Chekhov’s Gun in the Age of Automation

TLDR;

Chekhov’s Gun is more than a writing principle, it’s a systems design law. It warns us that everything we put on the wall should matter, and if it doesn’t, it shouldn’t be there. In modern work, we’ve violated this rule. Our workflows are full of unused triggers, abandoned policies, and rituals no one questions. This post reframes Chekhov’s Gun as a tool for clarity, focus, and transformation, especially in systems thinking, automation, and human psychology.

Anton Chekhov famously said:

This wasn’t just about plays. It was about intention. Economy. Discipline.

Now look around the modern workplace. SOPs no one reads. Tools no one uses. Slack channels no one checks. Teams burning out in the name of “efficiency” while buried under redundant steps and legacy tasks that serve no current purpose.

The modern enterprise violates Chekhov’s law constantly. And the cost are often hidden, not just in money, but in human clarity.

I used to work in logistics at a Fortune 500 company. One day I noticed a monthly ritual, physically rotating out bins of paperwork. When I asked why, nobody knew. Eventually, I uncovered that it stemmed from a regulation that had long since changed. For years, the team had been maintaining a prop in the system that served no function. A dusty gun on the wall that never fired.

The moment I questioned it, that “gun” finally went off, and the entire process unraveled. We rebuilt it. What had been ritual became irrelevant. That’s the power of spotting unfired triggers.

I define meaningful work as work that engages your full presence. Where your cognitive energy isn’t eaten by email pings and redundant checklists. Where your workflows aren’t loaded with dead triggers.

That’s why automation isn’t just a convenience, it’s a form of narrative discipline. It removes the props that will never matter, and it guarantees that the ones that stay will have impact.

In one engagement, we automated inbound shipment paperwork routing at a major manufacturer. Before, someone had to manually notify the right person and rely on (often lost) paperwork handoffs. Sometimes they didn’t. Shipments would stall. Hours were lost.

That notification was the gun. Automation made sure it fired.

Behavior change follows the same rule. Most teams are not failing because they lack resources. They’re failing because the signals are buried. People ignore them. Or worse, they’ve accepted dysfunction as normal.

When someone tells me, “That’s just how we’ve always done it,” I hear the click of a safety switch. A setup waiting for a shot.

Once you show them that a five-minute automation can save hours, their perception of work changes. They stop tolerating clutter. They start scanning for silent weapons.

This is where transformation begins, not in tools, but in awareness.

A mental health nonprofit I worked with had a grant tracking nightmare. After receiving a large award, they were handed a 50-page PDF detailing dozens of deliverables, each with a deadline and consequence.

They had someone reading those PDFs manually and entering dates into a calendar. Deadlines were missed. Stress was high.

We built an AI system that scanned the PDFs, extracted deliverables, and auto-assigned tasks to internal staff. The team didn’t even know that was possible. The grant requirements were the Chekhov’s Gun, fully loaded, yet buried in bureaucracy.

We surfaced it. And the circle finally closed.

Chekhov’s Gun is a narrative device, but it’s also a system design principle. Every item in a system must be there for a reason. If not, it must be stripped out. Of course you must be creative and open-minded on REASON, it doesn’t do you any favors to think of tooling, workflows or positions in your organization as expendable unless you come to that conclusion intentionally.

One of the primary tenets of Stoicism insists on removing what is unnecessary. But it is ruthless about intention. Those who adopt this mindset are obsessed with clarity.

In stoic thought, energy must not be wasted on what we cannot control. In systems, attention must not be wasted on tools and tasks that do not move the plot forward.

The average company is full of unfired guns.

These are not just inefficiencies. They are psychological costs. They clutter the narrative. They waste attention—the most valuable currency in any organization.

People burn out not just from overwork, but from incoherent systems. From unresolved setups. From guns that never fire.

Whether you're a leader, a nonprofit director, or a systems thinker, you are a director. Your organization is the play. Every field, form, policy, and tool is a prop.

Your job is to ask: Does this fire?

If it doesn’t, remove it.If it does, make it fire without fail.

That is how you reclaim clarity.That is how you make room for reflection and innovation.That is how you write a better second act.

Chekhov’s Gun is not a metaphor, it is a mandate.

It’s the principle that binds together good storytelling, strong systems, and meaningful work. It asks us to examine every element in our workflows, our policies, and our culture, and demand they justify their existence.

You don’t need more tools.You need cleaner stages.And sharper triggers.

That’s the future of work.

Want to go deeper? I help organizations uncover the unused guns in their systems, remove the ones that don’t serve, and build automation that ensures the right ones fire. If your team is buried in props, it’s time to rewrite the script.

Let’s talk.