Draft OKRs

Proposed onboarding OKRs — next quarter

Objective: Help new teams experience shared value quickly and keep collaborating.

The targets for KRs 2 and 3 are proposed, pending a feasibility review before leadership approval. They are not forecasts of retention impact.

Measurement and quality guardrails

• Freeze cohort eligibility, “active,” membership, and shared-note definitions before the quarter starts. Use consistent definitions for baselines and results.
• Score week-4 retention only on cohorts that have reached week 4; report immature cohorts separately.
• Reconcile the data before approval: the supplied segment figures imply approximately 32% overall retention, rather than 34%. Confirm whether they use different cohorts or definitions.
• Track onboarding reliability alongside these KRs. Critical onboarding defects are release blockers, not a bug-count target.
• Improve collaboration through genuine value—not forced invitations or changes that artificially inflate membership.

Candidate initiatives — not scored key results

Prioritize the checklist, invite-flow improvements, a small set of useful templates, and lifecycle emails according to their expected contribution to these outcomes. Use interviews and funnel analysis to choose and refine experiments.

Defer dark mode and AI summaries unless evidence shows they address a major onboarding barrier. Publish help content where research identifies a specific need.

Note to the squad

I replaced three broad objectives and a shipping checklist with one focused objective and measurable user outcomes. Launches, interviews, articles, and bug fixes are ways to make progress; completing them does not prove that onboarding improved.

Early team participation is our strongest available signal: teams with three or more people joining in week 1 have much higher week-4 retention. That is correlation, not proof of causation, so we’ll test whether our changes improve retention rather than assume invitations alone will do it.

I also narrowed the scope for our five-engineer, one-designer squad. NPS is too broad to diagnose this onboarding problem, while dark mode and AI summaries would compete with the core work.

Because OKR scores now affect bonuses, I want targets, scoring rules, guardrails, and shared ownership agreed before the quarter—not adjusted afterward. We should review the bonus linkage with leadership and HR so it does not reward metric manipulation or discourage honest experiments.

Onboarding squad OKRs, next quarter

Objective 1: New teams get their teammates in during week 1, and stay (supports the company goal: make Fieldnote the place new teams get started)

• KR1: Raise the share of new teams with 3+ people in week 1 from 29% to 45%.
• KR2: Cut the median time from sign-up to the first note someone else opens from 3 days to 1 day.
• KR3: Raise the share of new teams active in week 4 from 34% to 40% (shared with the company KR).

Planned bets, not KRs: onboarding checklist, invite flow redesign, 5 templates, onboarding emails. We'll drop or swap any of them if they aren't moving KR1 and KR2.

Objective 2: Keep the product dependable while we change onboarding

• KR1: Zero open P1 bugs at quarter end, and no P1 open longer than 5 days at any point.

Backlog, not this quarter: dark mode, AI summaries, NPS target, help articles.

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Note to the squad

Thanks for the draft. Here's what I changed and why.

1. Outcomes, not deliverables. Most of the draft listed things we'd ship. We could ship all of it and leave week-4 activity flat. The checklist, invite redesign, templates and emails are now the bets we make to hit the KRs.

2. One clear line to the company goal. Teams where 3+ people join in week 1 are still active in week 4 58% of the time, versus 21% for everyone else, and only 29% of teams reach 3+ today. So KR1 is about getting more teams to that point. Reaching 40% overall probably needs about 45% of teams there, assuming the relationship holds. KR2 measures how quickly a new team sees value from a teammate.

3. Cut and moved. Dark mode, AI summaries and the NPS target have no clear link to the company goal, and NPS isn't something onboarding alone can move. They go to the backlog, not the bin. User interviews and help articles are useful, but as activities inside Objective 1, not KRs. "Fix 50 bugs" rewarded volume over impact, so it became a P1 guardrail.

4. Two caveats to settle before Friday. - The data implies a week-4 rate of about 32% (0.29×58% + 0.71×21%), not the 34% in the company KR. Likely a definition or timing difference, but I'll confirm which baseline we're using. - The 58% vs 21% gap is correlation. Teams that invite people quickly may already be more committed, so the real lift from nudging invites will probably be smaller. That's why KR3 sits next to KR1, so we'll see whether the outcome really moves.

5. The bonus link. Since scores now affect everyone's multiplier, the safe play is to pick easy, output-style KRs. I've deliberately not done that. KR1 and KR2 are stretch targets, and I'd rather be upfront about it than quietly sandbag. Before Friday I'll ask leadership and HR how scores convert to multipliers, and I'll push for 0.7 on stretch KRs to count as a good result. I'll share the answer as soon as I have it. If you think a target is unrealistic, tell me before Friday so we can adjust it openly.

Please reply with objections or number challenges by Thursday noon.

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.