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.

I work in the Finance office of a small company. My work is very self-directed with a light-touch from my manager. Suits me.

Nice that you have made it work :)

Beancounter you have to account for every six minutes nowadays!

OP I work for a very specialised lawyer in his mid 50s and our firm has spent decades trying to get him to be more organised, submit timesheets, bill clients and deal with his own credit control and financial hygiene generally but he just can't do it. He loves being a lawyer but hates the admin that comes with it. I watch everything he does all day - I have full visibility of his emails, all calls made and received, all documents worked on, all work related conversations, and record absolutely everything in the time recording system, plus also provide legal support. There was no other way around it as he simply would not (or could not) comply.

Last paragraph of this is spot on! If no one else can record what he’s doing because only he has that information then no one will ever know if it’s accurate or not! You can just make up what you report to your boss, after all there will be nothing to say your wrong😂. Writing something down doesn’t make it true

“. Ask yourself, what would be the effect on the business if he just estimated times or made it all up?”

that would depend on our customers feeling they had got value.

I wish I had the luxury of that problem

Unicorn it’s good that works for you. At least you have control.

Why would the clients care if it’s an estimate or not? Have you ever measured your satisfaction in something by time spent rather than by result achieved?

Yes it's good to have control but is exasperating at times. My boss used to work on a deal for months and when it completed and was time to bill he used to read through his emails and calendar and estimate the time he had spent, then report to the client with that amount. It caused a lot of issues as clients nowadays want regular WIP reports and proper narratives and breakdowns, and managers nowadays need to see utilisation levels throughout the month.

It's a difficult situation and I would hate to manage someone like this.

What has "nice" to do with efficient and productive? I think you as his manager need to have a proper discussion with him about the difference between being self employed and being an employee. Its not about ageism or being offensive, its about making clear what the tasks in his new position are....and gently point out that he can't cherrypick the bits he likes or finds easy.
I think you need to really dig down into why he can't/won't produce the data you are asking for....what he finds difficult and so on...because you need facts.
Then a difficult conversation with your boss once you have gathered your facts.....how replaceble is the bloke? How big is the benefit to the firm in having him in their employ? Is it big enough to rewrite the requirements to accommodate new guy's needs? and this looks like its needed ASAP. If your boss likes data he needs facts and then its his decision as to how to proceed...so you need to identify new guy's performance gap plus any facts about the gap...then a cost benefit analysis of contunuing to employ him (and by cost benefit I don't mean just cashflow)...then an analysis of what you would be able to do and what you know you can't...then the suggested options with any comments you feel you want to add.

Is there actually any point to the level of data your boss requires

I'm guessing the time records will be used for billing, possibly even directly (though I imaging there will be a manual review and approve process.

I be would encourage you to be quite direct (for England) with him. Ask him to tell you the purpose of the time recording system. What will happen if he does not provide accurate records.

Then, make sure you go back to him and make him make the necessary changes every.single.time. Once he feels the pain himself and understands the connection between these mistakes, there is a chance he will grasp the necessary.

Even people who have worked themselves into a niche can recognise when they realise the impact of mistakes.

If he just can't do it then can he generate sufficient profits to justify an admin / paralegal whose role would include doing the timesheets.

Whatever else you do, don't let it slide. Good luck.

“If he just can't do it then can he generate sufficient profits to justify an admin / paralegal whose role would include doing the timesheets.“

nope -we bill by timesheet!

I'm also ex Big 5, we used to joke about the behaviours which would be tolerated compared to the ultimate sin of not filling in a time sheet correctly, on time.

First offence would involve a phone call from a partner. No one wants to be known to a partner for messing up their input to invoicing.

Never heard of any second offences.

Ours used to be that you had to sing in the Christmas choir..second offenses got a solo, and third offenses someone else wrote their solo for them. That only happened once!

I just can't get my head around how he's got away with not doing timesheets for so long. I don't work in law but in am in an adjacent field and we use them- complete a task, update timesheet. Yes it’s a bit shit, but it’s part of the job.

From timesheets flow your revenue projections, your WIP, your billings, calculation of your effective hourly rate (for fixed fee stuff, which he seems to love!) and it's a management tool as well. It’s not just numbers for numbers’ sake.

I agree with @godmum56. You’ve got to get to the reason why he can’t or won’t submit these. There’s no doubt it could be a neurodivergence related issue, but equally it could be him just not bothering because no one’s ever really rolled his balls over it before. He likely feels his niche area of expertise will protect him, but you can only allow so much leeway. In these circumstances you can’t allow people to be insulated from the very basic requirements of the job, especially if his attitude begins to spread into other areas of his work or influence other staff and their morale.

Are any of the junior members of the team incredibly skilled drafting a completely detailed procedural document including a why we do it section and a key risks and remediation section if it's not done?

Can you introduce a mandatory procedural for the team that must be 100% adhered to?

some problems with this.....first there must be a decision that its worth risking losing the bloke to enforce compliance...and that's above the OP's pay grade...Secondly you could write a detailed procedural document including the why we do it section and if the employee CANNOT do it then its not going to work.
Under normal management circs, yes you lay down what you want/need to be done, tell the employees and away you go....bottom line is staff comply or in the final event they get managed out...yes the manager may help...may support them to comply and so on but its my way or the highway....but this employee seems to have an extra value to the company so the question here is how great is the value...how far can/should the system be changed to keep the golden goose?
Oh also as the manager, I'd be writing the procedure or at least working closely with the writer.

I'm a lawyer and you could be my boss writing this about me. I've always found timesheets a ballache but totally understand the importance of them and have always exceeded time and revenue targets by a huge percentage (always achieved bonus when others havent). my current employer has a totally fucked up view of admin though. There are no secretaries and the time recording system is practically unusable as its been designed by accountants rather than lawyers, particularly when being used from home as it times out constantly. Its outrageous that clients are being charged my hefty hourly rate to do secretarial and other admin tasks. Where i work excuses are made constantly for the poor system but I have worked somewhere that is run properly and it doesn't need to be difficult. Maybe just have a chat with him and see what the difficulties are. It might be your actual processes. A lawyer shouldn't need timesheets to demonstrate they need admin support by the way. I regularly billed x5 a month at my old firm on a similar hourly rate but these days i fuck about doing my own word processing and filing whilst swearing at a software system that makes no sense. Its soul destroying. I've tried expressing my frustrations but come up against a constant wall of process over outcome.

Re our systems, it’s not that. I only need him to do time recording which uses a basic but bullet proof package plus the document management system which basically works.

I do hear you: our file opening system is beyond frustrating/slow. It drives us all mad so I plan to continue to shield him from that.

Ok, armed with your messages and insights I’ve drafted something explaining why it matters.
am cautiously optimistic
thanks all!

......but how would the secretary know what he is doing with his time ?
Surely he would have to tell him or her, in which case, why can't he just "tell" the time sheet ?

Updating to say we’ve had lots of chats. He seems not to listen but then refers to them next time.
he did some timesheets but doesn’t file anything and makes long meandering calls.
i think it’s a long history of ADHD or similar with some dreadful coping strategies that make him dysfunctional in an office.
it’s clear that he is hiding his work from me.
he has also expressed concern that the office manager is spying on him.

he recently divorced and I wonder if his ex wife organised him.

I don’t think he’s ready for office life. We may have to call a halt to this before he commits to renting a flat etc.

it sounds like that would be both sensible and kind.

Thank you.

Do you mean exit him? If so I would really start raising it with your boss (he is top boss yes?) and getting his but in to it being an option. If you have any HR support internally or externally get that in too so you are protected.

once you have that is it ultimatum time - shape up or ship out?

I work for a law firm that has lots of lawyers who used to work for traditional firms where they always had a secretary outside their office, etc. rarely input their own timesheets, however they still had to work out the timesheets, time, etc. The firm I now work for encourages all people (no matter what age/position) to do this themselves and they are all doing fine.

I find it hard to believe a 50 something lawyer cannot get to grips with this, he must have been doing timesheets for years (especially the 6minute sections).

I have one lawyer who is ABSOLUTELY determined to make herself look ditzy and 'oh I just can't do it, can you please do it for me' and I say no that's not the firm ethos, you know it's not. I think she thinks if she just keeps trying I'll do it for her and I've been told by management to push back (politely!) but not to do it. I think this is what he's doing to you.