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that their organisations didn’t let them download software, still blocked Social Media sites and used old fashioned and out of date technology.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.

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