How to sell for founders who hate selling

startup-selling.jpg

Sales is probably the most misunderstood part of running a startup.

Many founders imagine it as a murky world of aggressive tactics, manipulation, and worse—deceit. Most of us have experienced this, encountering salespeople who won't take "no" for an answer, more focused on their commission than on solving our problem.

But here’s the surprising thing: those salespeople who approach their job that way generally don’t do well. The harder you try to sell, the fewer clients you end up with.

If you've ever wondered why, it's because the key to selling isn’t about pushing harder. It’s not about pushing at all.

Here we’ll explain why selling isn't what you think it is and share how founders—especially those who hate the idea of sales—can shift your mindset to turn sales into something natural, even enjoyable.

The problem with traditional sales

When most people think of sales, they imagine a high-pressure world full of closing tactics, rehearsed objections, and fast-talking pitches.

This model of selling, unfortunately, has been perpetuated for decades, even though it doesn’t work anymore—and it never really did. People don’t like being sold to.

The minute someone senses that your objective is to "close the deal" rather than solve their problem, trust is eroded.

Think about your own experiences. When you walk into a store and a salesperson approaches you with, “Can I help you find something?” how do you usually react? You probably avoid them, right?

That’s because, whether consciously or not, you know they’re trying to push you towards a purchase rather than understand what you need.

This sets up an adversarial relationship: the seller is trying to "win," and the customer is trying to resist.

But what if we flipped that? What if sales was no longer about selling but about serving?

Stop selling, start helping

The biggest mental shift you can make as a founder is to stop thinking of sales as selling and start thinking of it as helping.

This might sound trivial, but it’s a profound change. When you think of sales as helping, you approach every conversation differently. Your goal isn't to close a deal. Your goal is to solve a problem.

Your potential customers aren’t just numbers or transactions—they’re real people with real problems. And your job is to determine if your product or service can genuinely solve one of those problems.

If it can, great. If it can’t, you move on. Either way, you’ve approached the situation from a place of empathy, not aggression.

One of the best analogies is to think of yourself as a doctor diagnosing a patient.

A good doctor doesn’t start prescribing medication the moment a patient walks in the door. They ask questions, listen carefully, and only after understanding the patient’s symptoms do they recommend a solution.

That same approach works wonders in sales: you diagnose before you prescribe.

The power of good questions

If selling is really about helping, then the most powerful tool in your arsenal is asking good questions.

But not just any questions. The questions need to be designed to uncover the customer’s real problems, motivations, and pain points. That’s where the conversation becomes meaningful.

Instead of asking, “Are you ready to buy?” a better question might be, “What’s the biggest challenge you’re facing right now in your business?” or “Why is solving this particular problem so important to you right now?”

These questions aren’t about pushing a product—they’re about understanding the customer’s world.

This approach serves three purposes:

  • It helps you genuinely understand the customer’s situation.
  • It builds trust by showing that you’re focused on solving their problem, not making a sale.
  • It opens up opportunities for you to offer a tailored solution.

But here’s the critical part: after you ask the questions, listen. Really listen.

Don’t just wait for your turn to speak or prepare your pitch in your head. People can tell when you’re truly paying attention, and it makes all the difference in building trust.

Selling through trust

Here’s the real secret of sales: it’s not about closing deals. It’s about opening relationships.

If your only focus is on closing, you may get a customer today, but you’ll probably lose them tomorrow. If your focus is on helping your customers succeed, you’ll start building long-term relationships.

That’s the key difference between average salespeople and great ones. Average salespeople are focused on the short-term: “How do I hit my numbers this month?”

Great salespeople—and founders, especially—are playing the long game: “How do I help this customer succeed so we can build something together over the long term?”

This approach has two huge advantages.

First, it’s much easier to build a relationship with someone than to sell to them. People want to do business with those they trust.

Second, relationships compound. The more trust and goodwill you build, the more customers come back to you. They refer you to their networks, and over time, your reputation grows.

In an industry like tech, where word-of-mouth and reputation are everything, this is gold.

A startup founder who builds a reputation for trustworthiness and delivering real value will be far more successful than someone who’s just focused on "closing deals."

Sales is a key part of growing your startup

Many founders think of sales as a necessary evil. Something they have to do, but they’d rather avoid. The truth is, sales is one of the most critical functions in any startup.

But it doesn’t have to feel slimy or manipulative. When you approach it as a way to help people, it becomes not just tolerable, but even enjoyable.

Sales, at its core, is about understanding people’s problems and offering solutions that make their lives better.

That’s why you started your company in the first place, right? To solve a problem and create value. The same applies to sales.

When you stop trying to sell and start trying to help, you’ll not only get better results, but you’ll also find that sales becomes something you can be proud of.

Final thoughts

If you’re a founder who hates selling, good news: you don’t need to “sell” in the traditional sense. In fact, you shouldn’t. The best salespeople aren’t focused on pushing products. They’re focused on solving problems, building trust, and creating long-term relationships.

Sales is one of the most critical functions for any startup, but it doesn’t have to feel like a necessary evil. When you shift your mindset from “selling” to “helping,” you’ll find that sales becomes something you enjoy rather than something you dread. And you’ll get better results because of it.

In the end, the best salespeople—and founders—aren’t selling anything. They’re helping. So stop trying to sell. Start helping. You’ll be surprised at how far it gets you.