Take the Work Seriously. Stop Taking Yourself So Seriously

You’re deep into a strategy planning session. The leadership team is working through something hard. Real decisions with real stakes, and that means real disagreement. Someone says something completely ridiculous, and there’s a beat of silence. Then a piece of candy flies across the room. This is what good strategic planning facilitation looks like, and it rarely looks the way people expect. 

This is normal. Well, for my sessions it is. 

The candy is part of something called the Bag of Appreciation, a simple practice where anyone in the room can throw a piece of candy to someone who just did something worth recognizing. Anyone who lived a value or said the thing nobody else would say to unlock the conversation.  

It’s real-time acknowledgment, and hits differently than a formal shoutout ever could. You can’t fake a piece of candy flying across a boardroom table! 

The False Equation 

At some point, we decided that important work means “serious faces,” full of corporate language. It required carefully constructed answers delivered in measured tones. Conflict surfaced only when absolutely necessary, and even then, handled gingerly. 

That’s not rigour. That’s performance. 

I once heard about a facilitator who made it their practice to “mine for conflict” between team members during sessions. They WANTED to bring tension to the surface. The outcome was that conversations were no longer about the issue but were now about the people.  

Nobody was solving problems. They were defending themselves, and that’s damaging. 

You can’t eliminate tension, and that shouldn’t be the goal. What we want to do is make sure the tension is pointed at the right thing. 

What I Really Want in the Room 

I ask clients how they feel during our sessions. The answers are usually some version of relaxed, energized, focused, confident. Then I ask how they feel afterward. The answer is almost always exhausted. 

That’s the point. 

They’re tired. They spent hours in a room. They were doing what needed to be done: 

• Genuinely hard thinking 
• Challenging assumptions 
• Having uncomfortable conversations 
• Making consequential decisions 
• Calling bullshit on things that needed to be called out 

When you force clarity where there was fog, you deal with what people are avoiding. That drives commitment to actual action. That’s heavy work.  

But they don’t experience the room as heavy. That’s intentional. 

Casual isn’t low rigour. Casual means the psychological weight of the room isn’t working against the thinking. People can laugh and still do hard things. In fact, they SHOULD laugh because it makes the hard things better. 

Lower the tension. Never lower the stakes. 

Why Fun Creates Better Strategic Thinking 

When people stop performative seriousness, half-formed ideas get spoken instead of edited before they leave someone’s mouth. Dumb questions get asked (and dumb questions are often the ones that crack open the real issue.) Leaders admit they don’t know, the only honest starting point for figuring something out.  

People challenge each other more freely because the stakes feel lower. Ridiculous ideas get floated, and, occasionally, a ridiculous idea reveals brilliance. Conflict becomes less threatening when the room isn’t already tense, and energy stays higher through work that is genuinely cognitively demanding. 

Fun isn’t a break from the work. Used properly, it improves the work. 

The Leader Sets the Emotional Rules 

This is true whether the leader in the room is the CEO or the facilitator. 

If the CEO is defensive, everyone becomes careful. If the facilitator is trying to demonstrate how clever they are, everyone starts performing for them. The emotional tone at the front of the room radiates outward and sets the operating conditions for everyone else. 

But if the person leading is calm, curious, willing to challenge, and occasionally willing to be a little ridiculous, they give everyone else permission to loosen their armour. 

You can create safety without creating comfort. Safety means people can say the hard thing without it costing them something. Comfort means nobody says the hard thing at all. One produces good strategy sessions while the other makes very pleasant ones where nothing changes. 

And Sometimes, Candy Flies 

The system isn’t candy, or sitting on the counter, or even swearing (which, yes, sometimes happens.)  

Those are expressions of something deeper: we take this business extremely seriously. We just don’t need to take ourselves seriously while we build it. 

And strangely enough, that tends to be exactly when the hardest work gets done. 

Bring this Energy into Your Next Planning Session 

The next time you’re in a room making hard decisions, notice what happens when someone loosens the tension instead of tightening it. More than any agenda or framework, that shift is usually what decides whether the room is thinking or performing. Let’s talk about how to improve your next planning session.