Why Product Teams Ignore Your Strategy

Breaking the Cycle of Strategic Fiction in Tech Companies

Every January used to feel like Groundhog Day – strategy sessions where I'd try to involve our product teams in planning the roadmap. But there was always a disconnect. Teams naturally focused on what they knew best – their immediate context, the challenges they faced daily, the opportunities right in front of them.

It's not that anyone was wrong. It's just hard for people immersed in specific product areas to suddenly rise several levels of abstraction higher. Meanwhile, leadership would work on the bigger picture, often without enough grounding in day-to-day realities.

Like Brian Chesky at Airbnb, being a hands-on founder helped bridge this gap. I lived in both worlds – the strategic vision and the product details. But I didn't want everything to depend so heavily on me.

Then something unexpected happened last year.

For the first time, I wasn't alone in seeing our future. Our CPO, Asya, synced with my vision – not through slide decks or strategy sessions, but by living it together. We pitched to investors in the Valley, got grilled in podcasts, walked the streets of New York between meetings, and watched each other explain our product to the world.

Somewhere between a tough investor question in Boston and a pitch in New York, our visions aligned. Not intellectually – viscerally.

That's when it hit me: strategy isn't something you write. It's something you live. Sometimes quite literally – like when Asya and I shared an Airbnb in Half Moon Bay, perched on a mountain in a house filled with crystals meant to ward off evil spirits. Nothing aligns strategic vision like debating product positioning while wondering if those crystals might interfere with our pitch deck.

Armed with this realization, we tried a completely different approach with our teams. And for the first time, it started working.

Let's talk about why strategic planning fails in most companies (the numbers are brutal) – and how we began turning fiction into reality at Welltory.

The Numbers Are Brutal

• 72% of strategic failures stem from disconnection between planners and doers — not from poor execution, but from flawed formulation (ISMA Research, 2024)

• While 89% of executives believe their strategy is clearly communicated, only 23% of frontline employees can actually articulate strategic priorities (Asana Research, 2023)

• Each management layer filters 18-22% of strategic content, meaning in a typical 5-layer organization, only 34% of the original strategy even reaches the operational level (Range Study, 2022)

This explains why most strategies never survive contact with reality — they're trapped in a fundamental disconnect between those who craft them and those meant to bring them to life.

The Real Reason: A Strategic Knowledge Gap

If we want product teams to participate in strategy — they need context. But here’s the paradox:

- Product teams don’t have enough context about the whole business: market, monetization, positioning, regulation, competitive dynamics.

- Leadership doesn’t have enough ground truth: user feedback, delivery friction, product reality.

"The top is too abstract, the bottom too narrow. And strategy dies in the middle."

This misalignment creates a broken loop:

- Executives create strategy without enough product insight.

- Teams ignore strategy because it feels irrelevant or ungrounded.

- Result: disconnected goals, weak execution, zero learning.

Weak execution - is a simple thing. When you make day-to-day decisions without strategic context, tons of your decisions are wrong or not optimal. So, this misalignment had tons of small consequences through the company’s processes.

People can’t just read the strategy. Recent neuroscience reinforces this: people don’t internalize strategy by listening to it. They need to formulate it themselves. fMRI studies show the brain retains 5x more strategic information when individuals discover or construct it themselves. The reward system (nucleus accumbens) activates 23% more strongly for self-generated ideas — increasing retention from 12% to 68% [PMC, 2023].

“Strategy fails when the people making it don’t know the details, and the people who know the details aren’t allowed to make it.”

The Symptoms of Dead Strategy

Let’s make this real. You might recognize your own company in some of these:

1. The PDF Strategy — the strategy deck is gorgeous. It lives in the CEO’s drive. No one else has read it. Everyone else is shipping tickets.

2. The Annual Offsite Illusion — you flew the team out, had sticky notes everywhere, inspirational talks. By February, you’re back to feature requests from sales.

3. Disconnected Roadmaps — one team is building gamification, another is rebuilding onboarding, and a third is launching a pricing experiment. None of it ladders up to a coherent bet.

4. Delivery Dominates — the only thing that matters is hitting sprint goals. Even if those sprints take you in circles. Velocity > direction.

5. No Feedback Loops — no one can tell you if the bet worked. Or if it was a bet. Or why you made it.

6. Strategic Mistrust — product managers nod when they hear the strategic vision… and then keep doing what they were doing. Because “strategy” feels abstract and out of touch. We had a really hard time syncing about bet on entertainment for a health app.

7. Strategic Overconfidence — leadership believes their 20-slide vision deck is all that’s needed. There’s no space for testing, refinement, or bottom-up feedback.

Even Spotify’s famous “squad model” eventually collapsed under its own weight. As former PM Jeremiah Lee noted, extreme autonomy led to chaos and fragmentation rather than innovation [source].

Google faced its own reckoning during the AI boom — forced to abandon its carefully planned roadmaps and switch into “Code Red” mode to compete with OpenAI’s lightning-fast iteration cycles [The Information].

If any of this feels familiar, you’re not alone. We lived it too.

What We Tried at Welltory

1. We started with a creative challenge

We launched a company-wide contest:

"How would you elegantly and efficiently move the company toward its new goal?"

We offered prizes — best concept overall, best from engineers, non-engineers, best feature idea, best long-term play, etc.

Some entries were wild but cool (like a reality show where people try to out-sleep each other). But others were deeply strategic. The winning idea tackled one of the hardest problems in digital health: food tracking. It proposed a new way to solve the core problem no one has cracked — how to get nutrition data without tedious manual logging or unreliable AI scans.

But more than the output, the process changed people’s mindset. Strategy became theirs. A lot of people spent a lot of time thinking about it.

2. We turned research into a shared process — and a context-building engine

Next, we mapped all the unknowns holding us back from making real bets — and assigned them out. But not based on job titles.

Engineers researched competitors. Designers unpacked reimbursement models. Marketers explored regulatory hurdles.

It wasn’t just cross-functional. It was contextual immersion. And it built the kind of strategic knowledge people usually assume they don’t need — until they do.

These learning dynamics are well-supported in organizational neuroscience. Context-building through domain switching and cross-functional exposure activates the Default Mode Network (DMN), enhancing concept integration and personal meaning formation [bioRxiv, 2024].

3. We ran team strategy sessions — but centered them on the company’s goals

Each team held a strategy session. But not “what’s our team plan?” Instead:

“What will it take for the company to reach its goal — and how can we help?”

Only once that was clear did teams consider their own roadmap. This one shift changed the entire quality of ideas.

We wrote more about this in [this post].

We were inspired by companies like Airbnb, where teams propose strategic bets and leadership helps refine and align them into the bigger picture [Lenny].

4. We have built our investor memo — together

Instead of leadership writing the memo alone, we co-created it. Teams contributed to:

- Competitive analysis

- Financial model inputs

- Strategic bets

- Risk narratives

AI team, data team, legal councils, product managers — everyone helped shape how we tell our story to investors. And in the process, many started seeing the business differently.

For the first time, we saw people ask themselves: “If I were an investor… would I bet on this?”.

What You Can Do Today

- In your next retro, ask: what did this teach us about our strategy?

- When reviewing roadmaps: what bet are we making, and what would falsify it?

- In your leadership sync: what knowledge do teams lack to think strategically?

- In your planning cycle: what if teams proposed, and leadership only gave feedback?

What’s Next

This was our first attempt at designing a more participatory, experience-driven strategy cycle. It’s far from perfect — but the change is real.

In our next essay, we’ll break down more about this Fractal Strategy framework: a new way to structure strategic learning, decision-making, and feedback loops inside product teams.

Because strategy isn’t what you write.

It’s how you think — together.