Lessons on facilitation from a Failed Workshop

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We’re kicking things off! The team has gathered, and everyone is thrilled to dive into the branding conversation. The Founder, we’ll call him Ted, came in early and wrote the title of today’s first session in big yet uncertain letters on the meeting room whiteboard: OUR VALUES. Below the title, there’s an awkward empty diagram. Now sitting in one of the chairs he arranged in a neat semicircle, Ted is flipping through a stack of stapled papers. That posture can’t be good for his spine. It’s clear that he didn’t have the time to prepare for this, but he’s hoping to catch up while everyone else settles in. After a few minutes, the room falls silent, except for the shuffling of paper—time to begin.

Ted stands up and solemnly walks up to the whiteboard. “The goal of today’s first session is to define what our brand values should be. Let’s start with brainstorming, and then we’ll pick the three values that are most important to us.” He reads aloud from his papers, then stands there waiting for someone, anyone, to say something. So the session begins, and for the first five minutes, words and ideas flow freely and aplenty: “Curiosity, audacity, playfulness, grit, ruckus, zest … ”. Ted only writes on the whiteboard the ones he likes. The meeting room door suddenly opens. Gina, the designer, is back from the restroom, realizing they’d started without her. Already somewhat pissed that she wasn’t leading the workshop as the company creative, she is now completely pissed and vows to keep her mouth shut for the rest of the session.

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An enthralling conversation between Colin from sales and Martha from marketing ensues about the different meanings and interpretations of the word “happiness” across individuals and cultures around the world. Ted has already decided the word happiness doesn’t belong on the whiteboard, but impressed by the fact that the team is taking this so seriously, he decides not to interrupt and starts answering emails on his phone instead.

Three hours later, the session ends in a synchronized sigh of relief. Everyone was looking forward to this coffee break for an hour. No one is looking forward to whatever session will come next or to the work they had planned for the day, which they now have less time to do. Ted, on the other hand, looks back at the whiteboard with pride. On it, three words circled over and over in red Sharpie: Passion, Sinergy, Excellence—sad trombone.

What went wrong? How did such a promising and exciting initiative spiral into a collection of platitudes and irreparable damage to the group’s trust in each other? The answer is simple: Ted has been a terrible facilitator.

Don’t get me wrong, Ted is a good guy. He’s hands-on, and people like him for that. He likely knew it would be hard and uncomfortable, yet he thought that leading the session himself would demonstrate his commitment to the brand. He stepped up to what he thought was his responsibility, but this time, his good intentions betrayed him.

Founders and CEOs make for poor facilitators

No matter how flat his company’s organizational chart was, Ted’s title loomed large—as executive titles always do. Facilitating a conversation and having the final say in it are irreconcilable responsibilities. So, while listening and fostering participation are, in fact, core skills for a CEO, facilitating a group conversation without bias requires a different kind of restraint. The sole goal for the facilitator should be helping the group discover the best solutions and insights collaboratively, without imposing authority or preferences.

Let the founder or CEO facilitate only as a last resort.

Come prepared

Ted was busy. Not only did he fail to prepare for the session properly, but he also couldn’t take the time to understand how the session fit into the broader context of the branding effort—and it showed. The team jumped right into the action, but without a clear roadmap, discussions quickly became unfocused and fragmented. Since no instructions were given, no one really knew how to steer the conversation back on course or noticed that it needed to be steered back on course in the first place.

If you’re planning to let someone from your team facilitate the branding exercises, make sure they have the time and space to prepare—this might mean stepping away from their usual responsibilities for a time because trying to juggle both will only result in stress and missed opportunities.

Set boundaries and goals

Ted started the meeting with a vague intention of “defining our brand values,” but he failed to describe what success looked like by the end of the session and how to get there. This left the team unsure of what they were trying to achieve and the discussion meandered as a result.

Before the session, clearly define the desired outcomes and set specific goals. Establish milestones so everyone knows what success looks like and how to get there. Make sure the team is aware of the phases of each exercise and the methods needed to navigate them, as this will help maintain focus and maximize productivity. Each exercise I’ll share in this book 

Garner support

Ted didn’t consider whether someone else in the group might have been better suited for the role, someone with the right experience or a stronger desire to facilitate, or someone who might have more easily garnered support from the rest of the team. Outside consultants have an advantage here—they’re typically viewed as experts or, at the very least, given the benefit of the doubt because they’ve been hired for the role. Professional facilitators also have a few tricks up their sleeves to convert even the most uncooperative participants.

When choosing a facilitator from within your team, do so transparently and democratically. The facilitator must have the team’s support; otherwise, it will be difficult to keep everyone engaged and cooperative throughout the session.

Here’s a facilitation tip that can help set you up for success as a facilitator: begin the workshop by asking participants to establish social rules for the sessions. As participants suggest guidelines—such as ‘raise your hand to speak’ or ‘avoid interrupting’—write them on the whiteboard. Keep going for about five to ten minutes, and I guarantee you’ll have a list of rules that will bulletproof your position as a facilitator. When you’re done, stick the sheet with the rules somewhere visible, and if you find yourself losing control during a session, refer participants back to the rules they created together.

Listen, challenge, and champion

Instead of digging into the team’s suggestions, asking follow-up questions, or pushing for more clarity, Ted simply noted the ideas he liked and moved on. Scribbling on the whiteboard gave him a false sense of productivity while he was, in fact, irritating everyone and collecting cliches. By failing to challenge the team and by outright dismissing the ideas that didn’t immediately resonate with him, Ted left everyone feeling unheard or just skating on the surface.

The facilitator should encourage equal participation and be ready to challenge the group to dig deeper or to champion ideas that might otherwise be unfairly dismissed or overlooked in the excitement of the conversation.

Stick to the schedule

Ted found himself in a difficult situation. He felt the added pressure of leading the conversation while trying to contribute his own ideas. He walked on eggshells because he didn’t want to be perceived as a dictator, so he refused to control the pace and flow of the conversation. As a result, he got tired, became distracted, and zoned out. Free, unchecked, open-ended discussions ensued, and with that, Ted committed the gravest facilitation sin: he let the session run over time. Being on time is one of the hardest, and possibly the most important part of a facilitator’s job. As many of my clients can attest, it is definitely the hardest part for me.

The problem with sessions running over time is that it not only derails the current agenda but also drains the team’s energy and focus. As the session turns into a marathon nobody has prepared for, people become less attentive, impatient, and frustrated—they start to check out. More insidiously, running overtime eats into people’s personal schedules, which breeds resentment and leads some to pull back to avoid prolonging the agony.

Wrap up

By the time people left the room, they couldn’t even remember what they had been talking about for so long.

A good facilitator always wraps up a session with a little celebration. They thank everyone for their participation, summarize the key takeaways, confirm the decisions made, recap the process, and share the next steps. This keeps the momentum going and prevents people from feeling like they’ve wasted their time and about to waste even more with whatever comes next.

Consider rotating the facilitator

Can you imagine Ted having the energy to lead the next session properly? Probably not. Since the facilitator job is deceivingly hard, unless you hire a professional or have one on your team, you may consider rotating people in the role throughout the exercises to share the responsibility. By taking a turn leading, everyone can own a bit of the process and put some skin in the game, which is likely to foster goodwill and smoother, more productive collaboration. Another perk of rotating the facilitator is that even if one of you bombs—it happens even to the best of us—no single session can derail the entire branding effort. Small, collaborative teams where members are comfortable with open communication and trust each other will love this approach.

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