28 Questions to Ask Your Boss in Your One-on-Ones
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?
What are the top outcomes I should focus on this quarter?
Aligns work with measurable priorities and reduces drift.
2What would make my work ‘excellent’ in your eyes?
What would make my work ‘excellent’ in your eyes?
Defines quality so you can hit the mark reliably.
3What’s one thing I could do that would make your week easier?
What’s one thing I could do that would make your week easier?
Shows leverage and service mindset.
4What am I not seeing about the risks in my plan?
What am I not seeing about the risks in my plan?
Surfaces blind spots before they become issues.
5Which stakeholders should I keep closer this month?
Which stakeholders should I keep closer this month?
Improves alignment and reduces rework later.
6Where should I say no or de-prioritize?
Where should I say no or de-prioritize?
Protects focus and throughput.
7What feedback do you have on my communication style?
What feedback do you have on my communication style?
Sharpens influence and reduces friction.
8If I had 10% more time, where should it go?
If I had 10% more time, where should it go?
Exposes highest-leverage activities.
9What’s the most valuable thing I can ship this week?
What’s the most valuable thing I can ship this week?
Drives near-term momentum and clarity.
10What does success look like for our team this quarter?
What does success look like for our team this quarter?
Connects individual work to team goals.
11What do you wish the team did more of—or less of?
What do you wish the team did more of—or less of?
Invites operational improvements you can lead.
12Where can I take more ownership?
Where can I take more ownership?
Signals growth and autonomy readiness.
13What would need to be true for me to earn the next level?
What would need to be true for me to earn the next level?
Defines promotion criteria in observable terms.
14How do I best keep you updated (format, cadence)?
How do I best keep you updated (format, cadence)?
Aligns reporting to your manager’s preferences.
15What’s the biggest unknown in our strategy?
What’s the biggest unknown in our strategy?
Targets exploration and risk reduction.
16Who should I learn from internally right now?
Who should I learn from internally right now?
Connects you to mentors and accelerates growth.
17What’s one behavior I should start, stop, and continue?
What’s one behavior I should start, stop, and continue?
Gives structured, actionable feedback.
18What decision can I make to unblock the team?
What decision can I make to unblock the team?
Shows initiative and bias to action.
19Is there a project I can lead end-to-end next?
Is there a project I can lead end-to-end next?
Invites scope that grows responsibility.
20How can I better support cross-functional partners?
How can I better support cross-functional partners?
Improves collaboration and outcomes.
21What assumptions should we test this sprint?
What assumptions should we test this sprint?
Promotes learning and reduces wasted work.
22Where do you see me adding the most value recently?
Where do you see me adding the most value recently?
Reinforces strengths to double down on.
23What would you change about how I run meetings?
What would you change about how I run meetings?
Improves efficiency and stakeholder engagement.
24What’s a risk if we keep doing things the current way?
What’s a risk if we keep doing things the current way?
Provokes constructive change thinking.
25How can I prepare for [upcoming review/launch]?
How can I prepare for [upcoming review/launch]?
Ensures readiness and reduces last-minute churn.
26Is there a stretch opportunity you’d trust me with?
Is there a stretch opportunity you’d trust me with?
Signals ambition and growth capacity.
27What should we stop discussing and just decide?
What should we stop discussing and just decide?
Cuts decision latency and drives action.
28What’s the best use of our 1:1 time for you?
What’s the best use of our 1:1 time for you?
Optimizes the meeting for mutual impact.
Want to learn more?
Run Great 1:1s
Want to learn more?
Run Great 1:1s
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.