customer development = learn & land customers

Good morning Predictable Revenue community,

Recently, I shared my thoughts on what I call “The Middle,” that messy stage where startups are trying to balance product development and generating revenue. After publishing, I had a follow-up conversation with my friend Kenny that really pushed me to clarify a few points. Our back-and-forth revealed some important insights that I want to share with you because it helped refine my thinking - and it might do the same for you.

Here’s the tl;dr:

• In early-stage customer calls, focus 99% on learning and only 1% on showing your product. Transition to selling gradually, but only if there’s clear interest.

• Added a new step in the process called Feedback Demo, this is the tipping point from learning to selling.

• The new customer development funnel stages look like this: Exploratory Customer Development, Focused Customer Development, Feedback Demo, & Real Sales Call.

• Early-stage sales conversations serve a dual purpose: learning from prospects while also preparing them to buy once you’ve built the solution.

Before I dive into our conversation, I’m looking for 3 beta testers that are looking at AI SDR type solutions. I’ve built a custom GPT based on the plays, signals, and messaging I’ve created for customers. I also scraped and loaded the entire Clay training library into it so it can help find the signals and then tell you how to implement them.

The ask, a 10 minute screen share to see if it produces any interesting ideas for you.

Kenny's First Challenge: Skepticism Around the Demo in Discovery

Kenny came in with a great point of skepticism, asking about the role of demoing the product  during a customer discovery call. He was also curious about when and how the switch from learning to selling happens, especially during early-stage conversations.

Kenny: I am just a little bit skeptical/curious about the demo part in the customer discovery interview.

I agreed that this was worth clarifying because my original phrasing could’ve led people to think I recommended pushing a demo too soon. I explained that the goal is learning first, with just a small, optional demo toward the end if there’s genuine interest.

Collin: To be super clear, this meeting is 99% learning & 1% show and tell. I only show and tell at the end of the meeting, after I’ve learned everything I need for that call, and only if they seem excited about it.

I emphasized that the demo is only there to sell the next meeting to the prospect. If a prospect is genuinely excited, then I might suggest showing what we’ve built. It’s important to make that transition carefully to avoid what I call the "bait-and-switch" feeling, where they might think you’re just trying to sell them something prematurely. That’s why I only share this at the end of the meeting while we’re wrapping up the conversation. In sales this is called the “hand on the doorknob question” because it’s designed to reignite one last quick conversation while you’re on your way out the door. 

The Transition from Learning to Selling

From there, Kenny brought up an essential question: when do we stop exploring the opportunity and start gathering feedback on the solution?

Kenny: At what point do we switch from trying to understand the opportunity to trying to gather feedback on the solution?

This led us into a discussion about timing. I realized that something was missing from my original process, the Feedback Demo. At this stage, you're ready to get feedback on what you’ve built - but it’s crucial to do this incrementally. The goal isn’t to overwhelm the prospect with every feature; instead, you should focus on the top three things they have highlighted as being the most important to them.

Collin: This should not be a continuous screenshare or demo, show one thing at a time and limit yourself to a 1-minute mini presentation for each. Remember, the goal is to get feedback and that can only happen if you shut up and listen.

This part of the process is about balancing. You’re baby-stepping them into the sales process without going full-on into a pitch. The biggest takeaway here is that listening trumps showing. You want to use these moments to gather insights on whether your solution addresses their pain points - not convince them it’s perfect.

Moving Toward Convincing: When Feedback Becomes Selling

Kenny also asked another great question that many founders struggle with: when do we move from gathering feedback to actually convincing someone that our solution is right for them?

Kenny: At what point do we switch from trying to gather feedback on the solution to trying to convince that the solution will address the needs?

This is where we really agreed that the transition is delicate. For me, the Feedback Demo serves as the tipping point from learning to selling. It’s about using what you’ve learned to guide the conversation towards solving their specific needs. You don’t want to hard-sell, but instead, you’re shifting the conversation subtly towards a potential fit. 

At this point, you’ve gathered enough information to know whether there’s a match between your product and their problem. This doesn’t mean you go all in with a traditional sales pitch, but the next meeting does begin a formal sales process in my books. 

Collin: The Feedback Demo is the tipping point from learning to selling.

The Role of Sales in the Learning Process

Kenny and I also dug into the fine line between learning and selling. He suggested that trying to validate your solution with “if I build this, would you buy it?” type questions is more about building a case for investors than anything else.

Kenny: The only reason to get people to answer "if I build this would you buy it?" type questions is to build a case for investors who don't know that answers to questions like that aren't actually reliable.

While I understand and agree with his point, I think it’s missing the core reason to ask the question. Asking that question isn’t about appeasing investors - it’s about having a reason to go back to those same people and ask them to buy once you’ve built it.

Collin: Strongly disagree. The only reason to ask the question is so you can go back to them after you’ve built it and ask for money.

At its core, this is part of the sales-learning loop. Yes, early-stage sales conversations are often about learning, but if you’re not asking people if they want to keep moving forward, you’re missing a critical part of the puzzle.

In the end, our conversation really helped sharpen my thinking around “The Middle.” Kenny’s questions challenged me to refine my thoughts on when to switch from learning to selling, how to handle demos, and the importance of balancing rapid iteration with validation.

So, where do you stand? Are you navigating “The Middle” in your startup right now? What challenges are you facing when it comes to balancing product and sales? Let me know - I’d love to hear your thoughts.

Collin