The Three-Phase OKR Maturity Ladder
No OKRs, then siloed team OKRs, then company OKRs with cross-org dependency mapping.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 90%
Pearl describes the OKR journey at Calendly as three distinct phases rather than a binary do-you-use-them question. The failure most companies get stuck in is phase two: each department has its own OKRs and they never connect, so lots of great work happens with no visibility into how it fits together. Phase three — company-level OKRs with tightly integrated department plans and explicit dependency mapping — is what makes the organization pull the same levers.
Origin
Annie Pearl's account of Calendly's OKR evolution across her first two-plus years as CPO, from roughly no OKRs at all through to company-level OKRs with cross-functional dependency mapping in 2023.
Core principles
- 01Great work with no connective tissue still fails — it is unclear how it fits together or how success is measured.
- 02Department-level OKRs that are not derived from company OKRs are just siloed to-do lists.
- 03OKRs need a strategy above them; Calendly could not write meaningful OKRs until the product strategy existed.
- 04Measure key results annually but instrument quarterly milestones so progress is visible more than twice a year.
How to run it
- 1
Diagnose which phase you are in
Phase 1: no OKRs — lots of great work, but unclear how it fits together or how success is measured. Phase 2: product-team OKRs derived from a product strategy, but each department runs its own siloed set. Phase 3: company OKRs with tightly integrated cross-department plans.
Watch out Phase 2 feels like success. It is the trap — every department is disciplined and the company is still uncoordinated.
- 2
Get a product strategy in place first
Calendly's phase-2 OKRs only became possible once a clear product strategy existed. Without a strategy, OKRs measure activity rather than direction.
- 3
Set a small number of company-level OKRs
Calendly runs about three company OKRs for the year. Keep the number small enough that every department can meaningfully line up behind them.
Pro tip Departments can still hold local objectives that do not roll up — the point is that the company OKRs are the ones everyone is pulling on.
- 4
Map dependencies across the whole company
Build the department plans in support of the company key results and explicitly map the cross-team dependencies, so you can see every lever that has to move to hit the top objective.
Pro tip Pearl calls dependency mapping the incredible transformation — it is what converts aligned intent into pulled levers.
- 5
Measure annually, milestone quarterly
Key results are measured on an annual basis, but quarterly milestones are set so progress can be checked far more frequently than annually or semi-annually. Product roadmaps then break down quarterly against those key results.
In the wild
When Pearl joined, Calendly had no clear product strategy and no OKRs guiding the work — plenty of great work happened, but it was unclear how it fit together or how success would be measured. Phase two brought a product strategy and matching product-team OKRs, while every other department ran its own siloed set. Entering the third year, the company set roughly three company OKRs with tightly integrated plans across every department.
→ Dependency mapping across the organization, with all levers being pulled toward the most important objective — a transformation Pearl calls incredible, and the biggest single OKR learning: connect them top to bottom.
Common mistakes
Stopping at product-team OKRs
A disciplined product team with its own OKRs sitting inside a company of departments each running their own siloed OKRs is not alignment. Nothing forces the departments to support each other's key results.
Writing OKRs before you have a strategy
Without a clear strategy above them, OKRs cannot say what winning looks like — they degenerate into measuring whatever the team was going to do anyway.
Only checking in annually or semi-annually
Annual key results with no quarterly milestones give you no chance to correct course. Calendly deliberately instruments quarterly milestones under annually-measured KRs.
Is it for you?
Best for
Scaling companies (roughly 150 to 600 people) where each function is individually well-run but cross-company execution keeps missing.
Not ideal for
Early startups where the whole company already sits in one room and OKR ceremony adds process without adding alignment.
From the transcript
“so I think it's just a kind of maturing of the business from almost you know no okrs to product team okrs to now company…”
“this has been a really incredible transformation of dependency mapping uh you know being able to make sure that we're pulling all the levers across…”
“okrs are are measured annually but we have Milestones across a quarterly basis so we can measure progress”
From the episode
Behind the scenes of Calendly’s rapid growth
Annie Pearl (CPO)