Four years ago, I was the one being mentored. Sean gave me topics to study, pushed me when I was stuck, and helped me land my first SRE job. Now I'm on the other side, mentoring interns coming into enterprise IT.
It's different than I expected.
What I Thought Mentoring Would Be
I assumed mentoring was mostly about answering questions. Someone gets stuck, you help them get unstuck. They don't know something, you explain it. Repeat until they're ready to work independently.
That's part of it. But the real work happens in places I didn't anticipate.
Lesson 1: If They're Not Comfortable, They Won't Ask Questions
Here's the first challenge with interns: if they don't feel comfortable, they won't ask questions. And if they don't ask questions, they will fail.
This is the foundation everything else builds on. You have to create an environment where they feel safe asking anything - about work, about school, about how things actually operate in enterprise IT versus what they learned in class. They're immersed in IT, but it's different from what they expected.
When I was learning, Sean created that space for me. No question was too basic. No topic was off limits. I try to do the same for my interns. The first few weeks are about building that trust so they'll actually tell me when they're stuck instead of spinning in silence.
Lesson 2: Let Them Struggle (A Little)
My instinct is to jump in when someone's stuck. I can see the answer. I could just tell them. It would take 30 seconds instead of 30 minutes.
But that's not how learning works.
The struggle is where the learning happens. When you fight through a problem yourself, you remember it. When someone hands you the answer, you forget it by next week.
Sean let me struggle. He'd watch me go down the wrong path, ask a few questions to nudge me back, but he didn't hand me solutions. At the time, I wondered why he didn't just tell me. Now I understand.
The balance is tricky. Let them struggle enough to learn, but not so long that they're demoralized. I'm still calibrating this.
Lesson 3: Explain the Why, Not Just the What
It's easy to show someone how to do something. Click here, run this command, configure it like this. Done.
But that creates someone who can follow instructions, not someone who can solve problems.
Every time I show an intern how to do something, I try to explain why it works that way. Why do we use this tool instead of that one? Why is this configuration pattern preferred? What would go wrong if we did it differently?
The "why" takes longer to explain. But it builds engineers who can adapt when they hit situations that don't match the instructions.
Lesson 4: Your Attitude Is Contagious
Interns are watching everything. How you respond to problems. How you talk about other teams. How you handle stress. Whether you complain about the work or engage with it.
If you treat production incidents as annoying interruptions, they'll learn to see them that way. If you treat them as opportunities to understand systems deeply, they'll learn that instead.
I didn't fully appreciate this until I caught an intern mimicking my troubleshooting approach - including a bad habit I didn't realize I had. They're learning from what you do, not just what you say.
Lesson 5: Give Real Work
Nothing is worse for an intern than busy work. They know when they're being given tasks that don't matter. It's demoralizing, and they don't learn much from it.
The best thing you can do is give them real problems. Stuff that actually needs to get done. Work that will go into production. It's riskier - they might break something. But that's why you're there to supervise.
Real work with real stakes creates real learning. Safe sandbox exercises create people who can only work in safe sandboxes.
Lesson 6: Pressure Makes Diamonds
I want my interns to have such a challenging internship that they go to their first real job and think it's easy.
One way I do this: I give timelines that are way too short. Intentionally. I'll assign something and give them a deadline that seems impossible. They look at me like I just asked them to eat an elephant.
If they would ask, I'd tell them the most logical answer: one bite at a time.
But here's what those impossible timelines actually teach:
- How to fail and miss a deadline - because they will, and they need to learn that's survivable
- How to stand up for themselves - to push back and ask for more time or clearer direction
- How to break big problems into small pieces - you can't eat an elephant whole
- How to make decisions under pressure - which is different from decisions you make with time to plan
And sometimes? They surprise everyone, themselves included, and knock it out of the park. That confidence boost is worth more than any safe assignment could provide.
Decisions made under pressure are different from those we make when we have time to plan. Enterprise IT will put them under pressure constantly. Better they learn to handle it now, with me there to catch them, than later when the stakes are real.
Lesson 7: Check In More Than You Think You Need To
Interns often won't tell you when they're stuck. They don't want to seem incompetent. They'll spin for hours trying to figure something out rather than ask for help.
I've learned to check in proactively. Not micromanaging - just quick touchpoints. "How's it going? Where are you at? Anything blocking you?"
Nine times out of ten, everything's fine. But that tenth time, you catch someone who's been stuck for two hours and was too embarrassed to say anything. A five-minute conversation saves half a day.
Lesson 8: Remember What It Was Like
It's easy to forget how overwhelming everything was at the beginning. The tools, the acronyms, the tribal knowledge, the unwritten rules. It all seems obvious now because I've been doing it for years.
When an intern asks something that seems basic, I try to remember asking Sean the same kind of questions. I try to answer the way he did - directly, without making them feel stupid for asking.
The gap between "knows nothing" and "knows enough to be useful" is smaller than it feels from the other side. A year of focused learning can bridge it. I'm proof of that.
What I'm Still Learning
I'm not a perfect mentor. I still jump in too fast sometimes. I still explain things in ways that make sense to me but not to them. I still misjudge how long tasks will take someone who's never done them before.
But I'm getting better. And watching interns grow - seeing them go from confused to confident - is one of the most rewarding parts of this job.
Sean invested a year in teaching me. Passing that forward is the least I can do.
- Seth Black, Co-Founder, The SRE Project