Faster Work, Harder Decisions

[Un]Churned Chapter 007

Work is moving faster, decisions are happening earlier, and the distance between leaders and the work is becoming more visible.

Here’s what’s been on my mind this week.

This CCO Won’t Ask His Team To Do What He Wouldn’t Do Himself ft. Jim Richmond (This Week’s [Un]Churned 🎙️)

This week’s [Un]Churned episode touched on something simple that’s quietly getting harder to practice: staying close to the work.

As things speed up, it’s easy to spend more time planning and building frameworks. That can feel like good leadership, but it also takes you further from the pressure your team feels. This distance can change your decisions without you noticing.

In this week’s episode, Jim Richmond, Chief Customer Officer at Smartling, talks about holding himself to the same standard he expects from his team. Knowing where something breaks because you’ve felt it break. Knowing when a push is reasonable because you’ve carried it yourself.

We also talk about how he uses AI to clear out the busy work so he can stay close to the parts of the job that require judgment. When the routine work disappears, what’s left are the kinds of interactions that actually impact retention.

Falling Behind, or Just Feeling It?

I shared a post this week because the questions felt more honest than any answer I was ready to give.

Recently, a few people I trust mentioned building things in hours that used to take weeks. They described rough versions being built and put into use almost immediately. I expected that to feel exciting. Instead, it left me uneasy.

I’ve spent years building in this space and watching cycles come and go, yet this moment feels different. The pace is faster, but what’s changed more is the expectation around speed. Decisions that once felt careful now feel slow, and that shift creates a kind of pressure I’m still trying to understand.

I don’t yet know what the right posture is, but pretending it isn’t there feels worse.

→ Read the post here, and let me know: does this resonate, or am I just behind?

Early Experiments, Better Decisions

This article from 3Sixty Insights describes a moment many teams now find themselves in before choosing a long-term solution. They build small tools with AI, test them in real-world use, and learn what actually matters. It’s less about speed and more about clarity. By building first, teams start to see the real problem they’re trying to solve.

Over time, these tools often reach their limits and become difficult to manage or scale. This process helps teams clarify their needs and pinpoint areas where they require support. If you’re interested in seeing an example of how early experimentation can lead to confident and well-prepared teams when scaling solutions.

→ Read the full post

Wrapping Up

The same pressure that creates anxiety for leaders is driving teams to experiment on their own. Faster cycles reward action, rough learning, and early signals. What matters is how those signals get absorbed, and whether they lead to clearer decisions or quiet workarounds.

See you next Monday 🧠

🌱 Josh

SVP, Strategy & Market Development @ Gainsight

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