Meet Randy Both

What called you into this work?

My life experiences have given me a heart to help others find joy in who they are, what they choose to do for a living, and how they engage with others to connect and build community around their work. Hard work, parenthood, executive management, success, and loss have all contributed to enabling me to come alongside others and help them embrace growth opportunities. 

It all started for me when my uncle (a New York Broadway playwright) wrote to me as a youthful, ambitious leader. We corresponded frequently from opposite sides of the country and the world. His, unbeknownst to me, deathbed parting shots were soulful and challenged me to grow where he knew I needed to grow. He pushed me to think more deeply about the meaning of work, my work, and the work of others who came into my life.

Twenty years after his passing, I was offered the opportunity to coach executives at Microsoft through a company called LeadersThrive. I had been unofficially doing this for 15 years in the corporate world and 10 years prior in athletics. More recently, Henley Leadership Group took over the coaching and facilitation programs that I had been doing. I’ve been inspired and have grown through the mentorship and partnership of the entire Henley team.

In short, I partner with individuals who want to grow and improve, striving to be better than they were yesterday. I’ve worked with CEO’s, Vice Presidents, Senior Leaders, and individuals who are just beginning their work journey. I lead leadership development programs, facilitate team development, and coach small groups, as well as work one-on-one with individuals to help them develop into the leaders they aspire to be - the leaders others want to follow. 

What is your approach to coaching and leadership development?

We’re all called to lead from time to time; some of us are called to lead most of the time. Our ability to do so successfully is limited by our curiosity, humility, and willingness to connect with others in a positive and authentic manner.

From my experience, leading requires an individual or team that wants to follow, and while there are many ways to force people to follow, long-term leadership success requires trust from followers. Trust is built when people feel safe enough to entrust someone else. I work with young and seasoned leaders to help them understand the behaviours that are building or destroying trust. With this baseline, I work with individuals to develop constructive approaches that improve their work processes.

What qualifies you to do this work?

• Certified Leadership Potential Coach - Korn Ferry 

• Executive Coach/Facilitator - Microsoft (7 years)

• Executive Leadership - Microsoft (11 Years), Startup CEO (5 Years), Small Business Owner (4 Years)

• Plus: workshops, retreats, trainings, counselors, and therapists

What are you exploring and learning these days?

I’m exploring the rapid evolution of AI in the context of being an authentic leader. I’m committed to examining how to sustain trust in a quickly changing workforce. Over the last two years, I’ve been helping leaders rewrite the narrative of their value and embrace AI as a key factor in how leaders can do more with less. While many are walking in fear, I’m helping align skills and behaviours that build trust and increase productivity.

What are you proud of personally?

I’m proud of the work that I’m doing with my life. I’ve built an amazing community, friendships, family, and businesses. I take each day as a new opportunity to learn and grow and build upon successes and failures…mostly the failures, as that is where we all can do better.  I have three children who are starting their independent lives, and it’s my biggest joy to see them thriving.

What are you proud of professionally?

I’m proud of the evolution. I raced as a younger corporate executive and worked hard, smart, and fast. I worked with a very small team to invent the smartphone, brought it to market worldwide, and lived to tell the tale. I’ve restructured entire companies and helped them grow through challenging times, including bankruptcy. I’ve taken over a failing executive team and transformed company strategy and product development by building trust and executing on consistent promises. I’ve started a company from nothing and built it into a thriving business with a strong leadership team.

What grounds your work?

I’m grounded in my faith and my belief that we are all called to do great work. When we find it, we need to learn how to embrace it and grow with others who want to help us deliver it.

I know what it feels like to need the insight and help of others to help me grow, and it brings me joy to do that for others.