The Value of the Unfinished Conversation

Some ideas land with a sense of closure.

You name them. You publish them. They feel done.

Others don’t work that way. They stick around. They resurface. They come back in different conversations, under different conditions. They shift slightly as the context around them changes.

Those ideas aren’t unfinished because they’re weak. They’re unfinished because the environment is dynamic.

What I Missed the First Time

Back in 2010, I wrote a post called “Why Is Soccer So Boring?” At the time, I compared watching the “beautiful game” to watching paint dry. My point was pretty straightforward: we don’t find things interesting until we understand what’s actually happening.

With the World Cup returning to the U.S. this year, that post came back to mind. Sixteen years later, I see it differently—not as a take on sports, but as an early sensemaking problem.

Back then, I thought soccer was boring because “nothing was happening” between the highlights. Today, I realize that’s where most of the game actually is. The movement without the ball. The positioning. The constant tension between possession and pressure.

If you only look at the score — the surface — you miss the strategy underneath.

The Same Pattern at Work

What struck me is how often the same thing happens at work.

We focus on outcomes. Milestones. Decisions. Dashboards. But much of the real work happens between those moments. The conversations that don’t make it into the recap. The tradeoffs that remain implicit. The alignment that quietly erodes over time.

I’ve written before about how context shapes judgment —  how people measure success differently depending on what situation actually demands. The same thing happens with ideas: what works in one context can still be directionally right later—and still be insufficient.

We tend to assume that good thinking ends in answers. That clarity means finality. We reward decisive conclusions and stable answers.

But organizational reality doesn’t work that way. It’s more like a game that keeps unfolding. Every decision changes the field a little. New constraints show up. Old assumptions stop holding. What worked last quarter may still be mostly right—AND no longer enough.

That’s where sensemaking actually lives.

A sensemaker’s job is never “done” because the context keeps moving. What made sense yesterday can still be directionally right and tactically incomplete today as roles change or new constraints appear. That doesn’t mean the interpretation was wrong. It just changed as the context did.

Why Sensemaking Never “Finishes”

I’ve written before about the role sensemakers play. What I’ve come to appreciate more over time is that their work doesn’t resolve—it keeps adapting as the context shifts.

I’ve noticed that this is where I spend more of my attention now.

I’m less interested in tidy conclusions than I used to be. More interested in the moments where something feels unresolved. Where the answer comes too quickly. Where there’s pressure to declare clarity before the complexity has really been worked through.

That friction is usually telling me something. Not that people are confused—but that the work isn’t finished yet.

Berkson's Bits

Sometimes it's the simple things in life that make all the difference. Try "hide self view" on video calls and realize how much of your attention was caught up in looking at yourself. I did. It was quite a bit.

What I'm Listening To...

I'm a big fan of the Cuban jazz pianist Alfredo Rodriguez. I see him live whenever he is in NYC and he never disappoints. I also love how playful he is on Instagram. Check him out. Especially his Instagram stories.

Lately, I’ve noticed that when something keeps coming back in my own work, it’s usually because I tried to close it too quickly the first time. I answered the question that was in front of me, but not the one underneath it. I’ve learned to pay attention to that feeling—not as a failure to decide, but as data that there’s still something worth noticing.

Some conversations aren’t meant to be wrapped up. They’re meant to be revisited as the game evolves.

And that’s worth sitting with.

Looking forward to continuing the conversation…
Alan