The other day, while teaching a facilitation workshop, one of the participants stopped me (Richard) mid-session.
“Wait—what did you just do there?” they asked.
They’d noticed how a single question had unlocked new insights for the group. It felt like magic to them—the kind of fluent improvisation that can seem mysterious when you’re learning a new skill.
That moment of curiosity from the participant—wanting to peek behind the curtain of facilitation—was fantastic. And it got me thinking about how anyone can develop this kind of natural facility with facilitation. How do you get to the point where asking the right question at the right moment feels effortless?
It turns out there are three key elements: imitation, repetition, and attention. Let’s break these down.
Start with Imitation
Here’s the thing: you don’t start by improvising. You don’t even start by making it up yourself. You start by borrowing what works.
Watching Bob Pike (a famous trainer of trainers) calmly and fluently facilitate a 110-person workshop was a revelation for me. He gave instructions so clearly, everyone always seemed to be doing the right thing…and it seemed so effortless.
I noticed that he avoided a trap I often fell into with larger groups. I’d finish giving instructions for an activity. Then, I’d ask something like, “Any questions?” In a smaller group, this usually worked fine. But with a larger group, the odds got higher that I’d have a participant ask a question that didn’t really need to be answered but that took a bunch of time and energy.
Bob asked, “What can I clarify about the instructions?” Usually nothing. But when there was a question, it was targeted and useful, and the activity moved forward.
I borrowed that for my own workshops.
Build Through Repetition
Copying something once or twice isn’t enough. You need to do it over and over, looking for opportunities to practice in real situations.
Think of it like learning a new language. You don’t become fluent by memorizing phrases and using them once. You need to use them in different contexts, with different people, until they become second nature.
In an earlier newsletter, I shared techniques for asking “why?” without using the word “why.” It took repetition for me to make this a habit. In the beginning, I just made a point of noticing when I wanted to ask “why?” and chose to ask one of two “what?” questions instead. I didn’t make up new questions on the spot. I just used my two pre-selected “what” questions until they became routine for me.
Sharpen with Attention
This is where the magic starts to happen. As you repeat these borrowed techniques, pay attention to:
- How they work in different situations
- What happens in the room when you use them
- How authentic they feel to you
- Which variations work better or worse
Some questions will feel natural coming from you. Others won’t. Some approaches will work beautifully with certain groups but fall flat with others.
For example, I noticed the Reflection step in the Focused Conversation approach brings really useful data about individuals’ internal state into the conversation, but questions that ask about “feelings” often felt awkward to me and to many of my participants. So, I started experimenting and found I could use questions about what was motivating, energizing, frustrating, or stressful as a way into a whole range of feelings.
Putting It All Together
Over time, you’re no longer imitating—you’re truly improvising. But you couldn’t have gotten there without first learning the vocabulary.
It’s like jazz musicians who spend years studying and practicing other people’s improvised solos on standard tunes before developing their own style. They need that foundation before they can start creating something new.
The next time you’re facilitating and someone does something that seems magical, don’t just admire it—borrow it. Use it repeatedly. Pay attention to how it works. And gradually, you’ll develop your own facilitation style that feels both natural and effective.
Give it a try and let us know how it goes!
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