Mistaking a partner for a vac schemer, deal-wrecking typos and costing clients thousands — lawyers annoymously share their TC blunders

By on

“The sinking feeling when I realised the error was horrifying,” one Reddit user wrote

Starting out your legal career can be a stressful time. Dealing with tight deadlines and sensitive information whilst trying to impress supervisors and meet high client expectations has seen some true howlers from newbies.

Lawyers have taken to Reddit to confess all from client roastings and embarrassing errors to deal-wrecking disasters. Legal Cheek has picked out some of the worst blunders from the thread so young lawyers can learn from the mistakes of others and avoid “the sinking feeling” or “the wave of cold sweat” when it suddenly dawns on you what you’ve done wrong…

Mistaken identity

Nothing is more awkward than not realising who you are really chatting to at a firm drinks event. One young lawyer recounts: “While a brand new associate at a City firm, I was at a vac scheme drinks event and got chatting to a young looking man who I assumed was one of the lucky vac schemers.”

“It turned out later that he was in fact a partner and one who was on the edges of the department I worked in, and who I’d never met,” they explain. “Luckily I didn’t really ask him questions identifiable as predicated on the vac scheme so I didn’t do the nightmare scenario of patronising him and showing I didn’t recognise him — the worst I asked was ‘so how’s it all going?’ (meaning the vac scheme) but he didn’t clock me.”

The lesson from this nearly very awkward encounter: “ask someone who they are […] — it’s less embarrassing than the alternative.” Surely that’s some advice, one rookie wished they had known before “flirting with a young looking female partner who they didn’t realise was a partner until they were several drinks in”.

In a more professionally embarrassing case of mistaken identity, one contributor tells how a trainee had instructed the wrong law firm on a multi-jurisdictional survey ahead of a big M&A transaction.

“The firm incurred several thousand pounds’ worth of fees before anyone realised,” they detail. Fortunately for the newbie, it was “not the end of the world as they weren’t conflicted and they were still reputable and on the shortlist of local counsel in that jurisdiction”.

Embarrassing typos

Sometimes just misspelling a name can throw a spanner into the works. One anonymous Reddit contributor “noticed that the spelling of the client’s name was incorrect on the mortgage offer”. After calling the bank, the offer was completely withdrawn and everyone had to start from scratch again. “We went in to the notice to complete period and I spent 2 weeks shaking with nerves,” they conclude.

Oops, that wasn’t meant for you…

According to the thread, this can range from copying a client into an email berating said client to sending your team’s arguments in a litigation to the opposing counsel.

Client confidentiality is also something that trainees are known for ruining. One online poster recalls “sending an email to a client regarding a highly confidential matter”, only to realise they had “inadvertently copied someone at a different client with a very similar name to the partner you work for. Erk.”

Applications are open for the Legal Cheek November UK Virtual Law Fair 2022

Equally some documents end up at the wrong destination: the bin or the shredder! One confessed to leaving a folder including documents with the original signature pages of the parties concerned on top of a dustbin under a desk overnight. The outcome: “said dustbin was emptied overnight. Cue panicked trainee having to re-obtain signatures.”

One self-described legal secretary tells a similar tale of woe. “Finally got signed documents from client,” they write. “Made copies. Put copies AND ORIGINAL in shredder.” Ouch!

Smart-arse karma

Occasionally, newbies enjoy flashes of brilliance. But according to Reddit, the highs of feeling like a legal genius can quickly be followed by the lows of realising you’ve actually messed up.

According to the thread, one keen-eyed pupil barrister spotted a mistake in a judges sentencing decision which they took to the Court of Appeal whilst in their second six… and won!

However, karma came around pretty fast. “3 weeks later I was back in front of that same judge who sarcastically asked me for my ‘expert guidance’ on the sentencing regime on my next case… which I sort of got wrong when but more of a matter of opinion on culpability,” they say. “He then said ‘don’t worry we all make mistakes from time to time and that’s what our peers are for’…”

The 2023 Legal Cheek Firms Most List

Another shared this story: “When I was in the clin neg/litigation team as a first seat trainee I was given a really esoteric research task on the final day before Christmas. Everyone had gone home but the associate had told me that the partner wanted it pre-Christmas.”

The confession continues: “I stayed in for ages searching and found literally the only QC to have ever opined on this particular point (can’t remember what it was). I always thought thinking outside of the box and independence were valued so took the initiative to email him on a no names basis describing the issue and asking him if he might be able to let me know what he thought.”

“He replied copying in the partner to the effect that a) he doesn’t give free advice and b) based on the point alone and my firm he was able to guess the case because his set was acting for the other side,” they write. “I went home for Christmas absolutely sh***ing myself.”

But fortunately, all’s well that ends well. “The partner was really nice about it when I came back in New Year and said he admired my initiative but that I have to be more careful about confidentiality going forward.”

Lucky escape!

There are some whose blunders have fortuitously gone unnoticed! One anonymous rookie confesses:

“My biggest one was making a mistake on the documents to register a specific type of charge over an asset that rendered the charge invalid. Nobody noticed until I realised about a year later what had happened. All that time, the lender had no security at all over the asset. Fortunately the loan was re-financed shortly after, and new security was put into place. But the sinking feeling when I realised the error was horrifying.”

But after everything, many a panicked trainee have their guardian associates to thank for avoiding a catastrophe, as this confession underlines: “As a very fresh trainee one of the partners put a letter on top of a folder and handed it to me saying ‘make sure this gets out in the post tonight to the other side’. Obviously I wouldn’t put the entire case folder, with the letter attached, in a box, and address that box to the opponent and pop it in the post room …. Would I?”

“Chatting with one of the associates in the pub that evening, the penny dropped. The wave of cold sweat hit me like a tsunami. The associate, once he stopped laughing, drove me to the sorting office where we were able retrieve the box,” they write. “The associate, once he stopped laughing, drove me to the sorting office where we were able retrieve the box [containing all the vital details of this case to the opponent in the litigation].”

For all the latest commercial awareness info, news and careers advice:

Sign up to the Legal Cheek Newsletter


Legal Officer With A 2:ii

“BuT wE wAnT tHE bEsT aNd If YoU mAkE oNe MiStAkE tHeN yOu MuSt Be ToO sTuPiD tO bE a LaWyEr!!!!”

And then the process of covering up the mistake wrecks life for everyone.

What a working culture


Scouser of Counsel

Covering up mistakes wrecks careers.

Better ‘fess up if you mess up.

Making a mistake doesn’t end a career.

Lying about it does.


Kirkland NQ

My most embarrassing moment was when as a fourth seat trainee I brought in a Ferrari brochure and started asking for advice on whether to treat myself to an SF90 or a Roma. A partner quietly took me aside and corrected me on my car brand choice.


Kirkland PA

Lemme guess, Lambo?



4/10, not great, not terrible.

Try harder son, your tired old shtick counts on you.



Yeah sure fresher, rather than sticking to your schtick, shouldn’t you be doing the reading for your next tort law seminar?



I once sent a letter to opposing counsel saying something like everything my client had done was “overboard”, when I meant to say ‘above board”.



I *knew* that thread would end up here. Taken right out of the Buzzfeed playbook.


Deal Sleds For Life

My moment was a couple months into my first seat; classic rookie move of miscalculating court deadlines. I thought I had one more day then I had (and that extra day was in the matter partner’s and the few associates/senior associates managing the day to day calendars too – and not just for that task but for all CPR/court requirements). It was a deadline for exchanging cost budgets on a multi party commercial dispute.

I was at a lunch with a group from my firm, including my seat supervising partner and another very senior partner of the firm. My work mobile started going off as the claimant and all co-defendants to the dispute started emailing with attached cost budgets. I immediately panic as ours wasn’t even drafted. I had to quietly excuse myself from the lunch to deal with an “urgent query” and sprinted back to the office. Immediately tell the partner and f/e’s, finish the budget, circulate a couple hours after deadline.

It ultimately didn’t matter because, like 99% of all commercial disputes, it settled shortly after. However it was very embarrassing sending the outlook calendar update for all the other court/CPR deadlines to the partner and f/e’s. End of seat feedback included a phrase to the effect of “made a dumb mistake, but approach to owning up to it and correcting it quickly was spot on”. I am grateful I didn’t qualify into a disputes team.


Man said "CPR deadlines" ROFL

Is this some kind of high street joke that I’m too BigLaw to understand?



As a pupil, my supervisor took me for lunch with clients after settling a case.

Towards the end of lunch, I started feeling a bit off colour. Then each and every person at the table went to the bathroom one by one – I thought it would be too weird and creepy for me to go as well (the kind of decision only an overthinking pupil would make).

I figured the clients were heading to the Tube and we would be heading back to Chambers – I could make it. I must make it.

Then, disaster struck. My supervisor offered to walk them to the Tube.

We started walking. I knew the time was nigh. A wave of unstoppable nausea overcame me. I looked around for salvation. A large wheelie bin. I peeled off from the group without a word, without breaking step, and marched towards the wheelie bin. I arrive at the wheelie bin unscathed.

The wheelie bin – it was locked.

The dam burst. I proceeded to vomit all over myself. My suit. My bag. My tenancy prospects.

My supervisor appeared from around the corner – no sign of his once cherished clients – and laughed. He made an attempt to retrieve his White Book from my bag, then thought better of it, and sent me home, soiled and bereft of dignity.

I had to take a few days off with a stomach bug.

Now, I am a tenant and have been for some years.

The moral of the story: if I could get taken on after that debacle, then you can too. We’re all human and the decent sets / firms will recognise that. If not, then you probably don’t want to build a career there. Cut yourself some slack.


Scouser of Counsel

Covering up mistakes wrecks careers.

Better ‘fess up if you mess up.

Making a mistake doesn’t end a career.

Lying about it does.


Comments are closed.