Fostering Connection During the Time of The Great Resignation; 10 Icebreaker Prompts to Invite Reflection and Learning for Your Team

As we adjust to less face time in the office and more hybrid work arrangements, it’s critical that leaders foster relationship building on a regular cadence. Especially during this time when many organizations are understaffed and work is piling up, it can be tempting to just focus on work and race to the holidays. It’s much more costly to organizations, however, to not consistently invest in seeing, understanding and knowing colleagues three dimensionally.

Here are a few prompts I have been using as meeting openers over the last year; these have allowed group members to get to know each other more deeply and also reflect and learn from and with one another. Some are classic rapport building questions you’ve heard before. Others are prompts I have come up with for this point in time during the pandemic when burnout is high and people are re-evaluating different dimensions of work and life.  

It’s important to think about the following before selecting the right tone and opening question for your group:

• Trust level and vulnerability in the group

• Personality and interests of the group

• Group size

• Context in terms of time of year and/or external events impacting group and team

• Regularity of group conversations

• Goals of a meeting and group/team

Below are merely example that I hope they will stimulate your own thinking to create your own relevant conversation starters and rapport builders.  

Reflective Prompts: 

1. What are you kickstarting and/or resetting this (year, month, week)?

2. What is a serendipitous or karmic story / experience that happened for you in recent weeks?

3. What are ways that you are incorporating humor/fun/lightness in your life and work? What suggestions do you have for our team on how to do that more or better?

4. We all have things in our work and lives we have put off or not completed. What are 1-2 things you have not completed or done that would be meaningful to tackle? What support or accountability might the group/team provide?

5. What has been taking head space for you this (morning, week, or month)?

6. What has been a rose, bud and/or thorn for you this (week, month, season of year)?

7. In the last month, have you been doing more “fire-fighting” or “fire-prevention” in your work and life? Tell us how.

8. What’s something you are really proud of personally and/or professionally from this last (week, month, quarter)?

9. What formal and/or informal strategies have you found to be most impactful for your professional growth?

10. What read or watch of late has been a guilty pleasure for you? What read or watch of late made you think?

Pandemic Related Prompts:

1. What were your biggest lessons in 2020?

2. How do things feel the same or different from past fall beginnings in September?

3. As we transition back to office, what do you hope to be cognizant of doing differently from pre-pandemic?

4. What are your reflections about how much has changed the last two years, both things seemingly big and small? What do you think will be long term impacts a decade from now?

Silly Prompts: 

1. When working from home, how has your wardrobe choices evolved above and below camera? (Keep your answers above the line professional!)

2. Most embarrassing story in Zoom or text realm

I find it’s less important what you ask in the end, and more important that you take the time and space to ask and create the safety for people to be honest and vulnerable with each other. Often any question is a Rorschach for people to share what is on their minds in a structured lens of a question. In a tight labor market, people are going to choose humane workplaces and cultures that value and see them as people and professionals and allow them to be their whole selves.