Strategy-Led Planning
A real, pre-aligned product strategy collapses annual planning from six weeks to three days
- Difficulty
- Advanced
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 90%
Instead of grinding through the standard four-to-six-week annual planning ritual, do the hard upfront work of a real product strategy that stakeholders are genuinely aligned on. With that in place, planning, prioritization, and escalation handling become fast because the strategy already answers most of the questions the ritual is trying to litigate.
Origin
Shreyas Doshi discovered this at Stripe while running Stripe Connect, when a real product strategy he'd built earlier in the year let him finish planning in three days while peers spent four-to-six weeks.
Core principles
- 01The annual planning ritual mostly produces a plan that is abandoned by late February anyway
- 02'Plans are useless but planning is everything' is a comforting phrase that excuses wasted effort
- 03A real strategy makes prioritization and escalation decisions fall out automatically
- 04False precision (8 vs 9 engineers) is theatre — you won't follow those numbers anyway
- 05Bend the rules: if a planning template doesn't make sense, don't fill it out
How to run it
- 1
Build a real product strategy, not a fake one
Do the upfront work to create a genuinely clear, cohesive product strategy for your area — distinct from the boilerplate strategy docs most teams produce to satisfy a template.
Watch out A 'strategy' that is just filled-in templates and buzzwords will not produce the downstream leverage.
- 2
Get real pre-alignment from everyone
Secure genuine alignment on the strategy with all stakeholders and executives before planning season, so the strategy is a shared, settled reference point rather than something to be re-argued.
Pro tip Front-loading alignment is where the time savings actually come from.
- 3
Time-box planning tightly and skip pointless artifacts
When planning season arrives, produce only the artifacts that are genuinely needed and give yourself very little time. Refuse to fill out templates that don't make sense for your situation.
Pro tip Doshi compressed planning for a major Stripe product into three days this way.
- 4
Route escalations through the strategy
When mid-year escalations arrive from sales or support, use the strategy as the rigorous framework for deciding what to do with them instead of reactively replanning.
Watch out Without a strategy you'll revise the plan ad hoc until nobody remembers the original plan.
In the wild
Because Doshi had built and aligned a real product strategy for Stripe Connect earlier in the year, his planning for that major product took about three days while peers were stuck in four-to-six-week planning cycles for their own products.
→ Dramatically less time in planning with a plan that actually held up, freeing him for higher-leverage work.
Common mistakes
Treating annual planning as sacred
Teams spend four-to-six weeks on spreadsheets, meetings, and dependency negotiation, then abandon the plan after the first customer escalations — Doshi found most plans are forgotten by the last week of February.
Arguing over false precision
Debating whether a team needs eight or nine engineers in 2025 wastes time on numbers nobody actually follows through on.
Is it for you?
Best for
Senior PMs and product leaders entering annual/quarterly planning who own a coherent product area
Not ideal for
Situations where no real strategy exists yet and can't be built in time — you can't shortcut planning on top of a vacuum
From the transcript
“because I had a real product strategy not one of those fake ones a real product strategy that I I had gotten alignment on with…”
“if a template doesn't make sense why should I fill it out”
“if you have that planning should be a breeze”
“should it be eight Engineers for this team in 2025 or nine Engineers for this team in 2025 like who cares”
From the episode
4 questions Shreyas Doshi wishes he’d asked himself sooner
Former PM leader at Stripe, Twitter, Google