Common challenges faced by Assistants

Executive and Personal Assistants have one of the most complex roles in any organisation, yet often go unrecognised for their hard work. While there are many positive aspects to being an Assistant, they inevitably face a variety of challenges on a daily basis that can affect efficiency and productivity.

In this article, we’ll explore some everyday struggles encountered by Assistants – from expectations management to paperwork overloads – and provide tips for managing them more effectively so you can get your day back on track! Here are common challenges faced by Assistants. We will cover the following:

Bouncing back from a mistake

Anyone who has worked in a high-pressure job will have made a mistake at some point in their career.

For those of us who have to multitask, juggle many different jobs, and work for several Executives and colleagues, the likelihood of making a mistake increases significantly. This is one of many common challenges faced by Assistants.

Now, I would love to say that I have never made any errors at work but, dear reader, I would be lying my backside off. I have made many mistakes throughout my career, some have not mattered, and nobody noticed, but some have significantly mattered, and everyone in the office knew about it.

Nothing is worse than getting that sinking feeling when you realise you have made a mistake. This is one of many common challenges faced by Assistants.

It is isolating and doesn’t disappear even when the panic kicks in. My worst mistake at work involved tickets to a sold-out international rugby game.

My company had several tickets for the England games, and I allocated the tickets to our Executive team to take clients for corporate hospitality. The tickets were first-come, first-serve, so I sent the initial email to the team asking them to get back to me if they wanted tickets. As you can imagine, the demand was high, and the tickets were immediately snapped up.

Like any diligent assistant, I put all the information regarding the tickets and who they would be on a spreadsheet. I received all the tickets a few weeks before the game and asked the executives to collect them. A few days before the match, all of the tickets had been collected, and I had used my spreadsheet to note down who had received the tickets. A very senior Executive came to my desk to collect his tickets a day before one of the England games. My heart started pounding as soon as the words came out of his mouth.

I didn’t have any tickets left, they had all been allocated, and his name wasn’t on my spreadsheet. The thought went through my head that he might be chancing his luck. But no, he had an email to prove that I had allocated tickets to him and another Executive. S***!

The panic had certainly set in, and I couldn’t make an excuse, so I told the Executive what had happened. He went berserk. He was taking significant clients and had already told them he had the tickets. It was a nightmare. The Executive had a fierce reputation and certainly not someone you would want to get on the wrong side of. He stormed off in search of my boss (who was luckily out for lunch).

After a few tears and more swear words in the privacy of the lady’s toilets, I racked my brains for a solution. Here is what I did.

Fess up and own your mistake

I ensured I was the first to see my boss as soon as he returned from lunch. He was a reasonably approachable guy, and I had a good relationship with him, which in this case, helped enormously.

After I tearfully confessed to everything, his reaction was a relief – he burst out laughing. He said he was sure I would fix the situation, and as I rarely made mistakes, he was happy to throw some money at the problem. I just had to ensure I satisfied both Executives and they got their tickets.

Fix the mistake

The problem was that tickets for this bloody rugby game were like gold dust. Getting the Executive into Willy Wonka’s chocolate factory would have been easier. It didn’t help that I didn’t know the first thing about rugby or how to secure tickets. I phoned a friend who was a big rugby fan. For the second time that day, I heard someone burst out laughing. I tried the official ticket line.

They had sold out months ago. I tried a few other official channels and asked every assistant I knew if they had spare tickets before I resorted to resale tickets. There were plenty of tickets still available, but of course, the price per ticket was ridiculous. It was the only way I would solve the problem, so, as my boss said, I threw some money at it and managed to secure four tickets. Problem solved but at quite a cost to my organisation and my confidence.

Regaining your mojo

For me, it helped that my boss was understanding.

I’m unsure how I would have reacted if he had also shouted at me. I probably would have burst into tears which wouldn’t have helped the situation or my reputation, come to think of it! Although I managed to get the tickets, everyone was happy (of course, the extortionate tickets were better than the original ones!) I was very much aware that I had made a colossal mistake.

I retraced my steps and realised I hadn’t remembered to add the Executive’s name to the spreadsheet once I had confirmed the tickets with him, which meant that when the other Executive requested the tickets, I thought they were still available. A simple mistake to make but not something I would usually do. I couldn’t even blame anyone else, this was my mistake, and I had no excuses.

So how did I get my confidence back?

First, this happened on a Friday, so I went out with some supportive friends and got very drunk that night. Over the weekend, I put my mistake into a little more perspective and decided to put it behind me and make a fresh start on Monday. I decided to work extra hard that week and prove I was a great assistant. At the end of the week, my boss joked that I should make mistakes more often. I was like a machine – everything I had been putting off was sorted. My Executives didn’t know what hit them! I also made a few changes to my work procedures. I relied too heavily on spreadsheets, so instead, I converted all relevant emails into reminders and tasks to check I had actioned them at the end of each day.

By the following Friday, I had almost forgotten the entire incident. However, I spent most of my time at the organisation avoiding that Executive. I also got a lovely reminder of my mistake at my leaving party – a rugby shirt!

Are you working in a hostile environment?

Everyone has the right to work in an environment based on respect that supports their wellbeing-. This is the necessary level of care employers offer, but unfortunately, many working environments do not offer this to their employees.

Working in what has been coined ‘hostile working environments’ can be an awful experience affecting your mental health. Firstly, I want to look at what a hostile environment is and, secondly, what you can do if you work in a hostile environment.

What is a hostile working environment?

This term is more widely used in the United States, but it defines our topic. The legal definition of a hostile working environment is “unwelcome or offensive behaviour in the workplace, which causes one or more employees to feel uncomfortable, scared, or intimidated in their place of employment”.

This behaviour can manifest itself in many different ways, including unwanted comments on, for example, your gender, race, nationality, age, sexual orientation, religion or disability (there are protected characteristics that can not be discriminated against).

These personal characteristics are protected by law, so the conduct of a ‘hostile working environment’ has legal connotations and can be prosecuted.

A hostile working environment is not a shitty boss or an annoying co-worker; it’s not a rubbish office or basic wages and zero benefits. Not that these examples don’t have an impact on your mental health. A hostile working environment consists of discriminatory conduct that can be reported as such.

What can you do if you are working in a hostile environment?

The first thing to say is that you do not have to put up with this behaviour. Wherever you are based, discriminatory and unwanted harassment is unacceptable, and you should be able to report the action to your Manager or HR representative.

I can’t speak for every country, but you can also take a legal approach, contact a solicitor in the UK, and even talk to ACAS for guidance and support.

If you don’t want to go straight down a legal route, you should do a few things to ensure that you protect yourself and that the behaviour is not ignored. Here are a few steps to follow:

Ask the employee to stop the behaviour directly or through your Manager or HR representative.

Document everything that happens.

Keep details on what happened, the comments or actions taken, the date and time, who was there, and where it happened. Keep copies of any supporting evidence – emails and messages (on all communication platforms).

If the behaviour continues, report it again to your manager or your HR representative. Meeting with you, the other employee, and your HR department might be worth mediating the conversation. If this meeting takes place, it should be recorded and documented.

You might also consider bringing another staff member to the meeting for support.

You can contact your trade union for advice. They might take up the case on your behalf – if there is a legal claim.

You can raise a formal grievance with your employer; this can be done with a solicitor’s advice, or you can raise the injury on your own. Either way, this is a formal complaint that your employer will have to take seriously.

If the environment is unbearable, you can, of course, consider resigning. Even if you work and live in a highly competitive market, there are always other opportunities for you. It is also worth noting that you can still seek legal advice after leaving the employer and making a complaint.

In the UK, this is called ‘constructive dismissal’. Whatever you decide, please take care of yourself and your wellbeing-. Nobody deserves to be mistreated at work, and you should seek advice immediately if you find yourself in a hostile environment. In the UK, there is a lot of advice on this issue on the Citizens Advice website.

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Dealing with personal issues at work

You might be the most professional Assistant in the biz, someone who works hard to keep their personal life as far away from their professional life as possible. Still, throughout your career (of all our careers), inevitably, something will happen to make the two collide.

That is how life works – we never know what it will throw at us.

So dealing with personal issues at work is something that we will all have to face at some point. Learning how to keep the problems from negatively impacting work will help in the long run. This is one of many common challenges faced by Assistants.

Here are eight tips I have used in my career to helping you stay focused at work and avoid burnout.

Try to use work as a distraction from what is happening at home by really getting stuck in your tasks. If you are not entirely focused on your work, now is an excellent time to do the jobs you have been putting off because they are dull. Do you have any filing or a load of photocopying to do? Use this time to get those basic tasks out of the way.

If you are not very busy at work, this is the time to get busy. Ask to sit in on meetings or do errands for other staff members, anything to keep your mind off your problems at home. Concentrating on other things can often cure the little worries you have in your personal life and put things into perspective.

Do talk to your trusted colleagues at work but try to keep this restricted to lunchtime or over a coffee away from the office. It is good to talk through your problems, and they may be able to help you with your work but don’t make this a regular occurrence as you don’t want to be too reliant on your colleagues.

If you’ve been burning the candle at both ends, you must realise that partying hard outside work will impact your time in the office. If you are suffering, remember you only have to get through 8 hours. Drink lots of coffee, take regular breaks, go straight home after work and have an early night!

Can you talk to your manager? If so, do. I’ve had times when I’ve needed to speak to my boss and explain why I’m not performing to my best. They had noticed and appreciated my honesty. My manager said I could leave early, get my issues sorted at home, and start again tomorrow. It helped greatly.

Many companies I’ve worked for have offered support through a helpline which covers quite a few issues, from money problems to legal advice to counselling. I’ve used the hotline a few times, and it does help. Even if the information is generic, it can point you in the right direction.

Plan something nice for the weekend ahead, even if it is time spent in your home relaxing. If the home is the problem, try to go out or do something that makes you feel relaxed. Trying to get the most out of your weekend will mean you can feel refreshed once you are back in the office on Monday.

If you need time off work to get your issues resolved, do take the time off you need. Take a personal day, a holiday or phone in sick. Your manager should understand if you need time away from the office urgently. If they don’t, that says much more about the company’s ethos towards its staff than you!

What to do when your day completely sucks

We’ve all been there. Unproductive day, with a conflict in the office, lost keys and wallet, train delays crappy email from the boss.

Whatever the problem, we’ve all had those days that completely suck. When nothing gets done, the hole you find yourself in gets bigger and bigger.

Time to pack up, call it quits and head back to bed?

Well, hold your horses. It’s not so easy to leave the office at 9.30 am and head home. People will start talking. So what can you do?

I thought I would share some tried and tested methods to get you back on track. Here are my tips on what to do when your day completely sucks! This is one of many common challenges that Assistants face for everyone who works!

Take a moment

Okay, this is my first piece of advice. Go to the bathroom, make a cup of tea, and take a moment to breathe. Sometimes just having a little time to yourself helps put things into perspective. Or at least give yourself a chance to take control of your emotions and pretend you are fine for the rest of the day.

Stick on some music

This does work wonders for me. If I lack energy but need to get through some stuff at my desk, rather than curl up into a ball, I put on my favourite music and try to get some energy, generally through the power of disco (if you don’t start feeling better after Pull Up To The Bumper by Grace Jones, I can’t help you!)

Hold fast until lunchtime, and then get the hell out of the office

If you can get through the morning, you’ve done well. Now, take your butt out of the office and go for a walk, meet some friends, buy some stuff from the shops, or do whatever you have to do to get some positive energy flowing so that you can come back in the afternoon and smash it.

Buy some, and then eat some chocolate

There is nothing wrong with giving yourself a treat when the day sucks and you need a quick pick me up. A whole bag of Haribo, you say?! I hear you, sister!

Rage clean

Okay, I’m sure I am not the only one that does this. But, when I am furious, I seem to channel all of my energy into what can only be described as an all-out assault on dust, mess and clutter. If you feel angry, now might be a good time to sort through your neglected office drawers! You know those piles of shoes you’ve got stashed under your desk? Get those bagged up and shipped out. If anyone asks, you are having a good sort-through and re-organising your workspace… while channelling that rage!

Call your person

In my case, that is my mum. That’s what they are there for, right? You can’t moan to your colleagues. It’s not very professional. You can’t cry to your friends, they don’t care, and if you moan to your other half, you might have to listen when they want to get something work-related off their chest. Your mum has to listen. That’s her job! *Thanks, mum* Whoever happens to be your person, give them a call and have a good moan.

Be super friendly to everyone.

It is incredible how much energy you can get from other people. So actually, when you feel like crap, try being super friendly to everyone. Seeing them smile and be happy can lift your mood.

Remember, nothing is permanent

If work or anything makes you miserable, remember it is only a blip on what will otherwise be your extraordinary life. Some of the sucky days pass by, and you forget about them. Or you might even laugh about them in a few years!

I stumbled across a profile on LinkedIn the other day of a guy who made my job difficult for a while. At the time I couldn’t stand him but, now, guess what..? Nothing! And that made me super happy!

So, these are just a few thoughts on what to do when your day completely sucks. Let me know what you do when it all gets too much.

How to keep a positive attitude at work

Let’s face it, being an Assistant can be pretty challenging and not every day are you going to be walking around your office with your glass half full, beaming from ear to ear.


Some days you will be massively p*ssed off and want to hide under your desk until you can leave at 5 pm! Hopefully, those days are few and far between, but whatever your outlook on life can be hard, always keep a positive attitude at work.

But we all know what it is like around someone with a negative outlook on life. It can be soul-destroying! Working with someone who, on the whole, has a positive outlook on life (even when things are going badly) has got to be better.

If you can keep a positive attitude at work, this could be the key to your success and here is why. When you are positive and open to new possibilities, you are more likely to say yes to new ways of working, and you tend to be more creative and come up with solutions to problems (rather than complain about them). So how do you keep a positive attitude at work?

Here are my 10 top tips:

Don’t criticise others unless it is constructive.

Do you need to pass on how you feel about someone? Do they need to know? Do other people need to know? Probably not! If someone rubs you up the wrong way, it is generally better to ignore them and let them go than criticise or moan about them to others. Trust me, the sooner you brush it off, the better for you. Other people’s bad behaviour and outlook on life is their problem, not yours!

Always come up with a potential solution when discussing a problem.

There will always be issues and problems that crop up at work. Yes, they are annoying, and yes, you could complain about them, but wouldn’t it be better if you fixed them? Positive people find solutions to problems, which is an excellent trait for an Assistant.

Surround yourself with other positive people.

Find other people in the office that have a great outlook on life. These are your tribe!

Don’t gossip… ever

Gossip is the worst and benefits no one, particularly in the office. Try not to get involved, as hard as it might seem.
Remember your sense of humour; this will see you through the worst times.

Take a break when you are having an awful day

Go for a walk, or read a book in your local cafe. Getting out of the office for an hour will give you some perspective on what is happening and a break to refocus on what you need to do to sort all that crap out!

Set some goals and strategies for your career

Working towards something more significant than the day-to-day grind will give you something to focus on. Seeing something through and working towards something challenging is exciting, and when you complete it, it will provide you with a real boost. So, goals help when the daily tasks get you down.

Reward yourself for your positive outlook, particularly when you’ve had a horrible day

Open that bottle of wine, buy that nice bag, watch that Netflix series, and spend time with the people that make you feel good.

There will always be things, situations or people that upset you

Life would be great if everyone were kind to each other, but that’s just not going to happen. So, instead, decide how you want to deal with these people, so they don’t upset you. Nobody at work should have that much power over you to the point they upset you every time you interact.

So instead of dreading seeing them, except that they will be horrible or cause you problems, know that you can deal with them. It is amazing how your attitude changes towards someone when you expect them to be terrible. You might even end up laughing about it.

Be kind to people

It can be hard when you are busy or your colleagues ask you neverending questions that have nothing to do with your work and eat into your time. I get it! But being kind to people and showing empathy and understanding (while sticking to your boundaries) makes you feel better.

A positive attitude at work can be the key to your success. People want to be around positive people with a can-do attitude.

Be one of those people.

The Executive and Personal Assistant role is multifaceted and essential, yet it can come with its unique set of struggles. Knowing how to approach these obstacles with good problem-solving and organisation skills is key for Assistants looking to maintain their efficiency and productivity in the long term.

Here we have outlined some daunting yet standard everyday challenges faced by Assistants so that you can tackle them head-on should they ever present themselves to you in the workplace. It’s important to recognise that while difficult moments arise, resources are available to help resolve any problems you may encounter quickly. If you’re feeling overwhelmed and unsure where to start, why not try our Assistant Mindset Online Course? With lectures full of practical tips and advice from industry experts, you’ll be better equipped to navigate the Assistant role confidently!