New Manager 90-Day Plan
First-time managers fail by improvising. Answer two questions and get a week-by-week 90-day roadmap: 1:1s with every report, stakeholder mapping, quick wins, first feedback conversations, and team norms — with milestone reviews at days 30, 60, and 90.
Your 90-day roadmap
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Questions to ask in Week 1 PRINT CARD
Ask these in every first 1:1. Tick each one once you've asked it — the goal is to listen, not to have answers.
Stakeholder map
List the people whose support your team needs: your manager, key peers, skip-level leaders, important partners. Revisit weekly.
| Name | Role / relationship | What they need from me |
|---|
Milestone reviews
Block 60 minutes alone for each review. Answer honestly — these prompts are how you catch drift early.
Day 30 — Do I understand?
- Can I explain what each report does and what success looks like for them?
- What surprised me most about the team or the work?
- What is my manager's honest read on my first month?
- What is my one biggest risk right now?
Day 60 — Is it working?
- Is feedback flowing both ways yet, or am I still guessing?
- Which relationships are strong? Which need repair?
- What one system, ritual, or process did I measurably improve?
- Who is thriving, and who am I avoiding a hard conversation with?
Day 90 — What's next?
- Would the team say we are clearer and more effective than 90 days ago?
- What are our goals for the next 90 days?
- What kind of manager am I becoming — and what must I develop next?
- What will I stop doing so I can lead instead of do?
Go Deeper with the Book
This plan is just the start. New Manager Made Simple by Kimani Upshur, M.Ed. takes you deeper into the same topic — the full first-90-days playbook, 1:1 systems, feedback scripts, and delegation frameworks you can use today.