Under Pressure: The Challenges of Leading (and liberating) as a Black Woman

Way to Win
4 min readAug 25, 2023

An analysis of workplace culture using concepts of design dynamics, and a roadmap to leverage organizational leadership as a means to liberate others.

By Eboni Speight
EVP and Chief Operations Officer for Way to Win

Workplace culture in the last decade has changed dramatically, and the pace of change became break-neck with the rise of MAGA, the onset of COVID, and the national reckoning on race. Change is hard, but it is inevitable. People of color, especially Black women, have endured harmful workplace practices for too long, forcing them to learn how to navigate and negotiate corrupt systems while not losing their identity and sense of self-worth in the process. My 20 year track record in the nonprofit industry with expertise in finance, human resources, and organizational development, have allowed me to identify core patterns I call proof pressures that work to undermine Black women in the workplace.

In the world of design dynamics, proof pressure is the maximum amount of force that can be applied to an object without causing significant damage. In the workplace, a similar phenomenon occurs where biases and microaggressions are experienced as emotional pressure, becoming yet another burden women of color must carry, while living up to impossible expectations and avoiding menacing assumptions about how they got the job in the first place.

It is hard to feel fully free and empowered to perform with excellence under these circumstances, yet many women of color manage to do so despite these obstacles, and they make it look easy.

A deeper analysis of proof pressure reveals two different types of these workplace challenges: error proofs and power proofs. Error proofs are unfair organizational pressures that force leaders to prove why they deserve the role they are in, or prove their competencies and expertise before being believed or accepted. It can also take the form of colleagues being hyper critical of your work, looking to blow minor errors and missteps out of proportion to undermine your credibility. Power proofs are unfair pressures from colleagues and peers who consistently challenge or delegitimize work products, wins, or outcomes, presenting a direct challenge to your own power or authority within the organization.

Throughout my career, I have found that when joining organizations as an executive, harmful interactions like those described above could start as early as week one. They often manifested as microaggressions, and discreet and even overt challenges to my competency and leadership ability. Even with decades of experience, my record of accomplishment and achievement would never be a legitimate endorsement of my capabilities, as it always is for white men (and in many instances, white women). If individuals have the audacity to treat me in this way — a Black woman who occupies a leadership position — one can only imagine the horrors experienced by women of color who are just starting out in their careers. This constant barrage of doubt, insubordination, and abuse creates proof pressure which can show up on day one, and last the entirety of a career.

Proof pressures have forced me to work longer hours, take on more responsibilities, and gain wins faster without recognition or due compensation. This is a common reality for Black women in leadership roles, and serves as both an ode to their tenacity and a clarion call for change. These phenomena have challenged our leadership team at Way to Win to constantly evaluate our own workplace practices and culture to root out this sneaky form of bias and workplace harm.

As the workforce continues to diversify and women of color find themselves securing jobs across organizational power structures, our new challenge as leaders and allies is to deconstruct these workplace harms, and foster an environment of belonging so that all employees can thrive.

To effectively confront these harmful practices, Way to Win has committed to meaningful and continued investment in our organizational culture. This calls on us all to acknowledge the workplace harms facing people of color, and commit to restoration if ever they appear. Way to Win is a majority minority organization with more than 70% of our staff identifying as a person of color. While diverse organizations tend to outperform their less diverse counterparts, we know that simply having Black and Brown faces in the organization isn’t enough. These individuals must feel empowered and encouraged to show up as their full selves. They must be encouraged to exercise the full panoply of their abilities. They must be encouraged to be free, and to lead. If this ethos was shared by more companies and organizations throughout the workforce, we can turn the weight of oppression into a collective force for change. And in doing so, we can hasten economic liberation for women of color in the workplace with a more conscious organizational leadership. Earlier I mentioned that Black women have been able to perform despite the burden of proof pressure. Imagine what could be achieved if we got rid of it altogether.

About the author: Eboni Speight is the Executive Vice President and Chief Operating Officer for Way to Win, a national strategy tank and donor collaborative that has played a key role in supporting progressive initiatives across the country. Eboni has over two decades of experience working with and leading nonprofit organizations, and is a nationally recognized expert on workplace culture, organizational leadership, and diversity, equity, and inclusion.



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