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Glenn Singleton Speaks Up

Founder & CEO, Courageous Conversation™ & Partner, Work Wider

We could not be more excited to launch The Wider View with this first interviewee, our very own advisor Glenn Singleton. Glenn has devoted over thirty years to constructing racial equity worldwide and developing leaders to do the same. He is also the author of COURAGEOUS CONVERSATIONS™ ABOUT RACE, a groundbreaking book recognized for effectively engaging, sustaining and deepening interracial dialogue. We are honored to have this opportunity to hear from him directly.

Finish this sentence: I wouldn’t be where I am today if it weren’t for ________________.

The perseverance of my elders and Ancestors. So much is said about the slow progress of achieving racial justice and equality in the United States.  Thus, I draw strength in recalling the harrowing experiences of racial inhumanity which those who came before me have endured. While BIPOC have yet to taste the sweet flavor of victory, we certainly have also come a very long way!

Resumes highlight professional and educational achievements. Which one of your life or personal experiences deserves to be on your resume?

Glancing at my professional resume, one instantly discovers that I have attended the finest of American academic institutions; from Hilton Elementary School #21 in Baltimore City, to The Park School, University of Pennsylvania, and Stanford University. Despite this, I continue to be met by skepticism, doubt, criticism, and outright dismissal by the larger society when I share my honest life learnings derived from these schools. NO degree, title, position or level of seniority has ever overshadowed the fact that Race Matters Most. Race was used to create the economic, political, and social foundations of our nation. An ability to persevere and triumph in my education, profession and life, more generally, despite ubiquitous racial injustices that I experience, deserves a spotlight on my resume.

What qualities do you look for when hiring someone on your team? What qualities do you avoid?

I try to avoid hiring lazy people. By this, I mean people who prefer not to carry out their own intellectual, emotional, and spiritual labor. Those who are quick to ask me for a solution, what they should do, rather than roll up their sleeves and join me in solving the problem at hand, exhaust me.

I prefer to be on a diverse team where people are curious and efficacious. I believe that teams thrive when there is expansive diversity of experience, belief, perspective and behavior. Not only do diverse teams offer us insights into the world which are not our own, but diverse teams also enhance our capacity and desire to wade into nuances and the discomfort afforded to us when diverse workers are present. Thus, I aim not to rehire myself.

One tangible step that every leader of an organization must take is to embrace feeling uncomfortable.”

What’s one piece of career advice you wish you could give to your younger self?

Growing up in a society where people are categorically granted permission to question my legitimacy and wisdom as a Black man, I would have told my younger self to “trust and believe in your own understandings of who you are and how you believe the world functions.” Due to the decades of self-doubt I endured, I am not as far in life as I could have been had I developed deeper self-confidence at an earlier age. This is a valuable lesson that I try to pass on to younger generations of BIPOC.

Which three books, podcasts, or new sources do you think everyone should read? Why?

First, in all humility, I believe everyone should read my two books; Courageous Conversations about Race and MORE Courageous Conversations about Race. Until we learn how to talk about race in a manner that is true to the topic and authentic to who we are as human beings, we will never achieve racial equality…or any other type of equality for that matter.

The third book should be a reread of your favorite book, but this time viewing through your newfound Courageous Conversation knowledge, skill, and capacity. For me, that third book is James Baldwin’s The Price of the Ticket, a collection of poems and short stories by the man I believe to be one of the greatest writers of all time.

Diversity, equity and inclusion is front and center right now. How do you express your commitment to diversity, equity and inclusion in your personal and professional life?

When I launched my company nearly 30 years ago to address systemic racial inequities in schools, never did I imagine that it would take so long for my society to recognize the need to uncover the role which race and racism play on institutional outcomes and human progress. Today, my central challenge is to stay focused, keeping my eyes on the prize. In my professional life, I express my commitment by continuously reminding those who are just arriving to the party, that they must do their own personal race work with family and friends before they can truly be a force in transforming their organizations. In my personal life I express my commitment through my unrelenting quest for equality in every aspect of my life.

What’s one tangible step every employer should take to help build a more representative organization?

One tangible step that every leader of an organization must take is to embrace feeling uncomfortable. Increasing organizational diversity and sustaining that diversity requires leaders to learn to facilitate awkward conversations about racial equity and inclusion, conversations which then need courageous leaders to examine and address policies and programs that yield racially disparate outcomes. Effectively leading through these sometimes painful conversations and transformations is the hallmark of an exceptional anti-racist employer.

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Glenn Singleton
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