Don’t Skip the Convo About Feelings at Your Next Team Retreat

We’re having a conversation with a nonprofit leader about facilitating a retreat for her team. We discuss the agenda, plan the day, talk about breakouts and collaborative exercises. We even make sure she and her team are thinking through snacks and movement.

And then the leader, inevitably, says something like, “You know, we don’t have to waste time talking about how the group is feeling. Let’s just focus on collaboration and getting the work done.”

Cue our bottom line: Yep, we’re definitely gonna get your team talking about their feelings. Nope, this won’t be the section that gets cut for time. 

That’s because talking about feelings unlocks your team’s creativity, purpose, and culture.

We get it: Conversations about feelings can get messy. These conversations feel risky to leaders because they aren’t confidently prepared to skillfully initiate or effectively close the discussion. What if someone gets upset or feels uncomfortable? Our team has goals, expectations, and metrics to meet — don’t feelings just get in the way? We won’t spend too much time or go too far beyond surface level, right?

Why It’s Smart to Make Space for Feelings 

When planning a staff meeting or retreat, most leaders find it much easier to build the agenda around strategy and tactics of the work itself — or they don’t gather their teams at all because that can open the door to turbulent, emotional conversations. 

But the nature of today’s workplace makes it more essential than ever for each individual to know that they’re valued, heard and aligned with a collective mission.  

How people are working together and how they're feeling about the work they’re doing

Some of this is a generational challenge. The leadership cohort consists mostly of forty-somethings, fifty-somethings, and sixty-somethings, many of them white, as teams increasingly skew younger and more diverse. Leaders bring to their roles a mindset they learned in the workplace: You put your head down, get the work done, put in the extra effort and you’ll get promoted and recognized. This new generation of workers, though, isn’t inclined to sacrifice their personal lives to work, to work outside of their scope without recognition or compensation, to go what was once perceived as “above and beyond” without a payoff for that effort. They’re also deeply attuned to what’s going on in the world and they’re frustrated by what they see as broken social systems. 

The emotional disconnect between leadership and teams can be especially acute in the nonprofit space because people bring their own passions and personal convictions to the work. Folks come into movement spaces to pursue careers precisely because they want to change those broken social systems, and often because they’re propelled by direct experience. But when their professional life involves addressing social ills AND the world feels like it’s a mess, folks experience a sort of emotional and sensory overload. 

And they can’t help but bring that overload to work; they talk about what’s wrong and share their personal experiences. They expect their leaders to have solutions to the existential, multidimensional crises happening in our world right now — which is unfair and unrealistic, but so is expecting people to show up and focus on a task at hand when the world seems like it’s on fire.

How to Let Feelings Into Team Engagements

Leaders aren’t equipped to manage through these emotional roadblocks, so their own tendencies toward fear and shutting down permeate the whole team. When these feelings of overwhelm are boxed up or ignored, collaboration,shared purpose and simply getting work done go out the window. Communication breaks down, conflict rises, people feel burned out. 

So what’s the solution? 

The answer is not to have a one-time conversation at an annual staff meeting — but rather a continued, constant commitment to reevaluating the way your team works and making space for changes. That means making time to slow down together … and yes, to air, acknowledge and accommodate feelings. And then, leaders have the responsibility to shift from expression to action — to build consensus around how the team wants to show up together, to work together, to be more effective together. 

As a leader, you should know that you’re not accountable for managing everyone on your team’s  emotions. You ARE accountable, though, for honoring the fact that people are having different experiences of, and feelings about, what’s happening around them at work and beyond. Be empathetic, be supportive, and be frank about your own limitations in what you control and what you influence. 

The hopeful news is that you’re not alone in making these important conversations happen. When we facilitate team retreats, we focus on seeing each individual as a human, not just a set of accountabilities and expectations. We emphasize hearing what folks have to say as a practice the whole team takes on. 

Discussing and exploring emotions and feelings unlocks your team’s potential to get creative, solve big problems, and pursue your organization’s highest calling. So absolutely, when we lead your retreat, we’ll start by talking about feelings. And you’ll end the day, if you slow down to do this work, in a different place from where you started. How can we help you? Let’s begin this journey together.


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In Service of the Group: The Facilitator’s Role