Sometimes people don’t get the message unless you hit them with the proverbial clue-by-four, and sometimes you need to attach a giant rock to it. You might be at that point. I’d start with “That’s fairly trivial, I’m sure you can figure it out.”, and head to “I would expect any developer working for me to know that. If you don’t, then that’s going to be a problem.”. Then follow through.

I’m assuming you’ve had the “George, you are a smart guy, you don’t need to come to me with all of these basic questions. What’s up with that?” type conversation.

Have you tried just telling him?

You’re trying subtle hints, and they aren’t working. Telling him about a joke site might get the point across to some people, but it didn’t work on him. Telling him you’re busy at the moment might have sounded like you have something to get done right now, but if not you’d be happy to help.

Some people can read incredibly subtle hints. Other people couldn’t pick up on a subtle hint to save their lives.

I was in a work situation (not programming related) where I was shuffled from one place to another, working for different bosses. I started worrying that maybe they didn’t like my work and wanted me to approach it in a different way, but they never said so, and whenever they told me they were going to send me somewhere else, they were always smiling and friendly and never said a word about bad performance or anything like that.

Finally they sent me to a new boss who immediately told me that they’d sent me there because they thought I was terrible and useless. They might have been sending all sorts of subtle hints, but they never once told me. The new boss told me what he wanted me to do, and I did it, and he was quite happy with me.

You want him to filter the issues he comes to you with. Have you tried, “I’d like for you to filter the issues you come to me with.”? You don’t want him to interrupt you while you’re in the zone for basic stuff. Have you told him that?

If you’re the manager and ‘professional authority’, its your job to manage him… not tell him to get lost and figure it out himself.

So.. you need to consider why he’s asking. Is it a political thing where he’s brown-nosing the boss? Is it a confidence thing where he needs to ask in order to be reassured he’s doing the right thing? Is it an authority thing where he feels he needs to make sure he has sign-off?

You need to sit down with him and have an adult conversation, including review and objectives for him, and in that formal chat you can give him some more authority to do what he feels is best. Bring up the good work he did and give praise for that, and tell him you were so impressed that you know he can do it, so he should not have any worries about doing it again without coming to you for guidance. Make it seem like a promotion to “independent worker” and he should be a happy, and more confident, puppy.

Don’t overdo it, ask to see his designs maybe so you can “keep in touch with the new code that’s going to go in” (nothing stopping you from reviewing it and giving feedback of course). As you’re the design authority, you should make time for initial meetings to go over requirements and suggested implementations which should make him feel like he’s done his bit in keeping you informed too.