New Assistants / Guide for Assistants who are new to the role / Working with multiple Executives

Chapter Five

Working with multiple Executives

Many new Assistants are asked to work with multiple Executives. In this chapter, you will find strategies to help manage their expectations, plan your work and deal with conflicting priorities.

Many Assistants are now being asked to work for more than one Director and quite often will complete tasks for whole departments of people.

Those one-on-one roles are becoming much more elusive and tend to be for high net-worth individuals, leading CEOs and private households. Most of us in the corporate world will be asked to support other people in the company, even if they arrange travel or do expenses.

How to juggle multiple Executive’s without dropping the ball

Over the years, I’ve had some roles that have required me to work for more than one boss. I’ve been Executive Assistant to the CFO, COO and Company Secretary. I’ve been PA to a Director and Administrative Manager for a whole department. I’ve even been Account Manager for 12 Committees.

These jobs were complex because I juggled multiple tasks, dealt with various personalities (sometimes within the same person), and worked too many different deadlines.

On top of that, I had to make my many bosses feel like they were the most critical part of my role, and I would always prioritise their needs first.

I believe this is and will become the norm for assistants, so we must adapt and learn how to juggle all of our boss’s demands without dropping any of the essential balls we have flung up in the air while also, you know, remaining sane!

So how do we do this? Well, here are a few tips that I have used in my multiple EA roles:

Communication is key

All of your Directors and colleagues know that you work for various people. Be clear that you can’t do everything for everyone all the time and that you must prioritise your work in the best way you see fit. Unfortunately, if you work for one Director that is senior to the rest, their needs will probably come first. If you clarify this from the outset, most of your colleagues will understand (especially if they report to that Director!)

You will also need to communicate regularly with each boss. The communication should be two-way.

They should tell you what they require of you, what they have coming up and any big projects that might take up a lot of your time. But, of course, you should also tell them the same things – what you have coming up, any work taking up a lot of your time and what you require of them!

Planning is key

Well, it is as important as communicating anyway! Assistants that support more than one boss have to be super organised. They have to be able to plan meticulously, and they can’t leave much to chance. Using task lists and keeping note of deadlines is crucial, as is your business knowledge. If you get to know the business, you will be much more aware of what to prioritise and what is essential.

You may also have to organise your bosses to plan what they need you to do. This can be tricky but worthwhile if you have multiple bosses and one of them is unorganised and asks you to do things without warning and with a short deadline.

Remember that all of you should share the same goals.

Suppose you have been asked to complete an urgent piece of work for someone and know it is critical and will benefit the company (for example, finishing a presentation for a client pitch). In that case, you can say this is a priority for the company, not just that one particular Director.

If another director asks you to complete an urgent workpiece, remind them that you all share the same goals, and client pitches come first! If you have two bosses demanding all of your time, it may be best to let them sort it out between them, they should have the same goals, but as we all know, this isn’t necessarily the case in business!

Offer solutions

If your multiple bosses are trying to get all your time, you must offer a solution to the problem because you are in the best position to tell them what your workload consists of and how much time you can dedicate to each one.

Offer a solution such as you work a certain number of hours for each one or devote all of your time on one particular day to Director X and another day to Director Y. If you have a consistently heavy workload, then you may have to push back on some of the work or at least ask for extensions on some of the not necessarily urgent deadlines. This can be hard, especially if you lack experience, but it is worth asking, and if they say no, then you know which bosses will work with you and be flexible and which ones you will have to work around.

It can be incredibly rewarding.

Believe it or not, working for multiple Directors can be satisfying, and you have to remind yourself of this so that you don’t get numerous bosses mad!

Your day can be very different. You can get involved in lots of various projects. As a result, you’re never bored. You avoid working for one Director that you dislike. You get to work with multiple personalities and learn to understand different working styles. You also get to know more people in your company, and I think you are respected for your ability to work for more than one boss.

So, on the whole, it can be great for you and your career! Honest!

20 ways to impress your Executive

20 Ways to Impress Your Executive

The worksheet gives you 20 ideas to elevate you in the Assistant role.

Meeting Agenda for Assistants and Executives

1:1 Meeting Template

The template you need to maximise the time spent with your Executive.

Ten tips for managing multiple Executives

Managing multiple Executives can be tricky and a constant juggling act. Here are my top ten tips:

  1. Communicate with your Executive every day. Remember, this is a two-way street! Your Executive should tell you what they require of you, what they have coming up and any big projects that might take up a lot of your time. You should also tell them the same things – what you have coming up, any work taking up a lot of your time and what you require of them!
  2. Prioritise on an hourly basis. You can only prioritise your work if you communicate regularly with your Executives. Once you know their needs, you can prioritise your day and workload accordingly. This will need to be reviewed throughout the day so that you can manage any emergencies or urgent requests.
  3. Plan meticulously. Assistants with more than one Exec can’t leave much to chance. Using task lists and keeping notes of deadlines is crucial.
  4. Understand the needs of the organisation. If you get to know the business, you will be much more aware of what to prioritise and what is essential.
  5. Manage your Executives. You may have to organise your Executives to plan what they need you to do for them. This can be tricky but worthwhile if you have multiple bosses and one of them is unorganised and asks you to do things without warning and with a short deadline.
  6. The result is the same. You are all working to make the organisation successful, and your Executive should be reminded of this when you have prioritised one Executive over the other. It is also worth reminding them that you have also put their work first in the past!
  7. If you have two bosses demanding all of your time, it may be best to let them sort it out between them, they should have the same goals, but as we all know, this isn’t necessarily the case in business! Set up a meeting for the three of you and discuss how you will work together.
  8. Offer solutions. If your multiple bosses are trying to get all your time, you must offer a solution to the problem because you are in the best position to tell them what your workload consists of and how much time you can dedicate to each one.
  9. Stand your ground. If you have a consistently heavy workload, you may have to push back on some work or ask for extensions on extreme deadlines. This can be hard, especially if you lack experience, but it is worth asking, and if they say no, then you know which bosses will work with you and be flexible and which ones you will have to work around.
  10. Working for multiple Executives can be great for your career. However, your day can be very different. You can get involved in lots of other projects. You get to work with multiple personalities, learn to understand different working styles, and get to know more people in your organisation.

Best tips from Assistants, on working with multiple Executives

Last month I asked everyone on the Practically Perfect PA social media platforms to give me their best tips on working with multiple managers. Here are the results. Enjoy… There are some brilliant tips here!

  • Here are my best tips for working with multiple managers. I look for ways to develop/enhance strong people skills and master my emotions. Building on social awareness and constructive work relationships.
  • The aim is to synergise with the Execs and colleagues, using emotional intelligence skills to achieve a thriving and motivating work environment and build solid partnerships. I am also committed to supporting my Executive and his team with professional maturity.
  • To have the perception to identify how what, where and when they need my support is a skill I seek to refine. Of course, it is unlikely that I would support everyone at once in my team. Still, it is also essential that I am clear about how to negotiate that same support and manage our mutual expectations realistically and honestly.
  • My best tip on working with multiple managers is to stay positive, work smart, keep the plates spinning by giving each one a bit of time every day, and prepare well; my old school tip is one notebook and coloured pens.
  • Working for 6 Directors allows me insight into different areas of the business. I agree to stay positive and always have a ‘can-do’ attitude… You never know where the next journey will take you.
  • I manage three, and I have learnt to manage their expectations and ensure that they know what they’re doing and what I’m doing. It means they tend to give me more advanced notice on some of the things they have coming up and need from me!
  • I rely heavily on Outlook to help with scheduling, simple reminders, shared calendars, etc. Also, having full access to each person’s calendar is a must. For example, if an exec is unexpectedly out of the office and a meeting scheduled needs to be cancelled, you can easily cancel it and manipulate their calendar. Outlook gives me life.
  • Keep their worlds apart. Personal integrity is crucial in a setup where you support more than two executives. You don’t want one Exec feeling neglected or that you favour one over the other, or that you have a better relationship with one or the other. If you fairly distribute your attention, you gain the trust and respect of all the executives you support.
  • Just be polite when working with multiple managers. Manage time and organise your time. When asked for support, ask when they want it for. Don’t be afraid to say you are tied up with something else, but you will ensure their job is complete for when they want it. It’s about common sense and juggling your work, but at the same time, managing yourself. Just relax and don’t panic. Keep a daily to-do list and give a rough time when completing each task. Once you get used to the directors and their expectations, you will realise that they never want the work when they say they do. But remember, the CEO comes first.
  • Patience, patience and patience
  • One thing for me is adapting to their different styles and tailoring my style to suit theirs. Also, taking the time to build relationships and trust with those that you manage is invaluable.
  • You are making the most of your time, so you’re not working over your hours. Ensure you’re up to speed with all aspects of their portfolios, not just parts.
  • Most importantly, please don’t spend your day thinking you have too much to do and aren’t paid enough to do it. Instead, grab the opportunity and show your bosses and colleagues how well you manage your job and enjoy the challenge. Finally, don’t let the work stress you out; you’re human and can only do as much as your day allows you to.
  • Outlook is critical for me with three executives.
  • Putting reminders for myself and my execs is essential. Also, getting to know their personalities is important. My execs have varying styles of ‘need’ for lack of a better word; knowing who needs to be kept on track with their calendars, who needs help with presentations – or who prefers to do that type of work themselves helps to manage my time. But also, being honest, I have been in periods where I literally cannot do everything at once, and I know I might be in the minority here, but I have had execs helping me set up boardrooms when needed. I may work between three people, but they can’t chop me into three people.
  • Be honest and speak up when you feel pressured; they know you do a demanding role. Just remember, they need us!
  • I support a CEO (Operational) and a President (Strategic), so keeping them as separate as possible is critical. However, both need different support to complete their day.
  • The ability to predict what may come next is a skill that is imperative to time management. E.g. Conference in another city – car checks, parking, roadworks, tolls, to try and think of any hurdles that may appear and having a ‘plan b’ really helps maintain that calm level when juggling workload.
  • An excellent can-do attitude, collaboration, and fantastic multitasking always get me going. However, sometimes you may need to pull off complete honesty when you are stretched by practising saying NO correctly.
  • I believe the foundation of managing +1 Exec is an appreciation & understanding of the business, the executives’ roles & priorities, and communication style. It’s helped me ‘put out the fires’ and know what task should be elevated to – DO NOW!!! Mutual respect and collaboration also go a long way, mainly when competing deadlines/interests exist.
  • Keep a different coloured folder for each Executive and keep anything to do with them in that folder (if you are old-fashioned like me, keep a paper list of questions to ask them). Then when you talk to them, you have to pick up their folder, and you don’t forget anything! If you are on Google calendar and are an absolute control freak, try having the folder’s colour match the colour of your calendar.
  • I work for several executives and find they usually need me at different times (conveniently). But I recommend, at the beginning of every week, letting them know which blocks of my time will be reserved especially for them (barring emergencies). Of course, sometimes this needs to be negotiated week-by-week or even day-by-day. But I think they find it reassuring that they ‘own’ significant pieces of my time and sometimes can even take it upon themselves to negotiate with each other if they need to take someone else’s designated time. Also, I think it’s reassuring to them when I speak highly of the other executives and don’t complain. If they never hear me talking someone down, they (maybe subconsciously) are reassured that I’m not complaining about them behind their backs.
  • All your bosses think they are equally important. So stay calm and don’t panic with the amount of work coming in; sit back and assess the critical tasks, and take it from there.
  • I have plastic legal folders for each Executive. I keep information that needs to be followed up on or items to discuss. In addition, I have weekly meetings scheduled with each, for 1/2 hour to an hour each, on different days so that I can catch up with them.
  • I have a BF (bring forward) accordion folder for the days of the month and another for the months of the year. So anything that needs bringing forward is put in there, and then each day, I go to that folder and pull out the documents.
  • I have full access to their emails, calendars and contact lists. In addition, all meetings are scheduled out of my calendar so that if there are any changes, I am “in control”.
  • Talk to them!
  • They must know what work/tasks you pick up for the others. So if you’re limited for time/capacity, they know about it. Or if their job is urgent, they learn to make sure you’re aware, so can you factor in the time?
  • Be honest with them – if they ask you to do something, and it’s going to be an hour before you can look at it – make them aware. Also, if you’re struggling, let them know. If they think you’re coping, they’ll keep putting work on you. Tell them if you need a bit of space – find out what work is urgent and what isn’t.
  • My trick: Send them both to meetings with their teams simultaneously. This gives me spare time to work on my projects and time to breathe and have the office just for myself. 🙂

Avoid the pain and start enjoying having more than one boss!

There are proven tips, tricks and techniques for managing multiple bosses or executives.

In this session, two experienced Executive Assistants reporting to multiple executives give their strategies for staying on top of the demanding task of managing numerous executives.

In this session with Natalie Egan, you will hear efficient advice to help you manage multiple executives.

The reality is apparent – the days of Assistant roles being confined to one-on-one settings are long gone. But that doesn’t mean you should approach your role as any less important. Instead, arm yourself with the skills and knowledge required to meet the demands of today’s workplaces head-on. Respond quickly to changing requests and prove yourself indispensable by taking ownership of multiple relationships.

If you’re looking for a comprehensive course to help develop your personal assistant capabilities, why not enrol on the Assistant Essentials Online Course? This course has been designed to equip Assistants with all the tools they need to succeed in an ever-changing professional environment and could be just what you need to take your career to the next level.

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Chapter six