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1on1-prep

1on1-prepSafety --Repository

Help leaders prepare effective 1:1 meetings with their direct reports. Use this skill when asked to: prepare a 1:1 agenda, generate discussion topics, create talking points for a specific person or situation, follow up on previous 1:1s, prepare for difficult 1:1 conversations, or structure career development discussions. The skill provides templates, question banks, and frameworks for different 1:1 types (regular check-ins, career conversations, performance concerns, etc.).

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Updated 1/18/2026

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SKILL.md

1:1 Preparation Skill

A framework for preparing and running effective 1:1 meetings that build trust, support growth, and surface issues early.

Why 1:1s Matter

1:1s are the most important meeting a manager has. They are:

  • Their meeting, not yours — The direct report sets the agenda
  • About them, not status — Save project updates for standups
  • Relationship-building time — Trust compounds over time
  • Early warning system — Problems surface here first

1:1 Principles

1. Consistency Over Intensity

  • Weekly or biweekly, same time, never cancel
  • 30 minutes minimum, 45-60 ideal
  • Rescheduling is okay; canceling erodes trust

2. They Own the Agenda

  • Ask them to bring topics
  • Your items come second
  • If they have nothing, dig deeper (that's a signal)

3. Listen More Than Talk

  • Aim for 70/30 ratio (them/you)
  • Ask follow-up questions
  • Silence is okay—let them think

4. Document and Follow Through

  • Take notes (or have them take notes)
  • Track action items
  • Start next 1:1 with previous action items

1:1 Types & Templates

Type 1: Regular Check-in (Weekly/Biweekly)

Purpose: Maintain connection, surface small issues before they grow

Template:

## 1:1 with [Name] — [Date]

### Their Topics (5-15 min)
- [Let them lead]

### How are you doing? (5 min)
- Energy level / workload
- Blockers or frustrations
- Anything I should know?

### Work Check-in (5-10 min)
- What's going well?
- What's challenging?
- Do you have what you need?

### Growth/Development (5 min)
- Any learning opportunities this week?
- Skills you want to develop?

### My Topics (5 min)
- [Your items — keep brief]

### Action Items
- [ ] ...

Type 2: Career Conversation (Monthly/Quarterly)

Purpose: Discuss long-term growth, aspirations, development

Template:

## Career Conversation with [Name] — [Date]

### Reflection
- What's energized you most in the last quarter?
- What's drained you?
- What accomplishment are you most proud of?

### Current Role
- What parts of your job do you love?
- What would you change if you could?
- Are you learning and growing?

### Future Direction
- Where do you see yourself in 1-2 years?
- What skills do you want to develop?
- What experiences do you want to have?

### Support Needed
- How can I help you get there?
- What opportunities should I look for?
- What's in your way?

### Action Items
- [ ] ...

Type 3: Performance Concern

Purpose: Address issues early, create clarity on expectations

Template:

## 1:1 with [Name] — [Date] — Performance Discussion

### Opening (be direct)
"I want to talk about something important. I care about your 
success here, which is why I'm raising this directly."

### The Issue (SBI format)
- Situation: [When/where]
- Behavior: [What specifically happened]
- Impact: [The effect on team/work/customers]

### Their Perspective
- "What's your view on this?"
- "What's getting in the way?"
- "Is there context I'm missing?"

### Expectations Going Forward
- [Specific, measurable changes needed]
- [Timeline for improvement]
- [Support you'll provide]

### Check Understanding
- "Can you summarize what we agreed?"
- "What questions do you have?"

### Action Items
- [ ] [Specific behavior change]
- [ ] [Follow-up date]
- [ ] [Support/resources to provide]

Type 4: New Team Member (First 90 Days)

Purpose: Accelerate onboarding, build relationship, identify gaps

Week 1-2 Focus:

- How are you settling in?
- What's confusing or unclear?
- Do you have everything you need (access, equipment, etc.)?
- Who have you met? Who should you meet?
- What questions do you have about the team/company?

Week 3-4 Focus:

- What's surprised you (good or bad)?
- What's different from your previous role?
- Where do you see quick wins?
- What processes seem inefficient?
- How's the pace—too fast, too slow?

Month 2-3 Focus:

- Where do you feel confident?
- Where do you still feel uncertain?
- What training or support do you need?
- How's your relationship with the team?
- What would make you more effective?

Type 5: Returning from Leave / Difficult Period

Purpose: Reintegrate thoughtfully, show care

Template:

- Welcome back. How are you really doing?
- What do you need from me right now?
- What pace feels right for ramping back up?
- What should I know but not share with others?
- How can I protect your time/energy?
- What's the best way to check in on how you're doing?

Question Bank by Situation

When They Seem Disengaged

  • "You've seemed quieter lately. What's on your mind?"
  • "On a scale of 1-10, how excited are you about your work right now?"
  • "What would need to change for this to be a 10?"
  • "Are you getting to do what you do best every day?"
  • "Is there something outside of work affecting you?"

When They're Frustrated

  • "Tell me more about that frustration."
  • "What's the root cause?"
  • "What have you tried so far?"
  • "What would need to change?"
  • "How can I help—do you want me to fix it, or just listen?"

When They Want Promotion

  • "What does that next level look like to you?"
  • "What gaps do you see between where you are and where you want to be?"
  • "What evidence would show you're ready?"
  • "What can you start doing now at that level?"
  • "How can I help you get there?"

When They're Overloaded

  • "Walk me through everything on your plate right now."
  • "What would you take off if you could?"
  • "What's urgent vs. important?"
  • "What can I take off your plate or delegate elsewhere?"
  • "Are you comfortable pushing back when asked to do more?"

When There's Team Conflict

  • "Help me understand what's happening with [person]."
  • "What's your role in this dynamic?"
  • "What have you tried to resolve it?"
  • "What outcome would you like to see?"
  • "Would it help if I facilitated a conversation?"

When They're a Top Performer

  • "What's keeping you here?"
  • "What might make you leave?"
  • "Are you being challenged enough?"
  • "What's the most interesting problem you'd want to work on?"
  • "How can I help you have more impact?"

When They're Quiet / Give One-Word Answers

  • "If you had a magic wand, what would you change?"
  • "What's the one thing you wish I understood better?"
  • "What feedback do you have for me?"
  • "What's something you've wanted to say but haven't?"
  • [Try walking 1:1s or informal coffee chats]

Questions to Ask Every 1:1

Pick 1-2 from this list to keep conversation flowing:

Opening

  • "What's top of mind for you?"
  • "What would make this a great week?"
  • "What's one thing you're excited about?"

Middle

  • "What's your biggest challenge right now?"
  • "What do you need from me?"
  • "Is there anything blocking you?"

Closing

  • "Is there anything we didn't cover?"
  • "What's one thing I can do to support you this week?"
  • "Anything else on your mind?"

Manager Self-Check

Before each 1:1, ask yourself:

Question
Did I review notes from last 1:1?
Did I follow through on my action items?
Do I know what they're working on?
Is there feedback I've been avoiding?
Have I thought about their career lately?
Am I in the right headspace to listen?

Getting Feedback on Yourself

Ask regularly (not every 1:1, but quarterly):

  • "What's one thing I could do differently to support you better?"
  • "What am I not seeing that I should be aware of?"
  • "If you were in my shoes, what would you do differently?"
  • "What should I start doing, stop doing, or keep doing?"
  • "On a scale of 1-10, how well am I supporting you? What would make it higher?"

Red Flags to Watch For

SignalWhat It Might Mean
Always says "everything's fine"Doesn't feel safe being honest
Never brings topicsDisengaged or doesn't see value
Frequently reschedulesAvoiding something
Only talks about tasksKeeping you at distance
Sudden mood/behavior changePersonal issue or job searching
Stops asking questionsChecked out
Complains about same thing repeatedlyFeels unheard

1:1 Anti-Patterns to Avoid

Status meeting — "Give me an update on your projects" ❌ Your meeting — You talk the whole time ❌ Skipping regularly — "We'll catch up next week" ❌ No notes — Forgetting what you discussed ❌ No follow-through — Not doing what you said you'd do ❌ Only when there's a problem — Makes 1:1s feel like trouble ❌ Multitasking — Checking Slack/email during meeting ❌ Rushing — Ending early when they clearly have more


Running the 1:1

First 2 Minutes

  • Warm up: "How are you? How was your weekend?"
  • Transition: "What would you like to talk about today?"

Their Agenda (First Half)

  • Listen actively
  • Ask follow-up questions
  • Take notes
  • Don't jump to solutions immediately

Your Items (Second Half)

  • Keep brief
  • Most important items only
  • Leave time for their reactions

Last 5 Minutes

  • Summarize key points
  • Confirm action items (who does what by when)
  • "Anything else before we wrap?"

After the 1:1

  1. Document — Update your notes within 24 hours
  2. Act — Do your action items promptly
  3. Follow up — If something urgent came up, check in before next 1:1
  4. Reflect — Did you learn something? Adjust?

Remember: The best 1:1s feel like conversations, not meetings.

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Licenseunknown
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Updated1/18/2026
Publisherjkbennemann

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