Things you shouldn’t say to your boss… Even though you are thinking it

If I had a pound for every time I bit my tongue while working as an assistant, well, I would be a very very wealthy lady! In our role, we are confronted with so many different situations and personality types it can be really difficult to think before we speak. But as assistants this is exactly what we have to do – particularly with our Executives. Maintaining a good relationship with your Executive is really important and sometimes you will have to forgo the urge to say exactly what is on your mind! There are always things you should say to your boss… Even though you are thinking it! Here are my top four:

That’s it… I’m outta here!

Okay, so yes, there have been a few occasions I wanted to storm into my Exec’s office and resign then and there before triumphantly grabbing my stuff and walking out the door. But, I didn’t… Because I didn’t have the guts and also it’s not cool. Even if you are heart set on leaving because you’ve just had enough, it is important you don’t burn your bridges. By all means, find another job, hand your resignation letter in and work your notice. You just never know what the future holds and you may one day need something from your ex-employer. Never ever threaten to leave without the intention of seeing it through… This is just a bad idea!

So, what exactly is in this for me?

Asking your Executive this question will open a huge Pandora’s box of stuff that is best not opened. As an assistant a lot of what you are asked to do isn’t going to benefit you in any way. It will, however, benefit your Executive, your colleagues and your business. That is your job. You benefit from seeing your Executive succeed and work more productively. You are the ultimate team player and, I think, the rewards are pretty amazing.

I’m sooooooo bored!

The work that assistants do can absolutely suck sometimes, but rather than speaking to your Executive about it you simply have to get on with the boring stuff. When the crap stuff outweighs the good stuff, then you can talk to your Executive about your workload and what motivates you. But this should be structured properly through one to one meetings with your Executive and you should have some idea as to what you want to do about the problem. Telling your boss that you are bored will cause two things to happen. Firstly, your Executive will be pretty pissed off that you are bringing this problem to them because at the end of the day you are paid to be in there and secondly, you will be given a load more crap work to do that fills your time rather than productive challenging work that will stretch you. Nobody wins when you tell your boss you are bored!

I’m not doing that

I admit, there have been loads and loads of times I wanted to tell my boss I’m not doing something they’ve asked me to do. But, then I remembered that this is part of my role and I sucked it up and did it anyway. I moaned about it afterwards with friends and family obviously, but not to my Executive! The debate about what an Assistant should or shouldn’t do for their Executive’s rumbles on… I think unless your Executive only asks you to do menial tasks you should do the odd thing that isn’t necessarily in your job spec (reload a stapler with staples found in their desk drawer for example…)

Working with an old school Executive

I recently organised an event for just over 150 assistants in Leeds and Edinburgh, where we showcased loads of office technology that would help Assistants and their Executives be more productive. During the course of the events you would not believe (or maybe you would!) how many of the Assistants mentioned that their organisations didn’t let them download software, still blocked Social Media sites and used old fashioned and out of date technology. There were also a bunch of Assistants that said although their organisations were very much working in the 21st century their Executives were not. A handful of assistants still had to manage paper diaries, print off and file emails along with every other bit of paper that passed by their Exec’s desk, type up hand written notes and take dictation. Old school stuff!

I must admit I was a bit shocked. I have been talking a lot recently about changes in office culture with the influx of Millenials coming into the workplace and taking senior positions. Many, many assistants will be supporting Millienial Executives and will need to keep up to date with all of the technology their Executives use on a daily basis. BUT and this is a big BUT. Many Assistants, millennial age or not, work for older Executives who do not and will not embrace new ways of working, new (or even kinda old) technology and expect their way of working to remain exactly how it has been for decades. Now, some Assistants may be completely used 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 own bubble?

Quite often old school Executives are incredibly resistant to change and we will come on to this. However, sometimes they just live in their own bubble where new ways of working just don’t cross their path. I had one Executive that had a bunch of the old style Rolodex business card holders dotted around his office. When I asked if he wanted me to put them onto his Outlook contacts he was delighted. When I told him that I could put an app on his new iPhone that scanned the business card directly into his Outlook contacts he was over the moon. If you have an old fashioned boss that just 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 make sure you are an expert so that they don’t get put off by any minor glitches.

Just resistant to change?

There is old school and then there are those that are just resistant to change. Don’t get me wrong, people who are resistant to change are incredibly difficult to deal with. Particularly, if you are proactive and can see that a few tweaks here and then will make a big difference. There are plenty of articles out there that will help you manage people resistant to change. Here is one I wrote a few years ago. 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 have a 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 problem tends to be that your Executive has everything in their paper diary, you work from that, but also put all of the appointments in Outlook or your online calendar. If anything changes out comes the eraser for the paper diary and then you have to make the same changes to the online diary. AHHHHHHHHH! So how do you get your Executive to move to an online calendar only. Firstly, have you actually 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 made it very clear you do not like working with two diaries, why would you expect them to change their routine?  If you have told them and still they refuse to give it up, ask yourself – what are they afraid of? Is it the lack of control, is it the technology itself, is it simply 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 so that they can 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 who is also old school in every way. 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 career. 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 lots of ideas and examples of changes I’d made in other organisations only to realise that these ideas were not welcome. I was quite frankly, pissed off. But over time I came to realise that my old fashioned Executive was brilliant at his job and despite being completely old fashioned had excellent systems in place that worked well for the department. 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 and acting inappropriately. Not everyone understands that ways of working have moved on. Can you be a little 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 just your Executive speak to like minded people in your office and ask how they deal with your Executive. Don’t accept that your Executive has all of the power because they don’t. You can manage up 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 really helped support my personal development. Not an easy choice but quite often the right one when it comes to working with bad managers.

How to make your Executive happy

This is a pretty fundamental question for assistants, isn’t it? How do you make your Executive happy? Some of them can be quite grumpy, can’t they! Aside from a lobotomy, there are a few other options that will ensure your Executive is happy with your performance and I thought I would share a few with you today.

Under-promise and over-deliver

I recently chaired a panel session at the PA show and this was one of the answers given by the panellists. It is so true, when it comes to working with an Executive a sure fire way of keeping them happy is to under-promise and over-deliver. Assistants should first and foremost deliver what they have promised, whether that is meeting a deadline or nabbing the hard to reserve tables, and then think about any additional work they can do that goes above and beyond their Executive’s expectations. Obviously, assistants can’t over-deliver on every single task (that would be crazy) but once in a while, making the effort will really keep that smile on even the most hard to please Executive’s face.

Return every call, reply to every email

This kinda goes without saying, but when you are absolutely slammed with work it can be difficult replying to every message, particularly if you get a gazillion messages from your Executive per day. To keep your Executive happy you must, must, must reply to everything. Even if it is a simple email that says you’ve received the message and you are working on it. I know this is time consuming, but keeping your Executive in the loop means they don’t have to chase you for a reply and they know that you are dealing with everything. It might be worth keeping a few standard replies in your draft folder if you get the same sort of email requests from your Executive.

Understand when something is urgent

It can take time to develop a good understanding of how your Executive goes about their day, their moods and their work style. It is really important that assistants do understand all of this though. It is the only way to create a truly great partnership with an Executive. Watch your Executive closely. I wouldn’t suggest stalking, but do get to a point where you know when they are at their most productive, when they need to be left alone and when you should schedule meetings for them. To keep them really happy you will also need to know everything about their day and what they have coming up that week, month, year. If they are having a particularly stressful time make sure you are around and there to help at any point. If they have given you a task during these periods make sure it is completed quickly and with the minimum amount of input from them. If you know they might require your help – be there.

Come with solutions

To make your Executive happy it is pretty vital that you do not cause them unnecessary hassle. As their Executive you must be the port in the storm. This can be an absolute pain in the arse, especially when you are really annoyed and just want to vent to your boss. But! As an Assistant you can’t be that kind of employee. If you have any issues or problems that you would like your Executive to resolve you must think of a solution to the problem and take that solution to your Executive. Never be that employee that gives your Executive more problems than answers. They don’t like those employees!

What is going on with your Exec?

The key to success in this role is a great relationship between the assistant and their boss. That kinda goes without saying right? Yes it kinda does… but actually it can be pretty difficult maintaining any good relationship when there are a gazillion other things going on. The day to day stuff takes over and it can be easy to neglect each other.

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Working with a micromanager

I’ve worked with a lot of Executives over the years and I have to say one of the trickiest personality types are those that micromanage their staff. The problem is that many of them do not realise that they are micromanagers and certainly wouldn’t admit their management style causes any issues if they were called up on it – which it often does! It can be really frustrating, especially for assistants, working with a micromanager.

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