Hey Babs: Dreading Upcoming Team Retreat

Jul 28, 2025

Facilitators, Ice-Breakers, and Not Trusting the Process.

Hey Babs,

I’m dreading an upcoming team retreat. While we work well as a team, we haven’t had a successful away meeting since before the pandemic. Not sure if the blame lies with the retreat facilitators or if the blame lies with us, but already we are rolling our eyes and making snarky remarks about “trusting the process”, ice breakers, and voting with dot stickers.

Even though I’m uncomfortable with how we are setting ourselves up for the event, I’m just as bad as the others in joining in on this, or maybe even worse as I believe that what we are doing now, in the lead up to the retreat, will guarantee the failure of the retreat.

Or maybe I’m wrong and this is how we bond and grow as a team.

As someone who facilitates team retreats, what do you think?

Lucy (not my real name)


Unless someone like you cares a whole awful lot,
Nothing is going to get better. It’s not.
― Dr. Seuss, The Lorax


Hey Lucy,

I really appreciate having this conversation about retreats. Failed or even not-so-great team retreats are disappointing for every one involved and can have a lasting affect right up to and into the the next retreat.

I’m wondering how common this is, given that this is about the sixth time in recent weeks that this topic has been brought to my attention.

Rather than laying blame, perhaps we can explore ways for you and your team to have a successful retreat.

  1. Instead of just trusting the process, be part of the process.

The facilitator was chosen because they meet your criteria or needs, including having the skills and experience for knowing how to design process and how to guide and hold space for the team’s conversations, ideas, engagement, and connections with each other.

But, the facilitator isn’t in the room alone. For the retreat to be successful, everyone needs to participate with good intentions and an open mind. After all, what may not have worked last time, may work this time. Retreats, like any situation, are not on repeat unless we choose for them to be on repeat.

  1. Resist joining in on the negative talk.

Eye-rolling and snarky remarks may bond the team, but it won’t be a team of courageous leaders. It will be a team of small-thinking, unhappy people with limited horizons. In the moment it might feel good, but that you have asked me about this, suggests that you have some unease about this approach to team-bonding.

Pay attention to that unease, check in with your values and ethics, and do different. I bet you dollars to doughnuts, that you are not alone in this unease and that your courage to do different will spread.

Having said that, don’t be surprised if others see you as letting the team down. It’s up to you to decide if joining in on the bad karma negativity is more important and easier to live with than addressing your unease and showing up with courage.

  1. As a team be purposeful about why and how you all want to show up for each other at the retreat.

Whatever the reason for the retreat (strategic planning, blue skying, bonding … ), a retreat should not be the same as the team’s usual business meeting. It is meant to be something different; a time carved out for fresh thinking, new ways of looking at challenges and opportunities, and for unearthing a diversity of perspectives, conversations, and ideas. So do it differently.

This could be the opening that the rest of the team has been looking for; for someone, like you, to ask “why are we having this retreat?”, “what do we want out of this retreat?”, and “how do we want to support each other to enjoy the retreat?”.

As a facilitator, I often send out the above questions in an anonymous-response survey in advance of retreats and then share the results as part of the retreat opening. Every single time it opens a conversation that quickly, and without drama, becomes an understanding of, and commitment to, everyone’s individual and shared responsibility for the success of the retreat. Every single time.

Again, thank you Lucy.

Babs


PS: As a facilitator with the upcoming fall nearly fully booked with retreats, I struggled with this “Hey Babs”. I feel that most every team that I have worked with has arrived at their retreat with some aspect, even if its just a teensy amount, of eye-rolling or not-so-positive commentary on ice-breakers, coloured markers, sticky-notes, break-out groups, and so on, along with the understandable dread of the unwise facilitator phrase, “trust the process”.

I get it.

Sometimes this has been the result of, as mentioned above, past retreat experiences and sometimes it has been the result of the team’s unhealthy practice of using negativity as a way of bonding with each other- a practice that will ALWAYS result in low trust, low creativity, low innovation, and all-round blahs. Snarky comments, including the ones disguised as humour, may feel like an amazing team glue, but they aren’t.

I have yet to have worked with a team that wanted to sabotage their team retreat or their team bonding – they were just stuck. But once they named the “stuck”, they were able to move forward and work on developing healthy team habits.

I have much gratitude to all of you that may not have trusted the process (why should you?), but did trust me enough to invite me in to design and guide a process that made the difference between a business-as-usual team meeting and a take-a-leap-forward team retreat.

You are courageous leaders.


Thank you to the many honest and courageous people who share their leadership stories with me to share with others. Some I share in “Hey Babs” and many are found in other posts. All stories are edited by me for brevity and anonymity. As with all my work, I hold dear your trust in my professional principles, including confidentiality.

You can find out more about the Courageous Leadership Project and my work as a coach and facilitator at courageous leaders.ca.


Photo by Pawel Czerwinski on Unsplash

Why work with me as your coach?

Because life and work is a demanding journey that requires attention and care.

I’ll help you expand and hone your self awareness and awareness of others, your expertise, and your wise and ethical behaviours while celebrating your resilience and courage for what is before you.

You can find out more about my coaching and leadership development services at courageousleaders.ca.

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