At work, I'm mentoring a junior colleague who was awarded a little less than $10k to spend on job-related training/certifications of his choice. The money expires in a year, and is a rare windfall in our organization.

If the kid was brand new and just starting out with fundamentals, I'd find a reputable programming generalist/web-tech boot camp and advise him to attend that.

Problem is, he's beyond that point. He's 2 years into self-taught work in the backend/security/cloud/DevOps space, and he is a natural. Fast learner, good at self-teaching, knows to avoid the superficial/shiny, cares about understanding "why".

As a result, he's already pretty productive and deep into a lot of what our specific job needs. But that means that "here's what a for-loop is, here's AWS/Terraform basics, here's a simple Kubernetes build-out"-type courses would waste of his time.

So, my question: what organized training do you buy to support or speed up an already-started, fast-learning person's career? Most trainings out there are occupied with helping people get started, correct deficiencies, or pivot into another area. As someone who was informally-taught, I'm at a bit of a loss: I want to recommend things that will accelerate his progress of learning things that he'd arrive at organically anyway, in time.

I've worked with some legendary engineers; this kid has the potential. Right now, he's productive, insightful, and a little bored with some of the more mundane work we do; he's on the cusp of starting that 1-2 year period that most engineers go through where he over-optimizes/over-refactors/over-automates everything he touches (for the record, I think everyone should go through that; it's an important learning experience). Even if left alone, I'm confident that he'll come out the other side of that with a pragmatic/flexible approach rather than ossifying and having to un-learn bad habits like some people (cough) do.

And he went from "what's AWS/Python/Ubuntu, I have no educational background in SWE" to where he's at now in like ... a year! Coupled with the fact that he's humble and a good communicator, I have zero doubt that if I check in on his career in 10 years, I'll be floored.

Question is: can we use this training money to make that 5?

The sky's the limit: weeks/months/in-person/online/whatever, we'll consider it. Both I and his boss know that there's a good chance of training him out of a job with us, but we care more about encouraging that than making him stay at this gig.

My impression of certification courses is that they're not great for someone who already has the skills--but that's not strongly held, and I'd love to hear otherwise!

I wish there were a training in like ... "software architecture aesthetics": how to become grug brained; how to know when to follow dogma and when to abandon it; how to intuit how to simplify/replatform big complex legacy systems; how to identify funny-smelling or bad ideas/implementations; when to switch to the new shiny tool and when to suspect it. But that stuff seems squarely in the "you gotta learn it from experience" category.

Right now, he wants to work primarily on backend/DevOps/data pipeline stuff, but he's open to learning about other areas. Any trainings that inform about the breadth of the field would be welcome, I'm sure.

Trainings for depth are also welcome: actual advanced AWS/DevOps/cloud engineering trainings seem pretty hard to find: "advanced" usually boils down to "stuff that a talented person who cares would pick up organically by their second year on the job anyway". If there are any advanced trainings that buck that trend, let me know!

The only restrictions are that the trainings have to be in or offered by the US (employer restriction), and have to look more or less like an organized educational opportunity (so no spending the money on parts to build a server rack, as fun and relevant as that would be).