new to management - big challenge with remote worker

[mytortoisehasgonemissingnow]

I need some management help please!
I'm a lawyer 6 months into management and have a new recruit in an ultra-specialised area of the law (and I mean ultra-specialised). it's something i've been pushing for for years and if I can make it work it will be really something.

He's a nice chap in his 50s. loves meeting the clients and they like him too. But he's been on his own for several years and is unfamiliar with modern time recording and filing systems.

The problem is that I can't seem to get the penny to drop about how important these are. I filled in the first few timesheets for him, then he did some yesterday but they are not reliable. Some have got client/file names mixed up, one says 3 hours which I think means 30 minutes, that sort of thing. I can't compare them to the file because he isn't filing stuff. I think it's an adjustment to your work being visible too.

He is fully remote. My ultimate boss lives and breathes data and I report in each month needing to show whether we have met targets (including for things like client satisfaction but principally financial). Right now I'm on course for saying I can't report in because the data is unreliable. That simply won't be acceptable to my boss.

My recruit has worked for himself for several years and is of a generation where you used to have secretaries to do the legwork. Also his culture is to say to clients "that'll cost around £5k" and then bill when the right moment comes.

Any advice? He finds hard things easy and easy things hard so we may be looking at reasonable adjustments to a degree, but my ultimate boss simply will not accept not having the data that he relies on to make decisions.

Quite.

Some people manage to resist learning things like this because there aren't consequences - it makes it 'your move' to fix.

A lot of bad workers skip basic requirements of their jobs, e.g. Answering internal emails, filing etc. It makes for an uneven playing field for those staff who realise that those tasks are part of their job as much as the other stuff.

Thank you all.

just a gentle point on the ageism accusation upthread. It is simple fact that people who started their careers in the 80s and early 90s were trained in the expectation of having a secretary. Ignorance of the processes controlled by the secretary was considered acceptable or even desirable/a mark of respect to the secretary’s expertise and your trust in her. Like trusting a skilled nurse to do a procedure that a doctor can’t do nowadays.
I remember being told “you’re not employed to type”. :)

as a status symbol the learned helplessness thing does still happen, as anyone who has seen “Suits” will know (Harvey has no mobile phone, etc, Donna runs everything)

I'm sorry OP but that is a load of absolute trite! I've worked in law firms for nearly 30 years and I can promise you that just wasn't the case. It may be that they were too busy to do it (I generally worked in Corporate) but the lawyers were still expected to be able to know the processes of 'how to' if needs be. In fact a lot of law firms have done away with dedicated secretaries and just have secretarial pools (as a way of clearing out a lot of older secretaries who actually weren't that good at what they did as they themselves hadn't moved on with the times).

I work with plenty of lawyers in their 50s, 60s and some in their 70s. They are perfectly capable. This guy is playing you if you think otherwise.

Maybe it was more forward thinking where you were in the 80s and early 90s :)