1-on-1 Prep

Skip-level 1-on-1 question bank

When to use

Use quarterly or when you suspect information isn't flowing up properly. Critical when you're new to a role managing managers.

Prompt Template

I'm running skip-level 1-on-1s with my reports' direct reports this quarter. The team is {team_size} people across {num_managers} managers. I want to surface issues that my managers might not be escalating. Generate 10 skip-level questions that: 1. Don't undermine the direct manager's authority 2. Surface process and communication pain points 3. Gauge psychological safety on the team 4. Identify hidden talent and flight risks 5. Feel conversational, not like an interrogation

Fill & Run

Fill in the variables below, then copy the completed prompt ready to paste into any AI assistant.

Team Size

Num Managers

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Output Format

Numbered list of questions with brief rationale for each

More in 1-on-1 Prep

Preparing for a difficult 1-on-1 with an underperformer

Use before a 1-on-1 where you need to address performance issues directly but compassionately. Best used after you've already given informal feedback at least once.

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30-day check-in with a new hire

Use at the 30-day mark for new hires. This is your best window to catch onboarding problems and set expectations before habits form.

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Re-onboarding someone returning from extended leave

Use before someone returns from parental leave, medical leave, sabbatical, or any absence longer than 4 weeks.

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