Just-In-Time Product Strategy: The Trap Startups Fall Into

If you've been around startups long enough, you eventually notice a pattern: teams don't fail because they move too slowly — they fail because they're constantly moving in different directions.

It's not always because engineering is unfocused, or product is weak, or leadership is unclear.

Sometimes, it's because strategy itself is happening just-in-time.

I've seen it a few times now.

You're humming along toward a clear goal…
and then everything pivots — because:

• an investor made a comment
• a board member asked a spicy question
• a competitor made noise
• growth stalled temporarily
• or someone suddenly became worried about a number buried in a spreadsheet

Suddenly the north star changes.
Again.

Even with great execution habits (like the weekly alignment rhythm I wrote about in the Execution Flywheel), there's a deeper layer here:

This is the part I've been thinking about a lot lately.
Not from a place of judgment — but from experience.

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The Part We Forget: Even CEOs Have Bosses

I think people forget this.

Even the most visionary founders have someone they're accountable to:

• boards
• investors
• large strategic partners

And those groups are often operating on different timelines — or playing a different game entirely.

Founders optimize for trajectory.
Boards optimize for risk-adjusted return.
Investors optimize for narrative consistency + future fundraising.

Those incentives don't always align cleanly.

Which is why some organizations end up with a new "top priority" every quarter…
or every month…
or every all-hands.

And to be fair — sometimes a pivot really is needed.
Markets shift.
Assumptions break.
Competitors release new products.

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The Hidden Cost of "Just-in-Time" Strategy

One pattern I've seen repeatedly:

Leadership can say, "Our #1 priority is growing our user base," and genuinely believe nothing else has to give.

Revenue should still grow.
CAC should remain low.
Engineering velocity should be stable.
The roadmap should continue as planned.

Not out of naïveté — but because they're leading from 30,000 feet.
From that altitude, it feels like a small steering adjustment.

But on the ground, inside the product and engineering org, that "slight turn" often means rethinking funnels, rebuilding onboarding, reshaping retention loops, shifting pricing considerations, re-sequencing the roadmap, and managing a thousand tiny dependencies that don't appear on any investor slide.

A pivot that feels small at the board level can be a full reorientation for the team actually building the product.

And if those tradeoffs aren't acknowledged explicitly, they don't disappear — they just show up later as missed timelines, odd prioritization choices, creeping tech debt, team burnout, confused users, or KPIs that stubbornly refuse to move.

Then everyone ends up surprised when the results don't match the directive:

• leadership: "Why aren't we seeing revenue?"
• product: "We shifted focus like you asked."
• engineering: "We're still paying for the last pivot."

This is the real cost of "just-in-time" strategy:

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When Great Execution Isn't Enough

This is the part where execution meets reality — and not all of it is in our control.

You can have:

• weekly goal-setting
• perfect alignment artifacts
• clean specs
• tight sprints
• unified communication
• and an engineering team rowing together

…and still miss the outcome if the strategy keeps shifting faster than the system can absorb.

This gap — the space between strategic intent and execution capacity — is where "just-in-time strategy" becomes dangerous.

It creates the illusion of decisiveness without the foundation to support it.

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How I Try to Bridge the Altitude Gap

When I'm interfacing with boards or investors, my default is to be direct — but grounded.

If someone says:

"Let's pivot toward X. That's the new priority."

I'll usually respond with:

It's not resistance — it's clarity.

Honestly, most stakeholders value this. They don't see the ripple effects from the ground level unless someone connects those dots.

But not every team has the same dynamics.
Some leaders can speak frankly; others need to tread lightly.
Some boards are partners; others are… more involved.

This is the messy middle where strategy meets execution — and it's rarely simple.

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The Altitude Gap: Where Strategy and Execution Fall Out of Sync

The part most founders, boards, and teams underestimate is the altitude gap — the distance between where strategy is set and where execution happens.

Product and engineering operate close to the ground.
Their world is made of constraints, sequencing, risk, dependencies, UX tradeoffs, system complexity, and the very real limits of team capacity. These are the mechanics that determine how and when something can be built.

Boards and investors operate at a much higher altitude.
Their world revolves around expectations, momentum, narrative, fundraising needs, external perception, and visible traction. Their levers are brand story, growth pressure, and market timing.

Neither altitude is wrong — they just run on different physics.

That's the tension early-stage teams navigate every day, whether they name it or not.

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When There Isn't a Neat Framework (And Why That's Okay)

I don't have a neat framework — and that's kind of the point.

This part of product leadership can be emotional, situational, and deeply human.

But here's what I've found helps more often than not:

1. Make the invisible tradeoffs visible

Not "yes" or "no" — get clarity.

"If we do X, here's what happens to Y. We can do it, but this is the tradeoff."

Most misalignment happens simply because these ripple effects were never outlined.

2. Clarify and confirm the desired impact of the pivot

Before shifting anything, I ask:

"What outcome are we expecting in the next 30–60 days?"

It's surprising how often the answer is vague — and the real problem is upstream ambiguity, not downstream execution.

3. Use data as an alignment tool

Data isn't emotional.
It's a shared language.
It grounds the conversation in reality instead of competing narratives or pressure.
Even the act of saying, "Here's what the metrics suggest," can reset the whole room.

4. Set expectations and close the loop

Sometimes the right answer is:
"Let me bring back a realistic plan by end of week."
Not to stall — but to ensure the pivot is translated into something actually executable.
This is where you balance urgency with feasibility:
moving fast, without pretending that impossible timelines are achievable.

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This Is the Part I Think We Don't Talk About Enough

I've shared my take, but I'm really curious how others have navigated this.

What's worked for *you* when strategy keeps shifting?

• How do you handle situations where strategy keeps shifting from above?
• How do you balance tactical execution with political expectations?
• How do you keep your team grounded when the ground keeps moving?

If you've been in these trenches, I'd genuinely love to hear your experiences.

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And if this is something you're dealing with right now…

This is the kind of work I help early-stage teams with — translating shifting strategy into something executable, reducing thrash, and creating a stable delivery rhythm even under pressure.