Interview with Michele Meyer-Shipp, Esq., CEO of Dress for Success Worldwide

Posted March 5, 2024

We sat down with CEO and Board Member of Dress for Success Worldwide Michele Meyer-Shipp, Esq., to discuss her career and leadership lessons she’s learned along the way. From a practicing lawyer to the Chief People & Culture Officer at Major League Baseball to transitioning to nonprofit leadership, Meyer-Shipp offers insights and advice for anyone considering making the leap from for-profit to nonprofit work and for existing leaders to become even more effective. Watch the video or read the transcript below for interview highlights.


Tell us about your career path up through joining Dress for Success Worldwide

Meyer-Shipp: I was an employment lawyer and I was very interested around helping people, you know, navigate through tough employment situations. That ultimately led me to discovering that I did not like litigation. I did not like the fight of litigation, but instead I actually liked helping companies and employees navigate the employee lifecycle. So everything around talent recruitment, talent development, talent support, mentorship, sponsorship, etc.

That took me on a journey of working in a host of HR and diversity leadership roles, where I really helped companies make sure that they had the right programs, processes, and development tools in place to help people thrive and, in particular, people who are underrepresented at the organization. I actually realized that I wanted to have the ability to directly impact more lives, but in particular the lives of those who needed us the most. And I didn’t know what that would look like, to be honest with you. So I took what I thought was going to be a sabbatical for a year to figure it out, and Dress For Success came knocking.


You’ve made diversity, equity, and inclusion efforts a big part of your work. Can you expand on why?

Meyer-Shipp: You know, for me, when I think about diversity, equity, and inclusion, I think about all of the dimensions of difference that make us each who we individually are. And you hear people talk about the more traditional descriptors of what diversity means around race, gender, sexual orientation, gender identity, ability, etc. I could go on and on, but it also is the very difference that you bring to the table. It could be your education, your socioeconomic background, your skill set, etc. It is the very uniqueness that we each bring that makes us diverse.

And I actually always say this when I’m in a room with a homogeneous team is that, even though this team may look homogeneous by gender or by race, there is diversity among us with respect to the qualities and the characteristics we bring to the table. And I can say, after more than 12 years of leading DEI for multiple organizations, that I live and breathe all things diversity, equity, inclusion and belonging.

And I really do believe that having an inclusive culture is at the heart of employee engagement, employee retention, innovation, and driving your business forward no matter what that business may be.


What’s your top piece of leadership advice for leaders in nonprofits or elsewhere?

Meyer-Shipp: Leading with a “people first” mindset has really helped me as a leader. There’s always a buzz in the office and there is not a moment that goes by that, you know, folks aren’t buzzing around, talking, collaborating with one another or taking a lunch break, you know, in our kitchen and sitting and talking about, you know, just life stuff outside of work. We do host and try to get the team together for team outings twice a year.

And we also, on a monthly basis, take time out to celebrate birthdays, anniversaries and other significant things. Just last night, we actually had an after work, in-office happy hour to celebrate a couple of cool business-related accomplishments, but also personal accomplishments for some of our team members. And that was a lot of fun. So I always start with people first.

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