Real Careers: Jacqueline (Jackie) Leib

Join me for today’s Real Careers interview with Jackie Leib of the US Midwest. 

Jacqueline (Jackie) M. Leib, CAP (Certified Administrative Professional), is Executive Assistant to her organization’s CFO. Here’s a look at her world.


My morning routine starts at 5:00 a.m. I go downstairs for a cup of coffee, sit in “my” chair and play the daily solitaire game. Then I read emails and plan my day. I get myself dressed, pack some fruit or veggies and head out the door.

My drive to work is about 25 – 30 minutes on weekdays. On the weekends or in the evening, it takes about 20 minutes. Who or what is on your commuting playlist/podcast? I like to listen to books on my way to work.  I am currently listening to Dare to Serve: How to Drive Superior Results by Serving Others by Cheryl Bachelder.

At the Office

Primary Responsibilities: I assist the CFO in day to day activities,  and also assist three  of our Board of Trustees’ Committee Chairs and the Director of Human Resources.

Morning Routines:  When I arrive at work, I open up my executive’s office and check his out box. I then turn on my desk lamp, fire up my computer and head upstairs to the cafeteria for breakfast. I’ll have created a to-do list before I left the office the night before, and I will have added to it based on emails that I read with my cup of coffee. I ask my executive if there is anything pressing on his agenda that I can help with, and then I dig in.

There is nothing in an administrative professional’s life at work that is typical … that is why I love it!

Note:  I plan for a day that rarely happens. Students lose their IDs and I need to make them new ones. A call comes in asking if the Little Theater is available on Wednesday at 3:00 for a meeting and I need to check availability and reserve the theater. An IT colleague will email me to ask if I am available to test out the new video conferencing software. The Director of Human Resources volunteers me to help a teacher figure out an issue with a Word document they received. There is nothing in an administrative professional’s life at work that is “typical” and, to be honest, that is why I love it!

How long is your work day? In the off season (November and December), I arrive 20 – 30 minutes prior to the start of my day and usually stay 45 minutes to an hour after work hours. I take my computer home with me every night and work on weekends, too. I am a volunteer-aholic!

We have a state of the art workout facility that all employees/spouses and family members can use free of cost

Given health risks associated with views that sitting is the new smoking, have you or your employer adopted any steps to support good health? I have days where I sit for hours working on a project. Other days, I am walking around our 150 acre campus. On the whole, I sit more than I stand or walk. I have been considering purchasing a sit/stand platform for my desk. My employer will donate $100 toward this purchase for anyone wishing to obtain one. Also, we have a state of the art workout facility on campus that all employees/spouses and family members can use free of cost. I have my moments when I take advantage of this benefit.

What might be a typical lunch?  As a boarding school employee, I receive three meals a day in the dining hall; this is a benefit. Lunch menus are rotated. As an example, yesterday’s lunch offerings included chicken fajitas, Spanish rice, sofrito black beans, hominy with cilantro and lime, steamed vegetables, grilled cheese quesadillas, chips and salsa, and pizza with cauliflower crust or pepperoni. This is in addition to a full salad bar and two choices of soup.

Are you involved in any employee groups/teams independent of your role?  Yes, I serve as an advisor to eight students and also serve on the Head of School Symposium which is studying Russia this year. I contribute to a Professional Learning Consortium and I just helped start a Thankful Therapy group with our students. During these monthly group meetings with students, we use our hands creatively while sharing what is on our mind. Last month we made thank you cards to share with our community.

Dealing with Challenges

What is the most challenging aspect of your day or career? Interruptions. I will be working on payroll or a project for my executive and the phone will ring. Someone will be asking for help, or calling to check availability of a room, or a student will stop by and say they lost their dorm room key. It is hard to truly concentrate on a project from start to finish.

Breathe deeply and begin!

What do you most enjoy about your career? I most enjoy the variety of work during any given day or week. One day I am working on preparing contracts for an external organization to use our auditorium, and the next I am on my way down to the city (Chicago) to help with a luncheon event involving speakers, alumni, current parents and students.

On Saying “No”

(Insert huge body laugh felt from my head to my toes!!!) I have notepads, mugs and stickers all referring to my inability to say “no”. Honestly, I love being able to say yes. I am a people pleaser and have always felt that it is part of my job  . . .  within reason.  After all, I do have my limits.

Jackie’s World

Map of worldI was born in the Midwest of the good ole USA and remain in the Midwest. I have been in or around the Chicagoland area my entire life. At heart, are you a city mouse or a country mouse? Hmm, I would say that I have moments of both. My family and I love to take the train into Chicago, walk around and see the sites, have a delicious meal, and then head home to the burbs. That being said, my vacations growing up were spent on my grandmother’s 80 acres in the Ozarks. These were the best vacations EVER!  My Mom and Dad retired to a farm near Galena Illinois, where my sister now lives.

How do you like to spend your time away from the office? I like to spend time with my husband and two sons, as well as my girlfriends. I am also a lifelong learner, so you will often catch me reading in my comfy chair or watching webinars.

How long have you been in this career? Gulp! 20+ years. What was your first such role? I interned for a company that sent me out to different law firms and financial planning companies to switch out the pages of laws, restrictions, etc. that had changed during the month. It was a very lonely job.

How did you learn about the opportunity that led to your current role? I stalked the school’s website! I started as an Office Manager for the External Relations (Advancement) Department and worked my way up to my current position.

Education has always been very important to me

How do you decompress or reward yourself after a tough day or week? Sadly, I reward myself with the most decadent chocolate I can find.  Mmmmmm, just thinking about it makes my mouth water.

Your ideal holiday or travel adventure? Of course it is anywhere my husband and boys go! That being said, it has changed over the years. When it was just my husband and me, we enjoyed sun, sea and sand. When the boys came, it was child-friendly amusement. Now I am into adventure and education. I am taking my first trip to London in the spring!


Education and Professional Development

Education has always been VERY important to me. I have an appetite for knowledge in multiple forms and avenues. I obtained my Associate Degree in Office Management and Administration in my early twenties. I went back to school and earned my Bachelor of Science in Business Administration and Management two years ago. This past April, I received my CAP designation (Certified Administrative Professional). Each month I sign up for webinars and take courses through from LinkedIn Training.

Jackie has earned Associate and Bachelor’s degrees as well as IAAP’s CAP (Certified Administrative Professional) credential

Peer and Professional Associations: I’m a member of IAAP, the International Association of Administrative Professionals and  IAEOP, the Illinois Association of Educational Office Professionals. I’m also a member of NAIS, the National Association of Independent Schools, NBOA, the National Business Office Association, ISACS, the Independent Schools Association of the Central States and NSLS, which is the National Society of Leadership and Success.

Have you held a leadership role in such organisations? Yes, I’m the Chicago NW Branch Director for IAAP and an Executive Board Member at NSLS. Independent of professional affiliations, I’m Committee Chair and Den Leader for Pack 72, Boy Scouts of America, and a board member of the Parents’ Associations for Butterfield School and Highland Middle School.

In serving others as a leader, I feel a sense of pride in watching people grow and step up to become leaders themselves.

Have you earned any certifications earned through the association? Yes; I earned my CAP (Certified Administrative Professional) credential through IAAP.

How have these networks or associations helped you? These organizations keep me up to date date on all things that pertain to my employer, my profession and my personal career. How have your professional networks benefited your employer? While attending an Administrative Assistants of ISACS (Independent Schools Association of the Central States) conference, we were able to discuss many common issues. I created a contact list from our emails and we now have a group of admins whom we can ask specific questions relating to independent schools issues – and we receive ideas on how other schools handle situations. Fellow group members email each other often, and ISACS is a great resource for individual members and our schools.

This past summer, I attended the IAAP Summit. When I returned to work, I wrote my executive and the Dean of Faculty to tell them about all the things I had learned. I am now slated to teach six classes to our faculty and staff on subjects I was exposed to at Summit.

 I feel a sense of pride in watching people grow and step up to become leaders themselves

What are the primary means of communication for members of your networks and professional associations? Email, videoconferencing and face to face conversations

Inspirational reads? Oh, goodness! I have a long list of people who have influenced me and my career. Joan Burge has been with me since I returned to full time Admin work.  Lucy Brazier’s Executive Secretary Magazine is a must read. Bonnie Low Kramen, Vickie Sokol Evans, Peggy Vasquez, Chrissy Scivicque, Melissa Esquibel, Rhonda Scharf, Sandy Geroux, Julie Perrine, Colette Carlson, Courtney Clark and Marie Herman … A CEO’s Secret Weapon by Jan Jones …The Definitive Personal Assistant & Secretarial Handbook: A Best Practice Guide for All Secretaries, PAs, Office Managers and Executive Assistants by Sue France … IAAP’s Office Pro Magazine … and blogs such as Musings of a High-Level Executive Assistant, Desk Demon, Office Ninjas, Exceptional EA, Practically Perfect PA, Audacious Admin and Executive Leadership Support Forum have all had a major impact on my career and professional development.

Recruitment is often competency-based. Which of the competencies you bring to the role are most relevant to success in your current position? First and foremost is the ability to adapt. After that, I would say that the competencies that I bring are leadership, self-management, innovation, emotional intelligence and communication.

What steps do you take when you recognise that you need to move beyond your comfort zone? I actually have been pushing myself most of my adult life to go beyond my comfort zone. My motto is to breathe deeply and begin!!


The Digital Age

Are the meetings you coordinate or attend primarily digital (relying on portals and/or PDFs of meeting materials), or paper-based? We are primarily digital. For my Board of Trustee committee meetings, we have a portal on our website. There, I post all of our documents, minutes and member information.

For internal committees, we use Google Groups.


Lessons Learned

Give us one or two of your best strategies for job interviews. Be honest, bring a portfolio of your work and follow up with a hand written “thank you for your time” note. Both Julie Perrine and Sandy Geroux have excellent ideas on how to build a portfolio and what to put in it.

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? Don’t sit at your desk waiting for people or projects to come your way.  Be a go-getter!

Advice for a new parent returning to the workplace? Read my blog!!!

Follow up on interviews with a hand written “thank you for your time” note

For those interested in promotion: I discuss this on my blog, in the article Professional Development is the Key to Your Success.


… and now, a note from Shelagh. Readers not familiar with some of the people and resources Jackie mentioned 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.

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 23 countries to date: Australia, Belgium, Brazil, Canada, England, Germany, 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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