Why CEOs Blow Up Good Product Work — And What Product Leaders Can Do About It
If you’ve been in product long enough, you’ve lived this scene:
Your team does everything right.
You run discovery. You validate the problem. You align cross-functionally.
Customers are excited.
Sales is relieved.
Even your CPO gives a thumbs up.
Then the CEO walks into the final review meeting.
Twenty minutes later, months of thoughtful work are suddenly upside down.
A new direction. A new mandate.
Often without a clear explanation.
It’s disorienting.
It’s frustrating.
And it happens far more often than people admit.
Product leaders quietly ask themselves:
Do CEOs know something we don’t?
Or are they simply not listening to the teams closest to customers, insights, and reality?
The truth is more complex — and far more interesting.
This pattern has followed me throughout my career
Across different organizations, I’ve seen multiple versions of this dynamic:
✔️ In one company, we worked hard to influence our leadership team to grant product enough autonomy to execute real strategy.
The result? One of the strongest product cycles of my career — clear wins, customer growth, and momentum that lifted the whole company.
✔️ In another, we built incredible things for years.
Customer adoption skyrocketed.
We were delivering value at scale.
But eventually, a major strategic redirection from the top unraveled years of sustained success.
(And I say this without blame — leadership complexities are real, and many factors contribute.)
✔️ At another company, product never had the conditions to truly lead.
Recommendations weren’t acted on, discovery was bypassed, and decisions were made reactively.
Every initiative struggled, not because the teams weren’t capable, but because the environment wasn’t built for product to succeed.
(I share this carefully — not as criticism, but as a reflection on what happens when product is asked to execute without clarity, alignment, or empowerment.)
And now, in my coaching practice, I see product managers and leaders living variations of these same stories every single week.
This isn’t about “good” CEOs and “bad” CEOs.
And it’s not about perfect product teams versus stubborn executives.
It’s about perspective gaps — and how they show up in the real world.
Truth #1: CEOs are playing a different game than Product
Good product teams optimize for:
Customer value
Evidence from research
Cohesive product strategy
Execution feasibility
CEOs optimize for:
Fundraising narratives
Investor expectations
Market positioning
Company survival
Strategic bets
Board pressure
Margin and runway
From Product’s vantage point, the roadmap is sound.
From the CEO’s vantage point, that same roadmap may:
Complicate operational scale
Undermine the story they need to tell investors
Threaten short-term revenue during a critical period
Pull the business away from the positioning they believe will win
Sometimes the CEO really is seeing a risk Product hasn’t internalized.
But because the “why” is rarely communicated, the shift feels arbitrary.
Truth #2: Founders often become anchored to the insights that made them successful
Founders succeed because they hold a deep intuition about the original product/market fit.
That intuition becomes their north star.
But as markets evolve, that north star sometimes points to a past version of the company rather than its future.
This shows up as:
Over-attachment to early product DNA
Fear of breaking the original magic
Gut-driven overrides rooted in identity, not data
Product sees:
“The market has changed — why are we stuck?”
The CEO feels:
“If we lose this, we lose who we are.”
Neither is wrong.
Both are incomplete.
Truth #3: Strategy misalignment always surfaces as last-minute roadmap blowups
If executives are not truly aligned on:
Target segments
Core product bets
Positioning
Differentiation strategy
Revenue model
Time horizons
…then that misalignment will always show up downstream as surprise vetoes.
Product teams make smart decisions inside their frame.
CEOs make abrupt decisions above that frame.
Both think they’re fixing the problem.
Neither realizes they’re working from different assumptions.
Truth #4: Sometimes it is fear, pressure, ego, or emotional overload
We have to name this too.
A CEO under pressure may:
Clamp down to regain control
React to a single big customer anecdote
Chase an urgent revenue patch
Override to soothe anxiety
Default to old patterns when stressed
This is not about villainizing CEOs.
Leadership comes with intense visibility and responsibility.
But emotional decision-making at the top can unintentionally destabilize product teams, especially when explanations are missing.
So who’s right — Product or the CEO?
The honest answer:
Both are holding a truth.
Neither has the whole truth.
And the system for sharing those truths is broken.
That’s why it feels impossible.
That’s why it feels personal.
That’s why even the best PMs question themselves.
And that’s why this pattern repeats across companies, industries, and product leaders.
What Product Leaders Can Actually Do
Here’s what consistently helps — across companies, across teams, and across the PMs I coach.
1. Get curious about the meta decision, not the decision
Instead of defending the roadmap, ask:
“What risk are we not addressing here?”
“What story are you trying to protect?”
“What has shifted in the business that we should account for?”
“What outcome do you most want to secure in the next 6–12 months?”
These questions elevate the conversation to the real level of decision-making — strategy, not features.
2. Translate your insights into CEO-language
PMs speak discovery.
CEOs speak risk, runway, narrative.
So articulate your work in terms of:
Revenue
Margin
Competitive position
Defensibility
Investment story
Strategic risk
Customer lifetime value
You’re not changing your work — you’re changing the format.
3. Pre-wire everything
Avoid surprises.
Send early memos.
Share assumptions.
Ask for constraints up front.
The product review should never be the first time the CEO engages with the direction.
4. Offer options, not ultimatums
Bring three versions of the plan:
Conservative – low risk
Balanced – medium risk
Bold – high reward
Let executives choose their risk appetite.
5. Protect the team when chaos becomes normal
If pattern after pattern repeats, and nothing changes, product leaders often have to:
Push for strategy artifacts
Clarify “empowerment” vs “execution”
Shield teams from thrash
Set boundaries on last-minute pivots
Advocate for clarity in decision-making
This is part of courageous product leadership.
A gentle mirror for CEOs
If you’re a CEO reading this:
Your clarity is stabilizing.
Your opacity is destabilizing.
Your veto is powerful.
Your context is essential.
When you override without explaining the why, product teams aren’t resisting you — they’re operating in the dark.
When you share your constraints, your fears, your bets, your vision…
Product doesn’t just align. It accelerates.
Great products are built when leaders share the same bet — even if they argue passionately on the way there.
Closing: What I’ve learned across companies and coaching PMs
After a career leading product in high-growth environments and now coaching PMs across the industry, here’s my honest reflection:
There is no single truth.
No single pattern.
No perfect playbook.
Sometimes the CEO is right.
Sometimes the product team is right.
Most of the time, each holds a piece of the puzzle.
But the breakthroughs happen when both sides:
Share context
Challenge assumptions
Name constraints
Align on the core bet
And operate from a place of partnership, not hierarchy
My hope is that these reflections create clarity — not conclusions, but a more grounded lens — for every product leader navigating this complex, high-stakes environment.
If you’re living this tension right now, you’re not alone.
And there are ways through it.