Mentoring Matters with Cynthia Whitfield-Story

Cynthia Whitfield-Story is the President and CEO of INSPIRE1, LLC Consulting & Coaching Firm. Before starting her own company, she worked for Allstate Insurance for almost 40 years, where she developed crucial mentoring relationships with the leaders she admired. Cynthia worked her way up to an executive-level at Allstate and after retiring, followed her passion for leadership coaching and development by starting INSPIRE1. She says, “I think it’s important for people to follow their passion, dream big and find a mentor who can turn those dreams into a reality.” Read more about the impact mentorship has had on Cynthia’s life.

Cynthia Whitfield-Story is the President and CEO of INSPIRE1, LLC Consulting & Coaching Firm, focusing on executive leadership coaching, strategy development and leveraging diversity, equity and inclusion in businesses and organizations. Before starting her own company, Cynthia worked for Allstate Insurance for almost 40 years. She started with Allstate as a claims representative and went on to hold various leadership roles in Operations, Accounting, Finance, Risk Management and Product Operations. In 2009, she was named vice president of Allstate’s Southern Region. Her success in developing and managing the strategic operating model for the region led her to her promotion to field senior vice president of the Southern Region in 2013.

During her time at Allstate, Cynthia found that what she loved most was developing her employees, her leaders and herself. For over 30 years, Cynthia has been a leadership coach, consultant and mentor focusing on strategy development and an integrated people-first approach. She is known for creating solutions to challenges and winning with accountability to achieve business results. She believes in being authentic, inspirational, challenging the status quo and creating an inclusive work environment. Her passion in these areas led her to start her own consulting company, INSPIRE1.

Cynthia also believes in giving back to the community and is a board chair-elect of the Nashville YWCA and a major sponsor for the AMEND Together program. As a strong advocate for mentorship, she is a board member for Big Brothers Big Sisters of Middle Tennessee and has served as president of the board. In 2019, Cynthia received the Big Brothers Big Sisters Jimmy Webb Volunteer Leadership award. She is a member of Leadership Nashville and serves on the board of directors for Advancing Women in Nashville and the board of FiftyForward. She is a Co-Chair for the Women Business Collaborative Nashville Advisory Council. In 2020, Cynthia was named one of Nashville Business Journal’s Women of Influence celebrating Nashville women making history as a community supporter.

Cynthia is a Guest Mentor for our upcoming event, Mentoring Matters. To grab a spot at her virtual table where she’ll be speaking about coaching and leadership development to engage, empower and elevate, click here.

It’s evident that mentorship has had a major impact on Cynthia’s life and is still a large part of it now. We sat down with Cynthia to learn more about her journey and how her experiences as a mentee and as a mentor led her to pursue her passion professionally.

What led you to a career as an executive leadership coach and consultant?

I’ve been doing leadership coaching, mentoring and sponsoring for almost my entire career. I was an executive with Allstate Insurance company for 40 years until I retired last November. In my time at Allstate, one thing that I always loved was developing my employees, my leaders and myself. I encouraged them to find mentors who could help them improve at whatever it was they were trying to be better at and could give them additional support and guidance around the things they wanted to pursue. I loved watching them grow and reach their goals.

After I retired from Allstate, I took some time off to think about what my next step would be. I knew I was most passionate about leadership development and coaching and decided that I wanted to make a career out of it and that’s when I started my company, INSPIRE1. I saw the opportunity to live my dream and I took it. Through my company, I get to work with executives and professionals on leadership development, strategic planning and DEI and help people build bridges to other destinations they may have never even thought about before. Those were the things that I loved in my career and now I get to live my passion every day.

Working in corporate America put me in a position to be able to build a career as an executive career coach and consultant and so did my mentors. When I decided to start my business, I went to a lot of people in the community that I respected as entrepreneurs and asked them if they would coach me. They became my mentors through this process. I think it’s important for people to follow their passion, dream big and find a mentor who can turn those dreams into a reality.

How has mentorship impacted your professional journey?

For me, seeking mentorship has always started from me being in a situation where I watch the room to see who the person is that everyone goes to. At some point in time, I get enough courage to go up to this person and say, “I’m trying to do X-Y-Z, would you consider mentoring me?” And what I can tell you is that no one has ever turned me down. These people that I sought out as mentors ended up being the ones to help me get promoted and put me in the right place and on the right projects to get me to that executive level. Mentorship is a way to help people get to the destination they want. I think it’s not only important professionally, but personally too. This skill of seeking mentorship is so important for a person’s career. Sometimes we just need to get out of our own way and ask for it. You’d be surprised at what can come if all you do is ask.

How do you approach mentorship?

My approach around mentoring has always been to meet people where they are. I’ve always based how I mentor off the needs of my mentee. But no matter who I am working with, one thing I do ensure is that I understand the goal they are trying to achieve and put plans in place to get there. Whether my mentee and I are emailing, texting or meeting in-person, we keep in constant contact, so I can make sure we’re setting intentional goals around what it is that they came to me for in the first place and that we continue to move towards those goals.

What’s the best advice you’ve received from a mentor?

In my career, I’ve met some wonderful people, but when I think of my answer to this question one of my bosses named Dave Prendergast comes to mind. Dave would always challenge my staff and me, and there was one specific meeting where he gave me a poem by Robert Frost called The Road Not Taken. The poem talks about making a choice between two roads, a road traveled extremely often and a road less traveled. When he first spoke to me about this poem, he was relating it to certain projects my team was working on and how we were going to achieve specific business results. And I remember looking at him and saying, “You know what, I’m going to take the road less traveled.” And I believe this choice made all the difference. From choosing that path less traveled in my career, I had to chop down trees, cut grass and have my share of ups and downs. It wasn’t always the smoothest ride, but it was important that I set a new standard and direction for myself, so that I could pursue the things I wanted most.

In that meeting, my staff and I decided this would be our mantra, “Take the road less traveled.” We decided to set higher standards for ourselves and through that, we were able to achieve goals that we’ve never reached before. Dave has gone from my boss, to my mentor, and now my lifelong friend. The beauty of mentorship is that you can get to that place where they become your friend and at some point, even a part of your family.

What would you tell your younger self?

First, I would say to my younger self, Mom and Dad were right about a lot of things in life, so listen to them. I would also say to be your authentic self. It’s okay to be unique and different, so be authentic to yourself and to others. Next, I would say to always be kind to people. We especially need this in our world today. Then lastly, I would say to pay it forward and look for opportunities to help people in your community on their journey and through their struggles.

Cynthia Whitfield-Story is serving as a Guest Mentor for our upcoming event Mentoring Matters, a professional group mentoring and networking event taking place virtually on September 22 from 5:30 PM – 6:30 PM. At this event, you’ll have the unique opportunity to spend an hour with Cynthia or another prominent leader of your choice. Cynthia’s discussion will be around coaching and leadership development to engage, empower and elevate. All proceeds go to supporting Big Brothers Big Sisters of Middle Tennessee’s programs and services.

Buy tickets to secure your spot today at