Draft OKRs

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.

To the Onboarding Squad:

Thanks for putting these together. I’ve rewritten our OKRs for leadership. Before I explain why, please note HR’s rule: our bonuses are now tied directly to our OKR scores. That means our OKRs must be about outcomes, not output, and they must tightly align with the company goal.

Here is what I changed:

1. Dropped the "feature laundry list." Draft 1 listed outputs (checklists, dark mode, 50 bugs). If we ship all those and week 4 retention doesn't budge, leadership fails us—and our bonuses drop. We need to focus on what happens to the user, not what we build.
2. Anchored on the Company Goal: Leadership wants week 4 team retention up from 34% to 40%. Our entire quarter must serve this.
3. Used our Data: Our data shows a massive retention cliff: teams where 3+ people join in week one retain at 58%, versus 21% for everyone else. Right now, only 29% hit that 3+ threshold. Furthermore, the median time to a shared note is 3 days—too slow.

Here is the finalized version going to leadership on Friday:

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Q3 Onboarding Squad OKRs

Objective: Get new teams collaborating faster so they stick around.

• KR 1: Raise the share of new teams with 3+ active members in week 1 from 29% to 40%. (Directly attacks our biggest retention lever).
• KR 2: Reduce the median time from sign-up to the first note opened by a second team member from 3 days to under 24 hours. (Accelerates "time-to-value" and teamwork).
• KR 3: Raise the share of new teams still active in week 4 from 34% to 40%. (Our direct contribution to the company goal).

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What this means for us: Features like the checklist, templates, AI summaries, and invite flow redesign are still our tools to hit these goals, but we’ll prioritize them based on whether they actually drive team invites and fast collaboration. Let’s crush this.

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.

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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.