One-on-Ones People Actually Want
Updated: 4 days ago
Engineering Leadership · Part 3
A weekly thirty minutes sounds trivial, and for most managers it is — a status update that could have been a Slack message. Done right, the one-on-one is the single most valuable half-hour on your calendar: the place trust gets built and small problems surface before they become resignations. This walks through running one-on-ones that matter — making it their meeting, the questions that open people up, and how to handle the moment they bring you something hard.
A weekly 30 minutes. Done right: most-valuable conversation of the week. Done wrong: status update theater.
Step 1: It's Their Meeting (10 min)
The 1:1 is for the engineer, not for you to extract status.
They set the agenda. You listen.
If they say "no agenda this week" — that's fine. Use the time for big-picture topics, career, or just walking.
If you constantly bring the agenda, they think it's your meeting. They stop preparing.
Step 2: Cadence (5 min)
Weekly. Same day; same time.
Skipping = signal of low priority. Rescheduling occasionally = fine.
30 minutes typical. New hires: 45-60. Established trust: 30 is enough.
Step 3: Shared Doc (10 min)
A shared doc per engineer:
## Standing topics
- Career goals
- Current project blockers
- Team feedback
## This week (2027-06-22)
- [agenda items they add]
- [your items, after theirs]
## Notes (your private)
- ...
Both edit. Add async between meetings. Look back at history.
Step 4: First Question (5 min)
"What's on your mind?"
Open. Lets them direct.
Not:
"What did you ship this week?"
That's status. Status goes in your team's standup.
Step 5: Topics They Bring (15 min)
Engineers raise:
Frustrations with the team / process
Feedback for you
Career questions
Confusion about scope / priorities
Personal stuff (sometimes)
Listen. Reflect back what you heard. Ask follow-ups. Don't jump to solutions.
"Sounds frustrating. Tell me more about when this happens."
Step 6: Topics You Bring (10 min)
After they're done:
Feedback (specific; timely)
Cross-team context they should know
Career conversations
Tough news (privately first)
Save feedback for 1:1s, not standups.
Step 7: Career Conversation (10 min)
Quarterly: zoom out.
Where do you want to be in 1 year?
What skills are you building?
What's missing from current scope?
Promotion path?
Not every week. Recurring conversation.
Without it: engineers' careers drift. They leave for somewhere that talks about growth.
Step 8: When They Bring a Problem (15 min)
Don't immediately:
Solve it
Promise to handle it
Dismiss it
Do:
Reflect ("It sounds like X")
Ask ("What have you tried?")
Co-decide ("What would help most?")
Coach, don't rescue.
For things you must handle: be clear about ownership and timeline.
Step 9: Tough Conversations (10 min)
For underperformance, conflict, hard feedback:
When a one-on-one keeps returning to the same performance gap, Handle Underperformance covers the next conversation.
Pick the 1:1 (private; in-context)
Be specific
Tie to impact
Listen to their side
Co-create a plan
"In yesterday's review, the tone toward Sarah came across harsh.
I noticed she stopped contributing after. Can we talk about what
was going on?"
Not in a group. Not over Slack. The 1:1 is for this.
Step 10: Track Patterns (5 min)
Notice over months:
Recurring themes (frustration, growth)
What energizes them
What drains them
Career trajectory
Use this for:
Project assignment
Promotion advocacy
Career conversations
Your notes are your memory. People feel seen when you remember.
What You Just Did
1:1s: their meeting, weekly, shared doc, open question, what they bring, what you bring, career, problems, tough conversations, patterns. The relationship that compounds.
Common Failure Modes
Status-update 1:1s. Wasted time; both annoyed.
Skip routinely. Signal: you don't care.
Solve every problem. They stop bringing real ones.
No career conversation. They leave; you didn't see it coming.
No notes; no memory. Same conversations every quarter.
Continue the Engineering Leadership path
Previous — Part 2: Delegate Without Losing Quality
Part of the Engineering Leadership learning path.
