How to sense when you’ve entered a dead-alley with your product?

Ton Dobbe
Ton Dobbe
Jul 9 · 4 min read

It’s a question I am exploring concerning the book I am writing on the ten traits to build a remarkable software business. When do we reach the moment when we should say ‘stop, enough is enough’ from a product strategy perspective.

What I often see is how we tend to get blind for those moments, and keep pouring resources into a product, module, or even feature that has lost its edge. As a result, it drains scarce development resources, which should be used to work on new projects that will create a shift in value — whether that’s something completely fresh or even the re-architecting of the current solution.

My take on this is that often it’s our self-talk that sits in the way. We’re so proud at what we have created that we keep making it better. Even when significant shifts happen in the market, we believe we can ‘fix’ it and technically meet the new norms and expectations. This way, just as an example, millions and millions of hours got invested in turning a host of traditional on-premise solutions into ‘cloud’ solutions. Sure, technically it will run in the cloud, but the question is whether that was the main goal of the shift, to begin with.

The challenge of avoiding conflict

So how come we have these blind spots? How come we have these severe hesitations to pull the plug and stop it / start over. One answer to this could be this one by Kevin Systrom, Co-founder of Instagram. He said this in an interview with Tim Ferris:

It’s important to realize how people are just wired not to be honest. Not that they lie, I mean, I guess technically it’s a lie, but I don’t think it like comes from a bad place. They’re just wired to avoid conflict.

What this means is that people will always aim to be polite with you, and therefore hide their true feelings about your product. They don’t want the confrontation. Also, because of this, we keep encouraged to keep pouring resources into ‘it,’ one scrum cycle after another, ‘hoping’ to get it right, while we should take a 30000 ft view and realize it hit a dead-end alley. He added this:

The more important your company gets, the higher up you go, the fewer people are willing to do it [being honest]. So, you have to like dig for it, and that’s one of the weirdest feelings ever: please tell me something negative.

[…], and when someone gives you feedback, you don’t respond defensively. You say, ‘thank you.’ You encourage this behavior.

The challenge of asking the right questions

However, there’s more to it. To me, it’s also about ‘how you ask your questions.’ Too often, we end up with customer input that looks like specs. Creating specs is not their task; it’s yours. The responsibility of the customer is to give insights into their objectives and aspirations, and the challenges they run into to achieve this.

Brian Chesky, a co-founder of Airbnb, shared some of his views in his interview with Reed Hoffman, Co-founder of Linkedin. In short: the secret is in how we communicate with our customers throughout the life-cycle of our solution. Brian has a simple method for extracting detailed feedback from users, and the magic is simple: He doesn’t ask about the product he already built. He asks about the product of their dreams.

We’d ask these questions like, “What can we do to surprise you? What can we do, not to make this better, but to make you tell everyone about it?” The answer to that will be different. If I say, “What can I do to make this better?” They’ll say something small. If I were to say, “Reid, what would it take for me to design something that you would tell every single person you’ve ever encountered?” When you start to ask these questions, it helps you think through this problem.

The lesson to learn from this is: Being customer focused is good; however, it’s your responsibility to ask the right questions. It’s about working with your customers to identify the existing and new roadblocks that prevent them from hitting their important objectives and aspirations.

This allows you to get the focus on the essence and reveal new clues early on in the process that you are on the right track or entering a dead alley. The earlier you identify this, the better your opportunity to shift course — even if that means starting over again.

I would value to hear your take on this.

Startup Grind

The life, work, and tactics of entrepreneurs around the world. Welcoming submissions on technology trends, product design, growth strategies, and venture investing. Learn more about how you can get involved at startupgrind.com.

Ton Dobbe

Written by

Ton Dobbe

I help business software CEOs reimagine what can be, to deliver remarkable impact (again)

Startup Grind

The life, work, and tactics of entrepreneurs around the world. Welcoming submissions on technology trends, product design, growth strategies, and venture investing. Learn more about how you can get involved at startupgrind.com.

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