Most one-on-ones drift because nobody planned them. The manager opens with "how's it going?", the report says "yeah good", and the next 25 minutes are status updates that should have been a Slack message. A good 1:1 question changes the entire shape of that meeting — it makes the report think, gives the manager information they couldn't get from a dashboard, and surfaces problems before they become resignations.
This is a working library of 60+ one-on-one questions, grouped by the situation you're in. Tick the questions that fit *this* meeting, copy them into your agenda, and run the meeting in 25 minutes instead of 45.
When to use which category
- Weekly check-in — short, low-stakes questions for the regular cadence
- Growth & career — once a month, deeper questions about trajectory
- Energy & blockers — when the report seems off, or wins have slowed
- Manager feedback — quarterly; uncomfortable but the highest-value
- Project & priorities — when scope has shifted or load is unclear
- Relationship & trust — for new managers or new reports
- Skip-level prep — if a skip-level meeting is coming, use the 1:1 meeting template to prep it
Why most 1:1 questions fail
They're too open-ended ("any thoughts?") or too closed ("everything fine?"). The best questions are specific and assumption-loaded — *"what's the most frustrating part of your week right now?"* assumes there is one and lets the report opt into the question size. *"What would you change about how I run our team if you could?"* assumes there's an answer and signals you genuinely want it.
How to use the agenda output
Tick 4–7 questions per meeting — fewer and you'll over-stretch each one, more and you'll skip half. Click "Copy agenda" to get a clean plain-text version you can paste into Notion, Linear, or wherever your 1:1 notes live. Each ticked question has an optional notes field so you can capture the answer in the moment.
For longer-running tracking (one-on-one history, theme trends, action items across meetings), the full LemTask app has dedicated 1:1 spaces. This page is the lightweight version for picking the questions themselves.