Most founders suck at selling

I made every single mistake in this article.

Creating a product from nothing, that people will actually use and eventually pay for, is incredibly challenging. It’s one of the hardest things I’ve ever done in my life. This article walks through some of the key sales mistakes I made during my time running Gondola.

Selling, for most founders, is a puzzle turned upside down. They often assume that offering any solution capable of addressing a business owner’s problem would automatically be the right solution. This mindset believes that if founders perceive a superior solution, the business owner will see it the same way and adopt it eagerly. The expectation is that showcasing one more feature will trigger an immediate desire to sign up.

Let’s set the record straight

In reality, prospects are indifferent to your product. They aren’t interested in your founder’s story, your background, the customers you serve, or the team you’ve assembled.

All they truly care about are themselves and the problems they’re striving to solve. This harsh reality is often misunderstood by many founders, leading to incorrect sales approaches. This post aims to dispel common misconceptions that early-stage founders have about sales and closing deals with new customers.

All of these key learnings came from my own experience as a founder. I made every single one of these mistakes.

Reality #1: Your prospect doesn’t care about your product

Whenever I meet with a founder for the first time, this is the most common recurring issue I see throughout their sales process. The common belief is that showcasing their platform or product will naturally attract prospects. However, the brutal truth is that prospects are indifferent to your product’s specifics, its features, or the order you present them.

Prospects primarily care about themselves, the issues they’re trying to solve, and maybe how you can make their daily lives more efficient and effective.

Recognizing this, your primary focus during initial conversations with potential buyers should revolve around grasping their current operations, understanding the changes planned within the next 90 days, and the sequence in which they intend to address these challenges. Exceptional sales skills involve understanding why they prioritize certain problems, along with the potential gains or losses tied to solving them. The most effective sellers I’ve worked with can quantify the monetary impact of these issues and the potential benefits of resolution.

To help with your discovery call process, here’s an outline of how mine typically go.

Discovery call outline:

1. Introduction and agenda
2. Understand current operations
3. Identify current challenges with operations and reasons
4. Understand their approach to solving the problem
5. High-level product overview: verbal explanation or live product demo
6. Next steps

This outline places considerable emphasis on understanding your buyers by asking thoughtful questions about their current operations, desired improvements, and strategies for tackling issues. Following this, you provide a high-level product overview aligned with their challenges and future resolutions.

Reality #2: Prospects’ solutions > your solutions

As sellers, we encounter buyers facing similar problems. Due to this familiarity, we assume that buyers want to address issues in a particular manner. However, this assumption can steer you off course.

After grasping the buyer’s current operations, your next objective is to understand their intended changes and how they aim to solve the problem.

While some buyers have a clear solution in mind, others seek expert suggestions on addressing the issue. Your role involves categorizing these buyers and tailoring your approach accordingly. If buyers have a clear solution, your goal is to grasp their approach and rationale. This will allow you to frame your product through their “ideal solution” lens and draw parallels to your solution. It’ll allow you to emphasize certain points and deemphasize other parts of your solution.

Selling is about discovering a need that you can solve. Not selling someone something they don’t need.

Reality #3: Focus on 2-3 features that solve their problems

Your job is to uncover a customer’s problems and needs and identify which parts of your solution can solve them.

Founders naturally take pride in what they’ve created. After all, they have spent hundreds or thousands of hours working on it. This pride often translates into showcasing the product extensively, under the assumption that demonstrating more will lead to stronger alignment with buyer problems and more closes.

However, this assumption is flawed.

After conducting proper discovery, your role as a seller is to spotlight two or three features that distinctly address the problems identified during the discovery phase. Clear connections between your solution and their problems make internal communication easier when buyers present to decision-makers. Overloading buyers with every product feature may confuse them and dilute your value proposition.

A good practice is to focus on demonstrating two or three key features, and allowing room for follow-up questions after each feature you’ve presented. This balanced approach maintains engagement and prevents lengthy monologues, in line with Gong’s finding that demos exceeding 76 seconds of uninterrupted pitching rarely lead to closed deals.

Gong’s research also shows how differently average reps and top performers handle discovery. Average reps ask all their questions at the beginning of the call. They frontload discovery, as if they’re completing a to-do list of questions before launching into their pitch. To them, discovery is a static event.

Top performers spread their discovery questions evenly across their sales calls. To them, discovery is an ongoing process, not an event.

Reality #4: Always be discovering

When a founder finally gains a grasp on a solid discovery process, one prevalent mistake they’ll make is treating discovery as a one-time event rather than an ongoing process.

Discovery should span the entire sales cycle, not just the initial call.

As you receive new information from prospects, be ready to ask further questions for clarity and to understand its impact. This applies to new insights about security requirements, workflows, and involved personnel.

Here are examples of situations where founders forget to ask further questions:

• Mid-demo: founders frequently forget to ask digging follow-up questions after they’ve shown a feature. It is incredibly important to ask questions beyond “did that make sense?” or “do you have any questions?”
• A new person joins the call: buyers will sometimes bring in additional people from their team to help with the evaluation. Ask this person new discovery questions, understand how you can make the call meaningful to them, and what they think a good solution to the problem might be.
• Feature requests: prospects will often ask if your product can do X or Y. Most often this is not a sincere feature request but an exploration of your product’s capabilities. Rather than answering directly, ask follow-up questions about why that feature is important and what they expect to gain from it.

Nailing the discovery phase is crucial for sales success

Consistently practicing thorough discovery deepens your understanding of customer needs and timelines, separating genuine opportunities from exploratory inquiries. If deals are stagnating or prospects go quiet after demos, start by reevaluating your discovery process.