One-on-One Meeting Questions for Managers: 50+ Questions, Sorted by Situation
50+ one on one meeting questions for managers, sorted by situation — weekly check-ins, career growth, performance, wellbeing, and upward feedback.
Conversation Cards & Leadership Tools for Managers
The Unstuck Box: Everything You Need for a Better Day at Work
Our boxes, books, and planners make it easy to improve how you think, lead, and collaborate at work.
- Master everyday leadership challenges
- Communicate clearly and confidently
- Stay organized, focused, and inspired
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NEW: AI Clarity
Not just a deck. AI Clarity gives you the tools to actually do something with AI.
Inside, you’ll get 100 powerful cards, ready-to-run AI workshops, and a live companion app that keeps you sharp as the tech evolves.
Transform Your Team
Empower your teams to break through business challenges with The Unstuck Box®.
- The Unstuck Box range builds collaboration, communication, and critical thinking skills in teams
- Fosters an innovative mindset and helps solve workplace problems from new angles
- Join industry leaders like Google, Amazon, and Harvard who use The Unstuck Box to tackle complex strategic challenges and drive innovation
Trusted by 50,000+ leaders
From organizations including...
Measurable Impact at global industrial leader Altrad
5,000+ employees
11-25% time savings
10/10 recommendation
Our client, in the L&D function at global industrial leader Altrad, reported concrete improvements after implementing The Unstuck Box® tools: significantly improved team problem-solving quality and decision-making speed, improved leadership facilitation skills and meeting engagement.
"We are stronger, more motivated, and eager to explore the next big challenge all with the help of The Unstuck Boxes!"
About Altrad
International leader in industrial services for Oil & Gas, Energy, and Construction sectors. Headquartered in France with 65,000+ employees globally.
Breakthrough in Leadership Facilitation at Hudl
501-5,000 employees
Up to 10% time savings
9/10 recommendation
An HR & Learning Development professional at Hudl experienced a significant transformation in company leadership and facilitation capabilities after implementing The Unstuck Box®. Beyond improved team problem-solving and decision-making processes, they achieved notable engagement improvements.
"Made our 1:1s more engaging, building more personal conversations."
About Hudl
Sports technology company providing video analysis tools for coaches and athletes. Founded in 2006, serves teams across multiple sports with backing from Accel Partners and Bain Capital.
Perfect Score from Leadership Development Consultant
50-500 employees
11-25% time savings
10/10 recommendation
Jon Winters, Leadership & People Development Coach at Empower You Consulting, gave The Unstuck Box® a perfect recommendation score after achieving significant improvements across team problem-solving, leadership skills, and meeting engagement.
"The Unstuck Boxes have been great tools for our leadership and people development."
About Empower You Coachsulting
Leadership development consultancy specializing in coaching, training, and speaking.
Why Leaders Choose The Unstuck Box
Grow Stronger Leaders
Coaches and managers get better, faster.
89.5%
report better leadership & facilitation
~40%
see significant improvement
- Scales great facilitation across teams
- Easy to run, easy to repeat
Win Back Meeting Time
Make meetings shorter and more useful.
55%
save 10%+ of meeting time
Up to 50%
of wasted hours reclaimed
- Example: 5,000+ hours/year back
- Less talk, more decisions
People Love It
Teams feel more engaged and productive.
NPS 70
with 80% promoters (9–10)
- 39% better meetings
- 28% clearer communication
- 22% higher engagement
Based on a 2025 survey of Unstuck Box customers.
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Unlock Enhanced Cognitive Skills
Learn new, simple ways to solve hard problems. Get tools that help you make better decisions at work and in life.
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Transform Team Dynamics
Boost your team's creativity and work together better. Our tools make teamwork smooth and lead to great results.
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Revolutionize Interpersonal Dynamics
Gain the skills to deal with tough people issues. Improve your relationships with clear and kind communication.
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Embrace the Mindset of Innovators
Think like top achievers. Use smart strategies to see things differently, make decisions faster, and succeed.
Let customers speak for us
Conflict Deck Is Awesome!
If you are an expert who often works and collaborates with other “experts,” I highly recommend this deck. It's been helpful!
Jessica Englehart
The Unstuck Box®: Workday Wisdom
The Unstuck Box®: Performance Improvement
Megan Fitzsimmons
The Unstuck Box®: Performance Improvement
High Impact Playbook
The playbook is a great resource that is jam-packed with valuable ideas and knowledge to help people leaders at any stage of their leadership journey leverage the most from their 1:1s. I’m getting so much out of it! Thanks unstuck Box!
Lisa B
The High-Impact 1:1 Playbook
Lives up to the name
I'm an overthinker, which can sometimes cause analysis paralysis, aka getting stuck! The Workplace Communication box help keep things simple, and keeps communication effective and flowing.
Andrea C
The Unstuck Box®: Workplace Communication
Original package lost, customer service did a great job replacing it!
I have ordered multiple unstuck boxes in the past. I genuiinely love using them with my corporate mentees. This was the first time I’ve ever had any issues receiving my packages. The original package was lost and once I reached out to customer service, someone quickly dispatched a new order. And i’m very satisfied with my purchase. I’ve shared unstuck box with multiple colleagues over the years and encouraged them to purchase. would recommend to anyone interested!
Jeremy Boco
The Unstuck Box®
The best 1:1 companion out there
This planner has been a brilliant addition. It helps my team and me stay on track before, during, and after our one-on-ones, ensuring that commitments are kept. It's such a great investment!
Lisa B
The Unstuck Box®: One to Ones Planner
great stuff
I have not opened them all yet but the one I have it looks great
Barbara Barclay
The Unstuck Box®: Workday Wisdom
Great Resource
Great insight and knowledge resource to build confidence for those that are new to, or building knowledge around AI
Ashleigh Smith
The Unstuck Box®: AI Clarity
A great tool
I find these cards a great tool when having conversations with my team.
Sometimes you find yourself asking similar questions, whereas these can help you take a different route and discuss things you wouldn't normally.
Tom Ride
The Unstuck Box®: One to Ones
A Helpful Resource for Managers
I’ve used several Unstuck Boxes, including Conflict Resolution, One-to-Ones, Performance Improvement, and Team Building. Each one was clear, practical, and easy to put into action with my team. I like that the materials are straightforward—no fluff—just useful prompts and tools that helped guide real conversations. The variety has been valuable for different situations, and it’s made my role easier when addressing tough topics.
Madison Wilson
The Unstuck Box
This notebook has a perfectly structured format for driving high quality one-on-ones. The notebook also is well made and high quality materials and design
Stephanie Tulgren
The Unstuck Box®: One to Ones Planner
Great tool for leaders
I was so excited to receive my pack! There were so many great questions included and it’s really helpful that they’re split into different categories. Great for using in team meetings and 121’s. Will be looking to purchase a different pack soon!
SPhillips
The Unstuck Box®: Team Building Cards
Incredible!!!
I wish I would have found Unstuck years ago! I had my first team meeting using Unstuck cards and it was a huge success! Feedback was that they wish I’d had that meeting a month ago!
Melinda M.
The Unstuck Box®: One to Ones
Very handy and useful
The cards are very useful for me, being new to AI, reading each card teaches me something new.
Cynthia Gan
The Unstuck Box®: AI Clarity
A Powerful Tool for Gaining Clarity
I recently tried out The Unstuck Box a toolkit of beautifully designed conversation cards and frameworks that help break mental blocks, spark meaningful ideas, and guide clarity during tough work moments or decision-making. Each prompt is easy to pick up and surprisingly actionable perfect to reach for during a moment of uncertainty or while planning. It’s thoughtful, practical, and genuinely helpful.
Shey Quinton
The Unstuck Box®: AI Clarity
Read the latest from The Unstuck Blog
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Effective Approaches to Workplace Conflict Resolution for Teams
Discover practical strategies for resolving workplace conflicts effectively, fostering collaboration and harmony within your team!
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Help! My boss keeps cancelling one-on-ones! 5 Strategies to Cope
Struggling with canceled one-on-ones? Discover 5 effective strategies to cope and enhance communication with your boss. Read the article for practical tips!
