One Sip at a Time

by Jul 30, 2026Leadership

What My Own Transcripts Taught Me About Teaching

By Henry Chidgey

Fifty-plus years of leading people. Switchman at eighteen. Running a hundred-and-twenty-five-person locomotive maintenance plant before I was thirty. A thousand people under my watch before I turned thirty-five. Senior roles at four railroads on two continents. You’d think by now I’d have the teaching part figured out.

Last week a stack of transcripts told me otherwise.

I want to walk you through what I found, why I believe it’s costing you the same thing it was costing me, and exactly what I’m doing differently now. This isn’t theory. This is a correction I’m making in my own work, in my seventies, because the evidence left me no choice. If a man my age can still find a flaw this size in his own methods, so can you — and the finding is the good news, not the bad.

The mirror I didn’t expect

Here’s how it happened. I mentor leaders and business owners, mostly folks in the skilled trades — people who run crews, shops, yards, and companies. A while back I started recording those mentoring conversations and reading the transcripts afterward. I use AI to help me review them, asking a simple question: what could I have done better? How do I do a better job of being a steward of these people who’ve entrusted me to help them grow?

I expected the transcripts to mostly pat me on the back. Confirm what I already knew. That’s what we all expect when we look in the mirror.

Instead, I found a pattern I could not unsee.

When I’m sitting with someone I believe in, I get excited. I see where they could go. I don’t just see their next step — I see ten steps down the road, the whole route, every switch they’ll need to throw between here and there. And in my excitement, I try to hand them all ten steps at once.

The man asked for a drink of water. I turned the fire hose on him.

Understand — nobody could have told me this. The people I mentor are too gracious to say it, and if one of them had worked up the nerve, I’d have argued. I’m giving you value. I’m giving you everything I’ve got. I had to see it in my own words, on paper, transcript after transcript, before I’d believe it. That’s the first lesson, and it comes before all the others: you cannot fix what you refuse to look at, and most of us never look. More on that at the end, because I’m going to ask you to look.

Why good leaders reach for the fire hose

Let’s be fair to ourselves for a minute, because the fire hose doesn’t come from a bad place. It comes from two good places, which is exactly what makes it hard to catch.

The first is care. You’ve been down the road your person is starting on. You paid tuition on every mistake waiting for them out there, and you’d spare them the cost if you could. So you try to hand them the whole map. That’s love, of a kind. It’s also useless, for reasons we’ll get to.

The second is sight. Experience gives you vision — you genuinely can see ten steps ahead, and seeing it, you feel an obligation to say it. Keeping it back feels like withholding.

But here’s what I’ve come to understand, and it took a story from a friend to crystallize it. He told me about a ninety-year-old Catholic priest who was asked, after nearly seventy years of hearing confession, what he’d learned about human beings. The old priest said: “There are no grownups.”

I said amen to that the moment I heard it, and I’ve been chewing on it since. Because there’s a framework I ran across years ago that says every conversation is one of a few kinds: adult to adult, parent to child, child to child. And the discipline — the real discipline — is deciding which conversation you’re in before you open your mouth.

Here’s what the transcripts showed me: the fire hose is what happens when a mentor slides, with the best intentions in the world, from an adult-to-adult conversation into a parent-to-child one. The moment I start pouring, I’ve stopped treating the person across from me as a capable adult who learns by doing, and started treating them as an empty vessel to fill. No wonder it doesn’t work. Nobody’s ever been poured into and come out wiser. Including you. Including me.

A soaked man can’t drink

Now let’s talk about why the fire hose fails, because the mechanics matter. If you don’t understand why it fails, you’ll quit doing it for a week and drift right back.

It’s not that the information is wrong. Mine was right. Every one of those ten steps I fed people was a step they’d eventually need. The problem is simpler and more stubborn than accuracy: a soaked man can’t drink.

When you dump everything you know on somebody in one sitting, three things happen, all bad.

First, nothing gets absorbed. The human mind doesn’t file ten new ideas at once; it files one, maybe two, and lets the rest run off like rain on packed ground. You didn’t teach ten things. You taught zero things loudly.

Second, nothing gets tried. Learning doesn’t happen in the conversation. It happens afterward, out on the job, when a person takes the one thing you gave them and gets it under their fingernails — tries it, fumbles it, adjusts, tries again. Hand somebody ten steps and they can’t try any of them, because they can’t remember where step one ended.

Third — and this is the one that cost me the most — they leave full instead of hungry. A person who leaves a conversation full has no reason to come back and no room left to think. A person who leaves hungry chews on what you gave them all week. They show up next time with questions, with results, with skin in the game. Hunger is the engine of growth, and I was smothering it with generosity.

Think about the best teacher you ever had. I’d wager money they left you wanting more — that you walked out of their presence with one idea burning a hole in your pocket, impatient to spend it. That was no accident. That was craft.

How the railroad actually taught me

It struck me, going through all this, that I already knew better. The proof was my own life. I just hadn’t connected it.

Nobody taught me railroading with a fire hose. When I hired on as a switchman at eighteen, no one sat me down and poured out everything there was to know about moving cars in a yard. It couldn’t be done, and the old heads knew it. The job came to me one cut of cars at a time, one shift at a time. An older man would show me one thing — how to read a switch list, how to protect the point, how to give a signal that couldn’t be misread, how to tie a handbrake, how to get up on top of a car, how to use a fusee — and then he’d let me do it. All shift. All week. Until it was in my hands and not just my head.

And here’s the part I’d forgotten: the waiting was the teaching. The stretch between one lesson and the next wasn’t dead time. It was where the lesson set up, like concrete. If that old switchman had given me everything he knew in my first week, I’d have retained none of it and probably gotten somebody hurt. Instead, the railroad gave me one-sip teaching, day after day, and fifty years later I can still feel every one of those lessons in my hands.

The blue-collar world already knows how people learn. Apprenticeship is one-sip teaching — that’s the whole design. Journeyman shows, apprentice does, time passes, repeat. We’ve run that system for centuries because it works. Then some of us get promoted, put on a supervisor’s hat or a mentor’s hat, and abandon the very method that made us — because now we’re important, and important people give speeches.

The transcripts caught me giving speeches.

What I’m doing differently — and what you can steal

So I’m restructuring how I do my one-on-ones. Not with a vague intention to “talk less” — vague intentions die by Thursday. With specific practices. Here they are; take any of them straight into your own crew conversations, your training, your foreman development.

One: Decide the sip before the session. Before I sit down with someone now, I ask myself: what is the ONE thing this person needs next? Not the ten things they’ll need eventually — the one thing that’s next. I write it down. If the conversation surfaces something more urgent, fine, I’ll adapt — but I walk in with one sip in my pocket, not a tanker truck.

Two: Stop while they’re still hungry. This is the hardest one for me, and it might be for you. When the one thing has landed — when I can see them turning it over — I stop. Even if there’s time left. Even if I’m dying to add the next piece. I say, “Let’s pick this up next week,” and I mean it. Ending early isn’t shortchanging them. It’s leaving room for the lesson to breathe.

Three: Hand them the summary. Instead of summarizing what we covered — more pouring — I hand the summary to them. “So tell me — what are you really taking from this?” or “What’s the first thing you’ll do with it?” Whatever they say, that’s what they learned, no matter what I said. If their summary misses the mark, I know the sip didn’t land, and I know what next week is for. You can run this with a crew hand at the tailgate in thirty seconds, and it’ll tell you more than an hour of talking.

Four: Treat the week between as the classroom. The session isn’t the classroom. The week is. So the session ends with something small enough to actually do before we meet again — one conversation to have, one thing to try, one thing to watch for. Small enough that there’s no excuse, real enough that it matters. Then next session opens with what happened. Now we’re not having conversations about their work; the conversation and the work are the same thing, with dirt and grass on it.

Five: Look in the mirror on a schedule. None of the above would exist if I hadn’t recorded my conversations and read them back. That practice is the one that found the flaw, and it’s the one I’d defend hardest. You don’t need fancy tools — a voice recorder on your phone and an honest hour will do it. Record yourself running a safety briefing, a crew huddle, a correction. Then read it or listen to it and ask the question I asked: where did I pour when I should have offered a sip? I’ll warn you: it stings. It’s supposed to. There are no grownups, remember — just people willing to keep looking, and people who’ve quit.

Where this all lands

I’ve spent a lot of years thinking about what leadership really is, and where I’ve landed is this: everything and everyone in your charge — your crew, your apprentice, your kids, your grandkids, that new hand who doesn’t know a torque wrench from a tire iron — has been placed in your care. You don’t own them. You’re their steward for a season. My name’s on the title of my ranch, but I’m not its owner; I just have it in my care for a while, and my job is to leave it better than I found it.

Teaching is stewardship of a person’s growth. And here’s what the fire hose really was, underneath the good intentions: it was me serving my own excitement instead of their growth. A steward doesn’t flood a pasture and call it irrigation. He waters what’s ready, at the rate the ground can take it, and he trusts the season to do its work.

That’s the correction I’m making. One sip. Then next week, another.

You’ve got somebody right now — I’d bet on it — who asked you for a drink of water this week and got the hose. The new hand. The young foreman. Maybe your own kid. Go back to them with one thing. Just one. Give it, then stop, and watch what hunger does.

And if you want to see what the mirror shows you, start recording. What you find might sting.

It might also be the best thing your teaching ever ran into.


Henry Chidgey is a leadership mentor to leaders and business owners in the skilled trades. He spent fifty-plus years in the railroad industry, from switchman to senior executive, and now writes and mentors from Lone Tree Ranch in Texas. His book is Leading in the Blue-Collar World.

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