Why I Asked My Product Team to Roast Me
A founder's experiment in building teams that think, not just ship
Here's a striking paradox of modern tech companies: While highly aligned organizations grow revenue 58% faster and are 72% more profitable than their peers, most strategic planning sessions still focus primarily on roadmaps and OKRs.
At Welltory, we're in the midst of reinventing our product – new architecture, new technologies, new market positioning. This transformation demands not just technical excellence but deep strategic understanding from every team member.
So when one of our core product teams gathered for their annual strategy session on a small island in the middle of nowhere (the best place for uninterrupted thinking), we decided to try something different. Instead of another roadmap review, we focused on expanding their strategic horizons. The results surprised us all.
What emerged wasn't just a better way to run a product team. It was a complete rethinking of what makes teams truly valuable in an age where AI can handle most routine tasks. And it started with a simple metaphor of a traveler in unknown lands...
From Feature Factory to Strategic Force
Think of a product team member as a traveler in an unknown land. To succeed, they need two fundamental things:
1. A Sense of Orientation
- Where am I on the map?
- Where am I going?
- Why this direction and not another?
2. Knowledge of the Terrain
- What dangers lie ahead?
- Where to find resources?
- How to navigate effectively?
This metaphor emerged when we challenged our basic assumptions about product teams. The traditional definition by Marty Cagan says a team must deliver business value, create user value, work efficiently, and avoid risks. But this session helped us discover what makes in-house teams truly valuable: their ability to both navigate strategically ("orientation") and deeply understand their environment ("terrain knowledge").
Learning Through Fire: What Actually Worked
Instead of PowerPoint presentations and documentation, we created experiences that forced real learning:
1. The Strategic Pitch Challenge
We split our product team into mini-teams and asked them to pitch our company to "investors" from different angles: business model excellence, user value and product-market fit, or technical capabilities. Here's the twist: we deliberately excluded subject matter experts from their areas of expertise.
A team pitching our technical architecture couldn't include engineers. Those explaining our user acquisition and monetization strategy couldn't include product managers or analysts. This wasn't just role-playing - it was a carefully designed exercise in discovering knowledge gaps.
When you have to explain something you don't fully understand, you can't hide behind jargon or assumptions. You have to build real understanding. The discomfort created natural curiosity and motivation to learn - not because someone told them to, but because they experienced the need firsthand.
2. The Founder's Hot Seat (or "Try to Break Our Strategy")
Every morning of our strategic session started with what we half-jokingly called "roasting the founder." The goal wasn't just to question strategy – it was to try to break it. Find the holes. Expose the weak logic. Discover hidden assumptions.
"Why focus on stress, not sleep?"
"What if Apple adds this feature tomorrow?"
"Why aren't we..."
"But what about..."
But here's the magic that happened: in trying to break the strategy, the team actually built something more valuable – a deep, intuitive understanding of how everything connects. Every challenge forced them to think through chain reactions. Every attempt to find a hole helped them see new connections.
It's like trying to break someone's chess strategy – you end up understanding the game at a much deeper level. By the end, the team wasn't just following a strategy they'd been told; they had built their own mental model of how all the pieces fit together.
3. The Team's Value Proposition
Then came the crucial question: "Why does the company need us? Why not outsource everything or just acquire successful startups in our space?"
The team had to articulate their unique value proposition to the company. This wasn't about defending jobs – it was about deeply understanding their strategic role. Why are we better than outsourcing? What value do we bring that you can't get by acquiring niche startups?
This exercise forced the team to think beyond just executing tasks. They had to understand their role in the company's broader strategy and articulate their unique contribution to its success.
4. The Future Scripts Exercise
Finally, we brought everything to our team's strategy. We ran two fascinating thought experiments about our yearly goals: First, teams had to imagine and describe in detail how we brilliantly achieved all our ambitious goals - what specific actions and decisions led to this success? Then came the flip side: what exactly did we do to completely fail these same goals?
This wasn't just positive/negative thinking. By forcing teams to think through detailed scenarios of both spectacular success and failure, we helped them understand dependencies, potential pitfalls, and success factors. It's amazing how much clearer your path becomes when you've already "lived through" both the best and worst possible outcomes.
The Minimum Knowledge Framework: Your Navigation Kit
Remember our traveler metaphor? Well, here's the essential knowledge that helps you navigate the product landscape. Think of it as your survival kit – not everything you might ever need, but the critical tools that make the difference between thriving and just surviving.
Market & Competition
Can you walk into a bar and explain why someone would choose us over Oura or Whoop? Not just feature comparison – real understanding of where the market is going and why investors are betting on certain trends.
User Understanding
Can you open our analytics right now and verify your hunch about user behavior? Have you talked to real users? Do you know what they actually value and pay for (not what we think they should)? Could you jump on support for a day if needed?
Technical Reality
You don't need to write code, but you should understand our systems like a traveler understands their gear. What breaks when we scale? How do features connect? What's our real AI capability (not the marketing version)?
Business Model
Where does money come from and go? What's our "aha moment" and how do we get users there? Which features drive revenue? A good product decision that ignores business reality is actually a bad decision.
Domain Knowledge
We're building health tech – you need to understand health. What actually impacts wellbeing? What can we realistically promise users? Enough knowledge to call BS on bad health advice.
Company Journey
What experiments failed and why? What keeps our CEO up at night? Why these priorities and not others? You should understand enough to meaningfully challenge strategic decisions.
Strategy Map & Team Role
Like any group of travelers, we need to know not just the terrain, but our destination and path. Can you articulate our mission beyond the obvious? Do you understand our key strategic bets and why we chose them? Most importantly – do you know your team's role in this journey?
It's not enough to know where we're going. You need to understand how your team depends on others and how they depend on you. Like a climbing expedition, each team has their crucial role – if the route finders don't coordinate with the base camp team, nobody reaches the summit.
The key? You don't need deep expertise in everything, but you need enough context to make smart decisions in your domain. Like our traveler needs to understand both the map (where we're going) and the terrain (what we're dealing with).
Think of it this way: AI can write code and design interfaces, but it can't understand why a technically perfect feature might fail in our specific context. That's where this knowledge makes all the difference.
The Hidden Enemies of Learning
During these exercises, we discovered two major cognitive biases that hold teams back:
1. The "Doing vs. Thinking" Fallacy
In tech, there's a persistent belief that thinking isn't "real work." We're trained to value shipping features, pushing code, and hitting metrics. Taking time to think, understand context, and build mental models feels wrong - almost guilty. This industrial-age mindset of valuing output over understanding is becoming increasingly dangerous in the AI era.
2. The Narrow Expertise Trap
We've been conditioned to value deep, narrow expertise - the specialist who knows everything about a specific domain. This made sense in a slower-moving world. But in an environment where technology and markets change rapidly, this narrow focus can become a liability. Yet many resist broadening their knowledge because "that's not my job" or "I need to stay focused on my expertise."
Looking Ahead
This strategic session was just our first experiment in rethinking how product teams learn and grow. As I watch specialized AI agents evolve for coding, design, and analytics, I'm increasingly convinced we're on the right track.
McKinsey defines strategy as "making non-obvious bets in the face of uncertainty that will create strong competitive advantages and high speed growth if executed well." This perfectly captures what AI can't do: think in uncertainty, see non-obvious connections, and hold complex contextual pictures that haven't yet become common knowledge.
While AI excels at predicting what's wanted based on past patterns, it can't truly think strategically or understand novel contexts. It can't make those non-obvious bets that come from a deep understanding of interconnected realities. After all, in a world of high speed, high uncertainty, and AI, our ability to think strategically and see non-obvious connections isn't just nice to have—it's a key to our survival.
We're now designing a year-long program to implement these principles across all our teams. While our experiments are just beginning, I'd love to hear what practices have worked in your experience.