Why You're Afraid To Close Deals (and how to fix it)

Title: Why You're Afraid To Close Deals (and how to fix it)

Read time: 4 min

Today, we’re diving into the mental side of sales, the part no one talks about but everyone feels. How to build emotional resilience, develop unshakable clarity, and finally stop getting derailed by rejection, self-doubt, or silence on the other end of the line.

Most founders think closing more deals is about better tactics, better decks, better pricing, better discovery calls. And yes, tactics matter. But what actually separates the top 1% of founder-sellers is how they think, how they handle pressure, and how they show up when no one’s watching.

Sales is a full-contact sport. It’s the business of rejection. You’re not just pitching. You’re constantly putting your identity on the line, dealing with rejection, chasing clarity, and fighting the urge to quit. If your internal state is cracked, your pitch will be too.

After working with close to 600 founding teams, I believe that a lot of founders break because they chase tactics before mastering their mindset. They know the playbook, but they still can’t bring themselves to follow through. They’re afraid to push. Afraid to challenge the buyer. Afraid to follow up again. And they confuse that fear with respecting the prospect’s time. You have to be relentless and fearless.

In reality, what’s holding them back isn’t strategy, it’s the unspoken fear that never gets addressed. In this issue we’ll unpack it.


When we are no longer able to change the situation, we are challenged to change ourselves.

~ Viktor Frankl

So what’s the secret to building this kind of mental resilience? How do you stop getting rattled by rejection, ghosting, or your own inner voice telling you you're not ready?

You train it. Just like your pitch. Just like your product.

Here’s how to harden your mindset, sharpen your execution, and start selling like someone who can’t be shaken:



1. Take 100% Responsibility

The moment you externalize your results, you lose. Whether it’s a bad quarter, a ghosted prospect, or a buyer who “doesn’t get it,” the second you blame anything other than your own execution, you’ve handed away your power. Don’t do this.

The best founders operate from one rule: Everything is your fault, even when it’s not.
That doesn’t mean you beat yourself up. It means you ask, What could I have done differently to create a better outcome?

That mindset shift alone separates professionals from tourists.


2. Obsess Over Process, Not Outcomes

You can’t control if someone signs. You can’t force timing. But you can control your process.

  • Did you ask the hard question?

  • Did you push on BANT / MEDDPICC?

  • Did you close the disco call with a demo booked?

  • Did you follow up with a clear recap and deadline?

When you master processes, outcomes take care of themselves. If you only measure yourself by closed deals, you’ll burn out. Measure your execution. Control the things you can.




3. Practice Under Pressure

Like boxing is the hurt business. Sales is the rejection business. It’s a pressure sport. And in most sports you have players who are participating, and others who want to win. The dogs. Most people only participate, that’s why they crack when stakes are high.

If you’re not role-playing your pitch every week, you’re winging it.
If you’re not practicing objection handling, you’re improvising when it matters most.
If you’re not training your voice, tonality, and delivery, you’re just hoping it lands.

Repetition gives you control. Control creates calm. Calm closes deals.



4. Flip Rejection Into Fuel

Rejection is part of the game. Big part. But for many founders, it hits too deep. It feels personal, especially when you’ve poured everything into the product. I know this feeling deeply, I’ve been in the sales business for a long time.

Here’s how I reframe: Rejection is the cleanest form of market feedback you’ll ever get. It’s not about you. It’s about your clarity. Your offer. Your process.

Start writing down the objection/pushback you hear. Write down why every deal didn’t close. Inside that pattern is where you understand how you need to show up better, more polished.



5. Train Your Voice to Become a Weapon

Your voice is your greatest sales asset, and most undertrained tool.

Monotone = low conviction.
Uncertain tone = low trust.
Weak pitch = weak response.

I’ve said this in so many issue. Spend 15-30 minutes a day reading your pitch out loud. Emphasize key words. Practice pausing. Inject energy and restraint where needed. Your tone says more than your words ever could. People buy conviction and enthusiasm.



6. The Singleness of Purpose Test

If you're still wondering whether this is going to work, your buyers can feel it.

Doubt isn’t just internal. It leaks into your tone, your body language, your follow-ups, and your ability to deliver on expectations. It makes you hesitate where you should lean in. It makes you seek validation instead of driving the process.

When you decide, to burn the boats. Go all the way in, fully, clearly, without a backup plan, that this will work, your energy shifts. You stop auditioning and start leading.

That kind of conviction shows up in every room you walk into. You become that dog. You stop avoiding tough questions and start asking them. You stop chasing and start qualifying.

Think about some of the most successful entrepreneurs and startups that have taken off, early on they had this aura, this energy like they’ve already seen the outcome. Buyers buy from those people. And that only happens when you stop trying to convince yourself, and decide to become that individual.


Key Takeaway

Having the proper mindset is everything.

Every hesitation, every soft close, every time you let a deal drift instead of challenging the prospect and pushing it forward, that’s your internal state bleeding into the sale.

You can’t fake conviction. Buyers won’t follow someone who’s unsure, and they won’t trust someone who’s trying to please everyone.

Your edge comes from being clear. Clear that this works. Clear that you’re the one to lead it. Clear that you’re not here to collect maybes.

When that’s real, it shows. You stop waiting. You start driving. And that’s when deals start closing on your terms. 💪



That’s it for today folks.


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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