Why Your Company Needs a Chief Failure Officer

The windshield is larger than the rearview mirror for a reason.

Yet, most businesses operate as if the rearview mirror is their primary display. Post-mortems, endless retrospectives, dissecting what went wrong long after the moment passed. But what if we stopped obsessing over what just happened and started accelerating what happens next?

The Problem with Failing Fast (and Stopping There)

“Fail fast” is startup gospel. But what’s often forgotten is the follow-through: fail often. One fast failure teaches very little. Frequent, intentional iteration? That’s where the gold is.

As Steven Bartlett put it, the goal isn’t simply to fall on your face; it’s to keep moving, adapting, and shipping faster than everyone else. It’s about learning velocity.

In short: don’t just fail fast, fail forward, continuously.

Enter the Chief Failure Officer (CFO)

Let’s get bold. Imagine appointing a Chief Failure Officer.

Their mission:

• Normalize smart risks
• Build repeatable learning loops
• Encourage faster releases
• Celebrate useful failure

This isn’t a vanity title. It’s a cultural shift. A CFO wouldn’t reward chaos; they’d reward teams that are learning faster than the market.

Think of it this way: if your competitors are shipping once a quarter and you’re running weekly experiments, you’re not playing the same game; they’re still drawing up strategy while you’re already on the field.

The Failing-More Playbook

And why it’s all about taking more shots on goal

Success isn’t about crafting the perfect play. It’s about taking more shots. In product development, marketing, sales—whatever your team is building—the winners are those who iterate the fastest and shoot the most.

Here’s how to operationalize this mindset:

1. Default to Experiments: Don’t debate in circles—reality test. Every idea gets an experiment baked in from the start.
2. Track Iteration Rate: How many shots are we taking? How often are we launching, testing, and tweaking? Track learning, not just outcomes.
3. Remove Ego from Outcomes: A missed shot is still forward motion. Celebrate bold attempts, not just wins.
4. Celebrate Recovery Speed: How fast can we adjust and retake the shot? Recovery time is a core KPI.
5. Make Failure Visible: Create internal dashboards or Slack/Teams channels that showcase experiments, learnings, and even failures. Visibility removes shame and increases confidence.

The goal is not to always score. The goal is to keep shooting until the scoreboard moves. The more shots you take, the more data you gather and the closer you get to product-market fit, campaign resonance, or breakthrough innovation.

Why the Windshield Matters More

Too many companies fixate on perfecting the past. But growth is a forward sport. The windshield? It’s where the action is.

Let’s stop obsessing over what went wrong and start optimizing for what’s next. Organizations that win in the long term aren’t perfect. They’re prolific. They get more shots on goal because they’ve built the habit of trying more, faster.

Final Thought

We live in a world that rewards momentum, not caution.

Perhaps it’s time to create a role or mindset that embodies that. Someone who ensures your team ships, learns, and grows faster than the market.

Call it a Chief Failure Officer. Call it a mindset shift. Either way, put your foot on the gas, and keep shooting.

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