managing-one-on-ones

This skill should be used when the user asks to "prepare for a 1:1", "prep my one-on-one", "generate an agenda", mentions "career conversation", "check-in with", "1:1 meeting", "one-on-one", or discusses meeting prep with a direct report.

Managing 1:1 Meetings

Agenda Generation Workflow

When preparing for an upcoming 1:1:

  1. Check calendar for the next 1:1 and identify the direct report
  2. Pull context from memory or project files for this person's goals, recent feedback, and open action items
  3. Check project tracker for their recent work, blockers, and completed items
  4. Check chat/messages for relevant recent context about this person
  5. Generate a structured agenda using the template below

Standard 1:1 Agenda Template

Structure every agenda with these sections:

  • Check-in (5 min): Energy level, how things are going personally
  • Their topics (15 min): Space for what they want to discuss
  • Progress & blockers (10 min): Current sprint work, obstacles, support needed
  • Action item review (5 min): Status of items from last 1:1
  • Growth & development (5 min): Progress toward career goals, skill development
  • My topics (5 min): Organizational updates, feedback, requests

Career Development Conversations

When preparing a career-focused 1:1:

  • Review the person's stated career goals from memory or previous notes
  • Identify recent projects that demonstrate growth areas
  • Prepare specific examples of strengths and development opportunities
  • Suggest stretch assignments aligned with their goals
  • Draft open-ended questions:
    • "What skills do you want to build this quarter?"
    • "Where do you feel stuck or under-challenged?"
    • "What would make this role more fulfilling?"
    • "Is there a project or area you'd like more ownership of?"

After the Meeting

  • Update notes for this person with new context, decisions, and commitments
  • Create action items tagged with the person's name
  • Flag any follow-ups that require escalation or cross-team coordination
  • Note any career development commitments made

Running Notes Format

Maintain a per-person running notes file with this structure:

# 1:1 Notes — [Name]

## [Date]
### Their topics
- ...
### My topics
- ...
### Action items
- [ ] [Owner] — Item description
### Notes
- Key decisions, context, career discussion points