Chapter Three

Understanding personality types at work

Improve your performance at work by understanding the personality types around you and how you can collaborate effectively with those you work with.

The workplace is full of individuals with different characteristics and personalities. Working alongside many other traits, cultures, and emotions can be tricky. Working collectively and collaboratively with our colleagues is essential for Assistants to succeed in the role.

It is even more essential for Assistants to understand the different personality types of those around them and how they can manage their needs and expectations and communicate effectively.

In this chapter, we will look at different personality types that Assistants often have to work with and how to build a relationship and partnership that works.

We will cover the following:

Working for a workaholic

To become a successful board-level director, you would expect that individual to be somewhat of a workaholic, if not extremely passionate about their job.

All of the Executives I have worked for have been passionate about their career and the organisation they work in; some have been what I would describe as workaholics. You know the type; they are always switched on, they are always available, and they are still on their iPhones.

Not to even begin mentioning the hours they work.

Working for a workaholic boss can be tricky for most people, but for Assistants, it can be challenging.

Are we supposed to match the hours that they do? Are we supposed to be in the office when they are in the office, and are we supposed to get through the work they do?

On top of that, how do you start supporting someone who considers their job the most important thing?

Here are some tips for those of you that are working for a workaholic.

Ask what is expected of you

With every new manager I have worked with, I have asked what they expect of me as their Assistant in the initial interviews. Once I was given the job, I asked the question again during the first meeting together. You must understand what your manager needs in an assistant and when they will require you to be around. I always ask what hours they work and when they arrive at the office and leave to know if I have to adjust my preferred hours.

Asking these types of questions in the early days of your relationship will set you in good stead. If you didn’t ask your boss this question when you started working for them, it’s not too late, particularly if you struggle to keep up with their demands. During your following review, ask that you discuss how you work together. They may not realise that you prefer to get into the office after the sun has risen or left before the world sleeps!

Set some boundaries

It is essential to set some boundaries with your boss and yourself. Getting sucked into a workaholic schedule can be easy, so you have to be quite disciplined. Discuss the hours you want to work, there will be times when you work long hours, but this shouldn’t be the norm.

Ideally, you want to get all your work done that day, go home at a reasonable time and not have to check your emails until you go to bed! If you are struggling with your workload and the demands of your manager, you will need to set some boundaries, and you will have to communicate your new position.

What is realistic for you?

The problem with workaholics, mainly when they are your boss, is that they may not realise they are workaholics. Secondly, not everyone else wants to work as hard as they do if they compare themselves to other executives in the organisation, fair enough.

But if they are comparing themselves to their staff, that is certainly not fair. To work successfully with a workaholic, you have to be strong and understand what is realistic for you. If you have other commitments outside of work, you shouldn’t feel wrong about that.

I’ve always said it is essential to match your work style with your boss, but at the same time, you must think about your preferred work style and how it might complement your manager’s. For instance, if you are racing through work to keep up with their demands but prefer a more systematic approach, you might end up making mistakes which they will undoubtedly pick you upon.

When working for a workaholic, you must think long and hard about your circumstances and what is realistic.

Try to get as much work done during your working hours

A compromise I have found to work well when working with a workaholic is this – you work hard when you are in the office.

Ensure your manager understands that you are doing everything you can to support them within your set boundaries. If you must work through your lunch but leave at a reasonable time, this is a compromise worth taking. If you try this approach, time management will be crucial, and you will also have to be pretty strict with those colleagues that interrupt you and take up an unnecessary amount of your precious time.

What are the positives?

Okay, I know I’ve just spent quite a bit writing about the negatives, but there are many positives when working with a workaholic.

They tend to be driven, successful and passionate.

Qualities that can be infectious. I always worked harder when I had a workaholic boss, but I was rewarded more frequently, and my efforts didn’t go unnoticed. I’ve worked for sluggish managers, which was much worse.

What can you do to free up their time?

Last but no means least, what can you, as their Assistant, do to free up their time so that they can go home early for a change?

Take a look at the tasks that take up a lot of their time and think of ways that you can help reduce their workload. For example, do they spend most of their day in meetings? Can their diary be structured, so they have a few hours to spend at their desk?

Are colleagues meeting with your boss when an email will do? Do they spend a lot of time doing their admin – that is something you will have to wrestle out of their hands immediately! Tell them you want to free up their time and work on solutions together. As much as a workaholic loves their job, they will appreciate getting away from the office early – at least occasionally!

Questions to Ask a New Executive

Use this guide to work in sync with your Executive from day one.

Checklist for Meeting Planning

Checklist for Meeting Planning

This checklist will help streamline planning for every meeting.

Does your Executive make decisions?

I’ve worked with several Executives over the years and seen many different management styles. Some Executives have been incredibly inspirational, others have been controlling and micromanaging your every move, and then there are those types of managers I want to discuss today. This manager never makes a decision.

The non-manager, so to speak!

These types of Executives will leave a decision unmade until someone else makes it for them, or the problem goes away. In this circumstance, everyone muddles along without clear objectives or knowing what is happening.

For Assistants in this situation, it can be pretty tough.

Often colleagues will ask you to make decisions on behalf of the boss, which is incredibly stressful. Colleagues might think you are not relaying information or questions back to your Executive when you have asked them on more than one occasion but have yet received a clear answer. You will often cover up for your boss when they cannot make any decisions.

The Executive may be technically brilliant at their job but unable to manage staff, so their assistants will also find themselves picking up the people management slack. This is great to start, but after several years working as an assistant with all this management experience, the thought of being promoted into a substantial management role is impossible, particularly with a manager who has no clue that their assistant is doing all the additional work.

In this situation, I have always found it hard to change a non-manager. I’ve had honest conversations about our working relationship. Still, their behaviour is so ingrained that most of the time, they don’t even realise their lack of leadership is causing any problems. If they know it, they tend to be good at their work, keeping them in a job and their boss happy, so why do they care what their staff think?

When I found myself in this situation (thankfully, it has only been once), I worked around my manager, accepted that he would never manage me exceptionally well and instead made the best of what I had. I didn’t stay in the role very long, but here are my tips if you work with a boss who never makes a decision.

  • Keep a list of everything you do, including your additional managerial tasks. I would also keep all of the emails or communications that contain details of the decisions that you have made. You have a list if your manager is interested in finding out what you do. Also, if your manager eventually gets found out, you will have documented evidence of your managerial experience. This can be used to prove you are ready for a promotion or a pay rise.
  • This type of boss will leave you to figure out your role and the type of work you want to do. Think about the positives – when you have eventually had enough and left this role, you will have additional expertise and skills. Proactively manage yourself by doing extra work that you find exciting and challenging. Ensure your colleagues know you are running the office and use that position to gain as much managerial experience as possible.
  • Although your boss is unaware of how much they rely on you, other team members will notice. Keep pleasing and supporting your colleagues – one may be promoted and want to take you with them. Alternatively, your current boss might be replaced by one of your colleagues. Either way, your good work will pay off.
  • In this situation, you have to be honest with your colleagues. Ensure they understand you are not the reason your boss is not getting back to them with decisions.
  • You also have to be assertive. Some staff members may exert authority if they realise their leader is not leading. These people will undoubtedly try to make support staff do work for them, which they should be doing themselves.
  • Should you keep your boss in the loop when it comes to decisions that you’ve made? I would say yes because you are covering yourself if a decision is ever questioned. I’ve found that managers that don’t care if they are bad at managing staff are good at blaming their team if anything goes wrong.
  • If the situation makes you frustrated and unhappy with your role, this is probably one to remove yourself from. You will have gained tremendous experience, so find a job that values those skills and rewards you for having them.

Working with an introvert

The key to a successful relationship between an assistant and their Executive is understanding how they operate. Let me rephrase that… the assistant should understand how the Executive works and adjust their style accordingly.

Most people fall into two personality camps- introverts and extroverts. Now obviously, people come in varying degrees of these types. Still, when building a successful relationship, it is worth noting what side of your Executive’s personality coin resides. I will look at the challenges facing assistants working with an extrovert, but today, let’s look at those reserved introverted types.

Communicating with an introvert

In my experience, introverts tend to listen more than they speak. It can be pretty tricky getting an introvert to say much at all. This can be frustrating for people used to talking, bouncing ideas off others and receiving direct instructions. It can also lead to people talking to introverts to cover up silences or awkward moments. Not suitable, especially for assistants. So how do you communicate? First, make sure you listen when they speak because they will have something important to say!

They probably aren’t happy having to repeat themselves, so make sure you remember any instructions they have given. If you have to clarify anything, ask specific questions (ideally with yes or no answers). Expect to use email as your primary source of communication.

Take the initiative

I find that introverted bosses let their staff take the initiative on projects and their workload. They don’t tend to micromanage, so assistants, in particular, can use this to their advantage and take on more work. Regarding feeding back, I suggest you use an online task list that you can share with your boss that way. You don’t have to let them know when you have actioned requests continually. They can see the evidence for themselves.

Prepare for meetings

Most introverts, I know, like to have space in their day to prepare for meetings. They want to go into an appointment with an idea of what they will say and how the discussion will pan out. An assistant can help with this process by ensuring they have all the necessary paperwork before the meeting and have time to prepare appropriately.


Introverts will not enjoy unnecessary interruptions and random conversations, so make sure you use all of your gatekeeping skills to keep your Executive away from scary Extroverts (incredibly pushy salespeople). Introverts like to regroup and spend time independently thinking through ideas and planning the next steps. Ensure you give them plenty of time in their diary for quiet reflection.

Create your sense of achievement

If things are going well, you probably will not hear much about it from your introverted Exec. This can be difficult for assistants who want to know if they are doing a good job (and really, who doesn’t!) Don’t take it personally. Just assume that silence is good and pat yourself on the back when you know you have achieved something.

Remember that working with an introvert brings rewards

Not all leaders need to be extroverts.

There is something pretty special about someone who can quietly encourage their workforce to shine. Introverts have unique qualities and can be fantastic bosses. I love this Ted Talk from Susan Cain called The Power of Introverts. If you work for an introvert, I highly recommend watching her talk.

Working with an old-school Executive

Many Assistants work for Executives who do not and will not embrace new ways of working, new (or even old) technology and expect their way of working to remain exactly how it has been for decades.

Some assistants may be used entirely to this style of working, but it can be frustrating if you want to introduce new ways of working and are shut down every time you mention it. If this is you, here are a few tips on working with an old school Executive.

Is your Executive living in their bubble?

Often, old school Executives are incredibly resistant to change, and we will come on to this. However, sometimes they live in a bubble where new working methods don’t cross their path. I had one Executive with many old-style Rolodex business card holders dotted around his office. He was delighted when I asked if he wanted me to put them onto his Outlook contacts.

He was over the moon when I told him I could put an app on his new iPhone that scanned the business card directly into his Outlook contacts. If you have an old-fashioned boss that needs a little encouragement, then take the time to suggest things to them.

Schedule time for tutorials and tell them about the benefits of new technology. You will probably have to manage the tech until they get the hang of it, so before you suggest something makes sure you are an expert so that they don’t get put off by any minor glitches.

Are they just resistant to change?

There is old school, and then there are those who resist change. Don’t get me wrong; people who resist change are incredibly challenging to deal with. Particularly if you are proactive and can see that a few tweaks here will make a big difference. There are plenty of articles out there that will help you manage people resistant to change.

It takes a lot of time to make changes, and sometimes you can feel like, ‘what is the point’ but trust me, it will be worth it in the end. Let’s look at the most common problem I hear from assistants – working with paper diaries. Just as a starting point – this would drive me nuts! The pain tends to be that your Executive has everything in their paper diary. You work from that and put all the appointments in Outlook or your online calendar.

If anything changes, outcomes the eraser for the paper diary, and then you have to make the same changes to the online schedule.

So how do you get your Executive to move to an online calendar only? Firstly, have you asked them to change to an Online calendar – do they know how much extra work you do to manage both aspects of the task? If you have not told them and clearly stated that you do not like working with two diaries, why would you expect them to change their routine?

If you have told them and still refuse to give it up, ask yourself – what are they afraid of? Is it the lack of control, the technology itself, or merely stubbornness? Once you have figured this out, you can slowly manage the changes that need to take place. A simple place to start is during your one-to-one meetings. Instead of working from the paper diary, ask them to open up the online calendar on their computer to see who is coming to the event and any additional details that might not be in the paper diary.

Keep doing this until they get used to looking at the computer. Change takes time, and you will have to be patient.

Old school in every way

So you’ve got an Executive who is resistant to change but is also old school.

They follow old-school management styles where what they say goes. They don’t collaborate on ideas. They expect you to drop everything when they ask, and even the mention of ‘working from home’ is looked upon with scorn and slight confusion.

Yup, I think most of us have probably encountered this type of Executive at some point in our careers. I know I certainly have. What to do?

Well, there are a few methods I’ve tried in the past… Briefly, here they are:

  • Is it me? I walked into a new job with many ideas and examples of changes I’d made in other organisations, only to realise that these ideas were unwelcome. I was, quite frankly, pissed off. But over time, I realised that my old-fashioned Executive was brilliant at his job and had excellent systems that worked well for the department despite being thoroughly old-fashioned. So in this instance, I had to adapt to his way of working rather than introduce changes that may have been better but weren’t all that necessary.
  • Not everyone is perfect. There are many reasons people are stuck doing what they have always done. Not everyone understands that ways of working have moved on. Can you be a bit more understanding of your Executive’s imperfections? If so, take the time to work out how they operate and how you can fit in.
  • Is it the culture? Is it just your Executive, or is the whole organisation like an old boys club? If it is only your Executive, speak to like-minded people in your office and ask how they deal with your Executive. Please don’t accept that your Executive has all the power because they don’t. You can manage and make proactive changes. You can also say no to requests and demand the same respect the rest of your colleagues get.
  • Bide your time. Old-fashioned managers won’t be around forever. They retire. If you are younger than them, you may consider waiting it out.
  • Quit. I did this, and I went on to work for some excellent, dynamic, forward-thinking Executives who helped support my personal development. Not an easy choice, but quite often the right one when working with bad managers.

Working with an incompetent Executive

Everyone moans about their boss. Fact!

Sometimes your Executive takes ages to get back to you on something. They are always in a meeting or out travelling. They never have enough time. They don’t manage your needs or expectations. They don’t make decisions or make the wrong decision and don’t lead effectively. These are all common gripes. But, for Assistants, we see the reasons behind these failings. They are mega busy, have so much responsibility, have enormous teams, and don’t have time for everyone.

They don’t delegate enough, or they delegate too much. They have problems at home, or they are also stretched. We see it all, and usually, we know there are reasons for these behaviours. We can offer support, so the team moans less about the boss and the work gets done. That is where we add value, right? But what happens when the support we offer isn’t enough? What happens when we are working with an incompetent Executive, and no matter the level of support, they suck at their job?


Easier said than done for some people. So, what can we do? How do we overcome the frustrations and support someone terrible at their job? Here are a few thoughts!

Please don’t make them into something worse than they are.

They are a person who is failing, don’t make them into a monster, because they probably are not. Remember that as an Assistant, you need to show empathy, even when their incompetence is soul-destroying!

Where is the incompetence?

Usually, people are promoted because they have the technical ability to get the job done or generate a lot of income for the business. Either way, very few people are promoted because of their people skills or leadership abilities. So, in your Executive’s case, where do the incompetencies lie? Is it that they can do the work but can’t manage the people?

Or do they spend too long managing the people that the business gets neglected? As their Assistant, you gain insights into the behaviours hidden from other staff members. Use that to your advantage. Work out the issues and then plan how you can help support those weaknesses.

How can you help?

The first thing to say is that your incompetent Executive will understand that they are not quite making the grade (even if they are outwardly the most egotistical person on the planet), which means they will have their barriers firmly in place. They will not ask for help, so you need to work out, on the sly, what it is that you can help with and then work out a plan to get them to trust you enough to accept your help.

To do this, you need to be the person that never moans about them. It would be best if you were on their team, on their side, and found a human angle you can work with.

They will never acknowledge their shortcomings if they are entirely unaware or in denial. You need to accept that and find a way to communicate with them. For example, if they are not giving you the access you need to do your job, you should say, “I need your help.

I want to be great in this role, and I know I can offer a lot of support, but I need you to help me with that [and list the specific things you want them to do – access to the calendar, make decisions on their behalf, attend meetings etc.]”.

Remember always to come prepared with solutions. They will have so many problems to fight, be the person that comes with answers.

Fill in the gaps.

Speak to your colleagues. What is your boss lacking? What are they not getting from your Executive? Where can you help? Do they need a sounding board, and your boss is too busy to listen? Do they need things signed off? Can you plan an effective way to get those decisions made quickly? Can you sign things off on your Executive’s behalf?

All of the above are examples of managing up, which you must do if your Executive is incompetent. Always think to yourself, what do you need to do for the good of the business?

Build your support network.

As an Assistant, you must have a support network in the office of different levels within the business. Doing this is even more critical if you work for an incompetent boss.

If you don’t have a network of people who all know that you are brilliant, everyone will think you are just as incompetent as your Executive, and the danger is that you get blamed for their incompetencies.

So, get out there, get known, and make sure everyone knows who you are rather than being perceived as only your Executive’s Assistant. Make sure you are known as someone who makes things happen despite your Executive. Get good at specific niche tasks that you could potentially move into if your Executive gets fired (which is likely if they are entirely rubbish).

Think strategically. Who do you want to impress the most? Probably your Executive’s boss, right? Well, yes, but shine in front of your Executive’s peers, make good connections with your HR representative, and ensure those key players know that you are not responsible for your Executive’s failings.

Look after your mental health.

There is no denying that working for an Executive who is floundering is a drain on everyone around them, but this is particularly true of Assistants. Concentrate on what you like about your role, the organisation or the other people around you. As soon as you start to feel resentful, angry and ultimately unmotivated, you will not be able to lead yourself and your colleagues out of this situation. And that is when it is probably time to move on.

How to work with a visionary manager

Someone starts every business with a vision. They are the driving force behind the company, and they want to change the world.

You might not work for the person who started the organisation. But, if you work for an Executive who is the creative thinker in your organisation, someone who innovates and drives change in the business – you are working for a visionary manager!

Working as an Assistant with a visionary manager has many advantages and disadvantages! We will look at how to work with a visionary manager, how you can support them, and what it means for your career. Firstly, let’s define a visionary manager.

What does it mean to be a visionary?

Author and speaker Josh Linkner defines a visionary as “willing to dream wildly and think ahead. When your organisation has a senior leader who focuses on what’s possible and breathes reinvention, you ­have a chance to reach those stellar, dreamed-about heights.”

It sounds incredible.

What an opportunity to work with someone who disrupts the status quo, innovates and drives the growth in the business! Visionary managers expect and often demand their team to create new ideas, think differently and embrace change. It is an exciting place to be, especially for Assistants. Working with a visionary brings so many opportunities because they will not work with their Assistant traditionally. They don’t work with anyone in a conventional way. The possibilities are endless.

But, with endless possibilities can come long hours, constant change, little structure and no strategy. Working in an environment with no clear path or plan of action can be stressful and frustrating. Many visionary leaders can make for bad managers because they are tasked with creating new ideas and thinking ahead rather than focusing on the here and now and dealing with the practical aspects of management. There are advantages and disadvantages when working with a visionary leader. Let’s look at how Assistants can work with and support a visionary.

Provide Structure.

This is the most critical skill you can bring to the table when working with a visionary. It would be best if you were an executor. The person that gets things done. You must provide the structure to get their ideas and concepts up and running. How do you do this?

Create a schedule that allows them time to brainstorm with their team. They will need time to spitball ideas, develop new strategies and bounce off other creative types. Structure these meetings to have a definite end time, and ensure you are strict with the time. Go to the sessions to take notes and track what has been discussed. If you can’t be there, find a facilitator in the organisation that can help structure the brainstorming sessions.

Giving them this time will also ensure they use the rest of their time to work more structured and strategically.

Understand the business.

You must know what is happening at all points of the day and in the organisation. This means you need to network as you have never networked before. You need to be involved in everything, you need to know what is going on, and everyone in the organisation needs to loop you in. You can only provide structure for your Executive if you are involved.

Remember, if you work for a visionary manager, you must inspire confidence because you will often be the lynchpin between your Executive and the rest of the team. You need to know your job inside out, and you will need everyone else to know that. Confidence does play a key role in how you work with a visionary.

Build Rapport.

Your Executive has to know that you have their back. You will be there for them and support them through every up and down they face. You have to build an unshakable rapport with them. Please get to know them, be in their life and understand how they think and function. Bethany Burns, EA to the CEO of BrewDog, calls this ‘comfortable intrusion’.

You have to get involved, and your Executive has to let you. It would be best if you also built rapport with everyone your Executive comes into contact with. Visionary leaders will have a strong team around them to execute the vision. Ensure you have a strong relationship with everyone in your Executive’s inner circle.

Constant Communication.

Your communication skills need to be on point for a few different reasons. Your visionary leader might struggle to communicate what they need from you and their team. You need to adapt to their way of communicating so that you are both on the same page and then you need to help disseminate information to the people around you. Again, having a good understanding of what is happening in the business will help with this. Communicating regularly with other assistants in your industry would be best.

This is a brilliant way to keep in the loop. Working with a visionary leader will mean that you will work at a fast pace. You don’t want to reinvent the wheel, so communicate with each other and share best practices. Back to communicating with your Executive – they will work at a fast pace, and they will have a lot of ideas that you need to capture.

This is where technology can help.

Find a tool that will help them offload their thoughts to you. This could be WhatsApp, Slack or even email. Use something that helps them get their ideas out of their heads and over to you for action.

Roll with the punches.

Steve Jobs springs to mind many famous cases of visionary leaders not treating their staff well. This isn’t the case for every innovative leader, but for many, the thoughts and feelings of their team are secondary to their vision. If you work for an Executive like this, it can be challenging, and you will need to develop a thick skin and learn to roll with the punches.

This isn’t for everyone; you need to decide your boundaries and how you want to be treated. Depending on the relationship you have with your Executive, you may also have to pull them up on behaviour that is not acceptable. This comes with confidence and practice. Speaking truth to power is not easy.

Just remember that your Executive will always win out at the end of the day. They often misbehave because they can. That is how business works. If they are innovating, making the business a lot of money, and genuinely leading change, their power and abilities will outweigh your feelings. Hopefully, times are changing, but it is slow progress. It would be best if you decided what works for you.

Share the vision.

This is my final point, and it is an important one.

You have to share the vision that your Executive is putting out in the world. If you don’t get on board, you will drown! You have to share their passion, enthusiasm and drive. You don’t have to work the same crazy hours or intensity, but you have to live and breathe the business.

Again, you have to ask yourself if this is truly what you want to do. If you succeed as an Assistant to a visionary leader, you must strap in and enjoy the ride!

As Assistants, it is important for us to form meaningful and successful relationships with our colleagues, no matter what their personality type may be.

By understanding these different personalities, we are better equipped to manage expectations as well as handle any issues that arise in the workplace. Staying collaborative and open-minded when dealing with co-workers’ different beliefs and values is essential. Working together successfully allows everyone to reach their peak potential.

If you want to cultivate more effective relationships in the workplace, consider enrolling in The Assistant Mindset Online Course. Here, you will learn more on how to work with different personality types and establish a healthy working environment that leads up successful collaborations built on trust, respect, and communication. You will be starting your first step towards being empowered as an Assistant!


Next Chapter:

Communicating your influence
Chapter Four