Been in a small firm that mainly does conveyancing and private client work for about three months now. I'm a legal assistant and I've been paired with a solicitor in the firm who is the quietest, meekest, least confrontational man in the world. Up until I joined and got my footing he had been working on his whole caseload on his own and has been increasingly notorious for never picking up the phone, never updating his clients until he needs something from them, ignoring angry phone calls and letting his cases slip, etc and has managed to latently piss off everyone in the firm. I think he's more or less just shy but getting him to delegate tasks to me is like pulling teeth even though I've literally made him a list of all the things I know how to do, I come to him throughout the day with suggestions of what I could be doing, updates on what I am doing, just trying to open the lines of communication. He's such a lovely person that everyone in the firm adores so he's not received the brunt of the frustration but it's definitely there, and it's frustrating to feel like you're sat next to someone who desperately needs help managing his cases and you and everyone else is telling him you can help him, but he just doesn't seem to want to delegate.
Basically, the TLDR here is that I need advice on how to "manage up" and get the world's shyest solicitor to start giving me tasks before his lack of communication irreparably pisses off his colleagues and clients. How do I be helpful and useful and not just annoying?