You’ve likely heard some leaders described as a servant leader. But what does that really mean? Servant leadership is a philosophy and set of practices that enriches the lives of individuals, builds better organizations, and ultimately creates a more just and caring world. Simply put, it is all about leading by lifting others.
Our guest, Chloe Drew, knows a thing or two about servant leadership. Throughout her career, from her corporate executive roles to her philanthropic and political engagement, Chloe has fought for the underdog and paved the way for others to get ahead. In this episode, Chloe shares her story and how she chose a divergent career path from her Harvard College classmates and followed her passion to help others.
Chloe Drew has 20 years of experience designing, scaling and leading strategies in human resources, corporate social impact, philanthropy and diversity, equity & inclusion. She currently works as an advisor and coach to CEOs and executive teams to develop customized inclusion and diversity strategies that help unlock the full potential of leaders and teams.
[03:04] Chloe’s journey
[08:13] Gaining clarity on your path
[10:35] Pushing past your fear of failure
[16:11] Excelling in a new & unfamiliar environment
[19:30] Tips for making difficult decisions
[23:32] Dynamics of imposter syndrome
[26:38] Asking your community for help
[29:39] How to stay ahead of the curve and be agile
[32:32] Advice on accelerating your success
“The best and most profound lessons of my life have been when I've completely failed.”– Chloe Drew
“Don’t expect to have the full picture when making a difficult decision, strive to get to feeling fairly confident in your decision.” – Chloe Drew
“Asking yourself ‘what outcome are you trying to achieve?’, will help drive out the noise, assumptions and biases.” – Chloe Drew
Chloe Drew has 20 years of experience designing, scaling and leading strategies in human resources, corporate social impact, philanthropy and diversity, equity & inclusion.
Currently she works as an advisor and coach to CEOs and executive teams across sectors – including technology, communications, financial services, sports and fashion – to develop customized inclusion and diversity strategies that help unlock the full potential of leaders and teams.
Before that Chloe was Chief People Officer at the real estate tech firm Compass where she supported a team of 2,500 employees nationally and oversaw the full employee experience through talent acquisition, total rewards, talent management, HR policy and diversity & inclusion. She also served as President of Philanthropy and launched the firm’s first community impact program engaging all employees and 15,000 real estate agents across Compass’s 20+ markets.
Previously she was Chief of Staff at the Markle Foundation leading HR, strategy and fundraising at the $125M independent foundation dedicated to harnessing the power of technology to advance economic inclusion. From 2013 - 2015 Chloe was Director of the New York City Mayor’s Office of Appointments where she ran the Administration’s effort to recruit Commissioners and senior staff for over 60 city agencies and 200 municipal boards and commissions. From 2008 to 2013 Chloe was Executive Director of the Council of Urban Professionals, a nonprofit network of diverse business leaders in New York and Los Angeles, and from 2002 to 2007 she was Campaign Director for Congresswoman Barbara Lee in California’s 13th District.
Chloe earned an A.B. from Harvard College in History and Literature. She has served on nonprofit boards including Wellesley College Centers for Women, Latino Justice, Dance Theatre of Harlem, Emerge America and Oakland Vote. She lives in Brooklyn with her husband and two young children.