Hello Reader,
This last week, I organized and shared my thoughts on LinkedIn about how I’ve approached planning with product leaders the last few years. In this week’s newsletter, I wanted to do a bit of a roundup to make the case for thinking beyond quarterly planning and how I’ve gone about operationalizing a higher-level planning cycle in the past.
If your team only plans at the annual and quarterly levels, you're not alone. Many product organizations rely on these planning cycles:
🗓️ Annual planning sets budgets, hiring plans, and multi-year strategy for each department.
🛠️ Quarterly planning drives execution through OKRs for each product area.
But as your organization grows, leaders at the VP and Director level are able to think longer term. They’ll begin to need a way to provide strategic context for their teams while staying aligned with other areas within the product team and functions at the company.
During the year, priorities shift, market conditions evolve, and execution teams end up reacting (or worse, ignoring) instead of adapting.
And yet, many product leaders stick to the annual and quarterly planning cycles, treating their annual plan as untouchable (or forgotten) and their quarterly plan as the only execution lens.
Of course, quarterly planning could absorb a strategic shift during the year. VPs and Directors should drive pivots when needed. However, beyond a certain scope, they end up having to pull off heroics and one-off activities to get the awareness and buy-in with cross-functional leadership they and their teams need. Plus, the quarterly planning timeline is often too tight to accommodate anything significant.
Planning for 6-month semesters
Imagine if your team had a structured, mid-cycle checkpoint to:
✅ Reassess product priorities based on market shifts.
✅ Adjust hiring plans & headcount allocations—within your existing budget.
✅ Rationalize team structures to avoid last-minute re-org chaos.
✅ Ensure strategy stays relevant—before the next quarterly plans are written.
This is where “semester planning” comes in.
It doesn't replace annual or quarterly planning. Instead, it ensures annual planning remains focused on company-wide priorities while allowing for smarter mid-year adjustments—without disrupting execution.
Key artifacts in semester planning
There are a few key artifacts at this level of planning that ensure strategy shapes execution—not the other way around:
📄 A semester plan document – The source of truth, for each product area, with:
- Vision & strategy input from CPO & executive team
- Investment strategy narrative, with stack-ranked initiatives tied to business goals
- Revised hiring plans & headcount allocation
- Funding status—what’s currently planned within current capacity, what’s on hold
- Fanout dependencies to ensure platform and other broad dependencies are accounted for
📊 Updated staff allocation and headcount plan – Aligns engineering, design, and PM resources to reflect headcount changes and real-world bandwidth.
📅 Revised product roadmap – A reflection of priorities, considering any changes to team allocation.
The rituals and communications of semester planning
Planning for the 6-12 month horizon isn’t a single event. It’s a series of rituals—the glue—that ensures strategy actually sticks.
🔹 Kickoff meeting – The CPO & product leadership set the stage with updated market conditions, strategy pivots, and business priorities. The supporting operations team provides a full timeline and key milestones to set expectations up-front.
🔹 Planning inputs available (milestone) – Leaders get access to latest finance budgets and forecasts, current team capacity, and customer insights so they’re not planning in the dark.
🔹 Plan writing (async) – Product leaders for each product area/vertical draft semester plans with their team leads, including initiatives, hiring adjustments, and trade-offs before any big meetings.
🔹 Review meetings (sync) – Leadership aligns across product verticals & cross-functional teams—before anything gets locked in to focus on initiatives that are on the bubble, cross-area trade-offs, and key dependencies.
🔹 Executive review and publish – CPO & executive leadership review aggregated plans, then publish to company & teams as input into quarterly planning.
A strong semester (6-12 month horizon, VP/Director-level) planning process doesn’t end when leadership signs off either. It includes structured communication milestones to ensure alignment.
📢 Publishing to company and functional leadership – Before teams see the plans for each product area, executives and cross-functional leaders (Finance, Marketing, Sales) get briefed on key shifts.
📢 Publishing to product & engineering teams – The final semester plans area shared as an input into quarterly planning—so teams execute with great context.
How often does your team recalibrate?
If your teams feel like they’re constantly reacting or trying to retrofit strategy into short-term delivery plans, this might be the missing piece.
Ask yourself:
🤔 Are our hiring and headcount plans still aligned with business needs?
🤔 Do we have a structured way to update priorities—or do we just react?
🤔 Are product leaders staying strategic, or getting pulled into quarterly execution?
I’d love to hear your thoughts.
Hit Reply and let me know: How does your team handle mid-year adjustments to product strategy, roadmap, and resourcing?
Have a great week,
Alex
