One-on-One Coaching

The 1:1 is the highest-leverage management tool you have. Done well, it surfaces problems before they become crises, accelerates career growth, and builds the trust that makes everything else possible. Done poorly, it's a status update meeting that neither person needs.

The fundamental rule: it's their meeting, not yours. Your job is to listen, ask questions, and create conditions for the engineer to solve their own problems.

For feedback on a specific PR or technical artifact, use the code-review skill.
For tracking team goals that surface in 1:1s, use the okr-engineering-alignment skill.

What 1:1s Are (and Are Not)

This ✅	Not this ❌
Private space for them to raise concerns	Status update (use standups/async for that)
Coaching toward growth and problem-solving	Manager directing what to do next
Feedback in both directions	Monologue of manager observations
Long-term relationship and trust building	A recurring calendar placeholder
Career development over time	Annual review as a surprise

1:1 Cadence and Format

Weekly 30 min for most engineers. This is the default.
Bi-weekly 45–60 min for senior ICs or engineers who are strong and self-directed.
Increase frequency for: new hires (weekly 60 min for 90 days), struggling engineers, engineers in a critical moment (promo cycle, PIP, major life event).

Structure (30-minute format):

Check-in (2 min): "How are you doing?" — and actually listen to the answer
Their agenda (15–20 min): What they brought; your job is to ask, not tell
Your agenda (5–8 min): Feedback, context to share, decisions they need to know
Close (2 min): Capture any commitments; confirm next week's agenda items

Don't cancel 1:1s. Reschedule if you must, but cancelling signals the engineer doesn't matter.

Listening vs. Problem-Solving Mode

Most managers default to problem-solving mode. The engineer describes a problem; the manager offers a solution. This feels helpful but prevents growth and creates dependency.

Switch between modes deliberately:

Mode	When to use	What it sounds like
Active listening	They're processing, venting, or figuring something out	"Tell me more." / "What's that like for you?"
Coaching	They need to think through a problem they can solve	GROW model questions (see below)
Advising	They've exhausted their own thinking and explicitly ask	"Here's what I'd consider..."
Directing	Urgent, safety, or they are very new	"Here's what I need you to do."

A useful question before responding: "Do they need me to listen, coach, advise, or direct right now?"

The GROW Coaching Model

Use GROW when an engineer is stuck on a problem they have the capability to solve themselves.

Goal

What do they want to achieve in this conversation?
(Not the problem — the outcome they want from discussing it)

"What would be most useful to focus on today?"
"What would a good outcome from this conversation look like?"
"What are you hoping to figure out?"

Reality

What is actually happening right now? (Facts, not interpretations)

"What's the situation as it stands today?"
"What have you already tried?"
"What's the impact of this problem — on you, on the team, on the work?"
"What's getting in the way?"

Options

What could they do? (Generate possibilities before evaluating)

"What are your options?"
"What else could you try?"
"If you couldn't fail, what would you do?"
"What would you tell a colleague in the same situation?"
"Is there anything you haven't considered?"

Will (Way Forward)

What will they actually do? (Commitment, not just ideas)

"Which of those options feels right?"
"What's the first step, and when will you take it?"
"What might get in the way — and how will you handle that?"
"How can I support you?"

GROW works because it respects the engineer's intelligence. They usually know what to do — they need space to reach the answer.

SBI Feedback Framework

Use SBI when delivering feedback — positive or developmental.

Situation → Behavior → Impact

Situation: Specific time and place — not "always" or "sometimes"
Behavior: Observable action — not interpretation or judgment
Impact: Effect on you, the team, the project — not character or intent

SBI Feedback Template

"I want to share some feedback about [something recent].

In [SITUATION: specific meeting/PR/incident], I noticed [BEHAVIOR: what you
specifically observed — not interpreted]. The impact was [IMPACT: concrete
effect on you, team, or work].

[For developmental feedback]: What's your take on that? / What was going
through your mind at that point?

[Optional]: Going forward, what would help is [specific alternative behavior]."

SBI Examples

Positive feedback:

"In yesterday's incident (Situation), you took ownership of the communication to stakeholders without being asked and kept updates going every 30 minutes (Behavior). That let the rest of the team stay heads-down on the fix and meant stakeholders weren't escalating to me (Impact). I really appreciated it."

Developmental feedback:

"In the architecture review on Tuesday (Situation), you talked over Sarah twice when she was making her point (Behavior). I could see her disengage for the rest of the meeting, and we may have lost her perspective on the design (Impact). What was happening for you in that moment?"

Anti-patterns to avoid:

"You're always late to things." (No situation, no behavior, judgment)
"I feel like you don't care about quality." (No situation, interpretation not behavior)
"People have noticed that..." (No situation, vague, cowardly)

Career Development Conversations

Hold a dedicated career conversation at least once per quarter — separate from regular 1:1 check-ins.

Career Conversation Framework (30–60 min)

Where they want to go (not where you think they should go):
- "Where do you see yourself in 2–3 years?"
- "What kind of problems do you want to be solving?"
- "What does 'success' look like for you — not just at work?"
Where they are now:
- "What are you most proud of in the last 6 months?"
- "Where do you feel most stretched? Most stagnant?"
- "What skills do you feel are underdeveloped?"
The gap and the path:
- "What would someone at [next level] be doing that you're not doing yet?"
- Share your own observations: use SBI to give specific evidence
- Identify 1–2 concrete growth areas to focus on this quarter
Commitments:
- What will they work on?
- How will you support them? (Sponsorship, stretch assignments, introductions)
- When will you check in on progress?

Question Bank by Scenario

New to the team (first 90 days)

"What's been the most confusing part of how we work?"
"What's been easier or harder than you expected?"
"What do you wish you'd known on day 1?"
"What would help you feel more confident right now?"
"Is there anything blocking your ability to contribute?"

Engineer who seems disengaged or checked out

"On a scale of 1–10, how excited are you about what you're working on right now?"
"What would make your work more interesting?"
"Is anything going on outside of work that's affecting things?" (offer, don't pry)
"What was the last time you felt really energized by your work here? What was different?"
"Is there a problem you wish someone would ask you to solve?"

Engineer who is stuck or struggling

"Walk me through what you've tried so far."
"What specifically is the blocker — is it unclear requirements, technical uncertainty, or something else?"
"Who else has faced this kind of problem — have you talked to them?"
"What would 'good enough for now' look like?"
"What would you do if you had to ship something by Friday?"

Promotion-ready engineer

"How would you describe your impact over the last 6 months to someone who doesn't know your work?"
"What have you done that you think is above your current level?"
"What's your read on where you stand? What do you think is still missing?"
"Who in the organization has visibility into your work besides me?"
"Are you comfortable advocating for yourself in a promotion conversation?"

Underperforming engineer

"I want to share some observations and get your perspective." (Then use SBI — give specific examples, ask for their take)
"What do you think is getting in the way?"
"What would it look like if things were going well?"
"What do you need from me to make progress on this?"
"I want to be direct: this is a pattern that needs to change. Let's agree on what specifically needs to be different."

Engineer under stress or burning out

"How are you really doing — not the work, you?"
"What's your capacity like right now?"
"Is there anything on your plate that could be dropped or handed off?"
"When did you last take a proper break?"
"What does your workload feel like — is it sustainable?"

Skip-Level 1:1s

Skip-levels (meeting with reports of your reports) give you signal on team health that you can't get any other way.

Frequency: Every 6–8 weeks for each skip-level report.

What to communicate upfront to the manager in between: "I'm doing skip-levels to get team context. I won't undermine you — if someone has feedback about you, I'll encourage them to share it with you directly, and I'll tell you I heard concerns."

Good skip-level questions:

"What's one thing the team is doing really well right now?"
"What's one thing you wish were different about how the team operates?"
"Do you feel like you know what success looks like in your role?"
"Is there anything you want leadership to know that might not be getting through?"
"How's [their manager] doing? Is there anything they could do differently to support the team better?"
"What are you most proud of recently?"

What to do with what you hear:

Information about team health → synthesize and act on patterns
Direct feedback about a manager → encourage them to share it directly; tell the manager you heard concerns (but don't share specifics)
Blockers you can remove → remove them promptly and visibly

30/60/90 Day Check-In Template

Use at day 30, day 60, and day 90 with new hires:

## [Name] — [Day 30 / 60 / 90] Check-In

### What's going well?
[Their answer — capture it]

### What's been harder than expected?
[Their answer]

### What's still unclear?
- About the codebase / systems?
- About how decisions get made?
- About what good looks like in this role?

### Feedback for the team / manager
- What could we do better in onboarding?
- Is there anything you needed that you didn't get?

### Their confidence level (1–10)
- Technical contribution: __
- Team integration: __
- Role clarity: __

### Commitments
- They will: [specific action]
- Manager will: [specific action]
- Review at: [next check-in date]

1:1 Preparation Template

Fill in before each 1:1 (takes 5 minutes):

## 1:1 Prep — [Name] — [Date]

### Their recent work
What have they shipped or worked on since last week?
What blockers or challenges might they be facing?

### My agenda items
- [ ] [Feedback to give — use SBI]
- [ ] [Context/decisions to share]
- [ ] [Career development thread to continue]

### Questions to ask
- [1–2 questions based on what I've observed or what they mentioned last week]

### From last 1:1
- They committed to: [X] — did it happen?
- I committed to: [Y] — did I follow through?

### Notes from this 1:1
[Fill during the meeting]

### Actions
- They: [commitment + deadline]
- Me: [commitment + deadline]

Output Format

When applying this skill, the agent should:

Ask which scenario applies (new engineer, struggling engineer, career conversation, etc.) before generating questions
Produce a 1:1 prep template populated with scenario-specific questions
If feedback is needed, draft it using the SBI framework with the details provided
If it's a GROW coaching scenario, provide the full GROW question sequence
Flag if the situation sounds like it warrants a more formal performance conversation vs. a coaching conversation

References

Camille Fournier: The Manager's Path — Core reference on 1:1s and engineering management
Michael Lopp: Managing Humans — Practical patterns for engineering manager 1:1s
LeadDev: How to have better 1:1s with your engineers
Sir John Whitmore: Coaching for Performance — Origin of the GROW model
Kim Scott: Radical Candor — Framework for feedback that is both caring and direct
LeadDev: Giving feedback that lands

one-on-one-coaching

SKILL.mdskills/manager/one-on-one-coaching/SKILL.md