The first 30 days
What the first month actually looks like.
Not a generic onboarding checklist. The actual plan I run with a new principal. Week by week, with the success metric that tells us whether we’re on track.
Week 1Days 1,5
Shadow & setup
01
- 30-min priorities call: your top 3 goals for the next 90 days, your top 3 annoyances right now.
- Tool access provisioned: inbox (read + send-as), calendar (read + propose), Slack, CRM, travel tools.
- Shadow you for 2 days, read-only on inbox, observe how you triage, what you flag, what you ignore.
- Draft your “Operating Manual”: preferences, stakeholders, tone, escalation triggers. You review.
- No live work yet. By Friday, I know your stack, your people, and your defaults.
Success metric
End of week 1: I can describe your week better than you can.
Week 2Days 6,12
Take inbox + calendar
02
- Inbox triage goes live: I handle 80% of inbound, escalate 20% with a recommended reply.
- Calendar: I propose all holds, protect your no-meeting blocks, flag conflicts before they happen.
- First stakeholder email drafted in your voice. You approve, I send.
- Daily 15-min check-in (async, written), what I handled, what I escalated, what I need from you.
- First travel coordination or small project runs end-to-end.
Success metric
End of week 2: you open your inbox 3× a day, not 30×.
Week 3Days 13,19
Own travel + reporting
03
- Travel goes fully to me: flights, hotels, visas, ground transport, itineraries, contingency plans.
- First recurring report (weekly metrics / board prep / investor update) drafted and delivered.
- Vendor & stakeholder coordination: I become the single point of contact for routine asks.
- Weekly check-in moves from daily to 3× weekly, then to 2×.
- Mid-month review: what’s working, what isn’t, what we change.
Success metric
End of week 3: you take one full day off inbox and nothing breaks.
Week 4Days 20,30
Propose improvements
04
- I propose 3 improvements to your current workflow (meeting load, inbox volume, reporting cadence).
- We agree on a monthly performance review format: 30 min, structured, no surprises.
- Daily check-ins move to weekly. Async Notion updates fill the gap.
- First “proper vacation” test: you take 2 consecutive days fully off, I hold the fort.
- 30-day review: confirm scope, adjust coverage window, plan the next 90 days.
Success metric
End of week 4: you can’t imagine doing this without me. (If you can, we part ways, no cost.)
The first week is a trial.
1 to 2 hours a day, on one real task. If it is useful, we scale up. If it is not, we stop there, no commitment, no awkward conversation. The risk is mine, not yours.
Send a briefForward this to your chief of staff or COO for review.