How do I politely encourage my new help desk colleague to troubleshoot more on their own?

I totally get where you're coming from. Instead of spoon-feeding, you can set some clear expectations. Next time he approaches you, redirect the conversation by saying, 'Hey, I'd love to help, but can you try this first: what troubleshooting steps do you think might work?' It could help him understand he's expected to put in some effort, and once he starts trying, he'll likely feel more confident.

I think there's a bit of a learning curve, and some people just need more time to adjust. It might be good to have a sit-down chat and let him know you'd appreciate it if he could try some basic troubleshooting before asking for help. Maybe even work together on a few issues to show him how you approach problems!

Sounds like he might just need a little push to build his confidence! You could try asking him guiding questions instead of giving direct answers. Like, say, 'What steps could you take to troubleshoot this issue?' This way, you'd be encouraging him to think for himself. Plus, it’ll help him develop a better problem-solving mindset moving forward. You might even ask him to document what he discovers along the way, so he has it to reference later!