Your First 10 B2B Sales Conversations Will Feel Weird. Here’s Why.

Estimated reading time: 6 minutes

Many founders know how to build software. Very few know how companies actually buy software. The first time a technical founder tries to sell their product, something strange happens. The conversation does not go the way they expected.

You show the product.
You explain the features.
You even solve the problem in front of them.

And the customer says: “Looks interesting. Let us think about it.”

Then nothing happens.

If this has happened to you, you are not doing anything unusual. Almost every technical founder goes through this phase.

The first few B2B sales conversations feel awkward because companies do not buy software the way founders expect them to.

You Expect the Product to Do the Selling

When you build software, you spend months thinking about the product.

You improve the UI.
You refine the features.
You fix edge cases.

Naturally you assume that when someone sees the product, they will understand its value immediately. Most companies don’t make decisions right after a demo. Even if they like the product, they still need time to process it.

There are questions that do not appear during the demo.

• How hard will this be to implement?
• What happens if something breaks?
• Who inside the company will own this tool?

These questions slow down the decision.

You Think You Are Talking to the Buyer

In your first few conversations, you often speak to the person who discovered the product.

They may like it.
They may even say they want to use it.

But they are not the one making the final decision. Inside most companies there are multiple people involved.

Someone controls the budget. Someone checks security. Someone evaluates risk. So even when the first conversation goes well, the process continues inside the company.

For founders this feels confusing. The meeting felt positive, yet nothing moves forward.

This is normal.

You Talk Too Much About Features

Technical founders love explaining how their product works.

They talk about architecture.
They talk about AI models.
They talk about integrations.

“Customers rarely care about these details at the start. They care about their problem.”

Imagine a hospital struggling to manage patient inquiries. If you start explaining vector databases or model accuracy, the conversation becomes abstract.

But if you ask questions like these, the discussion becomes clearer.

• How are you handling patient queries today?
• How many calls do you receive every day?
• What part of the process frustrates your team?

Now the customer starts describing the real situation.

Good sales conversations usually look like this. The customer talks more than the founder.

You Expect Fast Decisions

Founders are used to moving quickly. You build a feature in two days. You fix a bug in one hour. You release updates every week.

B2B sales does not follow that pace.

Even when a company likes your product, the process can take weeks or months.

• Someone needs to evaluate the tool.
• Someone needs to approve the budget.
• Someone needs to check whether it fits the current workflow.

In the beginning this delay feels frustrating. Later you realize it is simply how companies operate.

You Realize Trust Matters More Than the Demo

During early conversations founders often focus on the demo. They want the product to look impressive. Customers are often evaluating something else.

They want to understand the person behind the product. They are asking quiet questions in their head.

• Will this founder respond when we need help?
• Do they understand our industry?
• Will this product continue improving?

These questions shape the decision more than most founders expect. Trust grows slowly through conversations.

The Conversation Changes Over Time

Your first few sales conversations feel uncomfortable.

You may explain the product poorly. You may talk too much. You may miss important questions. After several conversations, patterns begin to appear.

Customers start describing the same problem in similar ways. You learn which questions lead to deeper discussions. You notice where people hesitate during the demo.

Gradually the conversation becomes easier. You begin to understand how customers think.

The Real Purpose of Early Sales Conversations

Many founders treat sales as a task.

In the early stage it is something more useful. Sales is how you learn what problem you are actually solving.

Customers explain how they work today. They show where things break. They reveal constraints you never considered.

Sometimes the biggest product insights come from these conversations.

Without them, founders often build features that nobody truly needs.

Why These Conversations Are Necessary

The first ten sales conversations rarely close deals. They do something more important. They teach the founder how customers make decisions.

You learn who inside the company influences the purchase. You learn what problems customers care about most. You learn how to explain your product in language they understand.

None of this comes from reading books about sales. It only comes from talking to people. For most technical founders, those first conversations feel strange.

That feeling disappears once you realize something simple. “You are not trying to convince people. You are trying to understand them.”

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Free companion tool: the first-10-conversations tracker

If you’re about to start these conversations, don’t just wing them, log them. I made a simple tracking sheet that captures the things that actually matter here: how each prospect describes the problem in their own words, where their workflow breaks today, who really influences the decision, and the product insight you walked away with. Ten rows, one per conversation.

Not sure who to have these conversations with yet? Start with the free ICP worksheet. And before the conversation comes the meeting: how to book your first B2B sales meetings in India. After it comes the number: how to price your first B2B deal. More like this in the Founder-Led B2B Marketing Playbook.