Business Leaders Willie Jackson Podcast

Business Leaders Having Uncomfortable Conversation About Race

By David Hassell, CEO of 15Five

Since late May 2020, there has been an accelerated evolution of the conversation around race in America and globally. With this latest round of high-profile deadly police encounters with Black Americans and the massive response to it, many of us are at a loss about how to best respond. Business leaders especially may be avoiding the conversation, afraid to risk their futures because they say the wrong thing. 

Shane and I welcomed Willie Jackson back to the podcast to continue the important conversation we began last time. Willie is a keynote speaker, consultant, and facilitator at ReadySet who helps leaders and organizations advance vital conversations in this arena, and he advises as a preliminary step to stay in your discomfort. When you get curious about that discomfort along with a willingness to be vulnerable and make mistakes, that leads to meaningful conversations that may in turn lead to long-lasting change in a country confronting its systemic racism. 

Click here to listen to more podcast interviews with thought leaders and experts.

How business leaders can create sustainable change

We recognize that this is a time of opportunity, and these opportunities go far beyond simply issuing statements of support and solidarity. We can use the current situation to make sure that our organizations have an equity-informed view of how they operate that leads to sustainable shifts toward inclusion.

Willie shares that being an ally is not enough. It takes more than just doing something within your comfort zone to feel like you’re on the right side of history. Actual meaningful change takes moving from the noun of “ally” to the verb of “accomplice”—taking action to restore equity and justice to a system that is sorely lacking in those fundamentally important principles. This means examining power and privilege and being vocal, even if it comes at personal cost.


In this episode we also discuss:

• Why it may feel awkward to discuss race and how to address these feelings

• Embracing the discomfort of not knowing what to say or do, getting informed, and taking the risk to speak out from a place of vulnerability and knowledge

• Creating the conditions so that your organizations organically develops into an equitable environment

• Acknowledging the social and historical context that affects everyone

• Being an accomplice rather than an ally


The following is a transcribed and edited portion of the Best-Self Management Podcast Episode 24, “Business Leaders Having Uncomfortable Conversation About Race w/ Willie Jackson”:

David: I’ve seen a lot of dialogue in social media where somebody comes out and says something, they’re clearly well-intentioned, someone calls them out on it, then they get defensive and say, “But wait a minute, my intentions are good.” And so that, that piece, I think, a key to helping people unwind so they can have the courage to go out and have conversations.

You want to be well intentioned, but you also have to recognize if you have impact it is your responsibility to own that impacts. So how do you help people navigate that really tricky emotional terrain and the fear that it comes along with?

Willie: There is such pressure right now for leaders and companies to make public statements about these issues: “We stand in support of Black Lives Matter”, or “We support inclusion in all its forms”. There’s a very lively conversation, and I know this because I’m supporting half these companies. There’s a lot of energy around how many of these statements don’t feel good enough? It’s like, “No, you need to call out white supremacy. You need to be anti-racist. You need to say ‘intersectionality’.” And I just picture people on their computer saying, “Okay, okay, okay!” And it feels like a hostage situation.

There’s such a shift of perceived power and influence that a lot of people with power are being extremely deferential to some of these voices—people who code as a minority identity. And some of that comes from a good place in righting historical wrongs, but we have to figure out a way of sustainably working with each other. And I think that involves taking the long view, which is to say this isn’t just about what we do before and up until Juneteenth or July 1st or what we do in Q3 and Q 4.

This is about how we fundamentally bake into the DNA of the company, an equity-informed view of what it means to attract, retain, promote, and elevate talent within our organization You want a natural process of people saying,”Hey, friends of all backgrounds, this is a fantastic place to work. I’m a better version of myself by working here and would love you to join me.”

If that can happen organically, if we can create the kinds of conditions where that can become true, that’s how we create sustainable shifts around inclusion instead of these more tokenistic. window-dressed tweets because you feel social pressure to. You may say, “okay, we have to do this”, but then there’s a disharmony between the actual work that’s involved in the day over day.

Willie Jackson is a keynote speaker, consultant, and facilitator at ReadySet who helps leaders and organizations advance vital conversations that unlock connections across differences. His belief in the transformative power of media to change narratives led him to found Abernathy, a magazine for black men backed by companies like Mailchimp, Atlassian, and WeWork. Willie served as Founding Technical Lead of Seth Godin’s altMBA program for high-performing individuals who want to level up and lead, and CTO of The Domino Project, an award-winning publishing company founded by business luminary Seth Godin and powered by Amazon.com. Willie is an avid houseplant aficionado and loves to spread the gospel of self-watering planters whenever possible.

David Hassell, CEO of 15Five

David Hassell is a business columnist, speaker, and serial entrepreneur who believes that when leaders institute cultural practices that support each person in being and becoming their best self, high performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David created the science-inspired Best-Self Management methodology that helps leaders and managers address the hidden factors that stimulate sustainable growth and development – things like intrinsic motivation, strengths, and psychological safety. David has been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.

Shane Metcalf is a keynote speaker on building a world-class workplace and one of the world’s leading pioneers in the space of cultural engineering and positive psychology. His insights have been featured in Inc, Fast Company, Washington Post, and Tech Crunch. As the Co-founder of 15Five, Shane and his team support HR Executives with data-driven continuous performance management. 15Five has won numerous awards for its company culture, including the prestigious Inc Best Workplaces award, and is ranked #3 in the U.S. on GlassDoor. Follow Shane on Twitter and LinkedIn.

Image Credit: Nathan Dumlao on Unsplash


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