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The 1:1 Agenda
Generator

Most people walk into their 1:1, get asked “what’s on your mind?” and freeze. This skill reads your last week of calendar, email, Slack and docs, then tells you what to raise, what’s stuck, what your manager will ask, and exactly what to say.

I own two businesses, so I don’t have a manager anymore. My team uses this before every 1:1 with me, and I really wish I’d had it back in my corporate job.

Promotions don’t happen because of what you do. They happen because of what your manager knows you did. This closes that gap every week.

Before You Start

It works best with your tools connected. In Claude, go to Customize (renamed Plugins on newer accounts), then Connectors, and add Google Calendar, Gmail and Slack, plus Notion, Google Drive, Linear or Atlassian (for Jira) if you use them. No connectors? It still works. It asks you to paste your notes instead.

Install The Skill
  1. Turn on file creation. Go to Settings > Capabilities and turn on Code execution and file creation (called Create and edit files in the newer layout).
  2. Upload it. Go to Customize (or Plugins) > Skills, click +, then Create skill > Upload a skill, and pick the ZIP. Don’t unzip it first.
  3. Check it’s on. Make sure 1:1 Prep is switched on in your skills list.

Skills work on every Claude plan, including Free. (Claude help: using skills)

Give It Your Context Once

The skill needs to know your role, your manager and your goals. Fill this in once and paste it into a Claude Project’s instructions (click Set project instructions). Then run your 1:1 prep inside that Project every week. If you skip this, the skill just asks you the first time.

My 1:1 Context
My 1:1 context (use this every time you prep a 1:1 for me): My role: [e.g. Senior Product Manager, Growth team] My team: [e.g. 4 engineers, 1 designer, 1 data scientist] My manager: [name and role, e.g. Sarah Chen, Director of Product] 1:1 cadence: [e.g. weekly, 30 minutes, Tuesdays at 2pm] My goals this quarter (the ones I'm measured on): 1. [e.g. Ship the new onboarding flow by end of quarter] 2. [e.g. Raise activation from 12% to 18%] 3. [e.g. Hire 2 engineers] What my manager cares about most right now: - [e.g. Retention numbers. She presents to the CEO in 4 weeks.] - [e.g. Hiring. We're behind on the plan.] - [If you don't know, write "not sure" and help me figure it out from my week.] What I'm building toward over time (not every 1:1): - [e.g. Promotion to Staff PM by year-end. I need to show cross-functional impact.] - [e.g. Leading the next big bet instead of maintaining old flows.] Tools I've connected: [e.g. Google Calendar, Gmail, Slack, Notion]
Run It
  1. 15 to 30 minutes before your 1:1, open a new chat in your Project with your connectors on.
  2. Type “Prep my 1:1”. Read the 7 parts, then copy the short agenda at the end.
  3. Send the agenda ahead. I like sharing it with the manager about 30 minutes before. It changes how they show up too.
What You Get Every Time

01

A 30-second summary

Headline win, headline blocker and one thing you’re noticing. This one is just for you.

02

Wins to make visible

Split into what your manager already knows and what they don’t. Only the second list goes in the agenda. Doing great work nobody sees is how people get passed over.

03

Blockers with the exact ask

The root cause, plus the specific thing you need from your manager. That could be a decision, an intro, air cover or permission to drop something.

04

Strategic patterns

One or two things you’re seeing across the work, and what you propose. This is the section that gets you promoted.

05

The thing you’ve been avoiding

The hardest topic on your plate, with a gentle way to bring it up. If there’s nothing, it says so.

06

Your manager’s questions, answered

The 3 to 5 questions they’re most likely to ask, each with a short answer ready to go. No more freezing.

07

Next week preview

Big meetings, decisions you’ll need from them and anything that could blow up if nobody flags it.

08

A paste-ready agenda

Under 200 words, split into updates, discussion topics, decisions needed and an FYI list, so your manager can read it in a minute.

3 Bonus Triggers

“Prep my skip-level” reframes everything for your manager’s manager, with less task detail and more business impact.

“Prep for [name]” runs the same flow for a peer or cross-functional partner and leads with shared work.

“What did I miss?” is a quick audit of last week for replies you owe, decisions you pushed and threads that went cold.

The Full Skill

Here’s everything inside the ZIP, if you’d rather read it first or paste it straight into a chat or Project instead of installing it.

one-on-one-prep / SKILL.md
--- name: one-on-one-prep description: Preps my 1:1 with my manager from my last week of calendar, email, Slack and docs. Use when I say "prep my 1:1", "prep my skip-level", "prep for [name]" or "what did I miss?" --- # 1:1 Prep Coach You are my 1:1 prep coach. Before each 1:1 with my manager, you go through my last week of work, surface what I should bring up, flag what's stuck, predict what my manager will ask, and draft talking points I can say out loud. ## Hard rules 1. Never make up work, wins, meetings or conversations. Only use what is in my connected tools or what I tell you. If you're unsure whether something happened, ask. 2. Be specific. "Acme deal slipped 2 weeks because of legal review," never "had a deal challenge." 3. Lead with what my manager cares about, not what I want to talk about. 4. Never hide blockers. Raise them before they turn into surprises. 5. Wins my manager already knows about: skip them. Wins they don't know about yet: make them visible. 6. Frame things in a career-forward way when it's honest, but don't turn every 1:1 into an ask. 7. If you see something I've been avoiding (an unanswered thread, a decision I keep pushing, a topic I dodge), raise it gently. ## My context Look for my context in this order: the Project instructions, my saved instructions or memory, then this chat. I need: - My role and team - My manager's name and role - 1:1 cadence (for example, weekly on Tuesdays, 30 minutes) - My 2 to 4 goals this quarter - What my manager cares about most right now - Longer-term things I'm building toward (promotion, scope, visibility) If any of this is missing, ask me for it in one short message before you start. Don't guess. Once I answer, suggest I paste it into my Project instructions so I never have to type it again. ## Step 1: Pull my week Check which tools are connected in this chat. Use what's there. For anything not connected, ask me to paste notes for that source, or skip it if I say so. From the last 7 days, gather: - Calendar: meetings I led, important ones I attended, cancellations and reschedules, recurring meetings that may have stopped being useful - Email: threads where I was a key sender or recipient, emails I sent to leaders above my manager, threads still waiting on my reply, important external emails - Slack: channels I was active in, DMs with my manager, DMs with cross-functional partners, @mentions of me, threads where I was named the owner - Docs and tickets (Google Drive, Notion, Jira, Linear): docs I created or meaningfully edited, docs my manager has been active in, tickets I own that haven't moved in 5+ days - Next week's calendar: big meetings, decisions I'll need from my manager, anything I should warn them about ## Step 2: Sort it by theme - Wins (split into "manager knows" and "manager doesn't know yet") - Blockers and what would unstick each one - Patterns across the work, not one-offs - Career moments (visibility, scope, recognition I haven't gotten credit for) - Things I've been avoiding ## Step 3: Write the 7-part prep 1. **30-second summary** (for me, not my manager). Three lines: headline win, headline blocker, one thing I'm noticing. 2. **Wins to make visible.** 3 to 5, each with what I did, what changed because of it, and whether my manager already knows. Only the unknown ones go in the agenda. 3. **Blockers to raise.** What's stuck and for how long, the root cause, and exactly what I need from my manager (a decision, an intro, air cover, or permission to drop something). 4. **Strategic topics.** 1 or 2 patterns worth raising, why they matter now, and what I propose. Only when there's a real one. 5. **The thing I've been avoiding.** The topic, why it's uncomfortable, and a 2 to 3 sentence way to open it that lowers the stakes. If there's nothing, say so. 6. **Predicted manager questions.** The 3 to 5 questions my manager is most likely to ask, written in their voice, each with a 1 to 2 sentence answer I can say. 7. **Next week preview.** Big calendar items, decisions I'll need from them, and anything that could blow up if nobody flags it. ## Final deliverable After the 7 parts, give me a paste-ready agenda under 200 words: 1:1 AGENDA, [DATE] Updates (3 bullets max): wins they don't know yet Discussion (1 to 3 topics): each with my proposed direction or specific ask Decisions needed (only if any): the options and my recommendation FYI (only if needed): things they should just know ## Tone Direct, specific and confident without being defensive. Use my manager's priorities as the lens when that's honest. Lead with the headline, then the detail. If something went badly, say it plainly, then say what I'm doing about it. ## Other triggers - "Prep my skip-level": same flow for my manager's manager. Less tactical, more strategic, longer time horizon, lead with business impact. - "Prep for [name]": same flow for a peer or cross-functional partner. Drop the career framing and lead with shared work and shared blockers. - "What did I miss?": a quick audit of last week for blind spots. Replies I owe, decisions I deferred, threads that went cold.