Innocent colloquialism or condescending…?

I had this with a one of my ex companies directors. He used to call me and other females 'girl', humiliating as an almost 40 year old. The last time he said it, my response was 'call me girl one more time!' I came to the office the next day, greeted by a huge bunch of flowers and an apology. I left a few months later for a better job, pay, prospects, benefits. That one comment has quadrupled my income, so thank you boi

I think how I'd tackle it would be:

Many thanks for your instructions however there are a few issues that need ironing out. We appreciate that you are new to this role so are happy to have a meeting to go through any of these if required.

A - Fee structure. The dept has a specific fee structure and there is a good reason for that based on tasks and staffing costs. We will be unable to do work at reduced fees so if reduced fees are quoted to clients in the future, then your dept will have to subsidise these. Please let me know the process that you have finaslised with your manager if this is a key requirement going forward. We need to be seen to be fair to all our clients and cannot risk being seen as favouring one client over another.

B - Tasks on offer. We offer the service of X and Y and refer back to our fee structure. Please desist in not being clear with clients about the work we offer. Again, we offer a fair service and adding tasks in that are not on offer or costed out affects the smooth running of our department.

C - Urgency of tasks. We operate on a planned work allocation basis and having work come through that you have made promises about without agreement puts our planned work into jeopardy which affects our other clients. Please refresh your knowledge on turnarounds before making promises to clients on our behalf.

D - Overfamiliarity. Our work is based on the understanding that any of our correspondence may end up in a court of law. Please desist from referring to myself or any of my team with overfamiliar greetings or sign offs, in particular the phrase 'my dear' which has been used several times. Please use formal business language for all correspondence.

As previous, we are more than happy for a meeting to go through our offer, fees, timescales, just let us know and we will make arrangements.

We have a new site worker who calls us 'poppet'. Gross

Definitely condescending.

If he was a very senior member of staff aged 80 and you were an 18 year old trainee it might just about be acceptable, but in the circumstances you describe definitely not!

I'd reply that the price of the legal work might seem expensive to him, but he doesn't have to keep calling you "dear".

To me it sounds like he is a condescending person and the "my dear" is part of it.

The problem is that from another person it might be an endearing colloquialism, so it's not the kind of thing you can pin down as him being an asshole.

I'd ignore it and concentrate on the issues where he is really being a problem, like timelines and fees.

@SpringDreams26 , It might be time to up your game and go fully professional 110%. Especially on how he speaks to you. That will also signal to your colleagues that you are NOT going along with the bullshit and neither should they. Don't let it become deniable as banter.
An unofficial coffee chat with someone in HR might be all that is needed.

This, 100%

Seems to me that he views the OP as some sort of admin/typist rather than a qualified professional.

His attitude seems to be a bit "Do as you are told, there's a good girl".

Perhaps he is trying to become a 'bit of a character', a pipe smoking old fogey that everybody loves. That is why he refers to the Good Working Relationship, it is special and favoured fee levels. Does he have exaggerated ways of speaking on the phone? Effusive thanks at any time.
I worked with a genuine character once, I said Good Morning, he would reply Good morning to you.

Is he trying to form his own team within the department? You might have been chosen to be is helpmeet.

I shall deal with [X] my dear, just get [X] done.

translates to me as

Shut up and get on with it.

You have a problem to deal with I’m afraid.

I dont mind certain phrases and im not offended by them but I would say they're usually from older generations. They are used as terms of endearment .
However I wouldn't accept it from a work colleague and due to his, and your age, I wouldn't believe it was innocently being used.

in the first instance id request he stops and then escalate it as needed. If he is going against work rules ie organising details without discussing with your department etc that is a whole different situation which should also be escalated.

Tell him he needs to use professional terms of address. Don’t say why. He knows why.

If he doesn’t like it and/or complains to anyone all you need to say is that you doubt he would address a man in that way.

Any change to the fee structure needs to be addressed to your boss, you are happy to forward his previous correspondence to them so they can apprise the matter…

Sounds patronising.
How about just a one line "by the way, I am not 'your dear' and find this somewhat unprofessional" added to a random email?

(One of my DC had a tutor for something that would always call me "flower" in every sentence whenever I had to speak to him. It grated a bit, but he'd been recommended and seemed good otherwise. After we had finished using him I heard from a friend that he'd been making dodgy comments about women in the street etc. in front of her DC... other DC will definitely NOT be going back to him!).

He is low-level bullying you. When he passes work to you slot it in to the timescale it deserves. Do not prioritise it, in fact, keep it until he chases you again for it. Make yourself the worst option, not the best. Send queries back to him, you are not paid to do extra work.

I manage a team of in house (public sector ) lawyers and if someone in my team was dealing with this I would want to know for several reasons

• inappropriate bypassing of the workflow system by the client
• client not sticking to agreed fees
• inappropriate tone and language

Is there any reason you haven't flagged it yet?

I've heard it used by a lot of older people, not by any particular race/sex. It has generally been used politely/kindly.
It doesn't tend to be used by younger people at all (same as I don't ever hear my kids using dear to mean expensive).
Wouldn't bother me really, if a term is old-fashioned but not offensive. It'll probably come round again, apparently Boomer language is now being used by the young ones! If he's being cheeky on other ways, OP, then tell him not to do those things.

Would you get away with calling him Sugar Tits?

Highly unprofessional and inappropriate. I would go through HR or send him a verbal warning. It's not acceptable.

If he sends work directly, either return it with a message that workload doesn't allow for it at this time, or forward it on to the central inbox for allocation. Attach a copy of the fees while you are doing it.

Lastly, and the point of this post, he often calls me “my dear” so I sent a perfectly professional email to which he responded “I shall deal with [X] my dear, just get [X] done.”

As far as this goes, they would be getting a reply from me along the lines of thank you for actioning this part of your job role, I will continue to action my part of the process in line with process and protocols.

Please refrain from using such condescending language when communicating with me in the future or I will be forced to take this further.

Ensure you cc your manager.

This would piss me right off.

I hate ‘dear’ in that context. It’s very outdated.