One On One

1:1 Meeting Prep & Notes

Great 1:1s are the highest-leverage activity a CTO has. They build trust, surface problems early, unblock people, and develop future leaders. This skill helps you prepare for and document them effectively.

1:1 Prep Template

Before each 1:1, quickly fill this out (5 min max):

# 1:1 Prep: [Person] — [Date]

## Their Context
- Current project/focus: [What are they working on?]
- Recent wins: [Ship something? Solve a hard problem?]
- Potential concerns: [Blockers, frustration signals, team dynamics?]

## My Agenda (pick 1-2, not all)
- [ ] Check in on [specific project/task]
- [ ] Give feedback on [specific behavior/output]
- [ ] Discuss [growth opportunity / career topic]
- [ ] Address [concern / issue]

## Questions to Ask
- [Open-ended questions, not yes/no]
- [Focus on their perspective, not yours]

## Key Message
[If there's ONE thing they should take away from this meeting, what is it?]

1:1 Notes Template

# 1:1 Notes: [Person] — [Date]

## Key Takeaways
- [Most important things discussed]

## Action Items
- [ ] [Owner]: [Specific action] — by [date]
- [ ] [Owner]: [Specific action] — by [date]

## Follow-up Topics
- [Things to revisit next time]

## Signals to Watch
- [Engagement, energy, concerns detected]

Types of 1:1 Conversations

Regular Check-in

Focus: Their priorities, blockers, and wellbeing.

Good questions:

• "What's the most important thing you're working on this week?"
• "What's slowing you down?"
• "Is there anything you need from me?"
• "How's the team dynamic feeling?"

Feedback Conversation

Structure: SBI (Situation-Behavior-Impact)

• Situation: "In yesterday's sprint review..."
• Behavior: "...you presented the technical trade-offs before recommending a solution..."
• Impact: "...which helped the team make an informed decision and got buy-in faster."

For constructive feedback, add:

• Request: "Going forward, I'd like to see [specific change]."
• Then ask: "What do you think? Does that resonate?"

Career Development

Focus: Their growth trajectory, not just current performance.

Questions to explore:

• "Where do you want to be in 1-2 years?"
• "What skills do you want to develop?"
• "What kind of work energizes you most?"
• "Is there a project or responsibility you'd like to take on?"

Map their answers to concrete opportunities: stretch assignments, mentoring, conference talks, tech lead roles.

Difficult Conversation

When you need to address underperformance, behavior issues, or deliver hard news.

Framework:

1. State the observation (facts, not interpretation): "I've noticed the last three PRs had significant bugs caught in review."
2. Share the impact: "This is slowing down the team's velocity and affecting the release timeline."
3. Seek their perspective: "I want to understand what's going on from your side."
4. Collaborate on a plan: "Let's figure out together how to improve this."
5. Set clear expectations: "Here's what I need to see in the next two weeks."

Skip-Level 1:1

Focus: Organizational health and hidden problems.

Questions:

• "What's the biggest thing slowing your team down?"
• "If you could change one thing about how we work, what would it be?"
• "Do you feel like you understand the company's direction?"
• "Is there anything you want me to know that I might not be hearing?"

Anti-Patterns to Avoid

• Status update meetings — If all you discuss is project status, use async updates instead. 1:1s are for the human stuff.
• Only talking when there's a problem — Regular cadence builds trust. Don't skip 1:1s when things are going well.
• Doing all the talking — Aim for the other person to talk 60-70% of the time. Your job is to listen and ask good questions.
• No follow-through — If you commit to an action item, do it. Nothing erodes trust faster than broken promises.

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: camilooscargbaptista
• Source: camilooscargbaptista/cto-toolkit
• License: MIT

Install and usage instructions live in the source repository linked above.