Thoughtful Team Builder Ice Breakers

What was the worst day of your life and why?
What would you most like to be remembered for when you are reminiscing about your life in your old age?
What aspect of your personality adds the most value to the world?
If you could change one thing about yourself, what change would you make?
If you could choose any one person, living or dead, whom would you most want to emulate? Share why.
Who had the most influence over the choices you eventually made for your life when you were growing up?

What was the best day of your life and why?
What soothes your spirit when you are unhappy or in a bad mood?
What talent do you have that is not utilized successfully in your workplace?
What are three things that you would change about your work environment that would make you a more successful employee?

If you had your work life to live over, at what point would you have chosen a different path that would have led you to more success and happiness?
What are the skills that you bring to your workplace that are currently underutilized?
What is one activity, which if you could do it every day at work, would most increase your appreciation of your current job?
Are you a day person or a night person and how does this affect how you work?
What words would you most like to hear from your boss that would help you feel motivated and successful in your job?
What would you like to do next in your current organization? What would you bring to the new position?
What are the most significant characteristics of the people who have been your best bosses during your career? What made them best bosses?
What are the most significant characteristics of the people who have been your worst bosses during your career? What made them the worst bosses?

Would you make a good boss? What makes you answer the question the way you did?
Do you get to do something at work every day that you love? If so, what is it? If not, what can you do about that?
Do you have a best friend at work? Who is it and what draws you to this person?
If you invited a child toa take your children to workday/event, what would you show the child about what you do at work? What would you tell the child about your job?
Looking at your whole life, not just your work life, what are three areas or activities in which you wish you were spending more of your time?
What five characteristics must your work environment or culture have to make you feel engaged, alive, excited, and contributing as an employee?
What are the one or two things in a work environment or culture that would absolutely drive you to look for a new job and leave?

What event do you remember most fondly from high school?
Who was your favorite elementary school teacher and why?
What's a favorite family memory that has stuck with you into your adult life? Why?
How do you use the information that you learned in your favorite class in your life today?
What spectator activities do you most enjoy attending and watching?
What was the most memorable event that you experienced in college?
What is the most memorable vacation you've taken in the past?
What's rocking your world this month?
What's the craziest thing you've ever done in your life?
What's your favorite activity to do locally and why?
Can you share three things about you that you think no one here knows?
What was your least favorite class in college and why?
What part of your current job is your favorite?

Share one thing that you love to do that you get to do nearly every day.
What's your most significant current challenge?
What would you like to accomplish in your job this year?
What is your favorite local restaurant and the meal you most enjoy eating when there?
What outdoor activities do you most enjoy? How often do you get time to participate?
What is one goal that you plan to accomplish during your adult lifetime?
Describe your dream vacation.
What do you enjoy in your favorite breakfast that you make at home?
What is the best meal that you have ever made for dinner?
If you could only travel to one more country, which country would you choose?

What are you most worried about at work this month?
What characteristic do you value the most in your coworkers?
What is the most important personal attribute that you bring to your job?
What are you most excited about in relation to your job this year?
What's one work-related skill that you'd like to develop, especially if you could do it easily?
What coworker characteristic do you find most irritating?
What's the one word that you'd like to hear from your boss?
If your workplace was a tree, what kind of a tree would it be and why?
What one factor or facet of work do you complain, moan, and groan about the most?
What's the single most important factor that you would change about your job?
What is the most significant factor that your organization has control over, that interferes with your success?

What is the single most significant factor, that your organization controls, that is fueling your success?
If you were the king of your workplace, what are the three missing factors that you would add?
What coworker habit drives you crazy or bugs you the most?
Describe the work culture in which you could most successfully contribute your best work. How far from your ideal is your current workplace?
You often hear that people are an organization's most important resource. Is that true for the organization that employs you?
How much money would you need to win to walk away from your current job?
What are the circumstances that would have to happen in your current job that would cause you to secretly job hunt?
When you have worked with a successful team, what factors were present in the working relationships?
When you have worked with an unsuccessful team, what contributed to its failure?