Mistakes Are Not Okay. How You Handle Them Is

I spent 20 years as Director of Computer Operations at Trader Joe’s, responsible for systems that could not go down. When a point-of-sale system fails across a retail chain, stores cannot process transactions. Customers leave. Revenue stops. The phone calls from regional managers start before you have finished diagnosing the problem.

In that environment, “mistakes are okay” is not a philosophy anyone takes seriously. Mistakes cost money, damage trust, and create cascading problems that take days to resolve. The systems I built were designed to prevent mistakes through redundancy, testing, and process controls. The goal was not to create a culture where people felt comfortable making errors. The goal was to create systems where errors were caught before they reached the customer.

But here is what I learned across two decades of managing teams and another decade of managing ghostwriting projects with 54 clients: the leaders who say “mistakes are not okay” and the leaders who say “mistakes are okay” are both wrong. The first group creates fear. The second group creates carelessness. Neither group is dealing with the actual problem, which is what happens after the mistake occurs.

The Real Problem with “Mistakes Are Okay”

The “mistakes are okay” philosophy became popular because it solved a real problem. In organizations where people were punished for errors, they stopped reporting them. Errors went underground. Small problems became large problems because nobody flagged them early enough to fix them cheaply. The solution was to create psychological safety, an environment where people could admit something went wrong without fearing for their job.

That was the right instinct. But somewhere along the way, “do not punish people for honest errors” became “celebrate failure” and eventually “mistakes are how we learn.” The message drifted from its original purpose. Instead of creating environments where errors get caught early, it created environments where errors get shrugged off. Instead of psychological safety, it produced intellectual laziness.

The leaders I have worked with who run the best organizations, the ones whose businesses grow and whose teams stay loyal, do not celebrate mistakes and do not punish them. They treat mistakes as information. Something went wrong. Why? What in the system allowed it? What changes prevent it from happening again? The focus is never on the person who made the error. The focus is always on the process that failed to catch it.

Fear Produces Worse Mistakes

Early in my management career, I inherited a team that had been managed through fear. People did not report problems. They hid them, worked around them, and hoped nobody noticed. The result was that small issues compounded into system failures that were far more expensive and disruptive than the original problems would have been.

The fix was not telling people “mistakes are okay.” The fix was showing them, through consistent behavior over months, that reporting a problem early would result in the problem getting fixed rather than the person getting blamed. That distinction matters. I did not lower the standard. I changed the response. The standard was the same: the systems needed to work. The response shifted from “who did this” to “what allowed this to happen and how do we prevent it.”

Within a year, problems that would have festered for weeks were getting flagged within hours. Not because people felt comfortable making mistakes, but because they felt safe reporting them. Those are different things. Comfortable making mistakes leads to sloppiness. Safe reporting mistakes leads to early detection, which is the single most valuable thing an organization can have.

What This Looks Like in Ghostwriting

I manage the same dynamic in every ghostwriting project. A book is a high-stakes deliverable. A factual error in a business book damages the author’s credibility permanently. A story that does not hold up under scrutiny becomes a liability. A structural decision that sends the book in the wrong direction wastes months of work if it is not caught early.

My clients are leaders who are used to being right. They run companies, manage teams, and make high-consequence decisions. When I tell them that a chapter is not working, or that a story they want to include does not support the book’s argument, or that a claim they are making needs verification, I am essentially telling a successful person that they made a mistake. How I deliver that message determines whether they hear it or resist it.

The clients who produce the best books are the ones who treat my feedback the same way I treated error reports at Trader Joe’s: as information, not as criticism. Something is not working. Why? What needs to change? The clients who produce weaker books are the ones who hear feedback as an attack on their judgment and dig in. The error does not get fixed because acknowledging it feels like losing.

This pattern shows up in every organization I have observed across 54 projects. The leaders whose businesses thrive are the ones who can hear “this is not working” without making it personal. The leaders whose businesses struggle are the ones who surround themselves with people who will not deliver bad news.

Systems Over Slogans

“Mistakes are okay” is a slogan. It sounds good in a LinkedIn post. It does not survive contact with reality because it does not tell anyone what to actually do.

What works is building systems that catch errors before they compound. In operations, that means redundancy, testing protocols, and review processes. In leadership, that means creating an environment where people flag problems early because they know the response will be problem-solving rather than blame. In writing, that means multiple rounds of review where every fact gets checked, every story gets verified, and every structural decision gets pressure-tested before the book goes to print.

The common thread is that none of these systems depend on how anyone feels about mistakes. They depend on process. A good process catches errors regardless of whether the organization celebrates them or fears them. The emotional environment matters because it affects whether people participate honestly in the process, but the process itself is what prevents small errors from becoming catastrophic failures.

At Trader Joe’s, the systems I built ran for years after I left because they did not depend on my personal management style. They were designed so that errors triggered responses, not investigations into who was at fault. That is what good systems do. They make the right response automatic rather than dependent on the leader’s personality or mood.

What Good Leaders Actually Do

The best leaders I have worked with, both as colleagues and as ghostwriting clients, share a set of habits around mistakes that have nothing to do with whether mistakes are “okay.”

They respond to the problem before they respond to the person. When something goes wrong, their first question is “what happened” not “who did this.” That question sets the tone for everything that follows. A team that hears “what happened” understands they are solving a problem. A team that hears “who did this” understands they are looking for someone to blame.

They distinguish between system failures and judgment failures. A system failure means the process allowed an error that should have been caught. The fix is a better process. A judgment failure means someone made a decision that was wrong given the information available. The fix is a conversation about decision-making, not a punishment for the outcome.

They make the post-error process visible. When an error gets caught and fixed, the team sees the fix. They understand what changed and why. This visibility builds confidence that reporting problems leads to improvements rather than consequences.

They hold standards without holding grudges. The expectation remains high. The response to falling short of that expectation is correction and support, not anger and punishment. People who consistently fall short eventually need a different conversation, but that conversation is about fit and capability, not about a single error.

Lead Better

If you are building an organization, managing a team, or leading any group of people through complex work, the question is not whether mistakes are okay. The question is what your systems do when mistakes happen. Build the systems. Train the responses. Create the environment where problems surface early. That is leadership. Everything else is a slogan.

If you are a leader whose book needs to reflect this kind of operational thinking, start with a conversation about your book and your goals. The leaders I work with have real management philosophy worth documenting. The book should reflect that philosophy with the same precision and clarity you bring to running your organization.

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