I am a PA to a very successful and senior investment banker. He works all hours and gives everything to his job. He sees my role as to do anything and everything necessary to help him be more productive. This includes many things which, in my opinion, fall well outside my job description and which I should not be asked to do, such as making doctors’ appointments for his wife, arranging parties for his children, and doing the payroll for his nanny and gardener.

If I complain I may be moved to another role in the bank, inevitably working for someone more junior, or at worst I may lose my job. Is there any other way to protest, or should I just shut up and get on with it?

Lucy’s Answer

There are two issues here. The first is whether your boss has any right to ask you to do these things. If he were a member of parliament he would be put in the stocks for such transgressions, but investment banks tend to take a more pragmatic view.

If he, as you say, works all hours, the shareholders should be only too delighted if his PA - whose labour is charged at a far lower rate – sorts out his home life so that he can go on toiling, uninterrupted by domestic concerns. His is an odd way to live, but that is another matter.

The second issue is whether you find it demeaning doing personal things for him. There is no intrinsic reason why this should be so: when you pick up the phone to make a doctor’s appointment for his wife you are using the same skills as when you make a business appointment for him, only the first is arguably more important.

It sounds from your message that you are a hierarchical sort of person, with your horror of working for someone more junior and your old-fashioned talk of job descriptions. Perhaps you feel that when you do regular work for him you are a colleague and when you do personal tasks you are a servant? This strikes me as a needlessly rigid way of looking at things.

Perhaps, though, the problem is not your misplaced sense of dignity, it is the fact that you do not like or respect him.

In that case I can see that doing personal things for him is intolerable. In which case what you need is not a discussion about your duties but a new boss.

Something else worries me about your problem: why can’t your boss’s wife make her own doctors’ appointments? Is she ill and therefore unable to lift the phone herself – or is she another workaholic investment banker who does not have such an obliging assistant?

I am on a panel of judges for an award for female entrepreneurs. We have just interviewed the short-listed candidates, most of whom were unimpressive. The most promising of these admitted during interview that she had had a sex change two years ago: until then she was a man.

I feel this disqualifies her as she was not a woman when she founded the business. I also feel that by not putting this relevant fact on the form she was deceiving us. Therefore I am inclined to disqualify her. The other judges on the panel do not agree and say that as the strongest candidate she deserves the award. Which of us is right?

Manager, male, 53

Lucy’s Answer

If you want to be pedantic about it – and it seems that you do – you could start by asking yourself whether she is a woman now. The answer to this is no, she isn’t. However she has had operations so that she can pass off as one and be treated as one. This means, surely, that she is eligible to enter this competition.

The next question is whether it matters that she was a man when she started the business. I don’t think it does. Evidently she wasn’t terribly happy with being one, so I can see no harm in stretching a point.

You say that you give her a black mark for not having been straight about it. I give you a black mark for having had that thought. What did you expect? That she would put full details of all operations she has had on the forms? The point is that she has changed her gender, which is a private matter for her and her doctor.

If you are still unhappy, reassure yourself with the thought that prizes are very silly things and the best person hardly ever wins. At least in this case you won’t be disappointing a brilliant born-woman candidate who deserves it, as you say the other candidates were feeble. This makes me think your prize is particularly silly: when I judged a similar award, there were lots of really good women entrepreneurs on the shortlist.

The others judges have already decided that you are a pedant, a meanie or a bigot. They may wonder, as I do, what principle you are defending: do you fear that, if you let this one through, lots of men will have sex changes just to get one of these awards? Give the award to her and stop worrying about it.

I have recently merged my management consultancy firm with another. Due diligence showed the chief executive to be well qualified, with an impressive MBA. However, I have recently seen copies of e-mails sent to his clients and to my horror his phrasing is clumsy and his spelling and punctuation make him look barely literate. He has a large ego, takes himself seriously and is proud of his achievements in business. But his e-mails go out under the merged company’s name and I am ashamed of them. How do I go about telling him he is not sufficiently literate? Is there anywhere he can go to recover what he must have missed at primary school?

Consultant, male, 62

Lucy’s Answer

No, there is nowhere your illiterate chief executive can go to learn what he should have learnt by the age of 10. People who did not master such things first time around do not suddenly pick them up later on.

And neither do they enjoy having their little lapses pointed out, especially when they have big egos. They particularly do not like having their spelling corrected by a new business partner during that most tricky of times when two companies are learning to co-habit following a merger. Though in your case, I wonder if it was a merger. I get the impression from your message that it was more like a takeover – in which case there is even more reason to keep quiet.

Instead you should console yourself with the fact that his prose is more damaging to your sensibilities than it is to profits. If he has built up a thriving business, evidently his clients either do not notice his mistakes or do not care. Your clients will presumably continue to deal with you and so they will be able to continue to enjoy your correct use of the subjunctive, semicolons, and the nice use of “none” as a singular noun.

A possible problem arises with new clients – for their sake perhaps you can get a spell-check program installed on your e-mail. Better still would be to stop worrying as this man is in good company.

Only a small minority of business people send e-mails complete with an elegant turn of phrase, perfect spelling and grammar, and most of those are about the same age as you.

One last thing. This man doesn’t sound as if he’s going to be terribly easy to work for. I suggest that you keep a stash of his worst messages and read them after bruising encounters with his ego – in order to rebuild your own.

I work for an investment bank in a team of 15, and I am the only woman. My colleagues endlessly stand around talking -both on business and private matters – as well as going out for coffee or drinks and to the gym.

I work long hours and don’t want to hang out with people from work. I hate the “team dinners” and usually don’t go as I feel I am unwelcome and prevent them from talking “man talk”. My managing director told me at my last appraisal I should spend more time with the team – which is ridiculous as I already spend 14 hours a day with them. Do I have to do as he says if I want to advance?
Banker, female, 24

Lucy’s Answer

When I was 22, I was the only woman on a male team in a bank. I often used to go out drinking with my colleagues and I gained two things from the experience: savage headaches and an even more savage anxiety over what I had said the night before. I doubt if any of my team-mates liked me any more for my copycat drinking and if my boss was impressed he never let on. It was all quite sad: I was trying to fit in and failing, not just because I was a woman but because I was altogether in the wrong job. It isn’t clear from your message if you are suited to banking or not. You don’t mention crying in the loo, so I assume that otherwise you are happy enough.

You ask if you can advance without hobnobbing. The answer is yes, at least for a bit. You think your sex is against you; actually it is rather in your favour. Being one in 15 means that if your manager fails to nurture you, he will be forced by HR to go on painful diversity training courses. I suspect he has told you to socialise because that is his crass way of nurturing you.

I suggest you forget about spending extra time with the team and concentrate on being more friendly during the 14 hours you are cooped up with them.

You say they spend time standing around talking. Surely you can manage this too? It is easy – you just need to stand around and talk. If you can’t do that, then you have quite a serious problem and need to think about quitting.

You mention coffee, drinks, the gym. Your strategy on these respectively is yes, no and no way. As for the team dinners, you should attend very occasionally and be as charming as you can. Otherwise just say no. Some of your team-mates may even grudgingly respect you for having a sliver of life outside.