Your 50th Latte Is Someone Else's First
Let’s Connect!
A coffee shop trainer explained something most managers never figure out: the person you're teaching for the fiftieth time is learning it for the first. Your patience isn't kindness. It's strategy.
I was at Stanford for a leadership program. Big classroom. Smart people. Slides about how to grow a company without breaking it.
At the break, I walked to the campus coffee shop for a cup. That's where I met a trainer named Sudha.
She teaches new managers. New ones arrive every few months. Her store sits on a college campus, so students come and go every semester. She teaches the same standards, the same rules, the same drinks, over and over and over.
So I asked her the question I actually wanted answered for my own company:
"How do you not get bored or drained doing this again and again?"
She said something I haven't stopped thinking about.
"It may be my 50th time teaching it. But it is their first time learning it."
I went to Stanford to study leadership. I found some of the best of it behind an espresso bar.
coffee unites us.
The problem almost every leader has and almost nobody names
If you lead people, you repeat yourself constantly.
You explain the mission. You fix the same mistake. You walk a new person through the same steps you walked the last three people through.
And a small voice inside you says: again?
Here's the thing. That voice shows up on your face.
The new person sees it. They don't know it's your fiftieth time. All they know is that the person who is supposed to help them looks tired of them.
So before they learn a single skill, they learn something else:
I am a problem here.
That's the message. Nobody meant to send it. It gets sent anyway.
Why this costs money, not just morale
This is where Sudha stopped being sweet and started being sharp.
She laid out the chain:
The trainer looks frustrated.
The new manager finishes training with low confidence.
A manager with low confidence can't fire up a team.
The team gets unhappy and people quit.
Now she has to train replacements.
Her words were blunt: "You're not helping me, and you're not helping the company."
Read that again, because it flips the usual logic.
Most people think impatience is a result of too much training. Sudha is saying impatience is a cause of it.
You get annoyed. The annoyance produces weak leaders. Weak leaders produce turnover. Turnover produces more training.
You built the treadmill you're complaining about.
Training and developing are two different jobs
Sudha doesn't only want people to learn the rules.
She wants them to leave her better than she found them.
Even if someone works there three months. Even if they quit and go somewhere completely different. She wants them walking out with more confidence, more skill, and their dignity intact.
She said she never wants an employee to think: my manager was always tired of teaching me.
Here's the difference in one line:
Training teaches you what to do. Development changes who you can become.
Companies spend fortunes building training programs. Almost none of them spend anything building people who are good at developing humans.
Those are not the same thing. One creates workers who follow instructions. The other creates people who can eventually replace you.
Only one of those lets you grow.
You are part of the lesson
I've spent months building training materials for my own company. Manuals. Checklists. Videos. All of it.
None of it survives a bad teacher.
If the person delivering the material looks bored, the boredom is part of the material.
People don't just learn what you teach them. They learn how you made them feel while you taught it.
Sudha said she stays optimistic on purpose, and that she needs a reason to do it. Not fake cheerfulness. An actual reason.
That's the part most advice skips. You can't rely on being in a good mood at 6 a.m. on your fiftieth run-through. Moods run out. Reasons don't.
Six things you can do the next time you have to repeat yourself
1. Say the math to yourself first. This is my fiftieth time. It is their first. Ten seconds of that changes your face before you open your mouth.
2. Know your reason, not your mood. Why does this specific person learning this specific thing matter? If you can't answer, you'll sound like you don't care, because you don't yet.
3. Watch your body, not your script. The sigh. The glance at the clock. The flat "okay, so, again." That's what they'll remember in five years, not your explanation.
4. Change one thing each round. Teach it backward. Ask them to teach it to you. Boredom usually comes from repeating it identically, not from repeating it.
5. Decide what "better" means before you start. Pick three things beyond the task. Confidence. Clarity. Feeling respected. Then check if they got them.
6. Build teachers, not students. The only real escape from endless repetition is people who can teach it without you. If you're still the only one who can explain it, that's bad design, not bad luck.
What I'm taking back to my own company
I've spent years building 787 Coffee. We grow our own coffee on our farm in Puerto Rico and serve it in 34 shops. I've obsessed over the bean, the roast, the machines, the art on the walls.The coffee is not the hard part. The people are.Sudha gave me a cleaner way to say what I want: We don't train humans to make coffee. We use coffee to develop humans.
Change the noun to whatever you build. Code. Food. Classrooms. Music.
You're not really in the business of the thing. You're in the business of who people become while they make it.
Let's get to work. 💯
Want the insider playbook that's helping thousands build wealth without traditional degrees?
Every month, I share the exact strategies, mindset shifts, and real-world tactics that successful entrepreneurs use to create financial freedom—including interviews with millionaires who started with nothing but ambition.
Join 15,000+ game-changers getting the SoyBrandon newsletter. No fluff. No theories. Just proven methods that work.
[Subscribe free here →] Because your breakthrough moment could be in the next email.
The bottom line
Repeating yourself isn't a break from leadership. It is leadership.
The mission you've explained a hundred times is brand new to somebody.
The standard you've shown a hundred times is brand new to somebody.
The lesson you're tired of is somebody's first day.
So the next time I think do I really have to explain this again, I'll remember a trainer at a campus coffee shop who decided that her fiftieth time would look exactly like her first.
Your 50th latte is someone else's first.
Teach it with energy.
Teach it with patience.
Teach it with purpose.
And most of all:
Don't just teach the latte. Develop the human.
Thank you, Sudha.
Gracias, gracias, gracias ☕
Frequently asked questions
What is the difference between training and developing someone?
Training teaches a person the tasks and rules of a job. Development builds their confidence, judgment and ownership so they can grow past it. Trained people follow the process. Developed people improve it and teach it to others.
How do you stay patient when you train the same thing over and over?
Remember the imbalance. Your fiftieth time is their first. The repetition is your burden, not theirs. Anchor yourself to a reason instead of a mood, change how you deliver it each round, and measure success by whether the learner left better rather than whether you felt fresh.
Why does a manager's attitude matter so much during onboarding?
Because attitude becomes part of the lesson. A frustrated trainer produces a new leader with low confidence. Low-confidence leaders struggle to motivate teams. That causes turnover, which causes more onboarding. Impatience creates the very workload the manager resents.
What does it mean to develop humans and not just train them?
It means treating someone's time with you as an investment in who they are becoming, no matter how long they stay. Even a person who leaves after three months should walk out with more confidence and capability than they arrived with.
Who is Brandon Ivan Peña?
Brandon Ivan Peña is an entrepreneur, artist, author and speaker who writes about leadership and growth. He is co-founder and CEO of 787 Coffee, a farm-to-cup coffee company, author of Creative Fucker, and host of the Spanish-language interview series Hablemos de Éxito.
Brandon Ivan Peña writes about leadership, creativity and growth for people who build things with other people. Entrepreneur, artist, author of Creative Fucker, TED speaker ("AI con Corazón"), and co-founder of 787 Coffee. More at soybrandon.com.
If this landed, send it to the person who trained you. Then send it to the person you're training now.