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Paper bag over head AccountingWEB Top 10 awkward accountancy stories

Accountants share their most embarrassing stories


From mistaking a partner for a photocopier engineer to ending up lying on a client’s driveway, here are our top 10 most awkward moments that prove even the most meticulous accountants can have an off day.

24th Jun 2024
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Accounting is often seen as what regular contributor WinterDragon described as “being null of any humanity”. Yet behind the tax returns, stories reveal the all-too-human side of the profession. 

WinterDragon came to Any Answers to share an embarrassing story and to make himself feel better, he asked other accountants: “In my moment of shame, have you ever done something similar?”

From getting a name wrong to falling over, the Any Answers community shared their own embarrassing experiences. Here are the top 10 awkward accountancy stories that might make you feel a bit better about your own mishaps. 

10. Name game fiascos 

Sometimes it’s the simplest mistakes that can lead to the most awkward moments. Getting a name wrong might seem minor, but for AccountingWEB member Jdopus, a simple slip of the tongue cost him a job opportunity and left a lasting impression of how important it is to get names right.

“When I was interviewing as a graduate I made the mistake of saying the name of the firm I had an interview with backwards, as in Smith Jones instead of Jones Smith. The interviewers were deeply affronted by this and made it clear that they had thrown out my application because of this,” Jdpous recalled. 

There might have been a bit of an overreaction on Smith Jones’ – oh wait Jones Smiths’ – part, but it serves as a reminder to think before we speak.

9. Lost in translation 

JB101 recounts a funny but awkward moment involving a client who took a colleague’s joke a bit too literally. “One of my colleagues jokingly told a client not to leave the country as he was having an HMRC investigation,” they said. “His wife phoned up to say that they were hoping to go shopping in Bristol but would cancel as they couldn’t leave the county.”

This story is a perfect example of how literal interpretation can lead to confusion, especially in the world of accountancy where clients often rely heavily on their accountant’s words.

8. The awkward case of mistaken identity 

Mistakes happen in every workplace, but few can match the embarrassment of mistaking a senior partner for someone else entirely. As Justin Bryant recalled: “I mistook a PwC partner for the photocopier engineer. I did not last there long after that.” 


7. A lucky accident 

Bernard Michael recalls a remarkable turn of events. “A client rang me to say that he’d gambled on the stock market following incorrect insider information and owed a stockbroker £300k,” he said. “My tongue-in-cheek advice was, ‘Do a deal with the broker or leave the country.’ The next day he rang me up from New York and asked me to tell the broker. I next heard from him two years ago when he told me he was running a very successful business in the US and was a millionaire ‘thanks to my advice’.”

Not an embarrassing story but definitely belongs here for being a crazy example of how a casual remark can lead to a life-changing decision.

6. A CGT love story?

WinterDragon recounts the story that kicked off this Any Answers post. “I was on the phone to a female client who had called to ask about capital gains tax on a residential property. I thought to check if there were any obvious pitfalls or complexities and I was unaware of this client’s personal circumstances, so I asked if she was married as she had said the property was her principal private residence before she began to let it out. The client told me she had never been married to which I replied: ‘Brilliant!’

“Before I had even finished speaking I had realised what I’d done and quickly tried to explain why I had asked that question – but not before the client had started laughing at a 20-something accountant being delighted at the fact she was single.”

Despite being single, she probably wasn’t ready to mingle over CGT.

5. Relationship status roulette 

As mentioned by Ireallyshouldknowthisbut and Roland196, accountants often find themselves playing a game of relationship roulette. 

Ireallyshouldknowthisbut admitted to frequent slip-ups during client Zoom calls. “I’ve put my foot in it more times than you would have thought possible,” they said. “A regular one I have is with a couple where I don’t know if they are married or not. I mention tax planning issues such as transfer of shares and one of them gives the other a hard stare and I have to backtrack quickly.”

Roland195 responded: “I’ll raise you the client where I know the two owners are married because of my diligent know-your-client work – just not entirely sure if it’s to each other.”

There’s clearly a fine line between financial advice and inadvertently triggering a domestic dispute, so it’s best to tread carefully.

4. Oops, wrong number 

“A colleague of mine was very nervous when calling clients so he used to write out a script beforehand,” said Yossarian. “I overheard a phone conversation where he launched into his monologue, not letting the person get a word in edgeways. Eventually, when he came to a stop there was a pause and I heard him say: ‘Have I got the wrong number?’ He’d misdialled and got a confused elderly lady.”

Just goes to show that sometimes being too organised can come back to bite you.

3. A high-pitched surprise 

Yossarian returned with another even more embarrassing story that left him blushing over a phone call mishap. 

“I once had a phone conversation with a client thinking he was his wife. He had quite a high-pitched squeaky voice and I was mortified when I realised my mistake. Fortunately, he was unfazed by it, and I suspect it probably wasn’t the first time it had happened.”

2. A not-so-smooth introduction 

WinterDragon offers up another story that unfolded when his father went to meet a prospective client. “He bumped his head into their handcrafted Japanese wind chimes. On the way out he carefully swerved his head around them – and that’s when his foot caught the step at the bottom of the door and he found himself lying down on the driveway.”

An awkward situation was made even more awkward when the potential client was having none of it. “My dad found this unfortunate series of events hilarious and began to laugh but the client just glared with a deadpan expression,” WinterDragon continued.

Next time, invite the client to your office instead.

1. First impressions matter right?

The story that tops all others is about Stanbu’s unforgettable first day in a new job. “I was a newly qualified accountant and on my first day with EY I was in a partner’s office when he said: ‘Could you pull the blind down please?’ So I did – right out of the ceiling!”

So here’s to Stanbu, for inadvertently bringing down the house – well, the blinds, at least. 

Do you have an embarrassing story to top any of these? Let us know in the comments below.

Replies (23)

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By Justin Bryant
24th Jun 2024 17:10

At least no-one here was caught having sex on the office desk.

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Replying to Justin Bryant:
By SteveHa
25th Jun 2024 16:05

No comment.

SteveHa, ex HMRC, attended a Christmas party in the office.

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the sea otter
By memyself-eye
24th Jun 2024 17:19

Sex on the office desk?
I would have done but my wife was working at the desk at the time and refused to give it up!

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By zxcvb
25th Jun 2024 09:19

In my first day at a local accountants, I was taken to the senior partner's office for an introduction. On the large desk were photos of his family, including his son who I quickly recognised as I had put him in hospital a few weeks earlier! (accidentally of course, I was a goalkeeper, he was a striker...)

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By Mr J Andrews
25th Jun 2024 09:21

I do hope the photocopier engineer was not offended.

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By unclejoe
25th Jun 2024 09:56

I had not been at the company very long, and I was introduced to the MD, who I had not met, at a social event. I was determined to be on my best behaviour and create an impression. He had an attractive woman with him and as I was introduced I said "And you must be Mrs xxx.", at which she turned to the MD and said very loudly "You have a WIFE!!!!".

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By JamesDS
25th Jun 2024 10:57

When very junior I turned up at a clients' house and failed to notice the Mezuzah on their front door and the Menora in the window. The client was working in the garden on a hot day and was obviously exhausted. I made a comment on this in greeting and he responded with "no rest for the wicked". I replied with a jovial "might as well be wicked then". I knew it was the wrong thing to say immediately, but didn't have the words to undo it.

Client took a very dim view of the remark and all business was terminated shortly thereafter, with the reason given being my lack of respect for their faith.

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Replying to JamesDS:
By Paul Crowley
27th Jun 2024 14:05

He started the wicked thing.
Leavers rarely give an honest reason.

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Replying to Paul Crowley:
By JamesDS
01st Jul 2024 17:25

You're right there, I suspect I was simply the precipitating event.

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By Dogracer
25th Jun 2024 12:06

This story dates back to the days when you could obtain the tax relief for maintenance payments provided they were made under a court order. A client mentioned to the partner that he was making payments for the benefit of his son Troy. Ever helpful the partner called the clients wife to remind the client to let us have the Court Order for payments for Troy so we could obtain the tax relief. The wife replied who’s Troy?

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By Tornado
25th Jun 2024 13:39

Some years ago I was having some difficulty in receiving payment for my invoice to a client but I felt it was in my interests to keep going with the work as I saw no particular reason why I would not be paid in the end, and I still had the upper hand.

I was mainly dealing with this client's wife and during one meeting I raised the point about the outstanding invoice and she said that she would pay it. I did not care much about where the money came and told her so, but was a bit puzzled as why no cheque book appeared to make payment to me.

It was not until several years later that it finally dawned on me as to how she intended to make payment. The debt was never paid and there have been no other similar offers.

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By stevenckay
25th Jun 2024 15:08

A friend of mine applied to 5 of the (then) big 6 accountancy firms. He was asked at one interview why he hadn't applied to Arthur Andersen and he replied, "I hear that they work you really hard there."

They thanked him for his interest and wished him well in his future career as he left, needless to say without a job offer.

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By Karen whitehead
25th Jun 2024 17:22

My first day at a new job, I was taking over as a manager from the previous incumbent and we had a period of overlap. It happened to be his birthday and we went out for lunch. I was at the front of the group as we returned from lunch tripped up the step at the entrance to the hallway, did a teetering trot trying to get my balance and grabbed hold of the banister at the bottom of the stairs, the momentum of the trip meant that I spun right around the banister and fell on my back with my legs in the air and my knickers on show to everyone in the office including all partners!! What a first impression!

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Replying to Karen whitehead:
By Justin Bryant
25th Jun 2024 17:40
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Johny Fartpants Picture
By johnny fartpants
25th Jun 2024 18:28

I have a couple of experiences from my earlier days in practice. Now I work as a sole practitioner. Perhaps this is why:

The first involved a new client who had bought their paperwork in and I was going through it with him. For some reason, part of the papers related to an insurance claim for a road traffic accident in his business van which the client was clearly still shaken by.

I tried to make light of the situation by remarking (on the other driver's details within the paperwork) "I'm not surprised he ran into you van, just look at his handwriting. What does he write with, a (add expletive here) hammer?"

There was a long silence before the client revealed that the other driver fainted at the wheel so wasn't able to write their details down at the scene of the accident and that it was in fact the client's own handwriting I had been commenting about!

I don't know what was worse. The long and protected silence that followed, the fact that the ground refused to swallow me up or the fact that I worked in an open plan office and had said this in full view of several of my colleagues.

Needless to say, I didn't get to deal with that client again.

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Johny Fartpants Picture
By johnny fartpants
25th Jun 2024 18:40

The second situation actually concerned a colleague rather than a client. This made is worse as it was much harder to avoid future contact with the guy concerned.

My employers were based at several sites all locally based and, to enable the smooth passing of information, they employed their own postman to deliver internal documents between sites.

One day, along with the usual paperwork, he also bought a picture of one of the receptionist's wedding day. The picture was from the 1970's, this was in the early noughties and fashion had obviously changed.

My colleagues were commenting on the receptionist's seventies clothes when I decided to but in, "Never mind her, look at the bloke in the top left corner". I then proceeded to mock his kipper tie, his flared trousers, the massive collars on his shirt before critiquing (quite unfavourably) his 70's hair cut.

Usually this kind of banter was well received but on this occasion it was met with complete silence. Needless to say, the 30 years had changed the appearance of the postman to such an extent I hadn't recognised him at all.


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By [email protected]
25th Jun 2024 21:47

In an effort to attract new clients, we used to invite local businessmen to a gut-busting breakfast at our expense at a nice restaurant at which I would give a quick talk on some wonderful tax planning opportunity. All our partners would attend to chat up the prospects and then back at the office I would email each partner with details of those deemed worthy of follow-up. I sent contact details of one businessman who'd seemed particularly interested, but the partner replied "No, I spoke to this guy - he's the monkey, not the organ grinder." The potential client responded instantly saying that actually, he owned the company, but wouldn't be doing business with us after all. The partner had sent his intended reply to the prospect instead of to me!

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By [email protected]
25th Jun 2024 21:57

I started out serving a few years in the old Inland Revenue, and once took a call from a taxpayer who had a query about purchase tax. I said that unfortunately we couldn't help him, he'd need to call HM Customs and Excise; at HMIT, we were responsible only for Income Tax, Corporation Tax and Capital Gains Tax. Quick as a flash, he came back with "I think you're responsible for a lot of heart attacks as well."

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By [email protected]
25th Jun 2024 22:07

In my days with Inland Revenue, I took a call from a lady who began "I'm phoning to let you know that I've just realised I made a mistake on my Tax Return." But I thought I recognised the voice. It was a wind-up call from a colleague in another part of the office. So I played along and replied "This is very serious, you'll go to jail without a doubt." But as the call progressed, I felt growing unease as it became apparent that the call was genuine. I got the file out, checked and confirmed that we'd already spotted the minor error and there would be no consequences. And I apologised for my flippant response to her opening gambit. She sounded relieved and was very forgiving.

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By Joe Alderson
27th Jun 2024 11:01

It predates my working in the accounting industry, I was working with mobile phones at the time and speaking to a potential customer. She was interested in a new phone but didn't know who she was with or what deal she was on. After getting more information from her, I asked "is it Virgin?" following which, there was a brief pause and she asked me "why do you want to know if I'm a virgin?". Fortunately, I was able to explain what I meant.

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By mcgregorian
27th Jun 2024 11:35

About 45 years ago (ouch) when I worked for one of the "Big 8" (I said it was a long time ago!) a student (not me - honestly) was doing a debtors' circularisation.

What could go wrong? A hundred letters into a hundred envelopes with a hundred reply paid envelopes.

If he had put the reply paid envelopes inside....

But he put the letter and the franked envelopes inside the rpes.

With the Post Office usual aplomb 80 envelopes were delivered to the office the next days with others following over a further few days.

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Replying to mcgregorian:
Mike Cooper HJS
By mike_uk_1983
28th Jun 2024 09:26

I remember something similar with sending letters out to clients and one of the junior staff used the registered office to send the letters out to but we were the registered office for a lot of the clients so the letters ended up coming back to us over the next few days!!

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Replying to mike_uk_1983:
By LJohnstone
28th Jun 2024 13:28

mike_uk_1983 wrote:

I remember something similar with sending letters out to clients and one of the junior staff used the registered office to send the letters out to but we were the registered office for a lot of the clients so the letters ended up coming back to us over the next few days!!

We've all done this, haven't we?


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