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Personal Assistant - Questions to ask your new boss

As a Personal Assistant, you know that temporary contracts, and therefore new starts can be frequent. Starting over often can become tiresome, but if you can master the art of settling in and getting to work fast, you will find that new starts get easier and easier every time.

The key to getting settled and figuring out how you can best be of assistance is to ask questions. Perhaps don’t ask a heap of questions all at once, but periodically asking a question or two from the following selection will show your boss that you are keen to get it right.

How do you take your tea and coffee?

This is an excellent place to start. Not only is sitting down with a cup of tea a great opportunity to ask questions, but if you can get a cuppa right then it will undoubtedly be appreciated. All being well, it won’t be long before they are making you a thank you brew too.

Have you worked with a Personal Assistant before and if so, what did you value most?

This question is a good way to get a measure of which traits your boss values most. If you ask this question and they say ‘my last assistant was always on time and kept a very tidy desk’ or if they cite loyalty or a keen sense of initiative, you know straight away that this is something to focus on. If, of course, you are the first assistant that your boss has ever had, then it will be up to you to help work out what their preferences are.

How do you prefer to receive information?

This is an important thing to agree on as soon as you are able. Some bosses want to be cc’d in on absolutely everything as and when it’s dealt with. Others prefer to receive less in their inboxes and instead receive an update at the end of each working day. Others place far more value on regular face to face catch ups than communicating by email.

If they have no preference feel free to suggest a way that has worked effectively for you in the past - initiative and experience go a long way in this job.

What are your short term and long term objectives?

You will be a far more valuable and effective PA if you have some sense of the goals and visions your boss is working towards. If you know what they are aiming for, you will support and anticipate their needs much more effectively.

What decisions can I make independently and which should I seek approval for?

This is crucial so you can quickly establish where your boundaries and freedoms lie. Most bosses want you to be pro-active but sometimes trust needs to be built up slowly before you go headlong into making decisions without checking first. Having said that, other bosses want to be consulted as little as possible and prefer you to shelter them from as much as you are able.

Do you see my role as gatekeeper and if so, how vigorously do you want me to protect your time?

The answer to this question can vary enormously. It also goes without saying that as time goes by you will become more in tune with who’s who, who your boss will always want to speak to and who they might prefer to avoid!

Apart from the specific tasks outlined in my job description are there any ‘informal’ tasks you would like me to take on, such as organising team socials?

This might be a question to save until you have got to grips with the basics and are confident you can cope with your workload. Some bosses ask their PA’s to perform more personal tasks such as collecting their dry cleaning. Some are very respectful and show appreciation for everything their PA does; others don’t. However, if you have a good relationship with your boss, you might find you want to take on extra work to make yourself utterly invaluable so that you’re fully supporting your boss in every area.

What is your life like outside work?

It would be a bit of a strange question to ask this question outright on day one, particularly seeing as at this stage, any boss would be within their rights to reply, ‘None of your business.’ Perhaps ask minor non-intrusive variations of this question, such as, do you have any hobbies? By understanding what your boss’ personal life entails, you can get a sense of how that person is likely to operate.

Is your boss a parent? If so, it might be important to them to try to get home at a reasonable hour wherever possible. You can usually get a few clues from pictures on their desk or by asking how their weekend or evening was. Does your boss have a wife, husband, or partner? If the answer is yes, make sure you get to know them, or at least learn to recognise their voice on the phone.

In one way or another, every boss’s personal situation affects their working life so, the sooner you have some understanding of it, the better.

Why did you hire me?

You don’t really need to know this; it’s just nice to know. You will have got the job for a reason and finding out what that reason was will be A/interesting and B/helpful so you can make sure you live up to expectations.

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