Real Careers: Debbi Shaffer

Exceptional EA showcases Real Careers, in which administrators from around the globe generously share the benefit of their experience. We’ve made virtual trips to Belgium, Brazil, Canada, England, Germany, Mauritius, the Netherlands, Northern Ireland, Norway, Republic of Ireland, Scotland, South Africa, Turkey, the USA and Wales, and now make our way to Washington, DC to visit with Debbi Shaffer.

Debbi Shaffer is an Executive Assistant who also blogs as Audacious Admin. Here’s a look at her world.

Not an Early Bird

To say I am not a morning person is a gross understatement. If it weren’t for coffee and B vitamins, I would never make it out of the house. My day begins with a cat jumping on me the moment the alarm clock rings. My husband is a lifesaver. He IS a morning person, so by the time my alarm sounds he has my vitamins, energy drink and coffee sitting on my bedside table. My co-workers really should send him thank you notes.

I live very close to my office. My commute is approximately three miles or five kilometers. I drive because I often need my car to perform work-related errands. Washington, DC is ranked in the top 10 US cities with the worst traffic, so my commute can be anywhere from 15 to 40 minutes.

Who or what is on your commuting playlist/podcast? Celtic Rock is always on my playlist. I produce a series of compilation CDs to raise awareness and funds to find a cure for breast cancer. I’m currently working on Volume IV, so I utilise my commute to listen to the songs bands have submitted for consideration or to arrange the tracks.

At the Office

Morning Routines: My schedule is 9:00 to 5:00, but I usually arrive around 8:00 a.m. I get coffee and log in to my computer, unlock both my executives’ offices and log them into their computers. Next I transcribe voicemails, check mailboxes, enter time, and print any items necessary for meetings that day. By the time I finish those tasks, one or both of my executives have arrived and we meet on any pending items.

One of the things I love most about being an executive assistant is that there is not a typical day. My duties and responsibilities change based on the project and event priorities. The fact that no two days are the same is what keeps me energized. I never know what challenges to expect, and I love a good challenge.

Primary Responsibilities: Travel coordination, calendar maintenance, drafting reports and correspondence, expense reporting, meeting and event planning, onboarding of staff, maintaining organisational charts, database management, time reporting, and email management, just to name a few

How long is your work day? My contracted hours are 9:00 to 5:00, but I rarely work my scheduled hours. I’ve come in as early as 4:00 a.m. and left after midnight. Fortunately, days that long are not standard operating procedure. I base my availability on what is happening in the office and where my executives are that week. If they are in the UK or Middle East, I might come in at 6:00 a.m. and leave at 3:00 p.m.

IMG_9639What might be a typical lunch? In addition to my job as an executive assistant, I run a charity organisation and a professional development company, so I usually spend my lunch hour catching up on items for these ventures. I’ll write blog posts, do research, catch up on correspondence, or conduct meetings while having lunch at my desk.

Do you work from home in your “off” hours, or during your commute? I’m guilty of rarely unplugging. Working for a global firm means it is often necessary to work outside standard work hours. I monitor my email from the time I wake up until the time I go to bed. If someone needs something urgently, I’ll happily work from home to help.

Dealing with Challenges

What is the most challenging aspect of your day or career? One of the biggest challenges for me is individuals who do not understand my role. The Assistant’s role has evolved and grown significantly. My executives and I are strategic business partners. It is frustrating when someone views me a wall they need to get around. I’ve observed people lurking around the executive offices waiting for me to be away from my desk to try to sneak in a few minutes with my boss.

What they don’t understand is that, by doing this, they derail something – whether it be scheduled work time or making my executive late for to a meeting, which can set off a chain reaction for the day. I wish they would understand they would get much further by enlisting my assistance.

My executives and I are strategic business partners

What do you most enjoy about your career? The absolute best thing about my career has always been the people. I’ve worked with some pretty amazing individuals, and have had some unbelievable opportunities thanks to the connections I’ve made.

On Saying “No”

I struggled for a long time with saying NO. I think many assistants have trouble saying no. I’ve learned the hard way it is okay to say NO. Not too long ago I over-committed myself to the point that I was on the brink of a breakdown.

On saying no: Please do not allow other peoples’ priorities to take precedence over your own

I wasn’t taking care of myself or nurturing the relationships that are most important to me, because I was busy saying YES to everyone. Please do not allow other peoples’ priorities to take precedence over your own.

Debbi’s World

Map of worldI was born in Baltimore, Maryland, USA, which is not too far from where I live currently, but I’ve lived in numerous places. I’m not sure I could recall all the places I’ve lived. I’ve spent the most time in Illinois, California and Washington, DC. I am 100% a city girl. I love the energy of big cities. I’ve never lived too far from a major metropolitan area. Honestly, I’m good for about two days in the country before I’m aching to get back to the city.

How do you like to spend your time outside the office? My husband would say my answer should be, “to be busy!” and that I don’t know how to sit still. Honestly, I don’t have a great deal of spare time but, when I do, I enjoy time with family and friends, travelling, attending concerts, reading, and shopping.

How do you pamper or reward yourself after a tough day or week? I reward myself with pampering often. I work hard and love to reward myself with a manicure, pedicure or massage, but shopping for a new outfit or pair of shoes is my favourite reward.

 A dream holiday or travel adventure? My ideal holiday includes a beach. My favourite destinations to date have been Bundoran, Ireland and Tamarindo, Costa Rica. I hope to get to Australia and New Zealand soon. Greece is also high on the list of places I’d like to visit. I’d love to take a Mediterranean cruise.

Education and Professional Development

Education: I was a terrible student. That fact that I graduated from high school at all is really quite amazing. School frustrated me because I was bored. For a long time, I thought I was dumb but as I got older I realised that was far from the truth. I tried college, but was more interested in what I was learning at work than in the classroom. I have a PhD from the University of Life.

For someone who hated school, I now spend a great deal of time and energy on learning. I belong to multiple continuing education platforms and take courses all the time. If someone tasks me with something I don’t know, I find a course and learn it. As I’ve transitioned into a professional development speaker, I really enjoy conducting training sessions because I always learn something new while teaching. The other day I saw something that said 80% of billionaires do not have a college degree. I don’t know if that is true or not, but I found it interesting. Bill Gates and Richard Branson are impressive examples.

Don’t be afraid to voice your ideas, observations and opinions

Peer and Professional Associations: I belong to several professional organisations, all of which have been helpful with my professional and personal development. I currently belong to the International Association of Administrative Professionals (IAAP), the Executive & Personal Assistants Association (EPAA), and WashingtonExec Assistants Committees. I’ve been offered leadership positions, but have declined due to time constraints.



Preferred form(s) of social media? Facebook and LinkedIn are my favourites. There simply are not enough hours in the day to master all the available applications.

Your dream app, or software, to help you in your career? My technology dream is for all software designers to understand the role of the executive assistant, so they will add features to make it easier to work as our bosses when necessary. I have to log in and out of computer profiles multiple times per day in order to do my job. If all software had a designate delegates feature, my life would be much easier.

I’ve learned the hard way that it is okay to say no

Awards and Recognition

The individuals I’ve been lucky to have worked with over my career have never been stingy with praise. I’ve received numerous forms of recognition, from employee of the month to the OfficeNinjas All-Star designation I referenced earlier.

Style and Substance

Toronto Style Copyright Shelagh DonnellyWhat is your go-to outfit to ensure confidence on an important day in the workplace? I’m really quite a clothes horse, so I have multiple power outfits in my closet. My go-to outfit would depend on the events of the day. I have a hot pink blazer I love that really makes a statement. As well, there is a grey Calvin Klein suit I gravitate to on important days.

What one or two cosmetics would your purse or travel bag be empty without? I have lip gloss and hand lotion with me at all times.

Heels or flats in the office?  Heels are preferred, but there are days I must break out the flats if I want to be able to walk the remainder of the week. On my busiest days my Fitbit has logged over 15 miles, which is tough on the knees in heels. For your commute? I drive myself, so I wear my heels, but I tend to slip them off and drive barefoot. Favourite brands of shoes, whether you wear them or they’re on your wish list? I don’t have a favourite designer; I have eclectic taste. My frustration is that I have large feet and many shoe designers don’t make my size.

Preferred scent: Flower Bomb by Viktor & Rolf

Communication and trust: crucial components of a strategic business partnership

What might we find in your desk drawer? My executives say my desk is like a mum purse. Pretty much everything you could ever need is in there: office supplies, medicines, first aid items and technology necessities. Just today I’ve been asked for Advil, rubber bands, a safety pin, glue, staples, a notepad, a phone charger, gum, a wireless mouse and a birthday candle. All were readily accessible at my fingertips.

Travel or travel planning advice? In my travel planning sessions, my favorite three tips are:

  • Think through every step of the trip as if YOU are the traveller.
  • Too much information is better than not enough information. I love the trips where my boss doesn’t call for any information because everything s/he needed to know was in the travel packet.
  • Think outside the box. Travel planning often requires creativity, research and persistence to get the best deals. I’ve saved my company thousands of dollars through creative travel planning.

Inspirational reads? Many books/authors have had an impact on my life. C.S. Lewis, Frank L. Baum and Dr. Seuss are some of my favourites. Recent favourites include What I Know for Sure by Oprah Winfrey, The CEO’s Secret Weapon by Jan Jones and Sway by Ori and Rom Brafman. I keep 100 Tips Using Office 2010 by Vickie Sokol Evans close by at all times. As a big Wizard of Oz fan, I really enjoyed Toto’s Reflections: The Leadership Lessons from the Wizard of Oz by Kevin Fickenscher.

If someone tasks me with something I don’t know, I find a course and learn it

Role models or mentors? I’ve been blessed to have many great role models and mentors, but my greatest has been my father. The biggest regrets in my professional life have been when I did not heed advice he offered.

Dad was a corporate executive and all of his assistants were role models for me. I joke that I’ve been in training for my career since birth. On the weekends, I loved to go to the office with him to play secretary. I grew up witnessing the value-add of a good assistant.

I’ve learned valuable lessons about who I want to be (and who I don’t want to be) from the executives I’ve supported.

I’m consistently amazed and inspired by the group of women I’m blessed to call friends. There is nothing these women can’t accomplish when they set their minds to a task. They push me to push my limits and to get comfortable outside my comfort zone.

Tell us about a career accomplishment of which you’re particularly proud. Earlier this year, over a dozen of my co-workers nominated me as an All-Star in an annual competition by OfficeNinjas. I was selected as one of the five 2016 All-Stars out of over 1,000 nominees. It was powerful and poignant to read the amazing things my team wrote about working with me. I needed more than one Kleenex.

I’m extremely proud of the Celtic Pink Ribbon compilation CDs I’ve produced. There are three to date, and I’m currently working on the fourth. It is hard to believe this little idea I had has been embraced by over 40 bands and raised so much money to help end breast cancer. I confess I get a little giddy when I receive orders from outside the US. I’m proud to say that there are copies of Celtic Pink Ribbon in Australia, England, Ireland, Scotland, Canada, and Mexico.

Do you have any career goals or accomplishments on your radar for the next five years? I’d like to obtain my Microsoft Office Certification this year. I’ve really enjoyed growing Audacious Admin over the past couple of years. I love developing programs to empower administrators and hope to continue to grow that business. To that end, I’d like to start working towards becoming a Certified Speaking Professional.

Lessons Learned

What bit of insight would have been most helpful to you in the early stages of your career? Not to be afraid to voice my ideas, observations and opinions. By keeping quiet, I was doing a disservice to both myself and my executives.

Manage the calendar; don’t let it manage you

Your most effective time management strategy? You need to manage the calendar. Don’t let the calendar manage you. I like to look ahead at least a week in advance to see what I need to prepare for. Every executive I’ve worked for has believed s/he has the ability be in two places at once, but I have yet to work for one who has mastered the skill. Double/triple/quadruple calendar bookings are addressed at our daily meetings. It helps me understand priorities and to set expectations for the people with whom they are meeting. A calendar appointment may have been sent requesting 90 minutes, but in reality they only get 30 minutes.

What are a couple of valuable early conversation topics you recommend an assistant initiate when beginning work with a new executive/principal? When I begin supporting a new executive, I schedule an interview with him/her. This is very different from the interview you had to get the position. During the appointment I ask questions on a wide variety of topics: family, favourite foods, allergies, medical conditions I need to be aware of, preferred methods of communication, travel preferences, memberships, expectations, and specifics I can do to add value to the partnership. From that initial conversation, I begin to build an executive dossier. This is a binder, kept under lock and key, that has all the particulars on my executives. I am constantly adding to these dossiers.

One important piece of advice: should you part ways with an executive, be sure to turn the dossier over to your executive, not to HR or your replacement. The dossiers I’ve created have contained a lot of personal information and only my executives should decide who receives that information. I’ve spent years building extensive dossiers and know my executives would definitely not want that level of detail passed on to a new assistant until they have built a relationship of trust with that individual.

Interview your new executive and build an executive dossier; then keep it under lock and key

Advice for new executives on how to best work with an assistant: Communication and trust are the crucial components to create a strategic business partnership with your assistant. You must make time for your assistant and teach her/him your business and goals. You wouldn’t hire a VP and not teach the newcomer your organisation’s mission and goals, so why would you not teach your assistant those things? Your assistant cannot be a strategic business partner if you don’t have full disclosure.

For those interested in promotion: As an assistant, you are fortunate to have the perfect seat in the organisation to view different roles, learn what is needed to be successful in those roles and make the connections to support advancement, if that is what you desire. I know many assistants who have successfully transitioned to leadership roles in their organisations.


… and now, a note from Shelagh. Readers not familiar with some of the people and resources Debbi referenced may be interested in checking the following links.

To explore a range of resources recommended by readers, click here for Exceptional EA’s Resources Page or click here to see all professional associations and networks recommended by peers.

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