Stop Reorganizing Your Roadmap Every Quarter (Do This Instead)
A field guide to navigating strategic whiplash
Last week I was shopping for a Sonos speaker. I own another Sonos product and logged in to my account to check out. This was what I saw:
I was hoping for a better price and decided to check other sites. I then opened an incognito window to shop, and lo and behold, the price was now $369!
The company that just announced a $12 billion strategy to get existing customers to buy more... was giving new customers a better deal.
I had to laugh. Not because it was funny, but because I have seen this movie before.
You probably have too.
Your CEO announces a strategic pivot in the quarterly all-hands. “We’re shifting from acquisition to retention.” Or “Enterprise is now the priority.” Or “We’re going upmarket.”
The strategy sounds great. The logic is sound. Leadership is aligned and all-in.
Then nothing changes.
Marketing keeps running acquisition campaigns. Sales keeps closing SMB deals. Product continues to add features for new users. Your roadmap gets shuffled. Again.
Three months later, leadership is frustrated that “the strategy isn’t working.” Six months later, they announce yet another pivot. Your roadmap gets reshuffled. Again.
And you’re stuck in the middle, watching the pattern repeat.
Here’s what I’ve learned:
You can’t always change the systems. But you can learn to read them. And reading them correctly by spotting the gap between stated strategy and embedded incentive is one of the most valuable skills you can develop as a product leader.
It’s the difference between:
Thrashing your roadmap every quarter chasing strategic announcements
Building credibility by predicting what will actually happen
Protecting your team’s focus for work that will actually get resourced and rewarded
Let me show you how.
The Pattern: Three Levels of Misalignment
When leadership announces a strategic pivot, misalignment happens at three levels. Learn to spot them, and you’ll know within 30 days whether the pivot is real or performative.
Level 1: Who Owns the New Number?
What to look for:
When strategy changes, someone needs to own the new primary metric. Not track it on a dashboard. Own it. As in: they get headcount for it, their roadmap prioritizes it, their 1:1s focus on it, their bonus depends on it.
The diagnostic questions:
After the strategic announcement, ask yourself:
Who owns [new strategic priority] as their primary KPI?
Is it their #1 metric or their #5 metric?
Did they get headcount allocated to support it?
Did their roadmap shift to reflect it?
Do they have the budget authority to move it?
Does the sales comp plan actually reflect it?
Example from my advisory practice:
My client, a SaaS company, announced that it was “shifting to enterprise.” I asked the VP of Product: “Who owns enterprise revenue as their primary KPI?”
Silence.
Then I looked at what actually happened:
Product roadmap: Still 70% features for SMB users (”protect existing revenue”)
No new PMs hired specifically for enterprise features
Sales comp still paid the same for $10K SMB deals as $100K enterprise deals
Marketing still measured on MQLs (which favored high-volume SMB)
Sprint planning: Enterprise features consistently deprioritized when timelines got tight
Nobody owned enterprise revenue. Which meant enterprise wasn’t actually the strategy—it was an aspiration.
What you can’t control:
You can’t assign ownership to others. You can’t allocate headcount to other teams. You may not even be able to influence those decisions.
What you can control:
You can spot the gap.
And you can use it to predict what will actually happen.
When no one owns the new metric, and there are no actual resources behind it, the old strategy continues. Save your team’s energy for work that aligns with what’s actually being resourced and measured, not what’s being announced.
Level 2: What Are the System Constraints?
What to look for:
Strategic pivots don’t happen in a vacuum. They happen inside systems that have inertia — roadmaps committed to customers, sprints already planned, engineering capacity already allocated, technical debt that cannot be delayed, comp. cycles that lock in annually, partner relationships built over years.
The diagnostic questions:
What’s already on the roadmap that can’t be stopped? (Customer commitments, contractual obligations, dependencies)
Where is engineering capacity already allocated? (What gets cut to make room for the new priority?)
What sprint/planning cycles constrain rapid change? (Are you mid-quarter? Mid-release cycle?)
How long ago was this year’s comp plan locked in? (Usually 3-6 months before the fiscal year)
What partner/customer commitments constrain pivoting? (APIs, integrations, SLAs)
Who has the authority to override these constraints? (And will they actually use it?)
Example from above, continued:
The company announced that it was “going upmarket so they can focus on quality over speed.”
But:
The roadmap had 3 major features committed to existing customers for the next two quarters
Engineering had just staffed two new teams focused on SMB feature velocity
Product demos in all-hands still celebrated “features shipped this quarter.”
The Q3 OKRs (set 6 weeks ago) were all about shipping velocity
No one got approval to slip committed dates in the name of quality
There was a hiring freeze with no signs of a thaw
Even if the product team wanted to pivot immediately, they had:
24 weeks of committed work over the next 2 quarters that they couldn’t stop
A team structure optimized for the old strategy
OKRs locked until next quarter
No air cover to miss commitments
The strategy was right. The timeline was impossible.
What you can’t control:
You can’t change the constraints. Roadmap commitments, team structures, and planning cycles, especially, are often locked in at the C-suite level.
What you can control:
You can map the constraints and predict a realistic timeline.
If roadmap commitments run through Q1 next year, and team reorgs happen in Q2, and OKRs are updated by then, the earliest you’ll see actual execution shift is 6 to 9 months from now.
Plan accordingly. Don’t burn your team out trying to execute a strategy that the systems won’t support for another two quarters.
Level 3: What Behavior Is Actually Being Rewarded?
What to look for:
This is the most important level because it reveals the truth.
Forget what the strategy says. Watch what gets demo’d in all-hands. Watch what gets people promoted. Watch what wins engineering resources in sprint planning when there’s a conflict. Watch what gets deprioritized when timelines slip.
The diagnostic questions:
What work got someone promoted recently?
What wins get celebrated in all-hands or demo days?
When engineering capacity is constrained, what gets staffed and what gets backlogged?
What does leadership actually review in planning meetings? (Look at their agendas)
What “misses” get you in trouble vs. excused?
When features compete for resources, which type wins?
Another example from my practice:
A company said, “customer experience is everything” and “quality over speed.”
Then they:
Cut the support team first during a downsizing, replacing them with AI agents
Promoted the Product Leader whose team shipped fastest, even though their features had the highest bug rates
Celebrated “features shipped this quarter” in every all-hands, not customer satisfaction improvements.
Consistently staffed new feature work over tech debt or quality improvements
Excused bugs as “we’ll fix it in the tech. debt sprint” (which never came)
When asked to choose between hitting a launch date or improving quality, always chose the date, citing competition
The stated priority: quality and customer experience. The rewarded behavior: ship fast, worry about quality later.
What you can’t control:
You can’t change what gets rewarded at the company level. That’s culture and leadership, which moves slowly.
What you can control:
You can align your roadmap and team’s work to what’s actually rewarded, not what’s stated.
If velocity is what gets celebrated and resourced, optimize for shipping. If acquisition features are what get staffed and demo’d, focus there. If you optimize for the stated strategy while everyone else optimizes for the embedded incentives, your roadmap will get deprioritized, and your team will get frustrated.
This isn’t cynical. It’s realistic.
How to Use This as a Product Leader
You’re not the CEO (no, not even of your own product). You can’t change comp. plans, rewrite OKRs, or restructure the organization.
But you can use pattern recognition to:
1. Protect Your Team from Roadmap Whiplash
When leadership announces a pivot, your team looks to you for direction. They’re asking: “Should we drop everything and reorganize the roadmap around this new priority?”
Instead of immediately reshuffling sprints, pause. Run the diagnostics above. Then tell your team:
If systems are aligned: “Yes, this is real. Here’s how we’re reprioritizing. Here’s what we’re stopping and what we’re starting.”
If systems aren’t aligned: “Leadership is serious about this direction. But the systems won’t support it until [Q3/next planning cycle/after this release]. Here’s what we’re continuing now, and here’s when we’ll shift.”
This prevents your team from:
Thrashing between priorities every quarter
Starting work that won’t get resourced or won’t make it to launch
Becoming cynical about every strategic announcement
Losing focus on work that’s actually getting measured
2. Build Credibility by Predicting Reality
The leaders who advance aren’t the ones who repeat strategy slides. They’re the ones who accurately predict what will actually ship and what will get deprioritized.
When you can say: “Leadership announced X, but based on [roadmap constraints/resource allocation/rewarded behaviors], here’s what I think will actually happen”—and then be proven right—you build enormous credibility.
Example:
Leadership announces: “We’re enterprise-focused now.”
You say (in your 1:1 with your director): “I think we’ll see some enterprise features ship in Q3-Q4 next year, but we won’t see the roadmap meaningfully shift until next planning cycle, when we can reallocate teams. In the meantime, we have 12 weeks of SMB commitments we can’t break. I’m planning to keep 70% of my roadmap on committed SMB work and explore 30% on early enterprise validation.”
Six months later, you’re proven right. Your director remembers that you called it. Your team stayed focused instead of thrashing.
3. Choose Your Battles Wisely
Not every strategy-incentive gap is worth fighting.
Some gaps are temporary (systems just need time to catch up). Some gaps are intentional (leadership knows but isn’t ready to communicate the constraints publicly). Some gaps are permanent (conflicting priorities that will never fully align).
Temporary gaps: Acknowledge them, plan for the transition timeline, protect your roadmap from short-term thrashing.
Intentional gaps: Work the back channels to understand the real constraints, plan your roadmap accordingly.
Permanent gaps: Accept that you’re operating in a company with conflicting priorities. Optimize for what’s actually rewarded, not what’s stated. Or start looking for a company with better alignment.
The mistake is treating every announcement as gospel and immediately reorganizing your roadmap. The wisdom is recognizing which announcements have teeth and which are aspirational.
4. Surface Contradictions (Carefully)
You can’t change the systems, but you can make the contradictions visible. But be careful, and do it right.
Bad approach: “This strategy won’t work because we don’t have the engineering capacity.”
(This makes you sound like a naysayer. Leadership already knows this. They’re either working on it or dealing with constraints you don’t see.)
Better approach: “I’m excited about this direction. To help my team plan the roadmap around it, I need clarity on a few things: Who owns [metric] as their primary KPI? When can we expect the headcount/capacity allocated to this? What existing roadmap commitments can we renegotiate? What’s the timeline for the shift?”
Frame it as seeking clarity to execute, not as poking holes in the strategy.
If you get clear answers, great—you have a timeline to plan against. If you get vague answers, that’s also useful data. It indicates the systems aren’t yet aligned, so you should plan conservatively.
5. Document the Pattern
When you spot strategy-incentive misalignment, document it. Not to be vindictive, but to build your own mental models.
Keep a simple log:
Date: Strategic announcement
Stated priority: What leadership said
System changes: What actually changed in roadmap/resourcing in the following 30/60/90 days
Outcome: What actually shipped vs. what was announced
Over time, you’ll see patterns:
Does your company typically align systems within one quarter? Two quarters? Never?
Which types of pivots get operationalized vs. which stay on slides?
Which leaders actually drive roadmap change vs. which just announce strategy?
This data makes you better at prediction. And prediction is power when you’re planning a roadmap.
The Sonos Example: Analysis in Action
Back to my Sonos speaker shopping experience. I dove into their February 2026 investor presentation. Slides 14, 15, and 16 summarize their growth strategy.
Sonos claims a $12B expansion opportunity targeting existing customers, selling direct to capture retail margin.
Three months later: New customers get 26% off. Existing customers get 15% off.
Running the diagnostics:
Level 1 - Ownership: Who owns “expansion revenue per existing customer” as the primary KPI? Unclear from public data. The new CMO just started in January (1 month before my screenshots). Metrics in last quarter’s earnings calls still emphasize new household growth, not expansion.
Level 2 - System Constraints:
CMO announced Nov 2025, started Jan 2026 (barely 1 month in role)
Promotional calendars are typically planned 6-12 months in advance
Best Buy drives 14% of Sonos’ revenue — can’t undercut them without consequences
Direct-to-consumer is 27% of revenue and declining, not growing
Pricing coordinated across all channels to maintain retailer relationships
Level 3 - Rewarded Behavior: Earnings calls celebrate “Era-started households” (new customer acquisition). Promotional pricing coordinated across channels (retail harmony prioritized over DTC margin). Customer forums show existing customers gaming the system, waiting for sales, and deleting cookies.
Prediction:
Systems won’t align until at least Q4 2026. Existing customer expansion won’t become the actual priority until:
CMO rebuilds go-to-market strategy (6+ months)
Comp plans cycle to reward expansion (next fiscal year)
Pricing strategy shifts (requires retailer renegotiation)
Marketing campaigns and promotional calendar reflect new priorities
In the meantime, new customer acquisition will remain the priority, regardless of the stated strategy.
Am I upset with Sonos?
No. They’re operating under real constraints. They’re in transition. The CEO has been in the role for 7 months. The CMO has been in the role for 1 month.
This is what strategic pivots look like in practice: messy, slow, contradictory.
But as a customer, I learned to read the incentives.
And the incentives told me: wait for the 26% sale, comparison shop across channels, act like a new customer.
So I did.
What This Means for You
You’re probably living some version of this right now.
Leadership announced a strategic pivot. Maybe it was quarters ago. Maybe it was last week.
You’re wondering: Is this real? Should I reorganize my roadmap? Should I reprioritize the backlog? Should I push back on commitments we made under the old strategy?
Here’s my advice:
Run the three-level diagnostic. It takes 30 minutes.
Level 1: Who owns the new metric as the primary KPI? (Ask your manager, check org announcements, watch for headcount/capacity allocation changes)
Level 2: What system constraints exist? (Check roadmap commitments, team allocations, planning cycle timing, comp cycle locks)
Level 3: What’s actually rewarded? (Watch what gets demo’d, who gets promoted, what wins engineering resources when there’s a conflict)
The answers tell you everything.
If all three align quickly (ownership is clear, capacity is being reallocated, behavior is shifting in planning meetings), the pivot is real. Reorganize your roadmap accordingly.
If one or two are misaligned but leadership is actively working on them, the pivot is real but slow. Plan for a 6-12 month transition. Keep current commitments while testing the new direction.
If none of them align and nothing is changing, the pivot is performative. Protect your roadmap. Execute on what’s actually rewarded. Don’t burn your team’s focus.
The Uncomfortable Truth
Here’s what nobody tells you about being a product leader at a growth-stage company:
Most strategic announcements don’t fully operationalize.
Not because leadership is incompetent or disingenuous. But because changing systems is hard, slow, and constrained by forces you can’t see from the middle.
Your job isn’t to reorganize your roadmap for every strategic announcement as if it’s gospel.
Your job is to:
Read the signals correctly
Predict what will actually happen
Protect your team from whiplash
Build credibility by being right about what matters
Prioritize work that’s actually getting resourced and rewarded, not just announced
This isn’t cynical. It’s realistic.
The PMs who thrive in the messy middle aren’t the true believers who reorganize their roadmaps every quarter. They’re the pattern recognizers who know how to read incentives and plan accordingly.
Strategy isn’t what gets announced. It’s what gets operationalized.
And until systems align with strategy, the systems win every time.
A Note for Leaders Reading This
If you’re announcing a strategic pivot, your PMs and product leaders are running these diagnostics whether you know it or not.
The best thing you can do is get ahead of it:
Explicitly state who owns the new metric as primary KPI
Allocate headcount and engineering capacity to support it
Share the timeline for system changes (roadmap shifts, resource reallocation, comp changes)
Acknowledge the constraints and what can’t change in the short term
Be transparent about what existing commitments you’re willing to renegotiate
Your PMs aren’t asking for perfection. They’re asking for clarity so they can make good decisions about how to prioritize their roadmap and allocate their team’s finite capacity.
Give them that clarity, and they’ll execute. Leave them guessing, and they’ll predict based on patterns—and their predictions might not be what you want.