The problem with "fail fast" is that it too often becomes "move fast." Failure is hidden or spun as success, speed is rewarded, and the learning part gets lost entirely. At its worst, "fail fast" is an excuse to rush into the next thing without pausing to understand what just happened.
What I want to promote instead is Observe Often. The shift in language is intentional—when we say “observe,” we bring focus back to what matters: seeing, measuring, and learning from what we do. And “often” reinforces frequency over haste. It’s not about reckless speed; it’s about small, deliberate moves and frequent feedback loops.
The “Often” Part: Small Steps, Big Insight
Observe Often is built on Create Simple Things in Small Steps. Big, risky changes don’t lend themselves to quick observation—you have to wait for the whole thing to ship before you can tell if it works. But when we design small, valuable, measurable changes, we can see results sooner and adapt faster.
Think of it as accelerating learning without risk to users:
Introduce a new algorithm and test it by logging it in production before rolling it out
Roll out a small UI tweak to improve conversion and watch user activity.
Introduce a new search filter to a small audience segment and monitor engagement.
Run an A/B test with two versions of a signup flow to see which reduces drop-off.
Each is small enough to limit risk, measurable enough to guide decisions, and valuable enough to be worth doing. This is not “sloppy fast”—it’s intentional, low-risk learning.
Observation is a Discipline
Observe Often means we start by clarifying the problem we’re solving and defining the outcomes we want. Then we decide what to measure at the solution level so we know if we’re making progress. Only then do we release the change, watch how it behaves, and learn from the results.
This isn’t just about product features. It applies to architecture, process, and team experiments too. When we change the way we deploy, run retros, or pair program, we should be observing those changes in the same way—looking for the signals that tell us we’re on the right track or need to adjust.
The Cultural Shift
When teams start Observing Often, decision-making gets sharper. They’re not just guessing; they have evidence. Emotional confidence builds because the team sees proof of progress. And because each change is small, recovery from mistakes is faster and less stressful. This creates a positive cycle—more confidence, more experimentation, more learning.
Why It Matters
Frequent observation is how you keep improving without overreaching. It’s how you build resilience into your team and your product. It’s how you avoid “fail fast” becoming “fail without learning.”
So don’t move fast. Don’t fail fast. Observe Often—and let small, measured steps keep you headed in the right direction.
Further Reading
Related Behaviors