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Q & A with Jan Jones: Part 11 – Can Executive Assistants be effective working remotely?

Jan Jones is the author of “The CEO’s Secret Weapon How Great Leaders and Their Assistants Maximize Productivity and Effectiveness”. The book debuted at #1 on Amazon’s Hot New Releases in the Office Management Category. It has received widespread acclaim from executives and
executive assistants worldwide. Jan spent 20 years as an esteemed
international executive assistant to well-known business people,
including personal development icon and author Tony Robbins. Jan is passionate about the executive assistant role and continues to champion the profession through speaking, mentoring and offering timeless,
practical advice that is relevant to the day-to-day role of the executive assistant.


For the past three years, FlyPrivate has been a proud partner and associate of Jan Jones. Jan brings valuable, actionable information to EAs across the globe. We hope you enjoy her blogs as much as we do!

Want more from Jan Jones? Check out her Q & A Series: Part 1-10!

FlyPrivateCan executive assistants be effective if they are working remotely?  What about virtual assistants? Can executives have their business needs met by using remote or virtual assistants?

Jan Jones: As the old saying goes, “there’s horses for courses”.
Meaning depending on the circumstances or conditions, assistants can be effective working remotely and many executives can have their business needs met by using remotely-located or virtual
assistants. We should take a closer look at the circumstances under which executives could function effectively using assistants who are working remotely, or are virtual assistants, to determine how
effective they can be.

Let’s take working remotely first. Actually, this is not something new. I was recently speaking with a former CEO of an international fast food organization. He told me that in the 1980s, within a few months of each other, several of his company’s assistants became pregnant, or wanted to leave due to their childcare situations. Since they had been with the company a long time and he didn’t want to lose their years of experience, he set them up with computers in their homes. He told them, “I don’t care when or how you work, just get the work done and deliver it on time.”  Technology today makes computers affordable and the internet gives us immense freedom to work from just about anywhere we choose, so it makes sense that remote and virtual assistants are gaining in popularity.

But how suitable is it for an executive who needs a certain level of support from an assistant? I checked in with two of the best, most celebrated executive assistants I know: Penni Pike former assistant to Sir Richard Branson for 31 years and Debbie Gross who spent over 25 years as assistant to John Chambers, former CEO and
current Executive Chairman of Cisco Systems. Both ladies are
featured in my book “The CEO’s Secret Weapon”.

Penni told me “Richard included me in everything”, which is how she came to know and understand the Virgin business and what
mattered most to her boss. When I asked her about assistants
working remotely she said, “I can’t understand that because I always worked so closely with Richard. He needed his assistant by his side. People at the very top have to have someone who works with them like that. Otherwise, if they need something urgently, the assistant is not there. Richard needs someone with him all the time.”

Debbie Gross said, “For administrative professionals, working
remotely has become more of the ‘norm’ in today’s business world partly due to the change in business models.  Many administrators support teams that are based around the world and are never
actually in a traditional office.  With the advance in video
technologies, it has definitely become easier to work remotely.

“That being said, one of the key roles I believe an administrator plays is their ability to build relationships across all levels and be the eyes and ears for the people they support.  Harder to do effectively from a ‘home-office’ environment. This was a critical component of my role supporting a CEO making working remotely not really an
option. John always expected me to be the ‘face’ of the office
especially when he traveled.  When he would check in while on the road he always asked how things were going at the office, so I felt it was key that I be present there. It was about noticing what was
going on around me with other members of the organization and
being able to feel the pulse and morale and share that with John.  He was pretty adamant that executive assistants be in the office, so I am not sure I would have been hired to support him if one of my
requirements was to work from home. Many senior level executives prefer to have their executive assistants in the office, especially the higher they are in their organizations.”

This has also been my experience in my career as an executive
assistant. My jobs were much too interactive with my boss, staff, clients and vendors for me to be outside the office. Like Debbie Gross, my executives counted on me to be their ‘eyes and ears’ and their ‘face’ to the world. Situations were constantly arising that needed my immediate attention. Leaving my desk to go pick up a sandwich at lunchtime could prove tricky. When I worked for bosses who were constantly traveling, on the rare days they were
scheduled to be in the office, I brought my lunch to work so I would not have to be away from my desk for more than a few minutes. Meetings were being set up, canceled or moved at a moment’s
notice, people would drop by unannounced, phone calls were being made, sometimes I was holding 2 or 3 calls at the same time, project approvals were needed, documents required signature, and there were always more travel arrangements to be made, changed or
canceled. Most executives I worked for were constantly calling out for me and I tried to always be within earshot, or have my assistant or someone listen out and let me know if I was being yelled for.  How would I have managed all this remotely?

I am currently working on a project with an assistant who is located remotely and I find it arduous. Work that should take 2 days is taking 5 or 6 due to the back and forth across international time zones. Yet, I am constantly meeting assistants who say they’ve negotiated with their executives to work remotely. Perhaps these executives have become accustomed to doing many tasks their assistants should be doing, or much of the work their assistants do for them is not of an urgent or time-sensitive nature.  Their assistants probably aren’t functioning as their liaison or deputy as I did, or as Gross and Pike did for their executives.

A big negative with the arrangement of assistants working remotely is the burden it places on assistants who are working at the office. I hear complaints that the remote assistants show themselves as “available”, but when they are contacted they don’t respond for hours, sometimes even an entire day goes by when they are not
responding to emails, texts or phone calls.  The urgency arises to schedule or re-schedule meetings, for example, but the assistant can’t be reached. If the executive is traveling, neither the executive nor their assistant can be reached and too much time is being spent by other assistants trying to contact them, cover for them, or
wasting time putting their own tasks on hold waiting for a response. I’ve inquired why these assistants don’t insist HR or the remote
assistant’s boss does something about it. HR tells them the boss agreed the assistant could work remotely when they hired them, so there’s nothing they can do. This is a cop-out by HR and the
executive. They must step up and consider the overall effects this situation has on the company. If this arrangement were impeding my workplace productivity, I would actively agitate for it to be changed. I would lobby HR not to allow executives to agree to letting their
assistants work remotely, but instead offer it as an option with
certain conditions, mainly that the assistant proves they are mature and responsible enough to warrant that privilege.

The bigger concern I have for assistants working remotely is how do they learn the business? How do they grow and expand in the role if they are not there to witness the daily ins and outs of the business environment? How do they develop a relationship of trust and
familiarity with their executive if they are not in physical proximity to each other? Ultimately, are they setting themselves up to become redundant? With warnings about A.I. and virtual assistants stepping in to fill many of the routine tasks assistants do, I would pay close
attention to developing skills and processes that make me more valuable and available to my executive.

The exception to this is assistants who have been with their
executive a long time, have built up a strong relationship with an
understanding of the business and each other. If the business is in a mature phase, or the executive’s role is such that they can be gone for periods of time, their assistants have the freedom to work remotely.

Penni mentioned that she thought assistants working remotely might get lonely. Debbie also addressed this from her experience at Cisco. “3 years ago I came to recognize that at Cisco, there was a whole administrative community that worked remotely and in
talking with several of these administrative professionals it became clear that they all felt a sense of isolation from the broader
administrative community.  As a result we pulled together this group and created an initiative known as G.R.A.C.E. – Global Remote
Administrators Connecting Effectively.  This is a group of remote
administrators who come together once a quarter to discuss the challenges they are facing, as well as review of best practices that help them feel connected.

“One of the key areas discussed was the challenge of developing a relationship with the leader because they were remote.  I strongly encourage administrative professionals who are working remotely to make it a point to travel to the corporate office at least once a year and even better, quarterly if they can, in order to ‘connect’ with their peers, meet the people they interface with across the
organization and become ‘visible’ – putting a face to the voice.  I also always suggest that remote administrators attend networking events and administrative conferences to learn and engage with
others in their profession. Working remotely certainly has its
advantages. However, administrative professionals can be even more effective by not isolating themselves. I feel that it is in our
administrative DNA that we connect with others and build strong relationships and that means we have to get out of ‘home-office’
environment to do that.  Many of Cisco’s G.R.A.C.E. members are now coming to the corporate office and networking with their peers, enriching their relationships and friendships and growing their knowledge and ultimately being of greater assistance to the leaders they support.”

Virtual Assistants: I often meet assistants who tell me they are
toying with the idea of trying out being a VA because they perceive it as a freeing experience. The purpose of including information about the VA profession in this article is to help assistants understand what it takes to survive and thrive as a VA.

Thanks to technology, there is a role for virtual assistants in the
business world. I remember from the pre-internet days, a friend of mine who worked at a large university would earn extra money
using her home computer to type students’ assignments, or
professors’ presentations. It stands to reason then, that with the freedom the internet offers us, that the virtual assistant profession would flourish.  Originally, this was a service that many
single-operator or small businesses used, but it is becoming more common for established businesses with ample resources to seek out the services of virtual assistants.

Penni Pike is an advisor for Time, etc., the virtual assistant service started in the UK, but now successfully established in the USA as well. Penni was brought on board by the company’s founder,
Barnaby Lashbrooke to guide them in setting up the business. He said Penni provided invaluable insight into how the EA-Executive
relationship should work and what kind of support executives need. Assistants chosen to work for Time, etc., go through a thorough
vetting process, not only for administrative skills, but for
inter-personal skills such as a client-focused viewpoint,
responsiveness to clients requests, attention to detail and so on. Their VAs are a mix of mid-to-high level, offering a range of skills that are “not all admin based, but include the strategic management side of business as well” said Barnaby.

He says the VA role is not suited for everyone. Many assistants are better suited to working in an office, so Time, etc., probes the prospective assistant’s reasons for wanting to be a VA. This is an
important aspect of the vetting process because it would be
disruptive if clients like working with a particular assistant and
develop an effective working relationship, only to find out the
assistant has moved on. Quality assistants with young families who need the flexibility of working from home, yet still need to bring in an income, are the most typical profile of a VA.

Anita Armas of Anita D. Armas Administrative Services from West Covina in California told me she started her VA business because she needed freedom and flexibility when she was looking for a way to be at home with her young children while still earning an income. Anita said, “I knew there was a way to use my skills and experience to do just that but wasn’t sure how, then I heard about virtual
assistants. My husband’s business was hit hard by the financial crisis of 2008 and I needed another way to bring in additional income, so I officially began marketing myself as a virtual assistant and I soon gained my first client.”

I asked Anita what mindset a person needs to be successful as a VA. “Aside from skills, in order to be successful as a virtual assistant one must be confident, resourceful, thick-skinned, adaptable, a great communicator and have a servant’s heart. As a VA business owner, my business success depends greatly on the success of my clients. A successful VA will not just be a “doer” but will be innovative and strategically invested in his or her clients business, in order to know how to best support their client. A willingness to learn and grow are key,” says Anita. She added that some of the pitfalls a VA can
experience include the client not seeing the VA as an autonomous business owner and leaning towards an employer/employee
mentality. The client feeling a sense of exclusivity, thinking they are the only client the VA has, and lack of communication between the VA and the client.

When assistants tell me they are considering becoming a VA, I
caution them that before they leave a secure, well-paying job with benefits and career advancement opportunities, they should
consider how the uncertainty of not immediately having a steady
income might impact them. They should consider whether or not they are cut out for working alone and whether they are sufficiently disciplined to get down to work every day when they have the
option to work at their own time and pace. It’s easy to romanticize being your own boss when you are operating from the safety of a
secure job. The reality of being self employed can be a wakeup call when you have to prospect for business, deal with unhappy clients, pay bills, collect payments and furnish your own healthcare. Many VAs thrive in the role and others, after a mild flirtation with
independence, gladly return to the security of a full time job.
Evaluate your skills, your disposition and your self-discipline
thoroughly before you venture into the VA world. It is not for
everyone, particularly if you decide not to work through a platform such as Time, etc., preferring to source business on your own.

What’s exciting about all this is the many options assistants of all
calibers and experience levels have at their disposal today.  When you get excited about the opportunities, be sure to think through the potential downsides, not just the upsides. Use this article to make a Pros and Cons list for yourself. I wish you success in whatever you decide.

Author: Jan Jones

©Copyright Jan Jones, 2015 “The CEO’s Secret Weapon”

Jan Jones Worldwide

Visit Amazon to purchase Jan Jones’ new book and visit her website: The CEO’s Secret Weapon.

The CEO’s Secret Weapon: How Great Leaders and Their Assistants Maximize Productivity and Effectiveness

Jan Jones


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All flights arranged by Private Business Jets, LLC DBA FlyPrivate are operated by Part 135 Certified Air Carriers. FlyPrivate will act as your agent for the purpose of obtaining charter service.