Business Leaders Having Uncomfortable Conversations About Race w/ Willie Jackson
Best-Self Management · 46 minutes ·

Business Leaders Having Uncomfortable Conversations About Race w/ Willie Jackson

Since late May 2020, there has been an accelerated evolution of the conversation around race and our roles as human beings, citizens, and business leaders. 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 because they are afraid to risk their futures because they said the wrong thing. 

Today, we welcome Willie Jackson back to the podcast to continue the important conversation we began last time. More and more difficult conversations are happening across the country and around the world that require vulnerability and discomfort. Staying in the discomfort and being curious about it along with a willingness to be vulnerable and make mistakes, will lead to meaningful conversations that may in turn lead to long-lasting change in a country drenched in systemic racism. 

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.

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.

How can you as a leader model become an accomplice in creating equity and inclusion in your organization? Let’s talk about it in the comments on the episode page!


In this episode

  • 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 our organizations organically develop into equitable environments
  • Acknowledging the social and historical context that affects everyone
  • Being an accomplice rather than an ally



“Many of us are ill-equipped to navigate the conversation at all. I think that it’s such an honest thing to say that it just feels awkward to name it. A lot of the conversation right now is about not burdening people of color in general, and black people specifically, about the dialogue.” [2:55]

“Talking about race is awkward. It is challenging. Like anything - running a business, making money, playing the piano - it takes practice.” [3:51]

“Acknowledging and repairing harm is a key part of how we can show up for each other.” [21:31]

“In order to fully participate at a baseline level, we might need to radically reimagine how we’re thinking about performance reviews, the stereotypes that get perpetuated, the training that managers get, because people don’t leave companies. People leave managers.” [27:12]

“It’s natural to want things to go back to normal. My fear is that we will forget that normal for a lot of people is suffering. It is fraught, and it brought about the conditions for the uprising that we’re seeing right now.” [31:16]



Find Willie Jackson online


Upheaval by Jared Diamond

Seeing White

Slavery by Another Name by Douglas A. Blackmon


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