Real Careers: Kimberleigh Deignan

Join me for today’s Real Careers interview with Kimberleigh Deigman.

Kimberleigh Deignan is a Senior Executive Administrator in Florida. Here’s a look at her world.

Starting the day with Finnegan and exercise

I typically wake around 4:30 am, stretch and load Finnegan my Havanese into his Dogger and circle the neighborhood for a couple of miles. This is more of a walk than a run, yet I’m pleased with my pace. Then it’s home to prepare for work. Since the pandemic,  I can work from my home office some days, and other days I head in to our corporate office. My husband, Jim, packs me a healthy lunch and snacks usually consisting of a sliced apple, grapes, or berries. Crystal Light sweet tea is included and often finished by the time I reach the office, about a 25-minute commute.

Who or what is on your commuting playlist/podcast? My playlist for exercise or driving is varied, and ranges from Sinatra to Big & Rich. Janis Joplin, Paolo Nutini, Peggy Lee, Roy Orbison, the Rolling Stones, the Tubes, Adele, Tim McGraw, and Uncle Kracker are a few others on my playlist.  I can listen to Christmas music or Disney themes for a pick-me-up any time of year.

At the office, independent of pandemic times

Primary Responsibilities: My primary role includes managing the CAO’s (Chief Administrative Officer’s) and HFHP (Health First Health Plan) Chief Executive Officer’s time. At both the corporate and home offices, I utilize three monitors. The far left monitor is for email, while the middle – the largest screen – is for calendar viewing and the far right is for instant messages. The calendar view is minimized for whatever project I am currently preparing. The large screen showing multiple executives’ calendars allows for more efficient planning.

Morning Routines: Each day I begin work between 6:30 and 7:00 am. Years ago, in a 1:1Microsoft training program with my executive, we learned to select the option for your calendar to open first. This allows you to review the day before jumping into email. I print the CAO’s calendar for the day to review with her when she arrives. During the day, I review both my executives’ calendars for conflicts and overbooking, and reach out to assistants to resolve, reschedule, or reduce meetings.

I sort and distribute to my executives any mail that has arrived. Often there are documents in my email that need to be printed and prepared for signatures. Once my executives arrive and sign documents, I scan and return them to their originating offices.

The pandemic has pushed virtual meetings and interviews forward in the corporate world

Given health risks associated with views that sitting is the new smoking, have you or your employer adopted any steps to support good health? Working for a healthcare system, we are conscious of good health habits. My desk is a sit-stand with an adjustable pedestal chair. Health First offers discounts on the purchase of a FitBit. Annually, I purchase a new FitBit and program it to vibrate and remind me that I need to achieve 250 steps per hour. Some days I do not need the reminder. While working at home, I have a standard writing desk and a pedestal chair.

Health First provides associates with fitness centers or membership at a local YMCA. Throughout the year, we have activities, including 5Ks, to promote physical fitness.

What might be a typical lunch? Usually I bring my lunch and I have been working a bit harder to find an empty office or conference room to eat in just to get away from my desk. If I choose to eat at my desk, I try to face away from my computer screens.

Inside the career

What is the most challenging aspect of your day or career? Probably the most challenging part of my day would be driving to and from work. I like to get where I am going and, fortunately, have only a 25-30 minute commute.

What do you most enjoy about your career? The role of Executive Assistant has been appealing to me for the variety of skills involved, and for the projects in which we participate or lead. Shortly after her 1996 Olympic win, Kerri Strug was in Louisville, Kentucky where I was working for Humana; I was able to plan and host a reception she attended. While working for the LCVB (Louisville Convention & Visitors Bureau), I was privileged to plan and host an annual event for wounded members of our military stationed at Fort Knox. This is where I met my first Medal of Honor recipient, Hershal W. Williams – or Woody, as he prefers to be called. I am proud to say I made lifelong friends from this group.

In college at SUNY (State University of New York) Fredonia, I was a math major. The EA role offers the opportunity to work with numbers, which for me is wonderful but could never be my full-time focus. I need more interactions and variety. Also while with the LCVB, I was able to partner with the University of Louisville’s athletic department on a bid to utilize the new KFC Yum! Center for playoffs. My presentation was a success.

It may not seem like a lot at the time, but the incremental increase of skills is valuable

Does your organisation make use of an intranet/SharePoint or other web portals? We utilize BoardEffect to communicate and survey their responses. This has been instrumental in keeping the Board informed during the pandemic.

On Saying “No”

In this role we are not supposed to say “no”, and often we already have a full plate when someone asks for one more thing. Generally, I begin with asking for their deadline. This allows me to see if the request fits within the time frame for my other projects. If I can not meet a person’s deadline, I explain my higher priority tasks and timeframes for completing them. If they agree to adjust their deadline, I can accommodate; if not, I suggest others who may be able to assist them.

Moving beyond your comfort zone? Research in order to complete the task and wow with results

Working through a pandemic

With your career currently a hybrid one, tell us about your experience with remote working. What are some of the challenges and benefits of working from home? The pandemic has certainly changed the way we operate. Previously, my role entailed remote working only when I had specific projects that were better accomplished working outside the office. The downside would be those times during the day when I need to catch my executive between meetings or get a signature.

My pets certainly have enjoyed the increased remote schedule. Last week, while I was participating in a virtual meeting with our cameras on, my youngest Bichon Frise, Derby, jumped on my lap. Everyone seemed to enjoy her pop-up visit.

Sometimes I feel more accomplished working remotely. An example would be when I can finish a meeting, get up to refill my beverage, throw a load of laundry in and return to my desk. By the end of the day, my work is completed, and I only need to fold laundry rather than starting it at that point in the day. It feels like I have more time at the end of the day.

Set a goal for how many new (even temporary) projects or tasks you can add next year

What would be your ideal work scenario once we settle in to new norms? Would you prefer to be back in the office, at home, or continue with a hybrid approach? With no immediate end in site for the pandemic, I feel a split schedule is most likely. I am pleased with this potential change and what may be the new normal. Our Health First executives are also working remotely some days and feeling accomplished. I am not sure if  we’ll work remotely as much in the future, once the pandemic is over, but feel it is now more of an option.

How would you rate your productivity when working remotely? Has your productivity increased or decreased, or does it depend on the day? Remote work has been accompanied by an increase in productivity and higher customer service ratings in our office. Personally, I feel more relaxed working at home. Maybe it is wearing a blouse and shorts for my virtual meetings, or just not having the commute time.

How many professional development-focused webinars do you estimate you’ve attended during the COVID-19 pandemic? I believe there have been five webinars so far and I signed up for three more this week. Do you enjoy learning via webinars, and/or are you very much looking forward to the next occasion you can attend an in-person conference or learning event? I do enjoy learning via webinars, but look forward to in-person conferences again some day. I have found that, even with live webinar training, it can be challenging to connect with other participants and the instructor.

What’s been your biggest career lesson/takeaway from the COVID-19 pandemic? I think the pandemic has pushed virtual meetings and interviews forward in the corporate world, where it may otherwise have been slow to progress. Financially, I think it is more effective to hold virtual interviews with candidates until the final round when a face to face meeting is essential.

What’s been your biggest life lesson/takeaway from the COVID-19 pandemic? With two of my sons living in other states as they serve in the military, and with the pandemic travel restrictions, time with our families is truly priceless.

Kimberleigh’s world

Map of worldI was born in Western New York. I lived 20 years in Louisville, Kentucky and four years in Nashville, Tennessee before moving to the Space Coast of Florida just over four years ago. At heart, are you a city mouse or a country mouse? Probably suburb life for everyday life, with an occasional trip to the city.

How long have you been in this career? It’s been 30+ years. What was your first such role? My first role as an assistant was as a Pediatric Dental Assistant; I also managed the front office. In that role, I acquired many skills I use to this day.

How do you like to spend your time away from the office? Living in Central Florida, I am a Disney-holic. With an annual pass, I go to Disney as much as possible. Whether it’s solo day trips or trips with friends and family when they come to visit, I love it all.

How do you decompress or reward yourself after a tough day or week? A video chat with one (or all) of our eight grandchildren is always a mood lifter. We have two Bichon Frise dogs, Bailey, and Derby, and two Havanese, Fiona Flynn and Finnegan. They give us daily rewards of love and puppy kisses.

Be genuine, try to speak in facts, do not gossip, and be a team player

Education and professional development 

While in high school, I was a secretary to our Athletic Director. In my senior year, I was selected to be in the inaugural class of County legislative interns. This provided a great deal of hands-on learning. I also began my college studies, at SUNY (State University of New York) Fredonia, while in high school.

Most of my employers have supported my attendance at conferences and, now, webinars.

Peer and Professional Associations:  I have belonged to IAAP, to ASAP and, in Louisville, to a group of Executive Assistants who work for a CEO or a board of directors. This was a by invitation only group, and I was honored to be included.

Working for Health First in Brevard County, Florida, I am part of a large group of administrative assistants. We work to share training and best practices.

Do you hold (or have you held) a leadership role in such your professional associations? While in Louisville, I was more active within IAAP; I served as Vice President of my chapter and as Professional Development chairman. For Administrative Professionals’ week, I planned and executed a full day of learning, lunch, and team building. This was a wonderful network of assistants. Connecting some local venders with the top executive assistants in the area was a bonus to the educational benefit and team building achieved. How did these leadership roles helped you? My roles in IAAP assisted with my event planning skills.

Inspiration and achievements

Tell us about a career accomplishment or two of which you’re particularly proud. While in Nashville, that was achieving my goal of increasing my executive’s time by 30% by taking on responsibilities to make his job easier.

Who has been your career/professional role model or mentor, and why? While working in the corporate office at Humana, founder David Jones had three assistants. They were wonderful role models with their work ethic, organizational skills, and their methods for keeping Mr. Jones in time. They shared insights with me, including remembering that “the devil is in the details”.

MOAA, Military Officers Association of America, honored Kimberleigh as a Kentucky Colonel for her efforts working with wounded warriors

Have you received any awards or recognition within this career? MOAA, which is Military Officers Association of America, presented me with the honor of being named a Kentucky Colonel for my efforts working with the wounded warriors at Ireland Army hospital at Fort Knox. This project began through my position at Executive Assistant to the CEO of the Louisville Convention and Visitor Bureau.

Inspirational reads? Simon Sinek; one of my executives introduced me to his writings.

What steps do you take when you recognise that you need to move beyond your comfort zone? When I have been given a task reflecting something I have never done before and am understandably anxious, I research everything I can in order to successfully accomplish the task. Not just complete the task, but really wow my boss. A few years back I was given the task of shooting a lip-dub video, and I included staff from every department. It had to be ready in 12 days. This put me way outside my comfort zone, but I dove into researching how to do this and everyone enjoyed their role in the project, and I could not have been any prouder of the finished product.

What skill(s) development or enhancement have you targeted for the next year? I recently began an on demand, Employee Engagement Essentials class, Intentional ListeningDo you have any career goals or accomplishments on your radar for the next five years? I would like to complete the new series of classes with the Disney Institute and elevate my career within Health First.

Travel Planning

Travel or travel planning recommendations? I implemented the Concur system when working with two past employers.

This offers ease of scheduling, tracking, and managing used tickets – all rolled into one system. The role of Concur Administrator was added to my responsibilities.

Lessons Learned

Give us one or two of your best strategies for job interviews. Be prepared – research the company and the executives interviewing you. Relax and be honest.  Do not oversell yourself. Remember, they need you.

What bit of insight would have been most helpful to you in the early stages of your career? “The devil is in the details” was a wonderful tip I received.

What advice might you offer a new parent returning to the workplace? It is okay to miss your child(ren). Talk to coworkers who have been where you are for support. Sometimes just talking about it and knowing others have survived it is helpful.

Interested in career growth? Keep building your skills, and network.

What are a couple of suggestions you’d offer that new assistant on the block, in terms of how to build effective business relationships within the office? Be genuine, try to speak in facts, do not gossip, and be a team player. Pitch in even if it is not directly your responsibility.

Your most effective time management strategy? Always schedule time for each item on your list of tasks.

What are a couple of valuable early conversation topics you recommend an assistant initiate when beginning work with a new executive/principal? From my experience, I have found it helps to get to know my executive, their personal likes, and dislikes. Finding even the smallest task that can make their day easier is a great beginning.

Remember, they need you

Your thoughts on goal setting? Taking on new tasks or responsibilities every year or quarter will increase your knowledge and skills. It may not seem like a lot at the time, but the incremental increase of skills is valuable. Set a goal for how many new (even temporary) projects or tasks you can add next year.

For those interested in promotion: Keep building your skills and network. Let your executive and talent acquisition team know of your desire for growth opportunities.


… and now, a note from Shelagh. Here are some links to  resources mentioned above.

  • ASAP, The American Society of Administrative Professionals
  • IAAP, International Association of Administrative Professionals

Shelagh showcases Real Careers, in which assistants from around the globe generously share the benefit of their experience.

We’ve made virtual trips to 25 countries to date: Australia, Belgium, Brazil, Canada, England, Finland, Germany,  Ghana, Greece, Italy, Mauritius, the Netherlands, New Zealand, Nigeria, Northern Ireland, Norway, Republic of Ireland, Scotland, South Africa, Sweden, Turkey, Uganda, the United Arab Emirates , the United States of America and Wales.

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