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How to deal with a difficult supervisor

As published in The Lawyer magazine (

(These tips are not confined to trainee lawyers, and can be used for different levels of seniority and in a range of sectors.)

When you are a trainee solicitor with limited time in each seat, you want to make a good impression, fast. What do you do then when you are, unfortunately, assigned a particularly difficult supervisor?


A difficult supervisor of course means different things to different people. To keep things simple, let us assume here that we do not just mean quirky or anti-social – we mean a combination of moody, unapproachable, unreasonable, and perhaps a little rude (but not the bullying, discriminatory kind – that behaviour should be reported to HR).

Accept the challenge

The first thing to do is accept the situation – it is unfortunate, but it is not going to change.

Chances are the firm knows the supervisor is difficult, so rather than openly complaining, gossiping and being miserable, you will impress people far more if you accept having drawn the short straw on this occasion and get on with handling things best you can, with your chin up.

Put differently, believe it or not, this is your chance to shine.

Get tips

If they are really that difficult, everyone probably finds them hard to work with.

Talk to the trainee you took over from and get tips. Observe how others in the team deal with them and emulate strategies where you can. Once you feel comfortable enough, consider asking their secretary for some pointers too – they may give some great advice.


Think carefully about how you can work together – every bit of synergy helps.

For example, if they are abrupt and tend to answer long emails in broken words, they are likely to respond better to brief communications. So keep your questions to the point (no waffling) and stick to bullet points in emails.

Or, if they seem constantly overloaded, send them a calendar invite and save all your questions on your various tasks for that catch up. This will make them value their time with you more.

Be brave

If you feel able to, sit down with them early on and ask how they like to work. For example, do they prefer you to print out drafts as well as email them? Do they want findings presented verbally or in a memo? Taking the lead and showing you are trying to make their life easier is likely to go down well and open up lines of communication.

Keep learning

This is your training contract so make sure your learning continues throughout, no matter what.

Look for the positives to help you do this – what are the advantages of having this supervisor? They may be exceptionally pedantic about grammar, which is great as this is your chance to really improve your written work. Maybe they assume you know things you never could have known – use the opportunity to work on your wider reading.

There is also long-term learning to be had. By observing and taking note of qualities you do not admire, you can really start thinking about the kind of lawyer you aspire to become.

Be nice

Be yourself, be genuine and be nice. Never underestimate how far this can get you.

If you know they like movies, mention a new film that has come out to lighten the atmosphere. If they are having a stressful day, offer them some tea (it is extremely difficult to be mean to anyone who offers you tea).

Many supervisors start off difficult but soften up after getting used to you – hopefully they will warm up after some time.

Do not take it personally

None of this is personal. This can be easy to forget, so keep reminding yourself. They may be stressed with work pressures or personal matters that have absolutely nothing to do with you. It is not about excusing their behaviour, but rather adopting a different perspective to take the edge off.

Sometimes laughing about how absurd it all is can help too. Consider compiling your personal top ten of the funniest things they do or say. Let the experience not only shape you into a more tenacious person, but also one with some truly brilliant stories to tell.

Look after yourself

None of your efforts will be effective if you do not prioritise taking care of yourself and keeping yourself sane. Do whatever it takes – go to the gym when you can, make fun lunch plans to break up the day, treat yourself in the evenings. If you are feeling happy in yourself you will be much better equipped to manage the situation.

Do not give up!

You may have been dealt a terrible card, but remember the situation will not last forever. Aim to get through it with your confidence and integrity intact, and more skills than you know what to do with.

(Want some extra support with all this? Why not consider some one-to-one coaching sessions with Red Arbre.)

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