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Perfect Icebreaker Questions & Activities for Training

Trainers always talk about “connections before content.” Icebreaker questions are critical starts to your training because they help learners connect with one another and with the topic they will be exploring. Looking for the perfect prompt for your next session. Let this be your guide!

For each category of prompts, we’ll share 5 to 10 examples. If you want more variety, you can purchase a Thumball, UNZIP-it! Pocket or UNZIP-it! PowerPoint Deck. If you want ALL THE PROMPTS for ALL THE TOPICS, explore the Trainers EXCHANGE website.

Get Acquainted Icebreaker Questions

Some getting-acquainted conversation starters will fill silences but not develop deep relationships. Others, which explore motivations, personality traits, history, goals, and accomplishments, will lead to deeper understanding. Understandably, with any conversation starter, the person answering always has the option to make light of a question rather than sharing deeply.  The themes listed below are (roughly) organized from skim-the-surface to dig-deeper discussion starters.

Favorites Thumball by Trainers Warehouse

Favorites Thumball  $31.95 BUY NOW


Although this content asks respondents to respond with “favorites,” we always recommend asking for “one of your favorites.” Somehow, that seems to make it all a bit easier to answer the question. These prompts, which are among our favorites, include a range of topics, such as:

  • Locations and destinations
  • Ways to spend time
  • Cuisines
  • Art forms
  • Preferences

Because every prompt is about YOU, most people can respond to these pretty easily. Here’s a spattering of the contents found on this Thumball:

  1. Favorite thing to spend money on
  2. Favorite thing about getting older
  3. Favorite compliment to receive
  4. Favorite bit of advice you’ve ever received
  5. Favorite fad or trend you hope comes back
  6. Favorite day of the week
  7. Favorite way to spend a Sunday morning
  8. Favorite way to feel healthy
  9. Favorite childhood memory
  10. Favorite mode of transportation

Find all the Favorites-style icebreaker questions in these great training tools from Trainers Warehouse

Which are You? Thumball by Trainers Warehouse

Which are You? Thumball  $31.95 BUY NOW


On this Thumball, you’ll find two words on each panel. They represent opposites. The goal is to understand if you are “this” or “that,” or if your preference lies somewhere in the middle. For instance:

  1. Work or Play
  2. Ask or Tell
  3. Highway or Back roads
  4. Self-serve or full-serve
  5. Sweet or salty
  6. Words or Pictures
  7. City or Country
  8. Imported or Domestic
  9. Letters or Numbers
  10. Store-bought or Homemade

As you use the ball to learn more about friends and colleagues, you’ll find that the topics are quite broad and can be applied to work, home, communication styles,  foods, activities, relationships,  purchases,  leadership, teams, and more.

As you play, you can reframe a prompt to your specific location, situation, or objective. Find the full range of prompts here:

Which are You and Why? Thumball  $31.95


UNZIP-IT! Pocket with Deck of Common Ground Conversation Starter Prompts

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Dig into subjects that explore commonalities and shared experiences, for instance:

  • Time: Ways to spend free time, weekends, vacations, etc.
  • Favorites: Favorite foods, activities, apps, show, books
  • People: Family and friends who impact your life
  • Growth: Goals, talents, or skills you’d like to develop
  • Moolah: What you’d spend money on
  • You: claims to fame and more…

Identify experiences and interests you share with others with prompts such as these:

  1. What does your perfect day look like?
  2. Favorite show(s) to watch
  3. What do you like to read?
  4. Sports I like to watch
  5. My favorite childhood memory
  6. What do you do regularly to stay healthy?
  7. Favorite art form (music, dance, art, theater, film)
  8. Who are the most important people in your life?
  9. Who in your family are you closest to?
  10. For good advice, who do you turn to first?

For more prompts, or to purchase the product, click here:

Remote PPT with icebreaker questions about What Makes You You

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This interesting grouping of “What…?” questions helps colleagues identify what makes each person special. The conversation starters cover a range of topics, including:

  • Skills and interests
  • Quirks, wishes, and facts
  • Motivations & fears
  • Likes & dislikes
  • Goals and contributions

This sampling of icebreaker questions will give you a sense of the questions:

  1. What are you good at, but embarrassed to admit?
  2. What is something you like to do the old-fashioned way?
  3. What could you give a 30-minute presentation on with no prep?
  4. What is something you think everyone should learn?
  5. What amazing thing did you do that no one was around to see?
  6. What are you looking forward to in the coming months?
  7. What is the most impressive thing you know how to do?
  8. What’s the dumbest thing you’ve done that turned out okay?
  9. What is something you can never seem to finish?
  10. What would annoy you about having yourself as a roommate?

Find the full sets of conversation prompts in these great training tools from Trainers Warehouse:

Getting to Know You Thumball

Getting To Know You Thumball $31.95 BUY NOW


Getting to Know You questions are intended to be thoughtful and easy-to-answer. With them, you’ll be able to spark conversation and help players know more about each. Questions will explore:

  • Experiences: memorable moments in your life
  • People: Family and friends who have affected your life
  • Most favorite and least favorite: Gifts, ages, sounds, chores
  • Activities: pastimes, hobbies, bucket list items, travel
  • Hopes, Fears and Wishes: the details that make you unique
  1. Least favorite mode of transportation
  2. A sound that you love
  3. A new skill you’d like to have (with no effort)
  4. The most difficult thing you’ve ever done?
  5. The age you’d most want to relive
  6. The age at which you became an adult
  7. An experience that made you a better person
  8. Something you did that got you in trouble
  9. One item on your bucket list
  10. Your claim to fame

Probing prompts that get to your phobias, wishes, and favorite moments, explore these resources:

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These prompts will help build relationships and tease out session objectives to help trainers kick off their learning sessions. Prompts primarily cover these three categories:

  • Getting to Know You:  dreams, peeves, wishes, decisions, frustrations, talents
  • Learning Styles: best teachers, preferred learning methods,  learning goals
  • Work Styles: proudest accomplishments, creative contributions, strengths
  1. I’m here because…
  2. I’ll be successful if…
  3. I’d like to change…
  4. Childhood dream
  5. A day I’d live over
  6. Most creative contribution
  7. I hope to learn…
  8. Oops! I forgot to…
  9. Greatest strength at work…
  10. I learn best by…

For more session opener icebreaker prompts about goals, motivations, and aspirations, consider the


The experiences in our lives shape who we are today. Engage your group in conversations about their past experiences and the people who influenced their growth and development. Icebreaker questions focusing on our past typically include:

  • Childhood memories: birthdays, vacations, regrets
  • Past experiences: scary moments, hospital visits, turning points, accomplishments
  • Daily life when you were younger: extracurricular activities, friendships, summer traditions
  • People & personalities: impact of birth order, mentors, grandparents
  • Challenges & accomplishments: difficult choices, challenging times, goals

Following is a selection of conversation starters that will help groups share the experiences that shaped them:

  1. A time you got in trouble at school
  2. A time you went to the hospital
  3. An important turning point in your life
  4. Describe your “group” in high school
  5. Extra-curricular activities you did
  6. How you spent your summers
  7. How you spent your time after school
  8. How your birth order affected you
  9. Something you hated as a child

You’ll find 32+ icebreaker questions focusing on past experiences in these Trainers Warehouse resources:

Topic-Specific Icebreaker Questions

Diversity Thumball by Trainers Warehouse

Diversity Thumball $31.95 BUY NOW


Address the factors and experiences that shape our understanding of differences in ethnicity, age, religion, and more. For instance,

  1. An instance when someone went out of their way to make you feel included?
  2. A time you went out of your way to make someone feel included?
  3. A time you shared an unpopular idea
  4. Describe a time you felt lonely in a big group of people
  5. What were your parents’ attitudes towards LGBT communities?
  6. Should companies/school close for all religious holidays? Why or why not?
  7. Name 2 ways in which men and women may be treated differently?
  8. Is it easier to be male or female? Why?
  9. What gives you hope that people are becoming more accepting of diversity?
  10. What’s your generation’s biggest challenge when it comes to acceptance?

Explore more Diversity-themed conversation prompts with the:


Gain personal and organizational insight. Explore us vs. them thinking, privilege and power, and community initiatives.

  1. A dominant aspect of my identity that influences how I feel & act
  2. An aspect of my identity that makes me feel proud is…
  3. With whom do you feel more/less safe in sharing emotions & experiences?
  4. What new initiatives could strengthen feelings of belonging?
  5. How can we create a culture of inclusion & equity?
  6. Something I’ve learned from people whose identities differ from mine
  7. In your mind, what does oppression look like?
  8. In what ways do you feel privileged?
  9. Why is it important for us to take action in DEI initiatives?
  10. What prevents people from stepping up as an ally for diversity and inclusion?

Consider the DEI Thumball by Trainers Warehouse for more DEI conversation starters and icebreaker questions ($31.95), or the DEI PowerPoint Deck with similar content.


“Toolbox Talks” are informal safety meetings that address workplace hazards and safe work practices. They help promote an organizational culture that is healthy, safe, and supportive. Use Toolbox Talks Thumball to supplement safety training, not replace it. It’s a great way to kick off safety initiatives, raise awareness, and identify areas to improve workplace safety.

  1. What should you do if someone’s doing something dangerous?
  2. What can you do if you’re bullied or harassed?
  3. What accidents happen most frequently in our environment?
  4. How are we “covered” in case of an accident? As Individuals? As company?
  5. What workplace activities are best not done alone?
  6. The safety rule that is hardest to comply with is…
  7. Do I feel safer in the summer or winter? Why?
  8. What do I look for on product warning labels?
  9. How does mobile phone use affect workplace safety?
  10. A safety protocol at work that should be changed is . . .

For more Toolbox Talks discussion prompts to help start conversations about workplace safety, try these Trainers Warehouse tools:

Be a Leader UNZIP-IT! Deck

Team Dynamics UNZIP-IT! Deck $29.95 BUY NOW


In this unique Leadership Thumball, find a full range of conversation starters, including:

  • Leadership traits that I have or aspire to have in myself and my team
  • Ways to motivate, inspire, and recognize employee contributions
  • Methods for dealing with disagreement, decision-making, and mistakes
  • Reflections on challenges, frustrations, delegation, and impatience
  • Approaches to promote growth and learning
  • Techniques to get buy-in, promote diversity, and share feedback

When prompting conversation, aim to include some reflective questions (past experiences) and others that are appreciative (questions that encourage participants to envision the future and focus on positive potential). A good range of leadership conversation prompts should cover vision, innovation, competence, integrity, continuous improvement, teamwork, accountability, diversity, and development. For instance:

  1. A time I used power in a positive way
  2. What makes me impatient?
  3. I get to know my staff by…
  4. What I like/dislike about coaching others
  5. In my role, I am most frustrated by…
  6. I foster learning by…
  7. I am least effective when…
  8. I last thanked a colleague or staff member when…
  9. I dislike having power because…
  10. I inspire creativity by…

Find additional icebreaker questions and conversation prompts that explore leadership qualities and experiences integrated into these Trainers Warehouse tools:


Promote team spirit, boost flagging energy, and initiate meaningful conversations with team dynamics conversation prompts. Indeed, with the right conversation prompts, you can tactfully explore how your group is working as a team. Discuss…

  • Benefits and drawbacks of teaming
  • Ways to make others feel heard, show respect, and draw in multiple perspectives
  • Systems to improve productivity and minimize duplication of efforts
  • Approaches to identify goals, work to completion and celebrate success
  • Management of disagreements, problems, and mistakes
  • Methods to develop consensus, show support, and motivate each other.

Effective teamwork is often based on:  Accountability * Motivation * Trust * Respect * Commitment * Diversity of Capabilities * Adaptability * Creative Freedom * Collaboration * Conflict Resolution * Communication

Rich conversation prompts might include these, i.e.:

  1. How should we manage disagreements?
  2. Give an example of a goal we are all working towards
  3. Do we have clearly defined team goals?
  4. Do we learn from our mistakes?
  5. Do we admit mistakes to each other?
  6. Give an example of a mistake we learned from.
  7. How can we support each other?
  8. Do we respect each other’s role in the team?
  9. When was the last time we had constructive conflict?
  10. How do we check that we are working toward the same goal?

To explore the factors that enhance or undermine your team’s success, consider more prompts on Trainers Warehouse’s Team Dynamics toos:


Resilience helps individuals adapt to difficult situations. To assist your groups in building resilience in their personal and professional lives, facilitate conversations that encourage optimism, positive thinking, compassion, and growth mindsets. The following 10 skills are most often associated with resilience. The questions that appear with them can help people begin to build that important skill.

  • Patience when facing situations that test your patience, how do you calm yourself?
  • Optimism what happiness might the future hold?
  • Gratitude – for whom and what are you grateful?
  • Acceptance – how might you productively respond to bad news?
  • Kindness – what are your preferred ways to spread happiness?
  • Purpose – what goals and accomplishments inspire you?
  • Forgiveness – when, why, and how can you forgive others?
  • Connection – do you regularly reach out to the people who create joy in your life?
  • Composure when you lose composure, how do you refocus your energy?
  • Listening – what techniques do you use to show you’re listening?

For more icebreaker questions to foster patience, acceptance, kindness & forgiveness, consider these:

Building Resilience Thumball


Use workplace happiness icebreaker prompts to enable colleagues to express their goals and articulate challenges. By focusing on positivity, workplace engagement, and meaningful relationships, conversations can elicit optimism and opportunities for a happier, more productive workplace. Discussion starters like these might get the ball rolling, e.g.:

  1. A new challenge I hope to take on at work?
  2. My top priorities for the day/week
  3. What risk would you take if you knew you couldn’t fail?
  4. What permission do you need/want to move forward?
  5. Something you’re thankful for at work
  6. The best thing about our organization is…
  7. I’d like coming to work more if…
  8. Our meetings would be more productive if…
  9. How do we encourage/discourage risk-taking?
  10. An area where I’d like more autonomy

Access additional happiness-at-work icebreaker questions, which emphasize  goals, achievements, hopes, and dreams, in these Trainers Warehouse exclusive tools:


Here’s another important topic for the workplace: Stress Management! Ideal conversation starters relating to stress management should cover this range of topics:

  • Causes of stress: tasks, chores, times of year, and situation that bring angst
  • Controlling stress: ways to minimize stress and focus on priorities
  • Sources of calm: hobbies, activities, quiet places that bring relaxation
  • Wellness practices: Sleep, exercise and diet that nourish you
  • Dealing with stress: what do you do (can you do) when you get stressed
  • Electronics: impact of technology and email on stress levels

For instance, you might ask:

  1. What forms of exercise are most enjoyable?
  2. Do you get as much sleep as you need?
  3. Is there a new hobby you’re hoping to start?
  4. What are your most dreaded household chores?
  5. When you’re busy, what’s first to get cut from your routine?
  6. If you took a “1-minute mental vacation,” where would you go?
  7. If you had one day left to live, what would you do?
  8. When stressed do you prefer company or solitude?
  9. What most relaxes you?
  10. How would you use two extra hours per day?

To help your group discover the causes of stress and the ways to manage it, consider more conversation prompts and icebreaker questions on Trainers Warehouse tools like these:


These prompts are excellent for any who are experiencing a life change. When facing difficult times, the challenge is to move beyond the past experience toward an unknown future. If your team is facing substantial change–as individuals or as a group–consider icebreaker questions that promote conversation about how to move forward, onward, and upward.

Address topics such as these:

  • People to seek out for assistance
  • Healthy habits — mentally and physically
  • Personal sources of strength  and joy
  • Methods to interrupt and reverse bad mojo

For instance:

  1. What’s the silver lining of a challenging time?
  2. A person I remember fondly
  3. My “go-to” indulgence
  4. When feeling blue, I prefer company/solitude because…
  5. Where do you find spiritual strength?
  6. I’ve learned to accept that…
  7. Something I accomplished recently
  8. An activity that relaxes and calms me
  9. My top priorities for the day/week
  10. Something that makes me proud

These Trainers Warehouse tools will have a range 30+ questions and prompts to discuss methods for managing change:


Emotional Intelligence (a.k.a. EQ) requires five skills: Self-Awareness [SA], Motivation [MO], Self-Regulation [SR], Empathy [EM], and Social Skills [SS]. Conversation prompts and icebreaker questions that develop EQ delve into these 5 topics.

For example:

  1. What contributes to distrust? (Empathy)
  2. How could someone regain composure after snapping? (Self-Regulation)
  3. What holds you back from being your best YOU? (Self-Awareness)
  4. How can I make colleagues feel valued?   (Motivation)
  5. What would your best friend say is your weakness? (Self-Awareness)
  6. How can we make others feel appreciated? (Empathy)
  7. Describe three ways to communicate non-verbally   (Social Skills)
  8. What could be a “blind spot” (a strength others might consider a weakness)  (Self-Awareness)
  9. What do you do if you find yourself overreacting to something?  (Self-Regulation)

Find more conversation starters to build self-awareness, empathy, motivation, and social skills on the Trainers Warehouse Emotional Intelligence Thumball.


Trust allows us to take risks, open up, and look for mutually beneficial solutions when conflicts occur. It gives us peace of mind when we need to rely on one another, and comfort to share our vulnerabilities. Like a bridge, trust also brings people together and deepens relationships. In turn, with strong relationships, we enjoy emotional support, confidence, reduced stress, good health, and happiness. Building trust starts with communication – asking the right questions and taking the time to listen. Discuss topics such as:

  • Causes of trust and distrust
  • People you entrust with secrets
  • Impact of promises, apologies, and lies
  • Ways to make others feel safe
  • Dealing with mistakes and resistance
  • Being genuine

Conversation starters that will help explore the topic of trust, and in the process, begin building trust include:

  1. What might be the impact of admitting mistakes?
  2. Are “white lies” okay? Why/why not?
  3. Who do you consider to be your “family”?
  4. What topics are hardest to discuss?
  5. How do you decide if someone is trustworthy?
  6. Do you tend to say “I don’t know” or make something up? Why?
  7. How can we build trust in one another?
  8. How do you make others feel safe?
  9. What is “active listening” and why is it important?
  10. Do you ever resist asking for help? When? Why?

Build bridges and explore issues of interpersonal trust #Building Trust Thumball



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