How Barbara Richard Started Her EF Coaching Business as an Assistant Principal (While Coaching for Another Practice)

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After more than 20 years in private education, Barbara hit a point where the workload as an assistant principal was no longer sustainable. When she transitioned into mental health work, she realized she had been teaching executive function skills for years, and the same challenges she saw in students were showing up with private practice clients, which pushed her to seek stronger training, structure, and confidence as a coach.

Barbara chose to get certified at EFCA and works one-on-one with Sean to help her move from coaching inside another person’s practice, where she earned a smaller portion of the fee, to building a more sustainable arrangement that allowed her to grow referrals and income through her own efforts.

Today, Barbara operates her own practice under the umbrella of Dr. Jennifer Bailey & Associates. As she continues to scale back her school role, she plans to increase her client load while maintaining flexibility and time for family.

In this interview, Barbara shares the decisions and steps that supported her transition, including how she created space through boundaries working at a school, how she navigated a difficult renegotiation, and how EFCA helped her grow as an EF coach.

What is Barbara's Background?

Barbara has a Master’s in Educational Leadership and has been in the private school world outside Atlanta for 20+ years.

Most of that time, she worked at a small school for neurodiverse students, first as a teacher and later as an administrator.

Now, she’s stepping out of school leadership and leaning fully into executive function coaching. She loves helping people find the strategy that actually fits them, build routines that stick, and adjust fast when something is not working. She also makes sure clients notice progress along the way, because small wins count.

Barbara got certified at EFCA and receives 1:1 coaching with Sean as she grows her practice. She currently operates her EF coaching practice under the umbrella of Dr. Jennifer Bailey & Associates, supporting high school students who need stronger skills, college students learning to manage new freedom, young adults navigating early career and adult responsibilities, and adults working through transitions.

You can reach Barbara at barbara.drjenniferbaileypsyd@gmail.com

Here is the full interview👇

1. After 20+ years as a school leader, what pulled you toward executive function coaching and why did you choose EFCA specifically?

I chose EFCA because as I changed careers from education to mental health, I realized I had been an EF Coach for years to my students.

They had the EF struggles that so many of the office clients had.

When the practice manager asked if I would help her clients, it was an easy task for me to take on part time.

While I had the basics, I knew that training would help me and my clients.

The reviews and outline of EFCA seemed the perfect fit and would give me the resources and confidence I needed.

2. Before transitioning to start your own practice, what did your work and life look like and what change were you most hungry for?

Before starting my own practice I was an Assistant Principal at a school for special needs students.

I was working about 50 hours per week, including time on weekends and holidays, breaks were non-existent for me.

Being a small school, there were only three administrators and most of the work fell on my shoulders.

It was incredibly stressful and I was almost unable to relax or step away.

I needed a new profession that could give me the joy of teaching/coaching with more flexibility for time and location and coaching has allowed me to accomplish those goals.

3. You started off coaching inside another person’s practice and earning a fraction of the coaching fee. What was working, and what became unsustainable?

It was great to start off in someone’s practice because I could get more confident with my new profession without having the stress of marketing and starting my practice from scratch.

Honestly, without Sean’s encouragement and guidance I would still be there today.

But, as I started to get referrals without the practice feeding me and realizing the financial loss, I had a tough conversation and began my own practice under the umbrella of her practice.  

4. What boundaries did you set in your school role that created space to build your own practice? What was the hardest boundary to hold and how did you make it stick?

In order to ensure that I have time to build my practice and ensure a smooth transition at school, I backed out slowly.

When we met as an administrative team to discuss the following academic year, the other administrators indicated they wanted me to continue as much as possible but without compromising my new goals.

Each year, I am able to shave off more hours and days in order to ensure I have time to move forward in my new career.

At this point, they are very cooperative and willing to work around my needs.

5. What made you decide to renegotiate with the practice you were working for and what negotiation moves helped you land a more sustainable arrangement?

With Sean’s encouragement, I had a very difficult discussion with the head of the practice as I was losing a significant percentage of my income.

Since I have built a referral network outside her practice, we agreed that I could separate those clients that come to me as a direct result of my efforts.

This allows me to have the income I am working for, unless the practice refers to me.

6. Why was transitioning to your own practice important for your lifestyle and income goals?

While I have deep respect for the head of the practice, losing a portion of my income would not have been sustainable as I leave the school.

Having my complete income allows me the income and flexibility to move into the next stage of my life with more control.

I want more time for family and hopefully grandchildren in the next few years.

7. What was your biggest fear before starting 1:1 coaching with Sean, and was there a moment when you thought, “I can actually do this”?

Imposter syndrome is ever present in my life and this was no exception.

While I can find the right approach for clients and can see their progress, insecurity keeps creeping in and holding me back.

With Sean’s coaching, I am now more confident and able to project this in conversations and meetings with clients, professionals, and professional agencies.

8. How did you get your first paying client? What steps did you take and what did you learn from that experience?

My first paying client was a client within the psychology practice in which I work.

A struggling college student that was dropping classes, missing work, forgetting tests, and not being accountable.

Together we got through a few tough semesters and into his dream college as a junior.

He now has goals to attain his master’s degree and while I don’t believe he “needs” coaching any longer, he does like the accountability of meeting with me weekly.

I learned a great deal from him including:

• one method does not work for all

• listening to his perspective is critical

• small steps are better than none

• setbacks happen

• coaching does help!

9. What tools, lessons, or systems from the certification or coaching with Sean have made the biggest difference in your ability to coach or grow your business?

I have used it all and am so grateful for everything from the spreadsheets to Google tips, articles, checklists, outlines, book suggestions, ongoing chats, etc.

Sean is a wealth of information and as each client needs something different, his resources have helped me so much.

I think the most frequently used items for me have been the planner and google tips but I do have clients that require me to revisit other resources and ideas.

10. What does your business look like today?

I currently have seven clients that I meet weekly and one that I meet every two weeks.

Given the four mornings at the school and a one night parenting class I instruct, all my clients are on two days.

This allows me time to take care of client needs, school needs, and office work on my days without clients.

As I scale back at the school, I hope to increase my client load to 10.

11. What impact has this work had on your clients and your own life?

Being able to step away from the duties of the school has given me more time to dedicate to my clients.

I have more time to:

• prepare

• create documents

• follow up

• schedule communication with parents, therapists, teachers, and counselors

I feel much more competent with this additional time and my clients and families are reaping the benefits.

12. What would you tell someone who’s on the fence about getting certified at EFCA and/or receiving coaching from Sean?

Absolutely sign up and don’t question it any longer.

The certification course is a wealth of information and coaching with Sean pushes you to a level of professionalism that was not a focus when I took the course.

His resources and encouragement are priceless.

13. What is your tech stack?

I am a Google girl:

• gmail

• google tasks, sheets, docs, etc.

Those are my first line of attack with clients and from there we have apps that we rely on for more specific timers, reminders, and note taking.

Thank you Barbara!

By recognizing that her years as an educator and assistant principal already gave her a strong foundation in executive function support, and then adding the structure, tools, and confidence from EFCA, Barbara built a coaching practice that is more sustainable and aligned with the life she wants.

Her story is a reminder that you can transition out of high stress school leadership without walking away from the parts of the work you love, and you can do it in a way that protects your time, income, and energy.

Thank you, Barbara, for sharing your journey and the courageous decisions that made this transition possible!

Interested in starting your own executive function coaching business?

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About Barbara

Barbara attained her Master’s degree in Educational Leadership and has been part of the private school community outside of Atlanta for over 20 years.

She has spent the majority of that time in a small school for neurodiverse students first as a

teacher and later as an administrator. Because of her work with this population and her desire to see each student maximize his or her potential, Barbara has been finding unique strategies throughout her career to help students find success in school, become more independent at home, and generally become more accountable. Her skill in this area has served her and her students well.

As she exits from the administrative team, she is excited to be a certified executive

function coach and continue to utilize her skills and individualized approach to help

others. Barbara’s passion for this work comes from both the challenge of finding the

individual strategy that works for each client, and the joy of seeing her clients

become successful. Working with Sean and EFCA gave her the skills she needed to facilitate this success.

Barbara encourages her clients to pivot when strategies don’t work while also supporting the fear of change. With her guidance, her clients work to create and follow routines and procedures. She also ensures that they become aware of and celebrate small victories along their path to success. Her suggestions and guidance along the way provide them with the support they need.

As part of the team at Dr. Jennifer Bailey & Associates, Barbara specializes in

working with several populations which include: college students who need

guidance balancing new found freedom and being full time students, post college

students trying to find work or new to the workforce and the responsibilities of

adulting, adults struggling with life changes or transitions, and high school students

lacking skills to be successful.