The Interview That Sparked This Essay

Joe 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 Arc

Joe’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 Feedback

If 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 Everything

Joe 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 Founders

You 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 adoption.

One of the most powerful tools you can use as a PM is explicitly framing your product decisions as explicit choices, rather than proposals seeking validation. For example:

Instead of saying:“We are planning to build a new onboarding flow. Here is the design. Thoughts?”

Say:“We are deciding between optimizing retention or acquisition next quarter. If we choose retention, the main lever is onboarding friction. Here are two possible approaches. Which outcome matters more to the business right now?”

In the second framing:

* The business goal is visible.

* The tradeoff is unavoidable.

* The decision owner is clear.

* The conversation becomes real.

This is how PMs build credibility and influence: not through slides or persuasion, but through framing decisions clearly.

Jaide’s Pivot: From Health Search to AI Translation

The result of Joe’s reframed feedback approach was unambiguous.

Across dozens of conversations with healthcare executives and hospital leaders, one pattern emerged consistently:

Translation was the urgent, budget-backed, economically meaningful problem.

As Joe put it, after talking to more than 40 healthcare decision-makers:

“Every single person told us to build the translation product. Not mostly. Not many. Every single one.”

This kind of clarity is rare in product strategy. When you get it, you do not ignore it. You move.

Jaide Health shifted its core focus to solving a very real, very measurable, and very painful problem in healthcare: the language gap affecting millions of patients.

More than 25 million patients in the United States do not speak English well enough to communicate with clinicians. This leads to measurable harm:

* Longer hospital stays

* Increased readmission rates

* Higher medical error rates

* Lower comprehension of discharge instructions

The status quo for translation relies on human interpreters who are expensive, limited, slow to schedule, and often unavailable after hours or in rare languages. Many clinicians, due to lack of resources, simply use Google Translate privately on their phones. They know this is not secure or compliant, but they feel like they have no better option.

So Jaide built a platform that integrates compliance, healthcare-specific terminology, workflow embedding, custom glossaries, discharge summaries, and real-time accessibility.

This is not simply “healthcare plus GPT”. It is targeted, workflow-integrated, risk-aware operational excellence.

Product managers should study this pattern closely.

The winning strategy was not inventing a new problem. It was solving a painful problem that everyone already agreed mattered.

The Core PM Lesson: Focus on Problems With Urgent Budgets Behind Them

A question I often ask PMs I coach:

Who loses sleep if this problem is not solved?

If the answer is:

* “Not sure”

* “Eventually the business will feel it”

* “It would improve the experience”

* “It could move a KPI if adoption increases”

Then you do not have a real problem yet.

Real product opportunities have:

* A user who is blocked from achieving something meaningful

* A measurable cost or consequence of inaction

* An internal champion with authority to push change

* An adjacent workflow that your product can attach to immediately

* A budget owner who is willing to pay now, not later

Healthcare translation checks every box. That is why Joe now has institutional adoption and a business with meaningful traction behind it.

Why PMs Struggle With This in Practice

If the lesson seems obvious, why do so many PMs fall into the encouragement trap?

The reason is emotional more than analytical.

It is uncomfortable to confront the possibility that your idea, feature, roadmap, strategy, or deck is not compelling enough yet. It is easier to seek validation than truth.

In my first startup, we kept our product in closed beta for months longer than we should have. We told ourselves we were refining the UX, improving onboarding, solidifying architecture. The real reason, which I only admitted years later, was that I was afraid the product was not good enough. I delayed reality to protect my ego.

In product work, speed of invalidation is as important as speed of iteration.

If something is not working, you need to know as quickly as possible. The faster you learn, the more shots you get. The best PMs do not fall in love with their solutions. They fall in love with the moments of clarity that allow them to change direction quickly.

Actionable Advice for Early and Mid Career PMs

Below are specific behaviors and habits you can put into practice immediately.

1. Always test product concepts as choices, not presentations

Instead of asking:“What do you think of this idea?”

Ask:“We are deciding between these two approaches. Which one is more important for you right now and why?”

This forces prioritization, not politeness.

2. Never ship a feature without observing real usage inside the workflow

A feature that exists but is not used does not exist.

Sit next to users. Watch screen behavior. Listen to their muttering. Ask where they hesitate. And most importantly, observe what they do after they close your product.

That is where the real friction lives.

3. Always ask: What is the cost of not solving this?

If there is no real cost of inaction, the feature will not drive adoption.

Impact must be felt, not imagined.

4. Look for users with strong emotional urgency, not polite agreement

When someone says:“This would be helpful.”

That is death.

When someone says:“I need this and I need it now.”

That is life.

Find urgency. Design around urgency. Ignore politeness.

5. Know the business model of your customer better than they do

This is where many PMs plateau.

If you want to be taken seriously by executives, you must understand:

* How your customer makes money

* What costs they must manage

* Which levers influence financial outcomes

When PMs learn to speak in revenue, cost, and risk instead of features, priorities, and backlog, their influence changes instantly.

The Broader Strategic Question: What Happens When Foundational Models Improve?

During our conversation, I asked Joe whether the rapid improvement of GPT-like translation will eventually make specialized healthcare translation unnecessary.

His answer was pragmatic:

“Our goal is to ride the wave. The best technology alone does not win. The integrated solution that solves the real problem wins.”

This is another crucial product lesson:

* Foundational models are table stakes.

* Differentiation comes from workflow integration, specialization, compliance, and trust.

* Adoption is driven by reducing operational friction.

In other words:

In AI-first product strategy, the model is the engine. The workflow is the vehicle. The customer problem is the road.

The Future of Product Work: Judgment Over Output

The world is changing. Tools are accelerating. Capabilities are compounding. But the core skill of product leadership remains the same:

Can you tell the difference between signal and noise, urgency and politeness, truth and encouragement?

That is judgment.

Product management will increasingly become less about writing PRDs or pushing execution and more about identifying the real problem worth solving, framing tradeoffs clearly, and navigating ambiguity with confidence and clarity.

The PMs who will thrive in the coming decade are those who learn how to ask better questions.

Closing

This conversation with Joe reminded me that most of the time, product failure is not the result of a bad idea. It is the result of insufficient clarity. The clarity does not come from thinking harder. It comes from testing real choices, with real users, in real workflows, and asking questions that force truth rather than encouragement.

If this resonates and you want help sharpening your product judgment, improving your influence with executives, developing clarity in your roadmap, or navigating career transitions, I work 1:1 with a small number of PMs, founders, and product executives.

You can learn more at tomleungcoaching.com.

OK. Enough pontificating. Let’s ship greatness.