Common Challenges Faced by Assistants

Executive and Personal Assistants have one of the most complex roles in any organization, yet they often go unrecognized 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 making a mistake
  • Working in a hostile environment
  • Dealing with personal issues at work
  • How to keep a positive attitude at work

 

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 realize 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-served, 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 Executive (who was luckily out for lunch).

After a few tears and more swear words in the privacy of the ladies’ room, 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 that 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 organization 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 realized 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 organization avoiding that Executive. I also got a lovely reminder of my mistake at my leaving party – a rugby shirt!

While learning to bounce back from a mistake is an essential skill for any Assistant, especially in a high-stakes role, sometimes the work environment itself can complicate recovery. In supportive workplaces, mistakes can serve as learning opportunities, but in a hostile environment, even small errors can be amplified, leading to undue stress and heightened tension. When working in a challenging setting, it’s crucial to manage mistakes effectively while also being mindful of the broader workplace culture. Understanding how to navigate both personal setbacks and an unsupportive or even hostile environment can help Assistants maintain resilience, ensuring they remain productive and focused, regardless of external pressures.

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 behavior in the workplace, which causes one or more employees to feel uncomfortable, scared, or intimidated in their place of employment.”

This behavior 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 cannot 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 lousy 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 behavior. 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 behavior is not ignored. Here are a few steps to follow:

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

  2. 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).

  1. If the behavior 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.

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

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

  4. You can raise a formal grievance with your employer; this can be done with a solicitor’s advice, or you can raise the grievance 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.

For U.S.-based Assistants, it’s important to know that the equivalent concept to “constructive dismissal” is often referred to as “constructive discharge.” Under U.S. labor law, constructive discharge occurs when an employee resigns due to intolerable working conditions that a reasonable person would find unbearable, essentially forcing them out of their job. If you believe you’re in this situation, consider consulting with an employment lawyer to discuss your rights and options. Federal laws, such as those enforced by the Equal Employment Opportunity Commission (EEOC), protect employees from discrimination and harassment based on race, gender, age, religion, disability, and other protected characteristics. In many cases, legal actions can be taken if you can demonstrate that the workplace conditions were so hostile that a reasonable person would feel compelled to leave. Before making any decisions, document all incidents thoroughly, seek support, and explore options within your company for reporting and addressing the issue.

Standard Daily Checklist Template for Assistants

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Our daily checklist for Executive Assistants is designed to streamline your workflow and ensure nothing slips through the cracks.

Dealing with personal issues at work

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

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

So, dealing with personal issues at work is something we’ll all face at some point. Learning how to keep 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’ve used in my career to help stay focused at work and avoid burnout.

  1. Try to use work as a distraction from what is happening at home by really diving into your tasks. If you aren’t entirely focused on your work, now is a good time to do the jobs you’ve been putting off because they’re 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.

  2. If you’re 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. Focusing on other things can often put your personal worries into perspective.

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

  4. If you’ve been burning the candle at both ends, you need to realize that partying hard outside of work will impact your time in the office. If you’re struggling, remember you only have to get through eight hours. Drink lots of coffee, take regular breaks, go straight home after work, and get a good night’s sleep!

  5. Can you talk to your manager? If so, do it. I’ve had times when I’ve needed to speak to my boss and explain why I’m not performing my best. They noticed and appreciated my honesty. My manager even said I could leave early, get my issues sorted at home, and start fresh the next day. It helped a lot.

  6. Many companies I’ve worked for have offered support through a helpline that covers various issues, from financial problems to legal advice to counseling. 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.

  7. Plan something nice for the weekend ahead, even if it’s time spent relaxing at home. If home is the problem, try to go out or do something that makes you feel relaxed. Making the most out of your weekend will help you feel refreshed when you’re back in the office on Monday.

  8. If you need time off work to deal with your issues, take the time you need. Use a personal day, a vacation day, or call 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 attitude toward its staff than it does about you.

What to do when your day completely sucks

We’ve all been there—an unproductive day, conflict in the office, lost keys or wallet, train delays, or a crappy email from the boss.

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

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

Well, hold on. It’s not so easy to leave the office at 9:30 a.m. and head home. People will start talking. So what can you do?

I thought I’d share some tried-and-true 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 and, really, everyone who works.

  1. 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 it gives you a chance to control your emotions and pretend you’re fine for the rest of the day.

  2. Put on some music
    This works wonders for me. If I lack energy but need to get through some stuff at my desk, rather than curling up into a ball, I put on my favorite music and try to boost my energy. Generally, disco does it for me (if you don’t start feeling better after “Pull Up To The Bumper” by Grace Jones, I can’t help you!).

  3. Hold fast until lunchtime, and then get out of the office
    If you can make it through the morning, you’ve done well. Now, take a break and go for a walk, meet some friends, buy something fun, or do whatever you need to get some positive energy flowing so you can come back in the afternoon and tackle the rest of the day.

  4. Buy some chocolate (and eat it)
    There’s nothing wrong with giving yourself a treat when the day sucks and you need a quick pick-me-up. A whole bag of candy, you say?! I hear you!

  5. Rage clean
    Okay, I can’t be the only one who does this. When I’m furious, I channel all my energy into what can only be described as an all-out assault on dust, mess, and clutter. If you’re angry, now might be a good time to sort through those neglected office drawers. Get those piles of shoes stashed under your desk bagged up and shipped out. If anyone asks, you’re having a good sort-through and re-organizing your workspace…while channeling that rage!

  6. Call your person
    For me, that’s my mom. That’s what they’re there for, right? You can’t complain to your colleagues; it’s not very professional. Your friends might not understand, and if you vent to your partner, you might have to listen when they want to get something work-related off their chest. Your mom has to listen. That’s her job! Thanks, Mom! Whoever your go-to person is, give them a call and vent a bit.

  7. Be super friendly to everyone
    It’s amazing 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.

  8. Remember, nothing is permanent
    If work or anything else is making you miserable, remember it’s just a blip in what will otherwise be an extraordinary life. Some of those tough days pass by, and you forget about them. Or, you might even laugh about them in a few years!

How to keep a positive attitude at work

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

Nope!

Some days, you’ll be completely pissed off and just want to hide under your desk until 5 pm when you can finally leave! Hopefully, those days are few and far between, but no matter what your outlook on life is, it can be hard to always keep a positive attitude at work.

We all know what it’s like to be around someone with a negative outlook on life. It can be soul-crushing! Working with someone who generally has a positive outlook on life (even when things aren’t going well) is definitely better.

If you can keep a positive attitude at work, it could be the key to your success. Here’s why: when you’re positive and open to new possibilities, you’re more likely to say yes to new ways of working, and you tend to be more creative, coming up with solutions to problems (rather than just complaining about them). So how do you keep a positive attitude at work?

Here are my top 10 tips:

  1. Don’t criticize others unless it’s constructive.
    Do you need to share how you feel about someone? Do they need to know? Do other people need to know? Probably not! If someone rubs you the wrong way, it’s usually better to ignore them and let it go rather than criticize or complain about them to others. Trust me, the sooner you brush it off, the better for you. Other people’s bad behavior and outlook on life are their problem, not yours!

  2. Always come up with a potential solution when discussing a problem.
    There will always be issues and problems that pop up at work. Yes, they’re annoying, and yes, you could complain about them, but wouldn’t it be better to just fix them? Positive people find solutions to problems, which is a great trait for an Assistant.

  3. Surround yourself with other positive people.
    Find others in the office who have a great outlook on life. These are your people!

  4. Don’t gossip…ever.
    Gossip is the worst and benefits no one, especially in the office. Try not to get involved, as tempting as it might be. Remember your sense of humor—it will get you through the worst times.

  5. Take a break when you’re having a terrible day.
    Go for a walk, or read a book at your local café. Getting out of the office for an hour can give you perspective on what’s happening and a chance to refocus on what you need to do to work things out!

  6. Set some goals and strategies for your career.
    Working toward something bigger than the day-to-day grind gives you something to focus on. Seeing a project through and working toward something challenging is exciting, and when you complete it, it will give you a real boost. Goals help when daily tasks get you down.

  7. Reward yourself for your positive outlook, especially when you’ve had a tough day.
    Open that bottle of wine, buy that nice bag, watch that Netflix series, or spend time with people who make you feel good.

  8. 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. Instead, decide how you want to deal with these people so they don’t upset you. Nobody at work should have so much power over you that they make you upset every time you interact.

    So, instead of dreading seeing them, expect them to be difficult or cause problems, and know that you can handle it. It’s amazing how your attitude changes toward someone when you expect them to be difficult. You might even end up laughing about it.

  9. Be kind to people.
    It can be hard when you’re busy, or your colleagues ask you never-ending 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 comes with unique struggles. Knowing how to approach these obstacles with good problem-solving and organization skills is key for Assistants who want to maintain efficiency and productivity long-term.

Here, we’ve outlined some daunting yet common challenges that Assistants face, so you can tackle them head-on if they ever arise. It’s important to recognize that while difficult moments may come, there are resources available to help resolve problems quickly. If you’re feeling overwhelmed and unsure where to start, why not try our Assistant Mindset Online Course? With practical tips and advice from industry experts, you’ll be better equipped to confidently navigate the Assistant role!

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Picture of Nicky Christmas

Nicky Christmas

I'm Nicky, the Founder and CEO of The EA Campus. Let’s continue the conversation over in our communities.

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