I will have a 14-year old shadow me at work – any advice?

I'd suggest helping him to see the 'whole' job. What do I mean by that? The best development (and developers) understand that they're not just writing code, but that code is the tool that they use to solve the real problem of the business.

That would mean spending a few minutes helping him to understand why you're writing the code you're writing and how it will impact the product or business.

Then, I'd walk him through your typical development process. Show him your ticketing system, how you identify user stories (if you're using agile) or features, how you groom those stories (e.g. things that make a story useful or not, the dialogues that you have with people to understand what you need to build), and the life cycle of a ticket.

Finally, (perhaps after a break), you could walk him through your development loop - Look at a ticket or feature, start exploring the code to see what you need to change, make an edit, run tests, commit your code, etc.

IMO, the important take away for him would be to see that development most often isn't a developer sitting at a desk typing at a computer all day. My experience has been that software development is an interactive experience with myself and other developers, myself and other teams, etc.

Not sure what kind of dev you do, but if you were so lucky to be working on front end, showing him how a change you make creates visible change on the screen that he sees as a user would be pretty powerful. Particularly if the thing you're working on is something that he could see after he leaves or that his friends might know about.

Giving him a task and putting him to the side might make him feel dismissed. I'd instead recommending using the time as an opportunity to practice teaching, and some basic pair programming. By all means, walk him through whatever tedious code you are writing. To you it is tedious, to him it is something completely new and exactly what he wants to see - what do you really do all day? If he hates it, he will choose another path, if he loves it, he'll follow up more on this path. Either way, the purpose is not for you to entertain, but to demonstrate.

I have conversations with my nieces and nephews about practically everything. Business, power dynamics, opportunity cost, risk, upside and downside, social interactions, reputation, local optima and global optima (if you could ever know them in real life), growth, compounding, mastery, competitive and comparative advantage, etc. I do that first without introducing the concept and by asking questions that lead them to extract the insight, then I'll put the term on that at the end with some references and the prior work on a topic.

I was putting some food in the microwave and my then 12 year old nephew was with me. We were in a short conversation about the price of things and he arrived at the concept of a loss leader. I mean he really understood it. Then I told him what it's called. I merely guided the conversation with questions that challenged his intuition, presented counter-examples to intuitive answers. He'd just "hmmm", then think about it for a few seconds, then upend his hypothesis. It was beautiful to watch.

I would focus on the “why” of the work more than the “how”. The details of your coding may not land, so be prepared to discuss the job and business more generally. Maybe they don’t end up coding. Help them understand how your role fits into the business as a whole. What do other people do that helps the business succeed.

Most of all, if they seem interested in anything you say, just ‘yes’ that and give them more even if it wasn’t your plan A.

Be careful what's in the other tabs -- you did already make sure anything NSFW is only logged in on your phone, which has notifications silenced on the lock screen in case your... partner or whatever... sends you a photo... right?

And yes, a short Python task is a good idea. Treat it like an interview -- get breakfast with him, tell him about the company, then let him try to program while you do email.

And otherwise, be very careful what you say, they will repeat it back to whoever they want, because they are minors and thus not subject to whatever weird NDAs you give them. (You'll probably want to write yourself a script.)

You've never met the kid so I'd say talk to them first and assess what they know about software. It might be unlikely but if they turn out a prodigy coder show them everything you do and have time for, like Morpheus teaching Neo. If they barely know how to turn on a PC, then your idea sounds good.

Btw the parents sound like helicopter parents going by your first sentence alone, I wouldn't mind them if they think their kid has to consider careers at 14.

As others have echoed, I'd suggest trying to talk to him and get a sense of his level of interest and knowledge. Many of us probably grew up trying to make QBasic games and trying to build our own computers in a much different era around that same age, so his level of interest in your real world coding tasks might surprise you.

Since the goal is discovery, I would have him shadow others colleagues too, so that he can discover more parts of the company. That would break the monotony, and increase the surface covered.

And of course first speak with him about what he is interested in.

Be professional 100% of the time. Do not try to be their friend. Be a good, patient mentor.

I think people are misunderstanding (or I am) the point of having someone “shadow” someone.

They basically follow you and see what you do. The entire point is you pretend they are not there.

That's kind of insane. The most I'd think a 14 year old would be interested in is learning some browser related tricks (inspecting requests, elements, etc). On the technical side of things, unix utilities like ping / nano would be a good bet.

For day to day related work, just show how you decide what to work on? Maybe go through an instance of investigating a task?

Give him a choice between the red pill and the blue pill. Put acid in both of them.

What's your day job?