one-on-one-prep

name

one-on-one-prep

description

Use when the user is preparing for a 1:1 — as a manager preparing to meet with a report, as an IC preparing to meet with their manager, or as a peer preparing for a regular sync. Trigger phrases include "I have a 1:1 with X tomorrow", "help me prep for my 1:1", "what should I bring up in my next 1:1?". Builds an agenda matched to the relationship and the moment, not a generic template. If the other person is a registered stakeholder, reads their reflection file first so the agenda carries what the user already knows — open loops, recent observations, questions worth asking.

1:1 Prep

A good 1:1 is the highest-leverage 30 minutes a manager and report have together. A bad one is a status update with extra steps. The difference is preparation.

This skill builds an agenda matched to who's meeting whom and what's actually going on, not a generic checklist.

Zeroth: load what you already know

Before asking the user anything, check the memory:

1. Profile. Read ~/bettersense-work-reflections/profile.md if present — role context and communication style.
2. The stakeholder file. Resolve the named person via ~/bettersense-work-reflections/stakeholders.json; if registered, read their <category>/<slug>.md in full. This is the payoff for every reflection the user has logged: the agenda should arrive pre-loaded, not blank.

From the stakeholder file, surface a short "worth raising" list before drafting the agenda:

• Open loops — anything a past entry says the user planned to ask, raise, or follow up on, with the entry date. Open loops corrode trust; this is where they get caught.
• Recent signals — observations from the last few entries that bear on this meeting (morale shifts, a growth ask, friction with a peer).
• Planned asks — any ask-category question entries where the user prepared a question but hasn't logged the answer yet. This meeting may be the moment.
• Staleness flags — topics the entries show haven't been touched in a long time (career conversation, feedback exchange).

Present it as: "From your reflections on [name]: [2–4 items]. Want any of these on the agenda?" — then build the agenda below. If the person isn't registered, proceed normally and mention once at the end that registering them (stakeholder-register) makes future preps arrive pre-loaded.

After the 1:1 happens, the natural bookend: "want to log how it went?" → stakeholder-reflect.

First: figure out the role

Confirm with the user before drafting:

• Manager → Report. The default case. Agenda emphasizes the report's growth and well-being; status comes last, if at all.
• Report → Manager. Different beast. Agenda emphasizes getting unblocked, surfacing feedback up, and managing visibility.
• Peer 1:1. Cross-functional sync. Agenda emphasizes alignment, dependencies, and trade-offs.
• Skip-level. With your manager's manager or a report's report. Agenda emphasizes signal-gathering and trust-building, not problem-solving.

If the user doesn't say which, ask. The wrong template applied to the right meeting is worse than no template.

Manager → Report

Default structure (30 min). Skip sections that don't fit, but be deliberate about it.

1. Personal check-in (3–5 min). Genuine, not performative. "How are you?" with attention. Watch energy, not just words. If something is clearly off, the rest of the agenda yields to that.
2. Their agenda first (10–15 min). Whatever they want to discuss. If they don't have anything, that's a signal — ask what's been on their mind, not what's on their task list.
3. Career & growth (5 min, every 2nd or 3rd meeting). What are they working toward in the next 6–18 months? What current work moves them closer? What's missing? Don't wait for the formal review cycle — by then it's late.
4. Feedback exchange (5 min). Give specific feedback (use the feedback-frameworks skill). Ask for feedback on yourself. The asking is the higher-leverage half.
5. Your asks (3 min, last). Anything you need from them — direction, context, visibility. Keep it short; this is not a status meeting.

Pre-meeting prep prompts to walk through with the user:

• What's the most important thing happening for this person right now?
• Anything from the last 1:1 that needs follow-up? (Open loops corrode trust.)
• Any feedback I've been holding that should land here? (Don't save up; deliver close to the event.)
• Anything I'm sensing but haven't asked about? (Mood shift, withdrawal from team, suddenly louder, etc.)
• What does this person need from me this week that I haven't given?

Report → Manager

Different goals. Build the agenda around three categories:

1. Get unblocked. What decisions, context, or air-cover do you need from your manager that you can't get elsewhere? Lead with these.
2. Manage upward visibility. What's going on that they should know about (good or bad), framed in their terms? Not a status update — a curated set of things that matter to them.
3. Calibrate. Are you on track? On what? What does great look like, in their eyes, this quarter? Most reports don't ask this enough.

Pre-meeting prep:

• What's one decision I need them to make / unblock / weigh in on?
• What's one piece of context they probably don't have that affects their thinking on something?
• What's one thing I want feedback on (specific, not "how am I doing?")?
• What do I want them to know about my workload / capacity right now?
• Is there feedback for them I've been avoiding? If so, plan how to deliver it (lean on feedback-frameworks).

Anti-pattern: walking in with a list of completed work. They can read the changelog. Use the time for things only a 1:1 can do.

Peer 1:1 (cross-functional)

The point is alignment, not friendship-building (that's a side effect).

1. What are you each working on this week that affects the other? Surface dependencies before they break.
2. Where might we be misaligned? Roadmap conflicts, resourcing tension, conflicting promises to stakeholders. Better to surface here than in a meeting with leadership watching.
3. What can I help you with? Concrete offer — beats "let me know if I can help" by a wide margin.

Run these every 2–4 weeks during periods of heavy collaboration; pause them when the work decouples.

Skip-level

Different rules: this person doesn't manage the user's day-to-day, so the conversation is about signal, not direction.

For the user as the report:

• Bring 2–3 things going well, with specifics.
• Bring 1–2 things you're wrestling with, framed as "here's how I'm thinking about it" rather than escalation.
• Ask about their priorities and pressures. Most skip-levels reveal more than the org chart suggests.

For the user as the skip-level manager:

• Listen 80%. Resist the urge to solve.
• Don't undercut the direct manager — anything that needs a decision goes back through them.
• Watch for patterns across multiple skip-levels: same complaint twice = systemic issue, not individual.

Exit signals

If the user says "stop", "exit", "I'm done", "skip this", "pause", or similar — stop immediately. Share whatever agenda has been built so far and end cleanly. Don't push to complete every section.

In the opening message, after confirming the role, add one short sentence: "You can say 'stop' at any time and I'll share what we have so far."

How to help the user

1. Confirm the role and the relationship state. New report? Long tenure? Recent friction? Recent promotion? These change the agenda.
2. Ask about open loops. What was the last 1:1 about? Anything left hanging? Open loops carried for weeks corrode the relationship; surface them.
3. Build the agenda in 4–6 bullets max. No one runs a 12-bullet 1:1 well.
4. Pair with feedback-frameworks if feedback is on the agenda. Pre-draft the feedback before the meeting.
5. Suggest one thing to not discuss. Most 1:1s are over-stuffed. Naming what's getting cut to next time is part of the prep.

Anti-patterns to flag

• The status report 1:1. "What did you ship this week" — replaceable by Slack. Don't waste the slot.
• Skipping recurring 1:1s during busy weeks. This is exactly when they matter most. Shorten, don't cancel.
• The manager monologue. If you talk more than 50% of a manager → report 1:1, you're doing it wrong.
• No follow-through. Things agreed in 1:1s that don't show up next time train people to disengage. Track them.
• Avoiding the hard topic for "another time." It's never another time. Plan it in.