“Training” an executive new to working with an Assistant is a fantastic opportunity to educate them in the art of administrative support explains Eth Lloyd

I was recently working with an Assistant, Lynda, on her Diploma in Business Administration. During our discussions she outlined how six months into her role she was allocated a new Executive, new to the organisation.  She described his first day, when she met him in reception and took him to his office. Lynda told me that as they walked together, he quite calmly told her “I’ve never had an assistant before and I’m not quite sure what you would be doing for me”.  She says he has confessed many times since (they have enjoyed a three-year working relationship), that he simply couldn’t function without an assistant now! In addition, after being allocated him, she was allocated a second new Executive.  Both had very different working styles and she adapted her support to suit each of them.

The organisation Lynda was working in at that time was going through a restructure. She decided that the new proposed structure did not provide her with the assistant role she preferred working in, nor any opportunity for advancement. Lynda made a personal strategic decision to look for another more suitable role. She was successful; and was told that one of the striking things about her was that she had clear and well-expressed ideas on how to “train” a new executive, which really impressed her new employer.

Lynda lists the day to day tasks she undertakes in the first stages of “training” an executive:

Diary Management

Manage all meetings and appointment requests.

  • Set-up a rule in your Executive’s inbox so that all emails relating to calendar appointments are sent straight through to a separate folder. This prevents their inbox filling up with these emails and acting as a distraction.
  • Discuss how you, as the Assistant, will learn which appointments to accept, which to delegate to some-one else and which require a decision from the Executive, freeing up their time.
  • Ensure the Executive always has a lunch-break of at least an hour in the day. Even if they don’t use the time as an actual lunch break, it is another way to ensure they have “desk time”.
  • Make sure the Executive’s personal preferences are met in the calendar – they may wish to have time for a run at least twice a week; they may need to drop their children at school so cannot attend meetings before 9am; they may need to leave the office at 4pm each day.
  • Use the diary to assist with meetings and meeting preparation. This is very much dependent on the Executive’s preferences, but you will establish these quite early in your working relationship.  For example, your Executive may wish for time between meetings for preparation/reading/coffee.  15-30 minutes is a good starting point but it depends on the length of the meeting.  If they have been in a 4-5 hour board meeting, an hour at least before the next meeting would probably be better than 15 minutes.
  • In Outlook Calendar there is the ability to categorise/colour code appointments. This could be useful for you both to identify different sorts of appointments, e.g. internal vs external meeting, board meetings, 1:1s, team meetings, placeholders, desk time, etc
  • Block all spare time during the day in the Executive’s calendar, as “desk time”. This means that anyone requesting an appointment will not see any free time for them at all, and will therefore need to contact you as the Assistant to request a meeting. This gives you the opportunity to specify the best time and day for the meeting to be held (taking account of your Executive’s preferences).
  • Encourage your Executive not to make appointments themselves in their diary! Instead they should ask you to do this, providing the reason, attendees, place and a timeframe. Obviously, if they are putting in a private/personal appointment they do not have to advise you all the details, so they retain some personal privacy. Perhaps in this instance they can mark the appointment as “private” and just tell you if it is in the office or out of the office.  With the Assistant managing most appointments, it will ensure the diary is kept clean and fewer errors will occur. If they wish to make appointments themselves, then simply request they email/advise you that they have done so – this again ensures fewer errors are made.
  • Ensure each appointment has all the information the Executive requires e.g. venue, subject, attendees, audio/video connections instructions, and any papers.

Daily meetings with the Assistant

Preferably in the morning, a daily meeting avoids constant interruptions to each other during the day. If your Executive is at a different site or is away from the office for work, then have that meeting by phone, skype, or other remote access.

Early on in your business relationship, daily meetings are an opportunity to get to know each other better and build rapport.  Lynda found that over time these meetings act as “grounding” or “sanity” time for the Executive in a busy day.

The meeting itself should be no more than 30 minutes but ensure your Executive understands a brief check-in later in the day could be necessary. The daily catch-up meetings could be used for:

  • Providing papers that need to be read in advance.
  • Checking and confirming the forward calendar/diary.
  • Discussing calendar conflicts or new requests.
  • Approving/signing items and papers.
  • The Executive providing you with action items from previous meetings, or upcoming meetings.
  • Both of you updating the other with items/projects you have been working on.
  • Sharing knowledge, e.g. the Executive advising his priorities or the Assistant advising of any issues they have noticed re staff morale (you may be their “eyes and ears” on the floor of your workplace and the information you have gathered may often be very important to them).

If the full scheduled time is not required, then both Assistant and Executive have some time back in their day, or they could use the time to go out for a coffee instead!

Daily Packs

Each afternoon build a “daily pack” for your Executive for the following day, containing their schedule and all the papers required for meetings, together with itineraries, notes, etc. This may be hard copy documents, through embedding documents into appointments, OneNote or other electronic processes, as you and your Executive agree which method best suits you both.

Key Contacts

Discuss with your Executive, how you would like to understand and know their key contacts/stakeholders and get to know their Assistants.  Explain the value of you forming a good relationship with those Assistants, describe how this relationship is crucial should urgent requests for appointments, information, meetings, etc., be required (after all it is the Assistant who makes the diary work!). Suggest you have the mandate to take those Assistants out to coffee/lunch every now and then.

Travel and Expenses

Book all travel for your Executive, even if they have done their own in the past.  Early on, establish their preferred airlines, seating, flight preferences, places to stay, etc and ensure these align with the organisation’s protocols. Have their profile lodged with the travel desk/agent.

Agree a method of keeping in contact when your Executive is away that suits you both.

Once a trip has finished, handle all expenses claims, credit card reconciliations, etc., again, even if they have been doing this before!  Be sure to strongly encourage them to keep all receipts and give them to you – perhaps have an “envelope” or “pocket” in travel documents/papers for these to be held in while away.

Dealing with Emails

Depending on the Executive’s preference it can be a big time save for them if the Assistant manages their inboxes. Once trust is built the Executive may request the Assistant to deal with some of the emails and reply on their behalf.

One effective way to manage an inbox is to categorise the emails.  This will enable the Executive to quickly see which items they need to attend to.

  • Examples of categories could be: Reading, FYI, Executive to Action, Assistant to Action, Circulate, etc.
  • There should also be a “completed” category, so that both the Executive and Assistant can mark when they have dealt with an email (to avoid double handling!).
  • Also use the “flag for action” to indicate when something needs to be done by a certain date.

Once emails have been dealt with, if they are to be kept, file them in appropriate folders in line with your organisations protocols. Folders can be agreed with your Executive and the Assistant can then do this.

Lynda recommends that you do not try to do this all at once! Determine which aspect to tackle first and build your Executive’s trust in your ability, knowledge and skills.  It is important to take it slowly and subtly and expect adaptations to be made that suit both of you even better.

Eth Lloyd, MNZM, worked as an Assistant for 30 years. She has a passion for the administrative profession and its value. She is a Life Member and past National President of the Association of Administrative Professionals New Zealand Inc (AdmiNZ). In 2018 ... (Read More)

5 comments on ““Training” an Executive new to working with an Assistant

  1. Serena on

    Thank you ! I am about to receive a new CEO into our organisation, I myself and new to the EA role and I have been wanting to compile a list of jobs/questions to ask the CEO when they get here. This will come in very handy.

  2. Eth Lloyd on

    Hi Serena, thank you for your comment and I have passed it on the Lynda who provided me with the material. I am sure that her tried methods will provide you with assistance but perhaps most importantly confidence in what to ask and tasks you can do. All the best

  3. Rachel Parker-Brown on

    I have to agree. I too will be receiving a new Executive and though not new to this role, it does make you think about existing systems and what is missing or could be improved, but equally what works well. This is an excellent tool to refer to and help me with this.
    Thank You

  4. Patty on

    I am currently working with a Manager who has never had an assistant before. And, I have recently transitioned back into an admin role. I feel that emails I send to my Manager should be read by him – he shouldn’t ignore them like he does so many others. Do I have the wrong idea?

  5. Eth Lloyd on

    Hi Patty, I certainly believe that your Manager should read your emails. However, if he overlooks others emails then perhaps he would prefer a different way of communicating with you? At the very least you perhaps need to have a conversation about how he wishes to receive communication from you and whether perhaps your emails need to be colour coded or have some trigger that he will respond to and then read. While we deserve to have our communications received and noted, if a method does not work for you and your Manager then try other methods until your settle on one that does work. I hope that helps. My apolgies for the slow response but the system would not allow me to respond at first and then I have been away.


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