Not Training Someone Is Irresponsible

The Tradition That Isn't One

Most companies hire someone, hand them a job description, and expect them to figure it out by watching whoever is already there. That is not onboarding, that is a manager abdicating a management duty and calling it culture.

The rationalization is almost always the same: "I had to learn it myself." Sometimes followed by "and I turned out fine." Both statements are probably true, and both completely miss the point. Whatever you learned through trial and error is now institutional knowledge sitting in your head, but refusing to write it down forces every new person to re-learn the same lessons at the same cost. That is a tax the company pays on every single hire, and it is entirely optional.

I have walked into more than a few roles over 33 years where the documentation situation was some combination of a shared drive nobody had touched in two years, a couple of Confluence pages written by someone who no longer worked there, and a buddy system where the buddy was also drowning. Every time, I built documentation as I went. Not because anyone asked. Because I could see immediately that the next person would be in the same hole if I didn't.

That is the move, but it should not have to be the new hire's move.

What "Documented" Actually Means

People hear documentation and immediately picture a 60-page playbook that takes three months to write. That is not what I am talking about.

Documented means: when someone asks you a predictable question, you can produce a written or recorded answer within an hour. That's the bar, not perfect and not exhaustive, just an hour.

If a new person on your team asks how to process a refund, or how to escalate a technical issue, or what the approval chain looks like for a budget exception, and your answer is "just ask me," you do not have a system. You have yourself, and yourself is not scalable.

The mechanics are not complicated. Keep a notes file open while you work. When you do something for the first time or teach someone something verbally, write down the steps right then. Record a short Loom walkthrough. Drop it in a shared folder with a name that makes it findable. That is it. You do not need a documentation strategy. You need a habit.

The bar for doing this has dropped by about 90% in the last two years. I use Superwhisper to dictate notes while I'm working. I run transcripts through Claude to clean them up into something readable. A process that used to take an hour to document now takes ten minutes. The people still not doing it are no longer invisible, they are making a visible choice.

The Vacation Test

Here is the clearest diagnostic I know. If you take two weeks off, completely off, phone in a drawer, can your team handle the predictable work without you?

Not the emergencies. Not the crises that require your specific judgment. The predictable, recurring, process-driven work that happens every week.

If the answer is no, the problem is not your team's skill. The problem is that the process lives in your head instead of somewhere accessible, and that is a documentation problem you own.

The vacation test is also a promotion test. The person directly below you on the org chart: could they step into your seat tomorrow with no scramble? Not perfectly, not forever. But competently, with access to the information they need? If you cannot honestly say yes, you are a bottleneck, and you have probably been telling yourself a story about being indispensable rather than confronting the reality that you have not done the work of making yourself replaceable.

Making yourself replaceable in your current role is how you get promoted. Every hiring manager and senior leader I have ever respected understood this. The managers who grip their institutional knowledge like a life raft are the ones who stall out.

The Status Move Nobody Talks About

The "I figured it out myself" stance is worth examining more closely, because it is not just a documentation failure. It is a worldview about what management is for.

If you believe that learning the job through struggle is character-building and that people who need help are somehow weaker for it, then refusing to document makes sense within that worldview. The problem is that the worldview treats onboarding like hazing. It signals that suffering from the confusion is the point, not the unfortunate side effect.

Anyone who comes up under that model will replicate it when it’s their turn. They will hand the next person a job description, stand back, and watch them flounder while telling themselves that is just how it is done. The dysfunction propagates through the culture, one manager at a time.

There is also a subtler thing happening. Some managers do not document because their knowledge is their leverage. They are the only one who knows how the thing works, which means they cannot be cut, cannot be questioned, cannot be easily replaced. That is not a stupid play for job security, but it is a corrosive one. It makes the team dependent and the manager indispensable for the wrong reasons.

Point being: if your value comes entirely from being the only person who knows something, your value disappears the day you write it down. Real managerial value comes from judgment, from relationships, from reading situations correctly and making good calls. That does not evaporate when you document the process for submitting a purchase order.

The Cost You Are Actually Paying

Let's be concrete about what undocumented operations actually cost.

Every time a new hire has to figure something out from scratch that a predecessor already figured out, you are paying for that discovery twice. Their salary is running during the weeks it takes them to get up to speed on things that could have been written down. Their mistakes during that period are costing you rework, correction cycles, and sometimes customer impact. And the person training them informally, the buddy who answers the questions, is splitting their attention between their own work and filling the documentation gap.

Then that new hire eventually figures it out, carries it in their head, and the cycle repeats.

I have seen this play out in call centers, in product teams, in operations. The teams that document consistently ramp new hires faster, sustain performance when people leave, and actually promote from within, because the institutional knowledge is in the system rather than locked in specific people.

What to Do Today

You do not need a documentation initiative. You do not need a knowledge management platform or a dedicated session to audit your processes.

Start with one thing. Pick the question your team asks you most often, the one that shows up in Slack or in your inbox on a repeating cycle. Write down the answer. Put it somewhere people can find it. Tell them it's there.

That is it. One question, one answer, one place.

Then do it again next week. The muscle builds faster than you think, and the payoff compounds. Teams that can operate without their manager making every call are teams that can grow. Managers who document are managers who can actually take a vacation, actually promote someone, actually step back.

The other version, where you are the keeper of everything and the answer to every question, sounds like control. It is actually a trap. And the new hire sitting across from you on day one, trying to decode a system with no written instructions, is not learning resilience. They are absorbing a lesson about what management looks like in your organization.

Make sure it is the right lesson.