And when something doesn't add up go right at it. Respectfully, directly, without flinching. Prospects respect that because it signals they're talking to someone who operates at a different level than everyone else they've spoken to.

3. Slip and Counter

Think about what makes a great boxer. It's not just one thing. It's speed, agility, timing, and fight IQ. It's knowing which punches are coming before they land, slipping them, and countering at exactly the right moment. The great ones don't get in the ring hoping the other guy doesn't throw the left hook. They've trained for the left hook. They've slipped it a thousand times in the gym so that when it comes in a real fight their body reacts without thinking. No panic, no hesitation. Just movement.

That's exactly what handling objections looks like when you've truly put in the work.

The prospect throws pricing. You're already moving. They bring up timing. You counter without missing a beat. They say they need to think about it. You know exactly where that's coming from and you go right to the heart of it. Nothing lands that you haven't already seen coming and trained for.

The six most common objections in any sales process are completely predictable. Here they are:

1. We don't have the budget for this right now

2. We can build this in house

3. We don't want to displace our employees

4. Our data isn't clean enough for this yet

5. We have concerns around data privacy and security

6. Come back to us in six months

You know they're coming so there's no excuse for not being ready. If you can’t rebut these objections with conviction and poise, you’re losing. Our clients can wrangle off polished rebuttals to every one of these objections and regain control of the conversation with grace. Write every single one of them down. Build your response to each one. Practice them until they feel like second nature and not like a script, so when they show up in a real conversation the last thing you want is to get caught flat footed on something you should have prepared for.

Objections aren't stop signs. They're information. They tell you exactly where the prospect's head is and what still needs to be addressed before the deal can move. When you start treating them that way they stop feeling like resistance and start feeling like the roadmap to the close.

Key Takeaway

I’ve spoken to a lot of people that play entrepreneur. They’re really not there yet. You have to become it.

The operators I've seen build real things and win in competitive markets all share the same DNA. They command every room they walk into. They ask the questions nobody else has the confidence to ask. And when the objections come they slip and counter without being shook.

That fierce determination to win isn't something you can fake. Find your why and let it drive everything you do. Because your competitors have theirs. And if you don't match that energy they will eat you for lunch.

Get in the gym. Put in the reps. Go win.

See you all next week!

Darren

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

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