We recently connected with Holly McIlwain and have shared our conversation below.

Holly, thanks for taking the time to share your stories with us today We’d love to hear the story behind how you got your first job in field that you currently practice in.

My first job was shucking corn in the back of my daddy’s pick up truck, in a bank parking lot in our small town. I cleaned houses with my mom.
I worked as tanning bed cleaner. It’s true. The 90s were weird.

Every job that I ever had required me to get over myself and think about the person I was preparing space for.
It’s like that in the field of People Operations (formerly known as HR!).

My journey to an “HR” title was bumpy, for sure. I spent 15 years in the nonprofit sector — convincing people to give two prized and limited resources — time and money — for the purpose of something bigger than themselves. Connecting people with talent to a purposeful project was invigorating. And heart wrenching. I’ve always been the kind of person to walk alongside people, and sometimes those pathways are bumpy. When it was time for me to leave nonprofit work, I walked into a management consulting firm and told my story. I found a temporary space, learned the art of being uncomfortable, and worked out the ways to align people with THEIR missions. That’s how the real fun began.

Over the next few years, I took brave step after brave step. I was mentored by an amazing woman, who created Winner Partners, a place where I hang my hat every chance I get, and had the courage to create books, platforms, and my own nonprofit, the Brave Women Project. In all my work, in all my dreams, I come back to this — people matter. When we are willing to be humbled in order to create the most perfect place for someone, the time is well spent and the rewards are multiplied. Do one brave thing every day. Do it scared. Let the action bolster movement.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

For years, I have served as a helpful role to those seeking inspiration, help, or advice. In 2000, I finally decided to own that role and be intentional about it. I started writing about my passions, my thoughts, and curious wonderings about our society. I founded the Brave Women Project with a mission to give others a taste of what goes on in my mind, and it has been a wild success ever since.

I wrote “For She Who Leads: Practical Wisdom from a Woman who Serves” as a guidebook and quick start for someone hoping to target their talent to the journey ahead. It has become a 24 hour retreat the I offer, and I get to accompany smart women on their brave journey.

As a constantly curious wanderer, I leverage my training and the usage of Behavior Assessments as part of Team Building, Dynamic Onboarding, Coaching, and Leadership Development. I’ve been trained and certified by Gallup, DDI, and TTI, which makes me a trusted partner and provider. I get to help people unlock their potential, with DATA to back it up! It’s super exciting work.

Most of my industry work is focused around Dynamic Onboarding & Training Experiences. My history in nonprofit taught me just how precious employee time is, and that dollars must stretch. Bringing together the two with memorable, purposeful, and ‘sticky’ experiences is both art and science. I will work with organization leaders and managers to create programs that reflect the proclaimed values and mission, while meeting the engagement needs of employees. I work alongside leaders to create experiences and opportunities for stakeholder feedback and options for DIY sustainable programs. (People leaders love that part!)

Perhaps my most significant contribution to industry as a people and culture enthusiast is Thoughtful Facilitation.
Sometimes, it takes an outsider to help foster the space for brave conversations. As Founder of Brave Women Project, and co-author of “For She Who Grieves: Practical Wisdom for Living Hope”; I help groups, teams, and organizations have the important conversations in the context of psychologically safe environments. Facilitation works best in the context of trusted relationships, so this would be another one of those project based offerings that I love.

Of all my work, I would say that I’m the most proud of For She Who Grieves — borne out of broken-heartedness and tragic loss, growing in the space of a nurturing friendship, and brought to life through the Brave Women Project.

What’s a lesson you had to unlearn and what’s the backstory?

Unlearning the question “What if I’m not enough” was hard.

The battle of ‘enoughness’ has been brutal.

Understanding how Imposter Syndrome impacts high performing women was part of my research for “For She Who Leads” and it is a lesson that I have to relearn occassionally.

I spent a lot of time in predominantly male industries, with strong male leadership making critical decisions. I had to learn how to communicate effectively, without diminishing my passion and compassion, in order to influence change and improvement. There were many days that I felt I needed to earn my place at the leadership table, although I had been recruited for the role I was in. Sometimes, brave action is unplanned, and just the thing that makes it possible to overcome ‘not enough’ and believe that I was right where I needed to be. For me, it was walking in to a senior leader’s office, who I had been reassigned to work with, and presenting my portfolio. He didn’t hire me, he didn’t recruitment, and he didn’t really know me. So I brought my portfolio, and walked him through my history. I proactively shared my suggestions for how my talent might align with his vision, and articulated ways that I could help him achieve it.

I wasn’t asked to do that.
It was a risk.
I was scared.

And it resulted in taking a chance, and he opened doors for me that changed my life.
He was a really smart man. He bet on me.

Putting training and knowledge aside, what else do you think really matters in terms of succeeding in your field?

There’s a statement that guides my daily life and decisions:

If you live your life according to your values, you will always have the life you deserve.

As a leadership practitioner and employee educator, I have the privilege of getting into very personal spaces with the people I serve. Business is pretty personal, after all.

The reason that I am successful is because I am committed to an integrated life — to living my life according to my values. I speak the truth to power. I honor the journey of others. I target talent to overcome obstacles. I coach as I live, and it is my brand. Because I live like this, work is easy. And making tough decisions is bathed in bravery.

Contact Info:

• Website: https://www.hollyjoy.info/workwithme
• Instagram: https://www.instagram.com/forshewhogrieves/
• Facebook: https://www.facebook.com/winnerpartners
• Linkedin: https://www.linkedin.com/in/hollyjoymcilwain/
• Other: www.winnerpartners.net www.bravewomenproject.com

Image Credits
headshots : dominique murray photography