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Interview with Business Leader - Heather Monahan - CEO of Boss In Heels

Updated: Sep 27, 2021

Heather Monahan is an American entrepreneur, a revered keynote speaker, a TEDx speaker and the founding CEO of Boss In Heels.

She was named one of the Top 40 Female Keynote Speakers for 2020 by Real Leaders. She is also a best-selling author of Confidence Creator, and Harper Collins Leadership is publishing her new book "Overcome Your Villain" in November 2021.

Heather’s has been featured on USA Today, CNN, Forbes, Fast Company, Gary V’s Audio Experience and The Steve Harvey Show.

We had the great pleasure of interviewing her, and we talked about her entrepreneurial journey, her book Confidence Creator, and her company, Boss In Heels.

Heather Monahan the Cosmo of Motivation

Hi Heather! It's an honour having you on the first cover of The Business Anecdote. We would like to start this interview by looking at your origin story. Please give us an overview ofyour background, initial career aspirations, when and how you got into entrepreneurship?

Heather: I grew up poor in Worcester Massachusetts. I was one of four kids and we were raised by a single mom who worked three jobs to put food on the table.

My childhood taught me that I never wanted to be poor so I started working at a very young age. I started with a paper route then working at diners and fast food restaurants and eventually becoming a waitress and bartender.

When I graduated college I got into sales, first in the wine business and then in radio. I was so focused on chasing a pay check, I really didn't think about much else.

That led me ultimately to becoming a VP of Sales, and then becoming a Chief Revenue Officer.

I had an incredibly successful career in corporate America, however I never felt fulfilled. That is why I eventually launched my personal brand which the company I worked for hated. They threatened me and told me to take it down. I knew what I was doing was trying to help others, and there was no negative intent so I refused to shut it down.

Eventually within a year I was fired. That is how I began my journey to becoming an entrepreneur.

Heather Monahan

What’s your book “Confidence creator” about, and what’s the inspiration behind it?

Heather: The inspiration behind my book comes from getting fired after a 20 year successful career in corporate America! That was an incredibly low moment for me, not knowing where my next pay check would come from. I had given so much of my life to the company that I worked for, and I had attributed a lot of self-worth to my title, pay check and team that I had built. I felt like I had lost everything when I got fired.

That ultimately reminded me of other low moments in my life like when I got divorced, and when I led my company through the recession, and countless others experiences. Thinking of all of those low moments helped me to remember how I eventually leveraged them to create confidence within me and bounce back.

My book Confidence Creator is a compilation of my low moments, how I learned to leverage them to create confidence, and how the reader can do that too.

Confidence Creator by Heather Monahan

Talk to us about the “Monahan Method”. How can this be used to elevate oneself in business and life?

Heather: The Monahan Method are the steps that I took to elevate myself in corporate America.

They include a variety of strategies like pitching myself for a job that didn't exist and closing that deal because I put myself in the other person's shoes ahead of time to anticipate their potential objections.

Another key strategy I share is to never take direction from someone who hasn't been where you are going. It also includes one of the most important lessons I have ever learned, Never take a No from someone who cannot give you a YES!

How have you used your brand to advocate for women empowerment, equality, diversity and Inclusivity?

Heather: In 2015 the Florida Diversity Council presented me with the Glass Ceiling Award for my work to advance women and advocate for diversity and inclusion in the workplace.

I absolutely use my voice and my brand to speak my truth which certainly includes advocating for equality, diversity and inclusion for all. For eight years I was a member of the Board of City Year Miami, working to empower and support at risk minority youth in our city. I was not only a board member but I also personally contributed thousands of dollars to the charity to help these children.

I have continued that work as a champion for women and minorities at large. Most recently being appointed to the Board of Directors of Healthlynked as their first and only female director. I believe glass ceilings are meant to be shattered and I am hoping that the small part that I contribute will help to pave the way for others, just like so many did before me.

Let’s talk about Boss In Heels LLC. Where did the idea come from and how did you validate its value generating potential?

Heather: The idea came from me growing up and only having one type of boss: a white male in his fifties wearing blue pant suits. I never questioned this when I was younger, it was simply who the boss was wherever I worked.

As I became more experienced I realized I had just as much potential as any male counterpart I worked with, so I started pitching myself for advancement. I advanced countless times and I finally reached the c-suite. The idea for "Boss In Heels" came from my life experience and the realization that a boss can look any way you want.

As a new entrepreneur I had no idea how to evaluate revenue generation potential, so I leaned on what I did know. I knew I needed to move fast and develop a product to sell. That is where my book "Confidence Creator" came from. Then when I was out selling books I stumbled into the speaking business. That exploded revenues for me until the pandemic hit. Then I looked at the messages people sent to me to see what problem I could solve for people from my computer. I found messages asking me if I ever offered consulting or coaching, so I put a post up on Linkedin announcing my new consulting and coaching business.

I had no idea what to charge but I offered a 100% money back guarantee because I knew I wanted to do a fantastic job for my clients. I charged too little at first but I amassed so many amazing reviews of my work and increased my prices. The whole process has changed immensely over the last three years and it continues to evolve as my goal is to drive revenue for my company while delivering products and services that help my clients achieve their goals.

What key challenges has “Boss In Heels” faced to date, and how have you navigated these?

Heather: I have faced countless challenges and more fails than I can remember! One of the big failures I had was partnering with Perry Ellis to launch a clothing line. We worked on it together for almost one year, only to be told "No" by HSN when we delivered the product line.

That was incredibly frustrating as it was my first year working for myself and I was sure we would sell the line into HSN with great success.

Next, I partnered with a skin care line to launch my own product and that fell apart as well. Then, I met with 5 different agents to bring my second book to life and none of those partnerships materialized. However, that was a major blessing in disguise, because it led me to my agent I am with now, and my deal with Harper Collins Leadership for my new book "Overcome Your Villains" which launches this November.d

Heather Monahan and Steve Harvey

What are your future plans for the “Boss In Heels” brand, and does the COVID-19 pandemic pose a constraint to these plans?

Heather: Absolutely! Covid-19 has made the last year incredibly difficult as I am a single mom raising a thirteen year old son in an apartment building.

For much of the year we stayed in our apartment to stay safe where I worked and he went to school virtually. It was incredibly isolating and my number one revenue generator the speaking business nearly disappeared overnight.

However a few amazing opportunities did arise from this awful year. I was brought on to teach Professional Selling & Sales Leadership at Harvard which was completely unexpected. Then I met someone in my coaching program that eventually nominated me for my new Board position with Healthlynked. I also used this time at home to finish writing my second book which will be out this November.

As far as future plans go, I am open! I know that I will continue taking major risks and moving my business forward to help others. However, this year taught me that there is no way to predict the future so simply trust yourself to figure it out along the way and enjoy the ride.

Before we conclude the interview, we would like to know what advice you have for female entrepreneurs aspiring to start a business?

Heather: Just start! So many women are paralyzed by fear or more specifically a fear of not being perfect. There is no such thing as perfect, the key is to move fast and break things.

Speed to market is critical in business and I can promise you this, whatever idea you have, someone else has it too, so get moving. I always think to myself, "Do I want to be the author of a book with 3 errors in it or the woman on her death bed telling her child about the book she never wrote."

That's it, once I think about that, I start taking action and figure it out along the way. That is the key! Successful people don't know the how but they trust themselves to figure it out along the way. Don't be afraid to ask for help! Strong people ask for help.

We have come to the end of the interview and would like to thank you participating in it. We look forward to the launch of your new book in November titled "Overcome Your Villains".

Heather: Thank you


You can pre-order Heather’s new book “Overcome Your Villain” on Amazon.

Overcome Your Villains by Heather Monahan

This interview was originally published in Issue#1 of The Business Anecdote magazine

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