08 Oct I Thought I Was Hosting a Leadership Experience. I Didn’t Expect to Be the One Learning. 

I co-hosted a dinner for a group of local senior HR executives at the Museum of Contemporary Art Arlington. 

When my co-host and I began planning the evening, I suggested we move beyond the traditional dinner discussion. Instead, I wanted everyone to experience firsthand something I’ve long believed: creativity isn’t just about making art. It’s a powerful way to spark fresh thinking, strengthen relationships, and help us see familiar challenges differently. 

So, we invited Arlington artist David Amoroso to lead us through a collaborative art experience. 

I expected it to be enjoyable.  I expected it to demonstrate the value of creativity in the workplace. 

What I didn’t expect was how much it would teach me about leadership. 

For one evening, I wasn’t the facilitator. I wasn’t leading the discussion. I was simply another participant. 

Sometimes the Hardest Part Is Simply Paying Attention 

We began with an exercise called contour drawing. The instructions sounded simple enough: keep your eyes on the object, not your paper, and let your pen continuously follow what you saw. The goal wasn’t perfection. It was observation.  

Except…I wasn’t listening as carefully as I thought. 

Somehow, I convinced myself the instructions were the opposite. I kept looking down at my paper instead of at the still life in front of me. 

Even after I corrected myself, I found another way to miss the point. 

I rushed. 

The exercise felt uncomfortable, and if I’m honest, I wanted to be finished. 

David kept coming back, gently pointing out details I’d skipped. 

“Slow down.” 

“Look again.” 

“You’re missing something.” 

I found myself thinking… 

“Do I really need to draw every little detail?” 

Later, it struck me how often organizations do exactly the same thing. 

When change feels uncomfortable, we rush toward completion instead of slowing down long enough to really observe what’s happening. 

Collaboration Rarely Looks the Way We Expect 

Then we passed our drawings to the person beside us.  A colleague to our left would begin painting what I had started, using only certain colors from the paint palette in front of us.  

Then we switched again and could adorn the new painting with any color we felt was missing.  So by the end, three people had contributed to every piece of artwork created that evening.  

I’ll admit something. 

I was more attached to my drawing than I expected. 

When I eventually saw how someone else had interpreted it, my first reaction wasn’t curiosity.  It was disappointment. 

Not because their work wasn’t great. 

It simply wasn’t what I had imagined. 

That realization stayed with me. 

We often say we want collaboration.  But collaboration means allowing other people to leave their fingerprints on the work.  And that almost always means the final result won’t look exactly the way we envisioned it. 

Constraints Can Become Catalysts 

The final surprise came from the watercolors. 

Each table received the same color palette, but were initially only allowed to use certain colors from the palette. So not only did the paintings have different dominant colors, some people embraced bold, saturated colors. Others, myself included, used much more water, creating softer washes and lighter transitions. 

Neither approach was right.  Neither was wrong. 

We simply saw the same assignment differently. 

It reminded me that leadership isn’t about giving everyone identical resources or expecting identical outcomes.  It’s about creating the conditions where different people can contribute in different ways. 

The best ideas often emerge not because constraints disappear, but because people respond creatively to them. 

Three Leadership Lessons I Didn’t Expect

By the end of the evening, I realized we hadn’t simply explored creativity. We had experienced many of the same dynamics leaders navigate every day. 

1. Slow down before rushing toward certainty. 

When we’re uncomfortable, our instinct is often to move faster. Leadership sometimes asks us to do the opposite; to observe more carefully before acting. 

2. Before changing someone’s work, seek to understand it. 

It’s easy to inherit a project and immediately start making changes. 

It’s much harder and far more valuable to first understand the original vision, the intent behind the work, and the problem someone was trying to solve. 

Understanding before changing is one of the simplest, and most overlooked, acts of leadership. 

3. Constraints don’t limit creativity. They reveal it. 

Great leadership isn’t about waiting for perfect conditions.  It’s about helping people do their best thinking with the time, resources, and information they have. 

Sometimes our greatest breakthroughs happen because of our constraints, not despite them.  

The View from the Participant’s Chair 

Ironically, my biggest takeaway had very little to do with art. 

It had to do with perspective. 

One of the unexpected realities of being a consultant and advisor for a long time is that you spend far more time designing learning experiences than participating in them. 

Somewhere along the way, it’s easy to forget what it feels like to be the person sitting in the chair: uncertain, uncomfortable, trying something new, making mistakes, and wondering if you’re getting it right. 

That dinner reminded me of something I hadn’t expected. 

It wasn’t really about creating art. It was about creating understanding. 

One realization especially stayed with me. 

Not one of us asked the person who started the drawing what they had envisioned. We simply picked up the paper and started making decisions. 

We could have asked.  We didn’t. 

And I couldn’t help thinking how often the same thing happens in organizations. 

Projects get handed off. New leaders inherit initiatives. Teams take over someone else’s work. 

Yet we rarely pause to ask: 

What were you trying to accomplish? 

What mattered most to you? 

What problem were you trying to solve? 

Instead, we often begin changing things before we fully understand what came before. Maybe that’s why so many transitions feel harder than they need to. 

That evening reminded me. 

And I left with a renewed appreciation for something I ask leaders to do every day: 

Stay curious. 

Stay teachable. 

Because leadership isn’t always about having the answers. 

Sometimes it’s about asking better questions. 

And sometimes…it’s about remembering what it feels like not to have the answers at all. 

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