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.

Id be honest with him and explain how important it is that your boss receives accurate data and the requirement for him to complete it correctly and on time.
Is it a training need do you think or just hes not in the habit of recording stuff .... maybe that you have to check daily or every few days with him until it becomes habit?

Is there any secretarial support available? If not, then I think you have to keep going back to him every time telling him it needs to be done properly. Don't you continue to do it for him. Is he on probation? You can extend that if he still doesn't do it properly. He is only in his 50s, everyone of that age will be used to using computers and if it is something he isn't used to, he will have to learn. Is there a course he can go on?

Fuck me, I'm in my 50s - there is no excuse for not being able to allocate your time to different clients.

You need to sit with him and show him your system and be very clear that his job could be on the line if he doesn't use it.

Have you directly explained it to him or are you just dropping hints?

Can you be really specific with him about the impacts? Not just that your boss won't have it, but very clear consequences of "if we cannot show ABC, we will not get/can't do XYZ"

Does he have any targets to meet re billable hours? If so, is this having an impact? He may suddenly decide to start doing it properly if its actually going to impact him

Also if he worked for himself previously, surely he has been doing this before? He can't have outsourced it completely

I’m in my fifties and am aware of how the modern world works!

Sounds like you need to do some re-training with him. Getting Clients names wrong is basic. You need to pull him up at every mistake. Don’t let his mistakes drag you down. Also, don’t cover his mistakes, or he’ll go on making them. It almost sounds like he’s not fit for purpose, and if these mistakes keep happening, you may need to have a disciplinary (or less extreme form). Age is no excuse.

Presumably you have tech to help with email filing and time recording, it isn’t all purely manual? Perhaps he needs more handholding from you or others on how to use these to smooth the process for him?

Nobody enjoys time recording and filing docs/emails. You can stress that but all you can really do is make incredibly clear that it is a complete non negotiable in the job.

I let this slide with a new hire in her 60s who was a heavy-hitter in the industry but useless at admin (timesheets, billing) and I've regretted it (and failed to fix it) for three years now. My advice is to push hard on this, right now, or you will repeat my mistake.

Surely if he has worked for himself for many years, then he will have had to have had some system for noting the time a piece of work takes.

You need to be direct and explain that this is part of the role.
Check in daily via zoom or teams or whatever and get him to fill in what he needs to fill in for the last 24 hours in front of you if that is what it takes. But do it NOW , at the start. If it is important to the company then it needs to be habit from the beginning, or it never will be.
Your time being spent supervising him doing this task now is clearly frustrating, BUT will save a lot of time down the line. Or, is there a peer that can do this instead of you ? Either way, if needs to be done now, not left.

Explain. Written procedure.
Make him do it daily. Check it first thing each morning. Allow 2 weeks of this. Then check twice a week

That's a really clear set of responses. Thank you!

this one hit home:
"I let this slide with a new hire in her 60s who was a heavy-hitter in the industry but useless at admin (timesheets, billing) and I've regretted it (and failed to fix it) for three years now. My advice is to push hard on this, right now, or you will repeat my mistake"

Is there actually any point to the level of data your boss requires or does he just like to have it. IME senior managers obsessed with data normally only want it so they can show it to their bosses and make it look like they are doing something. If you can explain the reason and purpose for the data gathering then he will likely find time to prioritise it, if you are asking him to simply collate data for the purposes of having data then don't be surprised if he can't be bothered.

Eastangular - you are giving me hope. He's a nice person and I think if he understood quite how critical this data is he would respond.

My boss is an entrepreneur who has only recently "let go" enough to appoint heads of department and stop line managing everyone himself. It's been a big transition and he absolutely depends on everyone's data. It is the basis of every decision, every spend authorisation, every end of probation review.

... every salary decision.... every appraisal.... every write-off, every apology.

it really "is" the business. far more than policies, systems and processes (we are still small enough to take quite nuanced decisions on more subtle issues)

I have found that if you give people the 'why' for data they will normally get it and oblige with gathering the info. I think unfortunately a lot of people have the experience of being asked to do meaningless tasks purely for the purpose of data gathering, strangely enough this doesn't really motivate people!

Of that generation - what on earth?! Those of us in our fifties are perfectly capable of understanding the modern world and secretaries haven’t been a ‘thing’ for many, many years. If you’re new to management I would encourage you to reframe your thinking on this quickly.

What you’re describing is a simple non-negotiable part of the work - it has nothing to do with age and everything to do with an attitude to the task. It doesn’t need to be over-complicated - you need to reiterate that neither you nor your boss are prepared to accept this, explain why it’s required, that it’s a key part of the role, and it needs to be immediately returned to him to correct every time there’s an error. If he continues then it’s a performance issue that needs to be managed.

I also suggest that your boss reviews his approach, as data will only get you so far when managing people. And as his business grows he will have far less control over the integrity of that data, as you are now finding.

I make these types of errors and have ADHD. Access to Work fund support workers to assist with admin. I’m late 30s and had to push for a diagnosis so at 50 they’re highly unlikely to be diagnosed if they have these type of difficulties.

Sitting with me each day to help me complete these tasks would be a work around but in all honesty I’d probably feel humiliated.

Hi OP where I work incomplete / inaccurate timesheets can result in disciplinary procedures. PP’s advice about 1. explaining why it’s needed 2. That it is mandatory 3. Training if required and finally 4. Emphasising that this could result
in disciplinary action should
do it.

For the first month or so perhaps you could do the weekly check ins via Teams.

I has a colleague who was sacked 15 years ago for failing to time record properly, it's not a new requirement.
However it does mean a different mindset, and he should be able to understand that you can't calculate an effective chargeable rate for him if you don't know how long he's spending on any given matter. Explain that your remit is to analyse how he is spending his time and whether it is cost effective for the firm.
I think you need to be very clear from the outset what the requirements are, because it sounds as if he is not compliant with the most basic client care issues.

If his specialism is that rare abnd desirable, surely it would make sense to hire a secretary with superb organisational skills to do this stuff for him. They won't cost a fraction of what he costs per hour, and he can focus on what he's good at.

i second this. such a waste of time having specialist staff spend their time on admin

My guess, as a 50 something person who isn’t particularly comfortable with unfamiliar technology, is that he isn’t completely clear about exactly what is expected of him and exactly how he is expected to do it, or the critical importance of it to his ultimate boss. He may see it as an admin task which should be delegated to admin staff.

You need to have a very direct conversation with him to make sure he understands these things. Spell it out. He also needs 1-1 hands-on training in how to use the systems / applications used for these processes.

I'm older than he is and had to get used to doing my own admin. One thing I found really helpful when I got busy was a VA (Virtual Assistant), who can not only do the admin, but put good processes in place for you too. Is that an option?