Leading with Heart: Jen Guidry of Brilliantly Bold On The Power of Authentic Women’s Leadership

An Interview With Pirie Jones Grossman

Pirie Jones Grossman
Authority Magazine
12 min readJan 14, 2024


You Achieve Long-Term and Sustainable Success: When you are authentic in leadership, there is no mask that you have to put on every day or there is no facade that you have to play in your role. By staying true to your values and principles you will create a lasting legacy.

In today’s dynamic world, the concept of leadership is continuously evolving. While traditional leadership models have often been male-dominated, there is a growing recognition of the unique strengths and perspectives that women bring to these roles. This series aims to explore how women can become more effective leaders by authentically embracing their femininity and innate strengths, rather than conforming to traditional male leadership styles. In this series, we are talking to successful women leaders, coaches, authors, and experts who can provide insights and personal stories on how embracing their inherent feminine qualities has enhanced their leadership abilities. As part of this series, we had the pleasure of interviewing Jen Guidry Fassler.

Recently retiring from being one of the Top Mortgage Loan Originators in America, one of the Top 10 Most Empowering Mortgage Women in the World and from leading teams and branches for almost her entire career, Jen Guidry Fassler has transitioned into a success and business coach. Her coaching style is marked by compassion, authenticity, and a deep understanding of the challenges faced by those striving for greatness. She owns Brilliantly Bold (BrilliantlyBold.com), and is a partner with Dr. Robb Kelly in 10XCoaching.online, where they encompass coaching people as a whole, including uncovering past childhood trauma in order to empower clients to reach their full potential. She is also a two-time award-winning author and motivational speaker.

Thank you so much for joining us in this interview series. Before we dive into our discussion about authentic, feminine leadership, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I started leading at a very young age. I was 23 years old and was running a branch for a national mortgage company. I was the “youngest” everything for many years at different companies…getting promotion after promotion. Before I was 30 years old, I was in charge of multiple branches in multiple states at one time.

Leadership is in my blood. I am naturally an ENTJ on the MBTI, which is a natural born leader…a commander. I was never afraid to take risks, driven to achieve my goals and I was known for building strong teams.

Now that I am not originating loans anymore, my focus is on helping others achieve success — whatever that looks like for them. I am a full-time coach to executives and entrepreneurs and like to specifically focus on helping other women. I also love doing motivational speeches, writing books (The Storm and Grit & Gratitude) and painting.

Can you share the most interesting story that happened to you since you started your career?

Gosh, the most interesting. That one is difficult. I will tell you a story about following my intuition versus doing what everyone else is doing.

About 10 years ago, I was part of a mortgage group that just decided to basically “stick it” to the company they were with and just outright leave without any notice or word literally in the middle of the night. We (including myself) had these huge offers to go work for another company that also had big promises.

My gut told me that the new company wasn’t good, and I also didn’t feel right about the abrupt leaving because it just wasn’t the right way to do things.

So, everyone left, except for myself, my assistant, Mary and one more loan officer. We decided to stay back and continue to work and everyone else left. We had this 6000 square foot office and there was now just the 3 of us. Everyone that left told us how foolish we were for staying, but we stuck to our guns.

Turns out, we made the right decision. The others quickly found out that the company with all of those promises, was basically just full of hot air.

Huge lesson: Listen to your intuition instead of doing what everyone else is doing.

What do you think makes your company stand out? Can you share a story?

When I was leading in mortgage, what made us stand out is that we all just worked hard and always did what was right for the client, even if that meant sending them somewhere else. We did things for the love of our clients versus being motivated by money. I have always said, “Money is a perk that you get when you do things for the right reason.”

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I have grit: You HAVE to have effort and passion for your goals. Success takes time and it is not easy. You must be in it for the long run.

I remember when I first moved to San Antonio in November 2005. I was told that it would be impossible to break into the iron-clad real estate cliques that were there. My goal was to be the Top Loan Officer in San Antonio. It took me almost 12 years, but I did it. I didn’t give up. Business got better every year. I kept doing things for the right reasons and by doing them in the right ways. It paid off and business exploded.

I was myself and I didn’t change. I remained goofy, had fun and didn’t ever feel like I had to be like every other person in a leadership position. I just did my own thing and didn’t conform to any style or rules. I believe that people followed and respected me because of this.

I am resilient. Throughout my journey, I faced numerous challenges, setbacks, and obstacles. However, my resilience allowed me to bounce back from failures, learn from my mistakes, and keep pushing forward, even when the odds seemed against me.

Resilience not only helped me weather tough times but also enabled me to maintain a positive and determined mindset. It allowed me to adapt to changing circumstances, stay focused on my goals, and lead my team through adversity with confidence.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

This happens almost every day. We have scenarios like this: I was leading a mortgage lending team during a challenging economic downturn. Interest rates were fluctuating, and the housing market was experiencing significant turbulence. Our team was presented with a crucial decision: whether to say and give our own advice on a mortgage application for a family who, on paper, seemed financially stable but had a few red flags in their financial history. On one hand, approving the application would mean meeting our targets for the month. On the other hand, saying what we REALLY thought that the client should do could potentially protect the family from taking on a mortgage they might struggle to repay in the long run. They were buying way too much of a home. One slip and this family was in big trouble.

The hard choice was between meeting short-term financial goals and considering the long-term financial well-being of our clients.

In the end, we decided to prioritize the well-being of the family and voice our opinion that we felt like they were buying too much of a home and that, while they qualified for this home on paper, they should really consider purchasing something less expensive. I believed that it was our responsibility to ensure that our clients could comfortably afford their mortgage payments and not be at risk of financial distress in the future. While this decision meant we might fall short of our monthly targets, it was in line with our commitment to responsible lending practices and ethical leadership. Even though we could still move forward with the existing home loan because they technically qualified, we felt like if we didn’t give our professional advice, that we would be unethical. The decision was up to them though, not us.

This experience taught me important lessons:

1. Ethical Leadership: It reinforced the importance of ethical leadership and making decisions that align with core values, even when it’s challenging.

2. Long-Term Vision: It emphasized the significance of considering the long-term consequences of decisions rather than focusing solely on short-term gains.

3.. Open Communication: I also realized the importance of transparent and open communication with the team, explaining the rationale behind the decision and its alignment with our values.

Ultimately, this difficult decision shaped my leadership style by emphasizing the significance of integrity, empathy, and a commitment to the well-being of both employees and clients. It reinforced my belief that authentic leadership involves making choices that serve the greater good, even when they are not the easiest or most immediately profitable options.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal experience where embracing your unique leadership style, which might not align with traditional expectations, led to a significant positive impact in your organization or team?

I was always just myself. I didn’t act like the other leaders or managers. I did my own thing and people liked me for it because I was real.

In your journey as a leader, how have you balanced demonstrating resilience, often seen as a masculine trait, with showing vulnerability, which is equally powerful, but typically feminine? Can you give an example where this balance created a meaningful difference?

You are going to fail, mess up and make a lot of mistakes as a leader. They key though is that you have to admit when you have and own it. You are human after all. Say you are sorry. Ask for forgiveness. Ask for feedback. It is all part of balancing the two traits. People will respect you for it.

As a woman in leadership, how have you navigated and challenged gender stereotypes, especially in situations where traditional male-dominated approaches are the norm? What strategies have you employed to remain authentic to your style?

It is best said from an excerpt of my book, Grit & Gratitude.

This is the fun part. How do we, as women, fit in to the male-dominated industry we are in while maintaining the respect we have earned, showing we know our stuff, and continuing to be taken seriously for what we know? It is a tough mix to juggle, but it is only the reality of what we need to do. When you work with a bunch of dudes, being a part of the team is important, which means that you will have to be one of the guys sometimes. It is by virtue of your circumstance and career choice. I don’t think it is wise to isolate yourself from everyone. You don’t want to be the outsider. You want them to feel comfortable in front of you while at the same time, not so comfortable that they stop treating you with respect.

Like I said earlier, if you have cast yourself to be the one that everyone has to walk on eggshells with, then being part of the team isn’t going to be real. It will be only superficial. People need to feel comfortable around you. When they do, they will want to include you. You want to be yourself as if you were around brothers. It seems so silly and simple, but it is true! It is important though, that when someone crosses the line, you deal with it swiftly and strongly so it doesn’t happen again. Don’t be the one who brings drama into the office or cries if someone makes you mad. Doing things like that will only serve to bring down your credibility.

Finally, don’t be afraid to speak up. Share your ideas. Provide feedback. Don’t just focus on the fact that you are a minority in your environment. Don’t expect special treatment on a daily basis because you are a woman. Work your tail off and show them who you are on the inside. You may have chosen a male-dominated field, so you are going to have to use your IQ and EQ in order to succeed in such an environment. Be strong. Be courageous. Don’t back down. We have a lot more work to do in these instances than other women in different fields. We can do it. One more thing. What I am not saying here is that you have to change who you are in order to work in a male-dominated industry or workplace. You may have to modify some of your behaviors.

How do you utilize emotional intelligence and active listening to create an inclusive environment in your team or organization? Could you share a specific instance where these qualities particularly enhanced team dynamics or performance?”

I have always had an open-door policy and my employees have always used it to talking to me both about their personal and professional life. People have always known that they can come to me and I will listen.

When they feel important, they just do better.

What role has mentorship played in developing your authentic leadership style, and how do you communicate authentically to inspire and empower both your mentors and mentees?

I have never been mentored, but I have mentored many. I just try to instill in everyone that you just have to be yourself. Don’t change. You don’t have to conform to what everyone thinks you have to act or need to be.

Ok super. Here is the main question of our interview. Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”? If you can, please share a story or an example for each.

1 . You Inspire Authenticity in Others: When you lead authentically, you serve as a role model for your team. When you’re true to yourself it encourages others to be true to themselves.

2 . You Increase Resilience: I am talking not just for yourself but for others that surround you also. Resilience not only helps you weather the tough times, but it also enables you to maintain a positive and determined mindset. You are always going to have changing circumstances, but resilience helps you stay focused on your goals and lead your team through adversity with confidence. When you are a resilient leader who is also authentic it will inspire others to be the same way.

3 . You Achieve Long-Term and Sustainable Success: When you are authentic in leadership, there is no mask that you have to put on every day or there is no facade that you have to play in your role. By staying true to your values and principles you will create a lasting legacy.

4 . You Increase Loyalty: Authenticity fosters a more loyal and dedicated team. When people see that they are heard and valued they tend to stick around a heck of a lot longer.

5 . You Empower Others: Simply said — when you are an authentic person you empower others to be the same way.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

I think the emotional drain would be the biggest issue because empathetic leaders sometimes absorb the emotions of other team members and we all know how draining that could be. Setting clear boundaries and delegating and sharing responsibilities helps with this pitfall.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

All phones get turned off as soon as you get home.

How can our readers further follow you online? @thejenguidry — Instagram or www.BrilliantlyBold.com

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About The Interviewer: Pirie is a TedX speaker, author and a Life Empowerment Coach. She is a co-host of Own your Throne podcast, inspiring women in the 2nd chapter of their lives. With over 20 years in front of the camera, Pirie Grossman understands the power of storytelling. After success in commercials and acting. She spent 10 years reporting for E! Entertainment Television, Entertainment Tonight, also hosted ABC’s “Every Woman”. Her work off-camera capitalizes on her strength, producing, bringing people together for unique experiences. She produced a Children’s Day of Compassion during the Dalai Lama’s visit here in 2005. 10,000 children attended, sharing ideas about compassion with His Holiness. From 2006–2009, Pirie Co-chaired the Special Olympics World Winter Games, in Idaho, welcoming 3,000 athletes from over 150 countries. She founded Destiny Productions to create Wellness Festivals and is an Advisory Board member of the Sun Valley Wellness Board.In February 2017, Pirie produced, “Love is Louder”, a Brain Health Summit, bringing in Kevin Hines, noted suicide survivor to Sun Valley who spoke to school kids about suicide. Sun Valley is in the top 5% highest suicide rate per capita in the Northwest, prompting a community initiative with St. Luke’s and other stake holders, to begin healing. She lives in Sun Valley with her two children, serves on the Board of Community School. She has her Master’s degree in Spiritual Psychology from the University of Santa Monica and is an Executive Life Empowerment Coach, where she helps people meet their dreams and goals! The difference between a dream and a goal is that a goal is a dream with a date on it!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.