Conversation Starters: Lessons Learned from a Kindergartener

Many of us, regarding our professional roles, struggle with starting conversations with others. We evaluate the importance of forming stage in team formation, kickoff meetings, and brainstorming sessions, where must consider icebreakers! As a speaker, one thing that I always think of in public speaking engagements is the icebreaker questions outside of weather or sports! As a conference organizer at least with PMI MassBay when I was the Vice President of Marketing and Communication, I had to think of icebreaker activities for team members to collaborate! 

As a friendly neighbor, I had the opportunity to babysit one kindergartener after school. While helping him assemble his bag, I noticed a check sheet, "Conversation Starters for Parents and Children!" It had the following items on the left. 

Conversation Starters for Parents and Children

1. Tell me about the best part of your day.
2. What was the hardest thing you had to do today?
3. Did any of your classmates do anything funny? What was funny about it? 
4. Tell me about what you read in class.
5. Who did you play with today? What did you play?
6. Do you think [subject] is too easy or too hard? Why do you think so?
7. What's the biggest difference between this year and last year?
8. What rules are different at school than our rules at home? Do you think they are fair?
9. Who did you sit with at lunch?
10. Can you show me something you learned or did today?

Wow! What a great list! When I started asking a few questions, the child started answering! No longer it was, "I don't know!" or shrugging of shoulders! Feeling happy seeing that in action, I thought how cool it would be to have such an open-ended conversation starter for team building, lessons learned sessions, or retrospectives.

Conversation Starters for Teams

1. Tell me about the best part of your work today. 
2. What was the most difficult thing you had to deal with today? 
3. Did any of your team members do anything that made you happy or sad? What was happy or sad about it?
4. Tell me about what you learned from your work today.
5. What stakeholders did you interact with today? What was the focus of your interactions? 
6. Do you think [Customer Service/IT Role/QA Role/PM Role, etc.] is too easy or too hard? Why do you think so? 
1. If you were to have someone switch their role with yours, what do you think they would so about your role and responsibilities?
2. How much are you willing to do a role swap and see how their role is for a day or two? If not, why?
7. What's the biggest difference between the last iteration and this iteration? (last project and this project, last year's customer interactions and this year's). 
1. What do you think contributed to it? 
2. What can we do differently to make it better?
3. What do you think would be a better outcome if you disagree or feel it can be better?
4.  What else?
8. What rules are different between your last role (or company) and this role (company)? Do you think our rules are fair? 
1. If you changed something, what would you change and why?
2. If you added something, what would you add and why?
3. If you deleted something, what would you delete and why?
9. Who else did you interact with outside of your core work responsibilities?
1. Who are they? 
2. What are they doing?
3. How is their work connected with ours?
4. How do these interactions demonstrate belonginess? 
10. Can you show me something you learned or did today (this week)? 

The most important thing for me is that I was able to learn at a time and place where I thought I knew. At least, I never thought I would learn something from a kindergartener babysitting event! Every interaction is a learning opportunity. 

What do you think we can add as open-ended questions to promote continuous team camaraderie and organizational belonginess?