the middle

Good morning Predictable Revenue community,

I just went through something I’ve put developers through more times than I can count. I sent what I thought was my "first draft" to the editor last week and now I realize I need to make some major changes - a whole feature section is missing! I had to laugh when I realized it. Now, I’m starting to really understand how frustrating it must be to work with non-technical leaders who are constantly changing their minds.

I woke up this morning with a graph in my head. On the left was the product journey and on the right was the revenue journey but there was this gray area in the middle where things were hazy. An idea I don’t think I’ve been able to articulate well enough has been that there is significant overlap between the two journeys. At some point in the middle, you’re doing both product and revenue work. This is where I got stuck. On the one hand, I wanted customers and on the other, I recognized that we didn’t know everything we needed to yet. I was stuck in this awkward messy middle, to paraphrase Scott Belsky. 

If you haven’t read Scott’s book, The Messy Middle, stop what you’re doing and go read it now. I don’t know Scott and there are no affiliate links here, it’s just a great book. A note on how we each use the words: Scott’s Messy Middle applies more broadly to the journey where I focus a little narrower on the gray area between finding a gap in the market and having a completed product with a sales motion behind it. 

TL;DR:

• Start selling is misleading advice

• You can sell in your customer development process but need to do it properly

The Middle 

In previous iterations I had mapped out the journeys as two separate paths for product and revenue. What struck me this morning was there was this middle ground where you’re both trying to figure out what to build and get some money from the process. The processes overlap! Many VCs I’ve talked to will say this is the stage that you need to just sell more. Which is terrible and great advice at the same time. It’s great advice because you need to get revenue asap and it’s terrible advice because you don’t have something to build a formal sales process behind. What you need to do is something in between both worlds. 

“Sell more” can be bad advice because when you switch into sales mode too early, you lock yourself into a fixed path when you should still be exploring. In this mode, you're focused on selling the same product to the same audience, which can close you off to valuable feedback. Instead, every potential customer interaction should be seen as a learning opportunity. If they buy, that's just a bonus. A sales-first mindset at this stage can actually prevent you from gaining the one thing you need more than revenue - insight. With only a few customers, you don’t know enough about the market yet, and your product isn’t fully developed. Their feedback is crucial for improving it.

Additionally, taking a sales posture too early can mislead potential customers. If you project too much confidence in your product, it may be disappointing for them to realize how early-stage your company actually is. This can damage the trust you’ve built with the prospect. You also risk giving them the impression that your first version is the final version. 

On the flip side, “sell more” is also good advice because if you don’t start generating revenue, you won’t have a company left to support the product. It’s easy to get stuck in “it must be perfect” mode, spending all your time building the perfect first version, only to run out of cash before you can take it to market. So, while learning is critical, balancing it with making sales is just as important to sustain your business.

Here’s where you can argue that I’m splitting hairs. You can and should sell as a part of your customer development process. It just needs to be handled differently than in a pure sales process. The primary goal of a customer development call is always learning. At the end of the call you can have a few calls to action. I always ask for a referral to someone else to talk to. I also will ask if they want to see what we’ve built or, if we’re super early, they want me to get in touch when we have something ready to show. The ratio of learning/asking questions to talking about your product should be 98% learning and 2% asks for help. Going too hard on the sales process at the end of customer development calls can make people feel like they’ve been bait and switched, which is not a great place to start with a prospect. 

How I think about this in practice is three different types of calls, Exploratory Customer Development, Focused Customer Development, and Sales. When I’m getting started, everything is Exploratory. As my product becomes real, I start switching from Exploratory to Focused. Once I have received at least one case study and one referral from active customers, I start thinking about switching to Sales Calls. 

Exploratory Customer Development: 

• Goal: Find a gap you think you can solve. I usually run these as day in the life interviews. 

• Call to Action: Ask for a referral to someone else they might know that you can interview. I’ll also ask if they would be open to checking out the tool when it’s ready. 

Focused Customer Development Calls

• Goal: Refine your thinking about a gap you’ve found. I also run these as day in the life interviews but I tend to steer them towards the gap earlier in the conversation. 

• Goal: I’m also trying to understand the impact solving the gap would have on their organization and all the variables that would go into solving it. 

• Call to Action: The call to action at the end of each meeting is a very soft ask if they’d like to take a look at what we’ve built so far. 

• To be super clear, this meeting is 98% learning 2% demo max. I intentionally structure it this way to avoid the bait and switch feeling. I will frame up the next meeting as a sales conversation with something like, “I’ll show you what we’ve built and if you think it might work for your organization then we can talk about what that might look like.” This gives them a heads up that we’re transitioning from learning to selling. 

Sales Calls 

• Goal: You know the gap that you solve, how your product solves it, and how you’ve helped your customers solve it before. Your goal is to see if the prospect is experiencing the gap and, if they are, how they feel about solving it right now.

• Call to Action: These look very similar to the Focused Customer Development Calls with one difference is the customer expects you to talk about how you can help at some point during the call. 

Here’s the picture with some rough milestones: 

Does this check with your experience or am I missing something? Are you currently in The Middle? Let me know.

Collin