Competitive Wargaming
Assign each squad one competitor for a quarter, then pool the intel on a presentation day.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 90%
Instead of asking every PM and designer to stay shallowly current on every competitor, Calendly assigns small groups to deeply own a single competitor for a quarter — living in that product, running a SWOT, and forming a view on where the competitor is heading. It culminates in a competitive wargaming day where each group presents, with prizes. The design insight is that competitive awareness is a distribution problem, not an individual-diligence problem.
Origin
A recurring ritual on Annie Pearl's product team at Calendly, run on roughly a quarterly interval.
Core principles
- 01Depth on one competitor beats shallow awareness of all of them — and the org still gets full coverage through pooling.
- 02Competitive intel must be tied back to your own strategy, not collected as trivia.
- 03The output is a directional view (where is this competitor going), not a feature checklist.
- 04Making it a game with prizes is what keeps it from becoming an unloved chore.
How to run it
- 1
Assign one competitor per group for the quarter
Split product managers and designers into groups and give each a single competitor to own for the full interval. Coverage across groups spans the market.
- 2
Immerse in the competitor's product
The group spends real time inside the competitor's product — using it, not reading about it — over the course of the quarter.
Pro tip Actual product usage surfaces the positioning and roadmap intent that marketing pages hide.
- 3
Run a SWOT and form a directional view
Produce a SWOT analysis and, more importantly, a point of view on where that competitor is going next and what that means for your strategy.
Watch out Stop at implications for your strategy. A backlog of copied features is the failure mode.
- 4
Hold wargaming day
Every group presents its competitor to the wider team on a single day. Add prizes and make it enjoyable. The whole org leaves with the full market picture in one sitting.
Pro tip Time it just before annual or quarterly strategy planning so the intel lands when decisions are being made.
In the wild
Calendly assigns groups to own a competitor for a quarter, has them immerse in the product and run a SWOT through the lens of where the competitor is heading, then runs a wargaming day where every team presents and prizes are awarded.
→ The team stays on top of the market without requiring every PM and designer to be deep in the weeds of many competitors — knowledge is aggregated through the event instead.
Common mistakes
Asking everyone to track everyone
Distributed shallow monitoring produces distributed shallow knowledge and quietly gets dropped. Ownership of one competitor with a public presentation deadline is what forces depth.
Turning competitive intel into a copy list
The exercise is framed against your own strategy — where is the competitor going and how should we think about that. Feature-parity chasing directly contradicts the where-to-play focus.
Is it for you?
Best for
Product orgs in a crowded category that need genuine market awareness without making every PM a part-time analyst.
Not ideal for
Category-creating products with no meaningful direct competitors, where the exercise manufactures rivals that do not matter.
From the transcript
“another fun one we do is something we call competitive work aiming so you know on a some sort of time interval at times has…”
“the competitor really trying to think through the lens of do a SWOT analysis really try to Think Through the lens of where's this uh…”
From the episode
Behind the scenes of Calendly’s rapid growth
Annie Pearl (CPO)