Men at Work: Advancing the Cause

Ryan Specialty’s Michael Blackshear is a DEI leader who knows that relationships are as important as data

By Ijeoma S. Nwatu

Photo by Andrew Collings.

As a young Syracuse University graduate in upstate New York, Michael Blackshear decided to venture into the insurance world, and the result is a career spanning more than 30 years in professional financial services in the areas of ethics, compliance, and risk management. Blackshear is senior vice president, chief compliance and privacy officer for Ryan Specialty, tasked with maintaining and developing an effective compliance and regulatory risk framework. Named one of the 2022 Most Influential Black Executives in Corporate America by Savoy magazine—a leading publication for Black culture, business, and entertainment coverage—Blackshear considers himself a craftsman in his work. He is also intentional about managing relationships. “You have to figure out your passion and what you enjoy,” he says. “For me, I’m already living that, because I’ve been deliberate in my career. If you don’t spend time managing relationships, regardless of how smart you are, you’ll have challenges being successful.”

In 2022, Blackshear spearheaded a newly formed diversity, equity, and inclusion effort charged with promoting DEI at Ryan Specialty and growing strategic partnerships within the insurance industry and with the communities that are home or workplaces for Ryan Specialty teammates. “It is my opinion that the insurance industry is still struggling with reaching people of color, women of color, and Black women [in particular],” Blackshear says. “The aim of an internal DEI focus is to authentically connect with and invest in people, with the goal of eventually becoming an industry leader in DEI.” While he admits he does not have all the answers, he roots his approach in data collection and analysis, which has and will continue to inform and shape his strategy and outreach.

Blackshear holds several degrees, including a bachelor’s in finance from Syracuse University’s Martin J. Whitman School of Management; an MBA from the Maurice R. Greenberg School of Risk Management, Insurance and Actuarial Science at St. John’s University; and a law degree from Fordham Law School. In addition to serving as an adjunct professor at Fordham Law School, Blackshear launched a $100,000 endowment in 2023 to support future generations of underrepresented students and increase diversity in the field of law. This was to honor his late father, the Honorable Cornelius Blackshear (former federal bankruptcy judge), who also attended the law school and passed away in 2021.

Blackshear also holds a certificate in managing ethics in organizations from Bentley College, and a certificate from Loyola University Chicago at the Diversity, Equity, and Inclusion Leadership Institute.

Diversity Woman: Tell us about your career trajectory and what you are most proud of.

Michael Blackshear: I have been in the insurance industry for over 30 years with a concentration in ethics, compliance, and risk management. I assumed additional responsibilities at Ryan Specialty as the head of diversity, equity, and inclusion during the summer of 2022.

I am most proud of seeing the growth and impact I have had on others’ careers. It is my belief that we all have an obligation to build and guide our future leaders.

DW: How does your firm advance women into leadership positions?

MB: We can do a better job. Our industry can do a better job. It is not enough. The foundation of our DEI program is to have an inclusive and equitable workplace where all employees are valued and evaluated on their performance and contributions.

It is about developing a practice where we give everyone what they need to be successful, where we ensure more visibility of diverse talent and actively move everyone closer to success by making systemic changes that level the playing field. We are still on our journey.

DW: What advice would you give mid-career women of color who are frustrated by the pace of their advancement into greater leadership? What steps should they take or avoid?

MB: Look for sponsors and allies, those who will be your advocates, particularly in the insurance industry. They don’t have to look like you, but they do have to be ready to advocate on your behalf. Identify a sponsor who will provide you with direct, honest, and critical feedback on how best to navigate your career and organization. This individual should be someone you trust, respect, and who has demonstrated a level of success.

Advancement is more than just being the smartest or most technically skilled practitioner in the room; that is just
one ingredient to success. It is also how well you manage, develop, grow, and maintain relationships. Do not wait for a favor or an ask; nourish relationships. Avoid beating yourself up when you fail. Have the courage to take risks. Lean into the storm.

About avoidance: Don’t let failure distract you from your goal. There will be failure, disappointment, and fear. Embrace these emotions to help strengthen your leadership style.

DW: You recently took on the task of promoting DEI at your firm. What does DEI mean to you, and how do you experience inclusivity within a workplace or industry?

MB: DEI means building a culture and environment where people can be their best selves and do their best work. I believe our firm, along with our industry, is still in the beginning stages of our maturity model. We have done a good job with recognizing, valuing, and leveraging our different perspectives and backgrounds to drive needed results. However, we still need to enhance the “belonging” aspects of our DEI framework.

DW: If a professional, particularly a woman of color, has the credentials and performance for a promotion yet doesn’t get it, what should that person’s next steps be?

MB: First is not to view this situation as a failure, but a learning, and begin to understand what those other factors were, other than “credentials” and “performance,” that were considered as factors for that promotion. 

It has been my experience that, for certain roles, if you make it into the top three, you are all well qualified for that role, and sometimes it is something else that will set you apart.

Advice I would recommend for women of color would be to take a moment to gather your thoughts, debrief on the process with someone you trust, get specific feedback, share with your trusted inner circle for a candid perspective, and do not let this experience define your value. Only you can define your value. 

DW: How should people put their full selves into their work and workspaces even if the company culture might not value DEI or is behind in prioritizing.MB: It is my belief that all organizations should strive for an inclusive and equitable workplace where all employees are valued and evaluated based on their performance and contributions, creating a culture where people can be their best self and do their best work.

I am realistic that my belief is not shared by all, and that our collective DEI journey will create conflict with some, navigate us through tough and uncomfortable conversations, and elicit emotional reactions for those who are directly impacted by our collective DEI journey. Nevertheless, we should all embrace the storm . . . since all storms will end. If something does not challenge us, then we will not evolve and change.

Be bold and bring your full self into your workspace, regardless of the culture. You are that catalyst for change.  Be honest with yourself about what you want to bring and who you want to bring it to. And last, see how you can support your organization’s efforts to move DEI forward. 

DW: Share a lesson or a piece of advice that has helped to shape your leadership style.

MB: Be aware that there will always be someone smarter than you in the room. Have the courage to tap that intellect and empower your talent so you can execute the necessary changes to see  real results. Leadership is about empowering others and trusting the talent in front of you. DW

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