The Difference Between Encouragement and Truth: Lessons From Building What People Actually Need

The Interview That Sparked This EssayJoe Corkery and I worked together at Google years ago, and he has since gone on to build a venture-backed company tackling a real and systemic problem in healthcare communication. This essay is my attempt to synthesize that conversation. It is written for early and mid career PMs in Silicon Valley who want to get sharper at product judgment, market discovery, customer validation, and knowing the difference between encouragement and signal. If you feel like you have ever shipped something, presented it to customers, and then heard polite nodding instead of movement and urgency, this is for you.Joe’s Unusual Career ArcJoe’s background is not typical for a founder. He is a software engineer. And a physician. And someone who has led business development in the pharmaceutical industry. That multidisciplinary profile allowed him to see something that many insiders miss: healthcare is full of problems that everyone acknowledges, yet very few organizations are structurally capable of solving.When Joe joined Google Cloud in 2014, he helped start the healthcare and life sciences product org. Yet the timing was difficult. As he put it:“The world wasn’t ready or Google wasn’t ready to do healthcare.” So instead of building healthcare products right away, he spent two years working on security, compliance, and privacy. That detour will matter later, because it set the foundation for everything he is now doing at Jaide.Years later, he left Google to build a healthcare company focused initially on guided healthcare search, particularly for women’s health. The idea resonated emotionally. Every customer interview validated the need. Investors said it was important. Healthcare organizations nodded enthusiastically.And yet, there was no traction.This created a familiar and emotionally challenging founder dilemma:* When everyone is encouraging you* But no one will pay you or adopt early* How do you know if you are early, unlucky, or wrong?This is the question at the heart of product strategy.False Positives: Why Encouragement Is Not FeedbackIf you have worked as a PM or founder for more than a few weeks, you have encountered positive feedback that turned out to be meaningless. People love your idea. Executives praise your clarity. Customers tell you they would definitely use it. Friends offer supportive high-fives.But then nothing moves.As Joe put it:“Everyone wanted to be supportive. But that makes it hard to know whether you’re actually on the right path.” This is not because people are dishonest. It is because people are kind, polite, and socially conditioned to encourage enthusiasm. In Silicon Valley especially, we celebrate ambition. We praise risk-taking. We cheer for the founder-in-the-garage mythology. If someone tells you that your idea is flawed, they fear they are crushing your passion.So even when we explicitly ask for brutal honesty, people soften their answers.This is the false positive trap.And if you misread encouragement as traction, you can waste months or even years.The Small Framing Change That Changes EverythingJoe eventually realized that the problem was not the idea itself. The problem was how he was asking for feedback.When you present your idea as the idea, people naturally react supportively:* “That’s really interesting.”* “I could see that being useful.”* “This is definitely needed.”But when you instead present two competing ideas and ask someone to help you choose, you change the psychology of the conversation entirely.Joe explained it this way:“When we said, ‘We are building this. What do you think?’ people wanted to be encouraging. But when we asked, ‘We are choosing between these two products. Which one should we build?’ it gave them permission to actually critique.” This shift is subtle, but powerful. Suddenly:* People contrast.* Their reasoning surfaces.* Their hesitation becomes visible.* Their priorities emerge with clarity.By asking someone to choose between two ideas, you activate their decision-making brain instead of their supportive brain.It is no different from usability testing. If you show someone a screen and ask what they think, they are polite. If you give them a task and ask them to complete it, their actual friction appears immediately.In product discovery, friction is truth.How This Applies to PMs, Not Just FoundersYou may be thinking: this is interesting for entrepreneurs, but I work inside a company. I have stakeholders, OKRs, a roadmap, and a backlog that already feels too full.This technique is actually more relevant for PMs inside companies than for founders.Inside organizations, political encouragement is even more pervasive:* Leaders say they want innovation, but are risk averse.* Cross-functional partners smile in meetings, but quietly maintain objections.* Engineers nod when you present the roadmap, but may not believe in it.* Customers say they like your idea, but do not prioritize ...