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 as well.

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 it is to 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 hard because I had to juggle multiple tasks, deal with various personalities (sometimes within the same person), and I had to work to lots of 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 bosses 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 of the time and that you need to prioritise your work in the best way you see fit. If you work for one Director that is senior to the rest, unfortunately, their needs will probably come first. If you make this clear 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 be telling 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 that is taking up a lot of your time and what you require of them!

Planning is key

Well, it is as important is 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 so that they can 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.

Remember that all of you should share the same goals.

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

If you are being asked by another Director to complete an urgent piece of work, then 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 the two of 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 all trying to get all of your time, then 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 you 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 workaround.

It can be incredibly rewarding.

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

Your day can be very different. You can get involved in lots of various projects. You’re never be bored, you avoid working for one Director that you dislike, you get to work for 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 the ability to work for more than one boss.

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

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’s every day. Remember this is a two way street! Your Executive’s should be telling 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 that is 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 are communicating regularly with your Executives. Once you are aware of their needs, you can prioritise your day and your 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 note 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 important.
  5. Manage your Executives. You may have to organise your Executives so that they can plan in advance what they need you to do for them. This can be tricky but worthwhile if you have multiple bosses and one of them is totally unorganised and asks you to do things without warning and with a short deadline.
  6. The end result is the same. You are all working to make the organisation successful, and your Executive’s 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 the two of 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 are going to work together.
  8. Offer solutions. If your multiple bosses are all trying to get all of your time then 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 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.
  10. Working for multiple Executives can be great for your career. Your day can be very different, you can get involved in lots of different projects, you get to work for multiple personalities and learn to understand different working styles and you 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 on 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 be able 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 being supportive of 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. It is unlikely that I would be able to support everyone at once in my team, but it is also important that I am clear about how to negotiate that same support and manage our mutual expectations realistically and honestly.
  • My best tips 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, prepare well and 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 not only do they know what they’re doing, but what I’m doing. I find 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 not only scheduling but simple reminders, shared calendars, etc. Also, having full access to each person’s calendar is a must. If an exec is unexpectedly out of the office and a meeting that they 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 very crucial in a setup where you find yourself supporting 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, then you gain trust and respect from 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 that you are tied up with something else but 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 manage yourself. Just relax and don’t panic. Keep a daily to-do list to start with and put a rough time of when you will complete 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 being adaptable to their different styles and tailoring your style to suit theirs. Taking the time to build relationships and trust with those that you manage, is invaluable.
  • Making the most of your time so that you’re not working over your hours. Make sure you’re up to speed with all aspects of their portfolios and not just parts of it.
  • Most importantly, don’t spend your day thinking you have too much to do and that you don’t get paid enough for doing it. Grab hold of the opportunity and show your bosses and colleagues how well you manage your job and that you enjoy the challenge. Finally, don’t let the work stress you out, you’re human and you are only able to do as much as your day allows you to.
  • Outlook is key for me with three executives.
  • Putting reminders for myself and my exec’s is essential. Also getting to know their personalities is important, my exec’s 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 really 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 exec’s 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 pressurised as they are fully aware that you do a really demanding role. Just remember they need us!
  • I support a CEO (Operational) and a President (Strategic) so for me the key is keeping them as separate as possible. Both need different support to successfully 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 to maintain that level of calm when you’re juggling workload.
  • A great can-do attitude, collaboration skills and fantastic multitasking skills are what always get me going. Sometimes you may need to pull off complete honesty when you are stretched a little bit, by practising how to say NO in a right way.
  • I believe the foundation of managing +1 Exec is an appreciation & understanding of the business as well as the executives’ roles & priorities along with their communication style. It’s helped me ‘to put out the fires’ and know what task should be elevated to – DO NOW!!! Mutual respect and collaboration also go a long way, especially when there are competing deadlines/interests.
  • 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, also keep a paper list of questions to ask them). Then when you talk to them, you just have to pick up their folder, and you don’t forget anything! If you are on Google calendar and are a real control freak, try having the colour of the folder, match the colour of their calendar.
  • I work for several executives and find that 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). 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 on themselves to negotiate with each other if they need to take someone else’s designated time. 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, either.
  • All your bosses think they are equally important. Stay calm and don’t panic with the amount of work coming in, sit back and assess the critical tasks, take it from there.
  • I have plastic legal folders for each Executive. In there, I keep information that needs to be followed up on or items to discuss. I have weekly meetings scheduled with each, for 1/2 hour to an hour each, 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. 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. All meetings are scheduled out of my calendar so that if there are any changes, I am “in control”.
  • Talk to them!
  • They need to know what work/tasks you’re picking up for the others so if you’re limited for time/capacity they know about it. Or if their task is urgent they know 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. If you need a bit of space, tell them – find out what work is urgent and what isn’t.
  • My trick: Send them both to meetings with their teams at the same time. This gives me spare time to work on my own 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 who currently report 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 exceptionally practical advice to help you manage multiple executives.

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Next chapter:

Building your personal brand and networking
Chapter six