100 Questions to Ask In a Team One-on-One

No.	Item	Definition
1.	Any blockers I can remove?	Looks for obstacles to clear.
2.	Anything you’re excited about?	Surfaces enthusiasm and opportunities.
3.	Anything you’re worried about?	Surfaces concerns and risks.
4.	Are expectations clear enough?	Checks understanding of expectations.
5.	Are priorities clear right now?	Checks alignment and clarity.
6.	Do you feel challenged enough?	Checks growth and stretch.
7.	Do you feel supported?	Checks support and inclusion.
8.	Do you have what you need?	Checks resources and support.
9.	Help me understand the issue.	Invites explanation and context.
10.	Help me understand your view.	Invites perspective and context.
11.	How are deadlines looking?	Checks timeline health.
12.	How are meetings working?	Checks meeting usefulness.
13.	How are things with the team?	Checks team dynamics and morale.
14.	How are you feeling about goals?	Checks goal alignment and confidence.
15.	How are you feeling lately?	Checks emotional state and wellbeing.
16.	How are you managing time?	Checks time management.
17.	How can I support you better?	Seeks better ways to help.
18.	How confident do you feel?	Checks confidence and readiness.
19.	How do you feel about work?	Checks overall work sentiment.
20.	How is collaboration going?	Checks teamwork and coordination.
21.	How is communication going?	Checks communication effectiveness.
22.	How is remote work going?	Checks remote work experience.
23.	How is your focus lately?	Checks concentration and attention.
24.	How is your motivation?	Checks drive and engagement.
25.	How is your work-life balance?	Checks balance and wellbeing.
26.	How’s your stress level?	Checks stress and pressure.
27.	How’s your workload feeling?	Checks workload and capacity.
28.	Is anything blocking progress?	Checks for current blockers.
29.	Is anything feeling off?	Invites subtle concerns.
30.	Tell me about your week.	Invites a broad update.
31.	Walk me through your priorities.	Reviews current priorities.
32.	What are others missing?	Surfaces overlooked context.
33.	What are you avoiding?	Surfaces hesitation or resistance.
34.	What are you concerned about?	Surfaces concerns and risks.
35.	What are you excited to do?	Explores motivating upcoming work.
36.	What are you learning now?	Explores current growth and learning.
37.	What are you not saying?	Invites unspoken concerns.
38.	What are you proud of lately?	Highlights recent accomplishments.
39.	What are you spending time on?	Checks time allocation.
40.	What are you struggling with?	Identifies current difficulties.
41.	What are you waiting on?	Finds dependencies and delays.
42.	What are your priorities now?	Clarifies current focus areas.
43.	What do you need from me?	Asks for support from manager.
44.	What do you want less of?	Identifies desired reductions.
45.	What do you want more of?	Identifies desired increases.
46.	What do you want to learn?	Explores future development interests.
47.	What feedback do you have?	Invites upward feedback.
48.	What feedback do you need?	Invites developmental feedback needs.
49.	What feels hardest right now?	Finds the toughest issue.
50.	What feels most important?	Clarifies strategic importance.
51.	What feels most urgent?	Clarifies immediate priorities.
52.	What goals feel unrealistic?	Surfaces misaligned expectations.
53.	What goals matter most now?	Identifies key current goals.
54.	What isn’t working well?	Finds ineffective practices.
55.	What progress are you proud of?	Highlights achievements and momentum.
56.	What should I know?	Invites important updates.
57.	What should we keep doing?	Identifies valuable ongoing practices.
58.	What should we start doing?	Identifies new helpful practices.
59.	What should we stop doing?	Identifies unhelpful practices.
60.	What surprised you recently?	Invites reflection on new developments.
61.	What would make work easier?	Seeks improvements and support.
62.	What would success look like?	Defines desired outcome.
63.	What’s been challenging?	Surfaces obstacles and frustrations.
64.	What’s been unclear lately?	Surfaces confusion or ambiguity.
65.	What’s changed since last time?	Reviews updates since prior meeting.
66.	What’s draining your energy?	Identifies demotivating work.
67.	What’s energizing you most?	Identifies motivating work.
68.	What’s going well for you?	Invites positives and recent wins.
69.	What’s helping you succeed?	Identifies effective supports.
70.	What’s not getting enough time?	Identifies neglected work.
71.	What’s one recent win?	Prompts a specific success.
72.	What’s one thing I missed?	Invites overlooked information.
73.	What’s one thing to celebrate?	Prompts recognition and positivity.
74.	What’s slowing you down?	Finds sources of delay.
75.	What’s taking too much time?	Identifies time drains.
76.	What’s top of mind today?	Opens with current concerns.
77.	What’s working especially well?	Finds effective practices.
78.	What’s your biggest challenge?	Identifies the main difficulty.
79.	What’s your biggest priority?	Identifies the main focus.
80.	When do you need my input?	Clarifies manager involvement timing.
81.	When should we check in next?	Sets next follow-up timing.
82.	Where are we making progress?	Finds momentum and success.
83.	Where are we misaligned?	Finds alignment gaps.
84.	Where are you feeling stuck?	Finds areas needing help.
85.	Where do you need clarity?	Identifies unclear areas.
86.	Where do you need support?	Identifies support needs.
87.	Where do you see opportunity?	Identifies possible gains.
88.	Where do you see risk?	Identifies possible problems.
89.	Which decisions need input?	Identifies pending decisions.
90.	Which relationships need work?	Identifies relationship challenges.
91.	Which skills are you building?	Explores skill development.
92.	Which skills need practice?	Identifies growth areas.
93.	Which tasks feel highest value?	Identifies valuable work.
94.	Which tasks feel lowest value?	Identifies low-value work.
95.	Which tradeoffs are you making?	Explores competing priorities.
96.	Who should be involved less?	Reduces unnecessary involvement.
97.	Who should be involved more?	Finds missing collaborators.
98.	Who’s been helpful lately?	Highlights support from others.
99.	Why does this matter to you?	Explores personal meaning and motivation.
100.	Why has this been difficult?	Explores root causes.