Draft OKRs

Here is the revised OKR draft along with the team note.

*

Proposed Q3 OKRs: Onboarding Squad

Objective 1: Accelerate new teams to their first collaborative moment * KR 1: Increase the share of new teams with 3+ members in Week 1 from 29% to 45%. * KR 2: Reduce median time from team creation to first collaborative note opened from 3 days to <24 hours. * KR 3: Contribute directly to the company goal by lifting new team Week 4 retention from 34% to 40%.

Objective 2: Deliver a seamless, zero-friction first-run experience * KR 1: Maintain zero open P1 bugs across the sign-up, invite, and first-note flows throughout the quarter. * KR 2: Increase invite-flow conversion (invites sent per new team) by 25%.

*

Note to the Squad

Team,

Thanks for pulling the initial draft together! Ahead of our review with leadership this Friday, I’ve refocused our OKRs. Here is what changed and why:

#### 1. We shifted from outputs to outcomes Shipping checklists, templates, and emails are solutions, not goals. If we ship all four and retention doesn’t budge, we haven’t succeeded. By framing our KRs around moving specific user behaviors (e.g., getting teams to collaborate faster), we give ourselves the flexibility to iterate, drop what isn’t working, and double down on what does.

#### 2. We’re anchoring on our biggest retention lever Our company goal is lifting Week 4 retention from 34% to 40%. Our data shows an undeniable path to get there: * Teams with 3+ members in Week 1 retain at 58% (vs. 21% for everyone else). * Currently, only 29% of teams hit that milestone. * It takes 3 full days for a teammate to open their first shared note.

Our primary job this quarter is simple: get teammates into the workspace and collaborating on day one. Every template, invite prompt, or checklist we build should serve that specific loop.

#### 3. We cut scope to protect our focus (and our bonuses) Now that HR ties our bonus multipliers directly to squad OKR completion, our OKRs must be focused, measurable, and within our sphere of influence: * Dropped AI summaries and Dark Mode: Both are cool features, but neither solves the core first-week team activation problem. They dilute our engineering capacity. * Dropped NPS (31 to 40): NPS is a lagging, noisy metric influenced by the entire product (pricing, bugs elsewhere, feature gaps), not just onboarding. * Refined bug targets: Fixing an arbitrary "50 bugs" incentivizes fixing trivial issues. Instead, we’re committing to zero critical bugs in our core onboarding and invitation paths.

Let’s chat through any questions at standup tomorrow so we’re fully aligned before Friday!

Onboarding squad OKRs: next quarter

Company goal we serve: Raise the share of new teams still active in week 4 from 34% to 40%.

Objective 1: Get new teams working together in their first week - KR1: Raise the share of new teams with 3+ people joining in week one from 29% to 45%. - KR2: Cut the median time from sign-up to the first note a teammate opens from 3 days to 1. - KR3 (shared with the company): Raise week-4 active new teams from 34% to 40%.

Objective 2: Learn what makes a new team stick - KR1: By week 4, interview 10 teams that stalled and 10 that stuck, and share the findings. - KR2: By mid-quarter, run a test showing whether adding invites causes better week-4 retention, or whether teams that invite were just more committed to begin with.

Guardrails (watched, not scored) - Zero open P1 bugs in sign-up, invite and first-note flows. - Free-to-paid conversion at the five-member mark doesn't drop.

Bets we'll try to move the KRs: the invite-flow redesign, the onboarding checklist, onboarding emails, and starter templates built for sharing. We'll drop any bet that doesn't move KR1 or KR2.

---

Note to the squad

Thanks for the draft. The work in it is good. Here's what I changed before Friday.

1. I swapped launches for results. "Ship the checklist" scores 100% even if nobody uses it. Leadership asked for more teams active in week 4, so we now measure the changes in behaviour that lead there. Your launches are still in the plan, as bets.

2. I built the plan around the strongest signal we have. Teams where 3+ people join in week one are 58% active at week 4. Everyone else is at 21%. Only 29% of teams reach 3+ today. Getting teammates in, and getting them to open each other's notes, is the main lever. That's why the invite redesign comes first.

3. I cut dark mode, AI summaries, help articles, the NPS target and "fix 50 bugs." Some of these are worth doing, but none clearly moves week-4 retention for new teams. Five engineers and one designer can't do them all and still do onboarding well. Quality is now a guardrail on the flows new teams actually touch.

4. I added a learning objective because our data may mislead us. Teams that invite people may stick because they were already serious, not because they invited. If so, pushing invites won't move retention much. A test early in the quarter tells us before we spend all of it.

5. Two things I'll raise with leadership: - The numbers don't add up. 29% × 58% + 71% × 21% gives about 32% week-4 retention, not 34%. The metrics may be defined differently. I'll check before Friday. - The gap is big. Even if invites cause retention, hitting 40% would mean about half of new teams reaching 3+ people, up from 29%. My 45% target for KR1 is already a stretch. I'll be upfront that the company KR probably needs other teams' help too.

6. The bonus link: I want to be straight with you. HR now sets each of our bonus multipliers from our OKR score. That rewards safe targets. The old draft was mostly launches we control, so it would likely have scored well. The new one has ambitious targets we may only partly hit. Good OKRs often land around 70%.

I don't think the answer is to lower the bar. Easy targets would make our OKRs useless to leadership and to us. I'll ask leadership and HR how a 70% score on a stretch target will be read for bonuses. I'll come back to you before we lock anything. If the answer is bad, we'll decide together how to handle it.

Happy to talk any of this through before Friday.

Proposed onboarding OKRs — next quarter

Objective: Help new teams start collaborating quickly and build a habit that lasts.

Measurement and scoring - Use consistent definitions of “new team,” membership and “active,” agreed with whoever owns company reporting. Exclude test accounts consistently. - For KR2, use a fixed observation window and report the share of teams that never reach the milestone alongside the median. A faster median must not hide more teams failing to collaborate. - Score week-4 retention only on cohorts old enough to observe it; agree the final reporting date before the quarter starts. - Treat these as proposed targets, not finalized bonus commitments, until we validate measurement, scope and feasibility.

Candidate work—not additional KRs

Prioritize the invite-flow redesign and a minimal onboarding checklist as the first experiments. Use interviews to understand why teammates do or don’t join. Test templates, onboarding emails and help content where evidence suggests they address a specific obstacle; do not commit to shipping every item.

Keep capacity for onboarding reliability. Before approval, agree measurable quality guardrails for sign-up, invitations and note access using current performance and existing incident standards. Do not trade reliability for activation gains.

Defer dark mode and AI summaries unless research establishes a stronger onboarding opportunity than the current priorities.

Note to the squad

I replaced three broad objectives and a delivery checklist with one focused objective and measurable user outcomes. Launches, bug counts and interviews describe work; they don’t establish whether onboarding helped teams succeed. NPS is useful context, but too broad to be our primary onboarding score.

Early team participation is our strongest current signal: teams with three or more people joining in week 1 retain at 58%, versus 21% for others. That is correlation, not proof that getting more people to join will cause higher retention. We should test changes and measure downstream retention—not optimize invitations alone.

We also need to reconcile the data before locking targets: the supplied segment rates and 29% participation share imply about 32% overall retention, rather than 34%. They may describe different cohorts or definitions.

Finally, because OKR scores now determine bonuses, scoring rules are part of the commitment. Before Friday’s sign-off, we should agree target realism, weights, cohort timing and treatment of material external dependencies with leadership and HR. The company retention target remains shared accountability, not an outcome onboarding controls alone. With five engineers and one designer, focused experiments and reliable core flows are a more credible plan than nine separate launches.