90-Day Plan Builder

Create a structured plan for your first 90 days in a new role

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The 30-60-90 Day Framework

Days 1-30: Learn & Absorb

  • Schedule 1:1s with key stakeholders (manager, peers, cross-functional partners)
  • Understand team dynamics, culture, and unwritten rules
  • Map out processes, tools, and systems
  • Ask lots of questions - it's expected and appreciated
  • Identify one "quick win" you can deliver
  • Don't try to change things yet - observe and learn

Days 31-60: Contribute & Build

  • Start taking ownership of projects/areas
  • Deliver on your quick win from phase 1
  • Begin building your network outside immediate team
  • Identify areas for improvement (but don't criticize)
  • Align with manager on expectations and priorities
  • Start forming opinions about what matters

Days 61-90: Lead & Impact

  • Drive initiatives from start to finish
  • Share ideas and propose improvements
  • Mentor or help onboard newer team members
  • Build reputation outside your immediate team
  • Set goals for the next quarter with your manager
  • Document your wins and impact

Key Relationships to Build

  • Your Manager: Weekly 1:1s, understand their priorities and communication style
  • Direct Peers: The people doing similar roles - learn from them
  • Skip-level: Your manager's manager - understand bigger picture
  • Cross-functional Partners: Design, PM, other eng teams you'll work with
  • Previous Role Holder: If accessible, gold mine of context
  • Team Admin/EA: Often the most helpful people in the building

Questions to Ask in First 30 Days

  • "What does success look like in this role after 90 days? 6 months?"
  • "What are the biggest challenges the team is facing right now?"
  • "Who should I definitely talk to as I get ramped up?"
  • "What do you wish you knew when you started?"
  • "How does this team typically communicate and make decisions?"
  • "What's the history behind [current project/system]?"
  • "What would be a quick win I could aim for early on?"
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Chester's Analysis