28 Questions to Ask Your Boss in Your One-on-Ones
High-signal prompts for productive 1:1s—clarify priorities, remove blockers, get feedback, and grow faster without wasting time.
1What are the top outcomes I should focus on this quarter?
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What are the top outcomes I should focus on this quarter?
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Why this works
Aligns work with measurable priorities and reduces drift.
2What would make my work ‘excellent’ in your eyes?
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What would make my work ‘excellent’ in your eyes?
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Why this works
Defines quality so you can hit the mark reliably.
3What’s one thing I could do that would make your week easier?
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What’s one thing I could do that would make your week easier?
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Why this works
Shows leverage and service mindset.
4What am I not seeing about the risks in my plan?
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What am I not seeing about the risks in my plan?
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Why this works
Surfaces blind spots before they become issues.
5Which stakeholders should I keep closer this month?
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Which stakeholders should I keep closer this month?
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Why this works
Improves alignment and reduces rework later.
6Where should I say no or de-prioritize?
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Where should I say no or de-prioritize?
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Why this works
Protects focus and throughput.
7What feedback do you have on my communication style?
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What feedback do you have on my communication style?
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Why this works
Sharpens influence and reduces friction.
8If I had 10% more time, where should it go?
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If I had 10% more time, where should it go?
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Why this works
Exposes highest-leverage activities.
9What’s the most valuable thing I can ship this week?
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What’s the most valuable thing I can ship this week?
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Why this works
Drives near-term momentum and clarity.
10What does success look like for our team this quarter?
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What does success look like for our team this quarter?
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Why this works
Connects individual work to team goals.
11What do you wish the team did more of—or less of?
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What do you wish the team did more of—or less of?
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Why this works
Invites operational improvements you can lead.
12Where can I take more ownership?
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Where can I take more ownership?
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Why this works
Signals growth and autonomy readiness.
13What would need to be true for me to earn the next level?
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What would need to be true for me to earn the next level?
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Why this works
Defines promotion criteria in observable terms.
14How do I best keep you updated (format, cadence)?
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How do I best keep you updated (format, cadence)?
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Why this works
Aligns reporting to your manager’s preferences.
15What’s the biggest unknown in our strategy?
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What’s the biggest unknown in our strategy?
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Why this works
Targets exploration and risk reduction.
16Who should I learn from internally right now?
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Who should I learn from internally right now?
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Why this works
Connects you to mentors and accelerates growth.
17What’s one behavior I should start, stop, and continue?
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What’s one behavior I should start, stop, and continue?
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Why this works
Gives structured, actionable feedback.
18What decision can I make to unblock the team?
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What decision can I make to unblock the team?
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Why this works
Shows initiative and bias to action.
19Is there a project I can lead end-to-end next?
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Is there a project I can lead end-to-end next?
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Why this works
Invites scope that grows responsibility.
20How can I better support cross-functional partners?
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How can I better support cross-functional partners?
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Why this works
Improves collaboration and outcomes.
21What assumptions should we test this sprint?
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What assumptions should we test this sprint?
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Why this works
Promotes learning and reduces wasted work.
22Where do you see me adding the most value recently?
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Where do you see me adding the most value recently?
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Why this works
Reinforces strengths to double down on.
23What would you change about how I run meetings?
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What would you change about how I run meetings?
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Why this works
Improves efficiency and stakeholder engagement.
24What’s a risk if we keep doing things the current way?
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What’s a risk if we keep doing things the current way?
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Why this works
Provokes constructive change thinking.
25How can I prepare for [upcoming review/launch]?
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How can I prepare for [upcoming review/launch]?
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Why this works
Ensures readiness and reduces last-minute churn.
26Is there a stretch opportunity you’d trust me with?
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Is there a stretch opportunity you’d trust me with?
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Why this works
Signals ambition and growth capacity.
27What should we stop discussing and just decide?
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What should we stop discussing and just decide?
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Why this works
Cuts decision latency and drives action.
28What’s the best use of our 1:1 time for you?
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What’s the best use of our 1:1 time for you?
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Why this works
Optimizes the meeting for mutual impact.
Run Great 1:1s
Expert tips and techniques for getting the most out of these questions.
Own the Agenda
Send a Doc
Share agenda + status 24 hours before to focus the conversation.
End With Actions
Capture owners and dates; follow up asynchronously.
Track Wins
Keep a running list to support reviews and morale.
30-Minute Template
Flow
Common Pitfalls
Status Only
Make space for feedback, growth, and decisions—not just updates.
Unclear Owners
Every next step needs a name and a date.