Product Operating Model Series: Learning Over Failure

Issue #221/ Wydanie #221

In today's edition, among other things:

💜 Editor’s Note: The Founder Mode Fallacy: Why CEO Product Ownership Is Treating Symptoms, Not Causes
💜 Product Operating Model Series: Learning Over Failure

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It will take you almost an hour to read this issue. Lots of content (or meat)! (For vegans - lots of tofu!).

Grab a notebook 📰 and your favorite beverage 🍵☕.

DeStaRe Foundation

Editor’s Note by Alex 💜

The Founder Mode Fallacy: Why CEO Product Ownership Is Treating Symptoms, Not Causes

Brian Chesky’s “founder mode” has become the product management community’s newest obsession. But here’s what nobody’s saying: Founder mode isn’t revealing CEO genius—it’s exposing product management’s 20-year failure to secure actual authority.

The narrative sounds compelling: Airbnb’s CEO personally oversees 50+ employees, reviews every project before it ships, and takes direct control of product decisions. The company is worth $79 billion and shipping 70 features per release. Meanwhile, traditional PM-led organizations are eliminating the role entirely, merging it with marketing, or watching CEOs reclaim product control.

The product management community responds with collective Stockholm syndrome: “See? We don’t need formal authority! We just need to ‘influence without power’ and ‘lead through storytelling!’” We’re celebrating the exact organizational dynamics that made us replaceable in the first place.

Here’s the uncomfortable truth the industry refuses to confront: Founder mode isn’t a solution to organizational dysfunction—it’s proof that we never built functioning product organizations to begin with.

Let me tell you what product management actually is in most companies. It’s not strategic leadership. It’s not customer advocacy. It’s not even product ownership in any meaningful sense.

Product management is a buffer layer—organizational shock absorbers positioned between executive vision and engineering execution to absorb cross-functional conflict while creating the illusion of user-centered decision-making.

Research on middle management reveals this function explicitly. Middle managers “occupy a central position in organizational hierarchies, where they are responsible for implementing senior management plans” while serving as “the bridge between senior leaders and frontline staff.” Their job isn’t to make strategic decisions—it’s to translate executive decisions into something implementable while managing the emotional labor of making teams feel heard.

When companies hire product managers, they’re not actually delegating strategic authority. They’re hiring diplomatic translators who can make “because the CEO said so” sound like “because our users need this.” The research confirms this: middle managers “interpret, communicate and translate organisational strategic goals into actions” while acting as “buffers to temper” organizational stress.

This explains a damning statistic: a seasoned PM with 10+ years experience reports “all the time it’s top-down. Crazy top-down, 9 out of 10 PMs just get told what to build!” Meanwhile, research shows only 24% of Product Owners feel empowered to actually do their jobs. The majority of PMs operate at what researcher Roman Pichler calls “level one empowerment”—deciding how to implement features that someone else decided to build.

When Chesky takes back product control, he’s not innovating. He’s just eliminating the buffer layer that was never given decision-making authority in the first place.

The product management profession spent two decades confusing activity with authority. We built elaborate frameworks—RICE prioritization, OKRs, Jobs-to-be-Done—and told ourselves this made us strategic. We facilitated workshops, synthesized research, and aligned stakeholders, believing these coordination activities proved our value.

But coordination without authority isn’t strategy. It’s project management with better slides.

Research on organizational empowerment reveals a brutal distinction. Strategic empowerment means authority to determine product direction, validate strategies, and allocate resources. Tactical empowerment means authority to decide implementation details within a predetermined scope. Most PMs have been operating with tactical empowerment while performing strategic theater.

This isn’t PMs’ fault—it’s how organizations designed the role. When companies “empowered” product teams, they typically meant: “You can decide how to build what we’ve already decided to build.” Research shows that when PMs lack strategic authority, “leadership gets involved in the details, thereby reducing autonomy” as a way to maintain control. The micromanagement PMs complain about isn’t executive dysfunction—it’s the natural consequence of operating without real authority.

Consider the cognitive dissonance: We celebrate PMs who “influence without authority” as if lacking formal power is somehow a professional strength. No other business function operates this way. Finance doesn’t influence budgets without authority. Legal doesn’t influence compliance without authority. But product management has normalized powerlessness as a virtue.

The Paul Adams quote captures this perfectly: “The underlying problem is almost always trust.” But that’s wrong. The underlying problem is that organizations never intended to give PMs trust-level authority in the first place. They hired PMs to absorb organizational friction, not to make strategic decisions.

Before we canonize founder mode, let’s examine what decades of organizational research reveals about CEO involvement in tactical product decisions.

Short-term: Sometimes Useful Research identifies legitimate scenarios for CEO involvement: training new employees, addressing underperformance, controlling high-risk situations, and establishing standards. This is founder mode’s valid use case—CEO as teacher, establishing quality bars through direct engagement.

Long-term: Systematically Destructive But research on sustained micromanagement (which is what daily product review really is) reveals consistent patterns:

Leadership studies show that managers who “put too much emphasis on daily operational details can miss the broader picture and fail to plan for departmental expansion.” When Chesky spends 35 hours per week reviewing work, he’s not demonstrating founder excellence—he’s exhibiting the same pattern that causes managers to “find themselves at considerable risk of burnout.”

Research on delegation proves the consequences: CEOs who excel at delegating generate 33% higher revenue (Gallup research). Not because delegation is some feel-good management philosophy, but because proper delegation enables specialized expertise to compound while freeing leadership to focus on genuine strategic work.

The micromanagement literature documents specific failure modes: decision bottlenecks (everything must pass through the CEO, slowing processes), reduced innovation (if the CEO is preoccupied with details, who’s thinking long-term?), dependence (what happens when the CEO is unavailable?), and suppressed talent development (teams never build decision-making muscles).

Marty Cagan, who knows something about product organizations, warned explicitly about the “CEO product manager” pattern, noting that teams end up feeling like “mercenaries” rather than empowered contributors. The research confirms this: when decision-making authority is centralized, “employees may feel that they aren’t given enough authority to make decisions or that senior management doesn’t adequately recognize their efforts.”

Here’s what nobody talks about: every company celebrating founder mode is simultaneously ensuring they’ll never develop internal product leadership capability.

Research on decision-making autonomy in organizations reveals a critical finding: “higher decision-making autonomy increases the probability of a subsidiary developing a product innovation.” When teams have authority to make product decisions, they develop the judgment, pattern recognition, and strategic thinking that creates genuine expertise.

Anders Ericsson’s research on expertise acquisition is unambiguous: developing expert-level performance requires deliberate practice—focused effort with immediate feedback on real decisions with real consequences. You cannot develop strategic product judgment by implementing someone else’s decisions. The neural pathways for strategic thinking only form through making actual strategic choices.

When Chesky reviews every decision, he’s preventing his product organization from developing the expertise that would make his involvement unnecessary. He’s creating learned helplessness disguised as quality control.

The research on empowerment confirms this pattern: “Employees that feel empowered are more inclined to take the initiative, feel important, and go above and beyond to accomplish collective goals.” When systematically denied decision-making authority, teams don’t just fail to develop capability—they actively learn that attempting strategic thinking is punished.

Consider Airbnb’s talent development strategy: they’re systematically training a product organization that can only execute well-reviewed decisions. What happens when Chesky leaves? When the company needs to 10x scale? When product complexity exceeds one person’s review capacity? They’ll face the same crisis Google faced post-Larry Page, Apple post-Jobs, Amazon post-Bezos—except these companies at least built product leadership benches during their founder era.

The real question isn’t whether CEOs should be involved in product decisions. It’s what organizational structures enable product teams to make decisions that CEOs want to be involved in reviewing.

Research on autonomy in product organizations identifies the actual pattern: “The underlying problem is almost always trust. If the lack of trust stems from the relationship, then a good place to start is the trust equation. If the lack of trust stems from hesitancy regarding competence, then it can be good to go through a PM skills competency matrix with leadership. However, most often, a lack of trust stems from leadership not feeling that there is enough alignment.”

Alignment, not authority, is the actual problem.

Amazon’s “Working Backwards” process isn’t about CEO control—it’s about creating alignment mechanisms that enable distributed decision-making. Every product starts with a press release defining customer value before any development begins. This isn’t Bezos reviewing every decision; it’s a system that ensures decisions align with customer value without requiring CEO approval.

Google’s OKR system (when properly implemented) creates alignment through shared objectives while leaving solution authority with teams. Spotify’s squad model enables autonomous decision-making within a clear strategic framework. These aren’t just “empowerment” theater—they’re systematic approaches to what researchers call “creating a shared brain” for decision-making.

The research on high-performing product organizations identifies consistent patterns: clear strategic direction from leadership, decision-making frameworks that enable local autonomy, capability development that builds expert judgment, and accountability systems that measure outcomes rather than activities.

Notice what’s missing? Daily CEO review. Personal oversight of 50 employees. Micromanagement rebranded as “standards-setting.”

The product management community faces an existential choice, and founder mode has clarified the stakes.

Option 1: Embrace Founder Mode Accept that product management was never meant to have strategic authority. Redefine the role as “CEO’s staff” or “implementation coordination” and stop pretending it’s strategic. Acknowledge that product success requires founder-level obsession and companies should either have founder-CEOs or shouldn’t exist.

This option is intellectually honest but practically catastrophic. It means every product organization is perpetually dependent on one person’s bandwidth, judgment, and availability. It means companies without product-obsessed founders cannot build great products. It means product management as a profession has no future.

Option 2: Demand Actual Authority Stop celebrating influence without power. Stop treating strategic empowerment as a “nice to have” instead of a requirement. Stop accepting that PMs should be grateful for coordination roles and storytelling opportunities.

Research proves that decision-making autonomy drives innovation, performance, and organizational capability. Teams with genuine authority develop expertise, make better decisions, and create sustainable competitive advantages. Organizations that properly delegate generate significantly higher revenue while building leadership benches that compound advantages over time.

But this requires something the product management community has been unwilling to demand: formal authority commensurate with accountability.

If PMs are responsible for product outcomes, they must have authority over product decisions. If they lack authority over decisions, they cannot be accountable for outcomes. The current situation—accountability without authority—is organizationally nonsensical and personally devastating.

Chesky’s founder mode moment is product management’s inflection point. For the first time, the industry is openly acknowledging what many have quietly experienced: most PMs don’t have real authority and many organizations are questioning whether they should.

We can respond with the familiar playbook—more frameworks, better storytelling, improved influence tactics—while pretending the fundamental power dynamics haven’t been exposed. Or we can acknowledge the brutal reality and demand systemic change.

If you want PMs to be implementation coordinators, call the role “Product Coordinator” and compensate accordingly. If you want strategic product leadership, grant actual decision-making authority and fire PMs who abuse it. Stop hiring people into roles with strategic accountability but tactical authority.

Research on organizational empowerment is explicit: “To transition from micromanagement to empowerment, leaders must first embrace a mindset shift. This involves recognizing the value of delegating authority and trusting in the capabilities of their team members.”

Implement what works: clear strategic frameworks that constrain decisions, capability development that builds expert judgment, decision-making systems that enable autonomous execution, and accountability structures that measure outcomes. This isn’t theory—it’s how every high-performing product organization actually operates.

For Product Managers: Stop Accepting Powerlessness as Professionalism

If you’re told to “influence without authority,” ask why this supposedly professional role lacks authority in the first place. If you’re accountable for outcomes but lack authority over decisions, document this misalignment and escalate it systematically.

The research is unambiguous: Product Owners who lack empowerment experience confusion and frustration. PMs operating without strategic authority cannot develop genuine expertise. Organizations that don’t delegate appropriately systematically underperform.

You have permission to demand: “I need level-three empowerment—authority over product strategy, not just feature implementation—or I need role clarity that I’m a feature coordinator, not a product manager.” This isn’t career-limiting audacity; it’s professional boundary-setting based on decades of organizational research.

For the Industry: Stop Celebrating Organizational Dysfunction

Prominent product leaders need to stop treating founder mode like innovation and start calling it what research proves it is: unsustainable micromanagement that prevents organizational capability development.

When Brian Chesky says he reviews every project before shipping, the response shouldn’t be admiration—it should be concern about Airbnb’s succession planning, organizational scalability, and leadership development strategy.

The industry needs to standardize around what research proves works: strategic empowerment for product leadership, systematic capability development, proper delegation structures, and accountability systems that enable autonomous decision-making within aligned frameworks.

Founder mode has done the product management community an accidental favor: it’s forced us to confront what we’ve been avoiding for two decades.

Most PMs don’t have real strategic authority. Most product organizations are structured around CEO decision-making with PM coordination support. Most “empowerment” is theater that makes teams feel heard while executives maintain actual control.

We can continue the comfortable fiction—celebrating influence without power, romanticizing storytelling over authority, pretending coordination equals strategy—while companies systematically eliminate or diminish the role.

Or we can acknowledge that product management as currently practiced isn’t working, demand the organizational changes that research proves enable success, and build the professional structures that make PM indispensable rather than replaceable.

The choice is binary: build genuine product organizations with appropriate authority structures, or admit that “product manager” is just a modern label for “CEO’s implementation staff.”

When your CEO next praises founder mode or suggests they need to be “more involved in product details,” you have a decision: nod along while your authority erodes, or respond with research-backed clarity: “That approach creates decision bottlenecks, prevents capability development, and generates 33% less revenue than proper delegation. Instead, let’s discuss the strategic alignment and capability development that would make your detailed involvement unnecessary.”

Will this be uncomfortable? Absolutely. But founder mode has already made everything uncomfortable. The question is whether you’ll accept diminishment disguised as innovation, or demand the organizational changes that decades of research prove actually work.

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Learning Over Failure: Quick Reference Guide

Product Operating Model Principle #20 from Marty Cagan’s Transformed

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Core Concept

“When you run an experiment in product discovery, there is no such concept of success or failure; there is only the question ‘What have we learned?’”

In many companies, deeply rooted fear of failure drives risk-averse behavior that prevents innovation. The learning-over-failure principle shifts focus from avoiding mistakes to rapidly discovering what works.

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Why This Matters

The Problem

• Fear of failure paralyzes teams and prevents innovation

• Organizations become unable to respond to market changes