The Jenga Moments in Family Business

“Running this company sometimes feels like I’m playing Jenga,” a second-gen CEO recently told me. “Every time I pull a block to make something better, I’m worried the whole thing might collapse.”

Over the years, I’ve heard versions of this comment many times.

Family business leaders often reach for game metaphors when they’re trying to describe the pressure they feel.

Jenga.
Chutes and Ladders.
Or (if they are older) even Pick-Up Sticks.

I find it interesting that such playful-sounding metaphors are all describing the same theme of fragility. 

I’ve started to think of moments of fragility in family enterprise as family business Jenga moments. These are gut-level moments when a leader becomes acutely aware that the
structure of the business may be more delicate than it appears.

Why is it important to spot Jenga moments?

For advisors, these moments are easy to misread, especially because from the outside, we often see systems ready to be analyzed, optimized, and redesigned.

But from the inside, the leader often has a different experience. They see a structure that has been carefully balanced, to the point where every move carries consequences.

I’ve seen clients loudly and emotionally resist change, only to find out later that their reaction stemmed from a Jenga moment I missed. 

I’ll never forget the rising gen who engaged us to evolve their brand, only to reject every change we recommended. I eventually found out that she was worried her mom would feel her legacy was being rejected, and that their longtime customers would think they had been purchased. Or the CEO who stopped a strategic plan because he was worried that their largest customer would see the growth as a sign that it wasn’t important anymore.

In that context, hesitation doesn’t always mean resistance to change.

It’s the recognition that pulling one block may shift several others.

I’ve found that spotting these hesitations and getting curious about them often uncovers a hidden risk that I would have otherwise missed. Once the root cause of the fragility is uncovered, we can easily create a stabilization plan.

But if you move too quickly (or overconfidently), you can accidentally send the pieces scattering across the floor.

Have you ever seen a Jenga moment?

I’m very curious to know if other advisors (i.e. you!) have seen these moments, or even heard these game metaphors used.

I feel like potentially collecting these stories could help unlock some patterns in when and how families can turn moments of fragility into an opportunity to make the whole structure more durable.

So… have you ever seen a moment like this? Let me know! I’d love to hear about the Jenga moments you’ve seen in your advisory work, and what happened next.

(Or, if you think I am off in some way, let me know that, too!)

meghan@sixpointcreative.com