A few years ago, I worked with a Director who did everything on paper. He rarely turned his computer on let alone sent an email or scheduled an appointment in his diary. He took his planner with him everywhere and expected it to be up to date with meetings, he wrote all of his notes in a notebook and asked for every document to be printed and put in a ring-binder for whatever meeting it was for. This was back in 2012, before online collaboration tools were popular, before Slack, before online cloud storage was a thing. It was a pain, but it was manageable! Imagine now, all these years later that Assistants are still working with a ‘paper person’. Recently on an Assistant forum, I read this exact complaint from a desperate EA who had an Executive who always does everything on paper. As much as we are all embracing technology, there are still Executive’s out there sticking with paper. Now, don’t get me wrong. I love a notebook, and I am an absolute sucker for a planner but everything on paper? Calendars? Board Papers? Business cards? Everything? That stresses me out! But, it is a problem that Assistants are facing, so I thought I would give you some tips on how to bring your Executive into the 21st century while working with the systems they are using.

Working with a ‘paper person’

  1. Remember, this isn’t personal. Annoying, yes. But, not personal. You Executive would have been working in this way for years and got pretty good at using their system. They are successful, despite the lack of technology and you’ve got to give them credit for that! So, firstly, when you want to change somebody or the processes around them, show empathy and be patient. This isn’t going to change overnight so you should start by embracing what you have and working with them.
  2. Are the papers in order? This is the next place to start. If the paperwork is well documented and in a sound filing system, learn the system and ask if you can take over managing the files. This is the first step in gaining their trust because I have found, if you are working with a paper person who is well organised, they are fiercely protective of their files. It is their comfort blanket, and you can’t just take it away from and put everything online. Once you have started managing the files, and they are used to not seeing them every day, you can slowly begin to transfer them to the cloud system. If they are massively unorganised and they have papers everywhere, you need to create a sound filing system for them. Start filing the document in folders and also on the cloud so that you are saving time in the long run.
  3. If their desk is a mess, start yourself a reminder every week, preferably when they are not in their office, to go in and tidy the desk and drawers. If they hate the idea of you invading their space, you might want to point out (subtly) that it doesn’t create a great impression if their office is unorganised and messy.
  4. Once you have their paperwork sorted, you want to look at how they use their calendar. If they are still using a paper diary, it is frustrating, trust me, I know, but there is a way around this problem. Firstly – you work from a digital calendar, be it Outlook or Google Calendar or whatever. You need to work from a digital calendar, and your Executive needs a digital calendar too. For the sole purpose of creating and excepting invitations to meetings. You can then schedule meetings, accept requests and manage their day as you would any other Executive. At the end of every day, print out their schedule for the next day and either give this document to them with the corresponding paperwork (you can read more about bring-up folders here) or write the meetings in their paper diary.
  5. The trick to managing someone’s schedule if they still use a paper diary is to try as hard as you can to keep meetings in the calendar without moving them too much. You have a 24-hour window but once the day arrives and your Executive is carrying around their paper diary you don’t have much time to tell them if meetings have been cancelled or moved – if they don’t like any technology, the chances of you being able to send them a quick message on their phone or tablet are slim. Another option is batching their meetings together, so they only have to say internal meetings on a Tuesday and external meetings on a Friday. Arrange for all of the internal meetings to be in their office so they don’t move around too much and see if you can attend external meetings with them, so you know (via your phone) if any meetings are delayed or cancelled.
  6. I heard many times of Executives asking their Assistant to print out emails, they then write a reply and ask the Assistant to type back the response. Again, this is crazy, but it happens. What can you do when your Executive doesn’t like to use email? Take over their inbox. But, again, this has to be a slow process (unless they hate email and love that you want to take it over). You can reply as, and when you know the answer, and you can print off any emails, you are unsure about. This is saving so much time, but they have to learn to trust that you know what you are doing.
  7. Should you introduce them to technology? Your job is to make them more successful, and technology can do that for them, but you have to take it slowly. They have obviously decided not to embrace technology for a reason, and it might be something that takes them out of their comfort zone, so move slowly. Start with small steps, what paperwork do they have in their office that can be digitalised without much fuss. Business cards, for example. Can you add their business cards to a contact database they can access on their phone? Start small and remember to show them what you are doing so that they know and feel in the loop.
  8. I saw this great tip on The State of the Executive Facebook forum. If your Executive likes to write a lot of notes, why not get a large whiteboard (or paint a wall with dry erase paint) so that they can jot ideas down on the fly. You can take pictures at the end of each day so that they don’t have scraps of paper or post-it notes all over their desk.
  9. Managing tasks and keeping up to date with what they have going on can be tricky with a paper person. This means that your one to one meetings are even more important because you need those updates on what is going on and what they are working on. You need to work even more closely with a paper person so that you can help manage their tasks and keep them on track. During the one to one ask your Executive to pull out their planner or notebook and go through the notes with them so you can pull out tasks and things that you can action on their behalf. Use the journal rather than an online collaborative tool. It might even be worth asking if you can get the journal at the end of the day to pull out notes and actionable tasks that you can add to an online task list.
  10. There are lots of great tools that your Executive can use to improve their productivity and make them more organised, but I would suggest you start with what you have. If they are used to using at least one piece of technology, be it their phone or say Outlook, try to get them to use the tools associated with that programme. So for example, they could capture their random thoughts on the notes app on their iPhone rather than on a random piece of paper (and then you can access the note and turn it into a task on their task list). If they are okay using Outlook, start using the task list on Outlook to help organise their priorities and use the calendar to block time for them. As I said, small steps but start with the technology they are already using.