When Planning Season Becomes Performance Season

Planning season comes around like clockwork. Budgets, OKRs, capacity models, prioritization frameworks—the rituals of focus and alignment. On paper, it’s a time for clarity. In reality, it often feels like an annual stage play: certainty (captured neatly in PowerPoint) built on incomplete understanding.

Every PM knows the pattern. The more polished the plan, too often the shakier the foundations beneath it.

The Fiction of Certainty

Most of what gets discussed in planning season isn’t strategy—it’s storytelling. Teams are expected to forecast impact on metrics that depend on problems they haven’t validated yet. Assumptions get turned into numbers because numbers look objective.

No one’s trying to deceive anyone. But everyone knows that the “expected revenue uplift” for a not-yet-designed feature is theater. Those figures still end up in executive decks, and then in budgets, and then in performance reviews. The fiction becomes fact by repetition.

When that happens, learning stops. Teams start defending the plan rather than interrogating it. Discovery debt compounds quietly under the weight of overconfidence.

The Diplomacy of Priorities

If every team’s priorities are “critical,” then none are. PMs spend weeks negotiating scope across teams, just to fit within headcount and calendar limits that were defined before anyone confirmed which problems were worth solving.

Frameworks like RICE or MoAR help structure the debate, but the inputs are still political. Impact and confidence are both guessed. Effort is a wish. The meeting becomes a contest of conviction rather than evidence.

What should be a portfolio conversation—balancing reversible bets against long-term investments—turns into a zero-sum fight for roadmap space.

Data Everywhere, Insight Somewhere (We Hope)

By late fall, dashboards are overflowing, but clarity is scarce. Planning season relies on what’s measurable, not necessarily what matters. Lagging indicators dominate. Customer understanding is often months old, filtered through sales anecdotes or quarterly NPS slides.

That’s why planning so often feels disconnected from reality: the evidence is stale, and the decision cadence has outpaced learning cadence.

Every PM has lived the moment where someone asks, “What proof do we have this is the right bet?” and the best available answer is “It’s aligned with our OKRs.”

The Politics of “No”

The hardest part of planning is choosing what to leave out.

A roadmap full of initiatives looks ambitious; a focused roadmap looks risky. The culture rewards inclusion, not exclusion. Saying “no” early feels dangerous. So half-decisions get parked as “stretch goals,” quietly guaranteeing over-commitment and future disappointment.

By the time the dust settles, the PM’s job has morphed from prioritization to damage control.

The Loop That’s Missing

The most effective plans don’t come from sharper decks or clever frameworks. They come from better learning loops.

Teams that enter planning season with fresh, grounded insight about their customers make faster, cleaner choices. They know which problems are truly consequential and which are noise. They can defend trade-offs with confidence, not spin.

What teams need isn’t extra research, but steadier engagement with the right people.

Where Catalytic Customers Change the Equation

This is where Catalytic Customers earn their place in the process. They’re not a focus group or advisory board in disguise. They’re experienced, constructively critical users of the category—people who care deeply about utility, not novelty.

When PMs maintain a standing relationship with a small set of Catalytic Customers, planning stops being guesswork. These customers:

• Surface meaningful problems early. They reveal where real friction lies before it turns into churn or backlog noise.

  
  

• Validate trade-offs. They can articulate what “good enough” looks like and what’s non-negotiable.

  
  

• Expose blind spots. They challenge internal logic without derailing momentum.

  
  

It means the team finds alignment sooner, with less waste along the way. You go into planning with credible evidence about what matters, which makes everything downstream—budget, capacity, prioritization—far less theatrical.

Catalytic Customers don’t replace your frameworks; they make them real. They ground RICE scores in something other than educated guesses. They give story points a human story behind them.

What Better Planning Feels Like

When discovery debt is low and Catalytic Customers are part of the rhythm, planning season feels different:

• The roadmap meeting is about sequencing, not speculation.

  
  

• OKRs are derived from genuine opportunity spaces, not just metric gaps.

  
  

• Teams can explain why each initiative matters, not just what it might deliver.

  
  

• Saying “no” becomes easier because the reasoning is clear and shared.

  
  

The process is still messy—it always will be—but it’s grounded. The plan becomes a set of hypotheses, not a performance of certainty.

Closing Thoughts

Planning season will always tempt teams to overstate what they know. The antidote isn’t more data or better slides—it’s better learning, built into the system year-round.

Catalytic Customers make that possible. They keep your assumptions honest, your priorities connected to real needs, and your plans defensible when the calendar flips.

If learning leads, planning starts to look a lot more like progress.

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Post-script

My book, The Catalytic Customer: Accelerating Innovation and Growth from the Outside In, explores how experienced, constructive customers can help product teams cut through noise, ground their decisions, and plan with real confidence. Available now on Amazon, or wherever books are sold.