I recently facilitated a board retreat for a nonprofit client. As a warm-up exercise, I asked the participants to pair up for two minutes and discuss the following questions.

As a board member, what do you need to be successful?

What does the organization need from you to be successful?

When I reconvened the full group, people took turns sharing their conversations. When her turn came, one woman began to quietly weep.

“What’s going on?” I asked, as gently as possible.

“I haven’t been very engaged,” she said, “and I feel bad about that. I would like to be doing so much more.”

We all sat silently for a moment, looking at her and beaming lots of love and goodwill in her direction. Another trustee got up, walked around the table, and gave her a hug.

“You’ve just demonstrated,” I said, “a deep, deep commitment to your organization.” Everyone nodded, and the energy in the room shifted a little.

The moment passed; we moved on. This was the beginning of a really productive retreat.

When crying happens

I facilitate 40 or 50 events per year – planning meetings, fundraising workshops, board retreats, community trainings, etc. Once or twice per year, somebody will cry.

Among the questions and exercises that have generated this response:

• When you were growing up, what messages did you learn about money? (A classic fundraising exercise borrowed from trainer and author Kim Klein.)
• Role plays to practice asking for gifts. I’ve seen tears in the middle of the role play, but more often when people acknowledge their fears during the small-group feedback that follows.
• During facilitated conversations about how to address a crisis, including the possibility of shutting down the organization.
• When people master something difficult, you might notice tears of joy and relief.

As noted, crying isn’t a common occurrence, but I’m always thankful when it happens.

What crying means

Nobody comes to a meeting or a workshop expecting (or wanting) to weep. The tears come in response to a meaningful experience, which might be joyful or painful.

As a group leader, you’ll be more successful when you embrace these moments, rather than ignore or avoid them. It’s an indicator that the group is doing meaningful work, and that the facilitator has helped to create a space that’s safe enough for people to honestly express their feelings.

One interesting aspect of being a fundraising trainer: you’re discussing money, and money goes deep. It generates all sorts of feelings about power and powerlessness, social class, gender, and many other dimensions of how people see themselves and their position in the world. These can be potent, emotional conversations.

Tears can also result from bullying, hurtful comments, or ignorant behavior. If you’re the facilitator or group leader, it’s absolutely your job to intervene, name it, and address it. In more than twenty years of facilitation, I’ve seen very little of that – but your experience might be different, depending on your topic and the types of groups you work with.

Creating a safe space 

To help people feel safe enough to express themselves, consider the following suggestions.

1. Be vulnerable. For example, as you introduce yourself, you might include a weakness or a fear. “I’m not very good at remembering names, and I feel bad about that. I don’t want to be disrespectful. If I ask for your name more for than once, please help me out.” Humility goes a long way in building trust.

2. Listen carefully with your full attention. When people speak, face them and make eye contact. Try not to cut them off. Acknowledge what they say. “Thanks, that’s a really helpful comment.”

3. Use lots of breakouts and pair conversations. Many participants are more comfortable, and more willing to open up, in the relative safety of these smaller groups.

4. If someone becomes emotional, honor that. Listen quietly before you respond. Crying in any sort of class, meeting, or workshop is courageous – treat the moment with dignity.

5. Sharing isn’t mandatory. Encourage people to take the time and space they need (perhaps in private, outside the room) to process their feelings.

When the facilitator cries

Many years ago, I participated in a planning retreat facilitated by an older man with many years of experience.

Our group got into a difficult conversation about race, class, and privilege. He facilitated with a light hand, gently encouraging us to ask hard questions and not saying much as we wrestled with the subject and challenged each other. The tension in the room rose and fell.

In the middle of the discussion, we noticed him crying. We all paused and turned to him.

“You’re doing really difficult work,” he said, choking up, “and I’m grateful. Keep going.”