The Accidental Facilitator: How I Learned to Break the Rules and Get Results
- Jessica Hall
- Aug 17
- 8 min read
I never chose to become a facilitator.
Right after joining 3Pillar, I had clients flying in from North Carolina for the day. Instead of the usual PowerPoint parade, I came up with a series of exercises I'd read about on Gamestorming to help us learn about their target customer and business objectives, then explore potential features together.
Sitting in the room was our head of sales. As he watched the session unfold, he saw something powerful: workshops could be a way to show our value and expertise to current and prospective clients. Not just talking about what we could do, but actually doing the work together.
So I became a facilitator.
I've never had formal training everything I know comes from experience, reading, and a lot of trial by fire. What I discovered along the way is that traditional facilitation doesn't work. At least, not if you want to actually get things done.
Breaking the Rules: Why Traditional Facilitation Fails
Here's what they tell you a facilitator should be: a neutral party who keeps time and makes sure people follow the rules of the exercise.
I tend to go my own way and do what feels right so rules are gonna get bent or ignored.
We're committed to our clients' success, and that calls for an engaged partner who can share insights from other verticals, trends, and their own experience. This doesn't mean letting your ego run wild, but it does mean being involved instead of neutral.
My core principle is simple: We need to do the work in the room. We need to make decisions in the room.
All the post-workshop report should do is capture that work, not try to change the conversation after everyone's gone home.
Too many workshops fail because they're designed to be safe, comfortable, and consensus-driven. But breakthrough thinking doesn't come from comfort. It comes from productive friction, hard decisions, and someone willing to call out the elephants in the room.
What I Do Differently
Instead of neutral facilitation, I:
Design the session to force tough decisions, not avoid them
Frame and focus relentlessly, if we're off track I bring us back
Change direction when needed because plans are useless, but planning is indispensable
Manage the energy like a conductor, knowing when to push and when to let things breathe
Connect the dots between exercises so everything builds toward our goal
Point out misalignment when I hear it, even when it's uncomfortable
Provide an outside perspective from other industries and experiences
Challenge assumptions and pressure test concepts in real-time
Force prioritization because there's always more we want to do than we can or should
Be vulnerable to make it safe for others to take risks
The result? My repeat clients kept coming back because I keep them on track without making them mad. It requires a soft touch and paying close attention to reactions, knowing when to let conversations run and when to rein them in.
The Foundation: What I Learned from The Art of Gathering
Before diving into my framework, I need to mention Priya Parker's brilliant book "The Art of Gathering." It fundamentally changed how I think about bringing people together.
Parker challenged me to be more thoughtful about the type of gathering I want to create—not just the logistics, but the deeper purpose. She pushes facilitators to think beyond the surface question of "what are we doing?" to the more important question of "why are we gathering, and what transformation do we want to create?"
Her work reinforced something I'd intuited but hadn't articulated: every gathering is an opportunity to create something that didn't exist before. In the corporate world, we often settle for information transfer or status updates disguised as workshops. But real workshops should be transformative, they should leave people thinking, feeling, or behaving differently than when they walked in.
Parker's emphasis on making bold invitations and being intentional about inclusion resonates deeply with my rule-breaking approach. If you're going to ask people to spend six hours of their lives with you, you better make sure those hours matter.
Her book is very much worth reading, especially if you want to move beyond traditional meeting formats toward something more meaningful.
The Framework: Three Questions That Drive Results
This approach grew out of my training as a ski instructor, where I had just a few minutes to assess a situation mostly through observation. In the corporate context, I can dig deeper, but the core assessment remains the same.
Every workshop design starts with three simple questions that I answer through interviews, observation, and research:
Where do we want to go?
What are we trying to achieve in this workshop?
What needs to be accomplished so we can move this idea, project, initiative, or strategy forward?
Where are we?
Where does the sponsor/client think the group is? Where does the team think they are?
What are the blockers and major roadblocks ahead?
What are the cultural norms when it comes to conflict and decision-making?
What people do you most need to work with, around, over, or under?
Does the team have a clear picture of the path ahead, or is it constantly changing?
How do we get there?
Think of it like crossing a creek with rocks of different shapes, sizes, and degrees of slipperiness. There are many paths across, but you have to focus on picking one rock at a time.
What do you need to achieve with each step?
What exercise will help achieve that step?
How do you tailor it for this specific group?
Putting It Together
I gather my team and draw this out on a whiteboard. The number of boxes represents the steps that will best fit our time period (usually a day). I aim for 30 to 45m per activity because after that people lose focus.
We talk through what needs to be accomplished in each step and which activity will work best. Having different activities is crucial, it provides variety and allows both extroverts and introverts to participate in their own ways.
The last step is always creating an action plan. We never want clients walking away without knowing how to move forward.
Preparation for Battle
As Dwight Eisenhower may have said: "In preparing for battle I have always found that plans are useless, but planning is indispensable."
My Preparation Principles
Have a flexible framework: I've developed a method for designing workshops that lets me customize the experience without creating from scratch every time. It's modular—we use different exercises to achieve client needs and slot them in as required.
Know enough to be dangerous, not much more: My clients are the experts. I can't be as knowledgeable as they are about their business. I need to know enough to ask good questions and raise possibilities, but anything more could box me into the same conventions preventing them from innovating.
Always have a plan, just don't always follow it: I reserve the right to throw out my plan if it's not serving the client's needs, and I've done it many times. Having the plan ensures I'm solving for the right things and gets me to Plan B quickly when needed.
Collaborative exercises beat conversations: Conversations easily fall into old patterns that prevent new thinking. Exercises allow people to think things through individually first, then share.
Offsite is better: Clients have more meaningful experiences when they leave daily office distractions behind.
In the Room: Making It Happen
Once we're in the session, everything becomes about energy management and productive tension.
Managing Energy and Momentum
Energy is the most precious resource. Different activities, movement opportunities, and breaks keep energy levels up. Know that the lunch coma is real and group productivity drops after about six hours.
I work in 30-44 minute blocks to maintain focus and productivity. Sometimes longer blocks work, but I have to work harder to keep people engaged. When lunch is involved, I do the heavy intellectual lifting beforehand and lighter work afterward.
The Art of Regulation
Regulate with charm. This is what kept my repeat clients come back. I keep them on track without making them mad. It requires paying close attention to reactions and knowing when to let conversations run versus when to pull them back.
Key techniques I use:
Provide connective tissue between ideas and exercises
State consensus views when I hear them forming
Know when to let it play out (productive work happening), when to push (avoiding decisions), and when to park it (tangential but important)
Bringing Things to the Surface
Sometimes participants aren't on the same page and don't realize it until someone brings it up. I ask "What does that mean to you?" constantly because the same words mean different things to different people.
When I hear misalignment, I call it out. It's uncomfortable in the moment but essential for real progress.
Troubleshooting: When Things Go Sideways
Every workshop hits rough patches. Here's how I handle the most common ones:
The Hardest Thing: Getting People to Say No
Deciding what not to do is the hardest thing to get people to do. Sometimes I have to stand in front of a group and ask several times what they aren't going to do, or physically make them remove features from their list.
Nobody wants to give things up, but without saying no, we don't have direction or strategy.
Parkinson's Law of Triviality
People argue about things that don't matter instead of tackling the big, scary decisions. When I see this happening, I stop it by asking directly: "Is this debate worth having right now?"
Usually it's not.
The Information Isn't in the Room
The answer is likely not in the room. If we don't have the information needed to make a decision, the conversation should focus on how to get it, or we park the topic. I don't allow precious time to be lost to random speculation.
Getting to Results: The Final Push
This is where most workshops fail. Everyone feels good about the discussion, but nothing concrete emerges.
Disagree and Commit
I've heard that at Intel they say "disagree and commit" meaning you should hash it out, but once the decision is made, everyone executes on it.
As a facilitator, I make sure tough conversations happen, then ask for explicit commitment.
The Action Plan Problem
We never let clients leave without knowing how to move forward. The last step of every workshop is creating a concrete action plan with owners and timelines.
Tools: The Practitioner's Guide
I design workshops with care because clients need to get out of their comfort zones, and they won't do that if they don't trust the process and me.
I fall back on my TV days and create a three-column facilitator's guide that lets me see at a glance how I'm doing on time while having all the information I need. We share it with attendees and post it on the wall to stay on schedule.
Column 1 – Time
My workshops run about six hours on a tight schedule to maintain energy and productivity. I work in 30-40 minute blocks, sometimes longer, but shorter blocks require less effort to keep people engaged.
Column 2 – Activity
The name of each exercise—just a quick reference to stay on schedule. Activities help groups tackle specific problems: sketching, business strategy mapping, using stickies to describe users, prioritizing development tasks.
Column 3 – Notes
The exact sequence of steps for each activity, plus key questions and goals. This is crucial when tailoring exercises for specific client needs.
All this planning is essential, but I almost always end up changing something during the session. Because I planned ahead, those changes go smoothly.
The Bigger Picture
Here's something I've learned: you can facilitate anytime, anywhere. If you're in a meeting that's going nowhere, get up, go to the whiteboard, and make it better.
Workshops are just a formalized version of what good leaders do every day, they help groups think clearly, make decisions, and move forward together.
The key is remembering that your job isn't to be neutral. Your job is to help people do their best work, even when that means pushing them outside their comfort zones.
Image: Some fun with watercolor, pen and rubbing alchol
