Lead With Empathy and Assume Best Intent: How a Former Private Banker Builds Teacher Pathways in Greater DC (with Anthony Dorado)
Anthony Dorado's road back to the program that trained him began when a busy CEO made time for him, and now he tries to give fifteen minutes to anyone who reaches out.
In this episode of The Stronger Podcast, Mike Montoya sits down with Anthony, Executive Director of City Teaching Alliance in Greater DC Metro, a nonprofit that prepares teachers for city schools, to talk about changing careers and leading with empathy.
Anthony grew up in Koreatown, Los Angeles, in a first-generation Mexican family. His parents were 16 when he was born, so his grandparents raised him in a home full of aunts and uncles. He started kindergarten without speaking English, was in English as a second language classes until high school, and found a mentor in his charter high school's founding principal.
He started out in private banking and left after almost two years because the work did not match his convictions. When his best friend, a teacher, asked if he wanted to teach math, he said why not, and fell in love with teaching. He joined Urban Teachers, now City Teaching Alliance, which pairs a master's degree with a teaching fellowship, and moved to Washington, DC. After working internationally as CEO of education for a private equity firm, he came back to lead the region where he trained.
Mike and Anthony get into how the four-year fellowship works, why classroom management is team management, and why Anthony assumes best intent when something goes wrong. He also lays out what is next for City Teaching Alliance, which now calls itself a workforce development organization: an accelerated pathway into teaching, a pathway for paraprofessionals, and a move into Virginia.
Tune in to hear what Anthony would tell his younger self in Los Angeles, starting with skateboarding.
Chapters:
- (01:11) - Stronger together, and where Anthony calls home
- (02:00) - Growing up in Koreatown in a house full of family
- (03:40) - Parents at 16, and the grandparents who raised him
- (05:30) - Starting kindergarten without speaking English
- (07:08) - A charter high school and the principal who became a mentor
- (09:08) - Leaving private banking to teach math
- (11:12) - Urban Teachers, a master's degree, and a move to Washington, DC
- (13:04) - I was in your seat ten years ago: teaching his own community
- (14:45) - Former students sending their graduation pictures
- (16:50) - How the four-year City Teaching Alliance fellowship works
- (19:18) - Why teacher preparation needs partners outside the system
- (21:17) - Coming back to lead, and giving anyone fifteen minutes
- (23:35) - Teaching as a proving ground and a pipeline into leadership
- (24:36) - Classroom management is team management
- (28:20) - Special education support depends on the school and its budget
- (29:39) - The gap between what kids need and what schools are funded for
- (31:33) - Leading with empathy and assuming best intent
- (33:09) - Leadership development, and a note to the funders
- (35:51) - Roots in the DMV, and new pathways into teaching
- (37:14) - Scaling City Teaching Alliance into Virginia
- (39:04) - Advice to his younger self: quit skateboarding
- (39:58) - Trusted mentors, and making fifteen minutes for others
Referenced in this episode:
City Teaching Alliance names Anthony Dorado executive director for Greater DC Metro: https://cityteachingalliance.org/blog/city-teaching-alliance-expands-leadership-team-with-three-new-executive-directors/
Urban Teachers renamed City Teaching Alliance: https://cityteachingalliance.org/urban-teachers-announces-name-change-to-city-teaching-alliance/
Public school spending per pupil, U.S. Census Bureau: https://www.census.gov/newsroom/press-releases/2026/school-system-finances.html
Urban Teachers renamed City Teaching Alliance: https://cityteachingalliance.org/urban-teachers-announces-name-change-to-city-teaching-alliance/
Public school spending per pupil, U.S. Census Bureau: https://www.census.gov/newsroom/press-releases/2026/school-system-finances.html
Links:
Anthony Dorado at City Teaching Alliance: https://cityteachingalliance.org/employees/anthony-dorado/
More about City Teaching Alliance: https://cityteachingalliance.org/
City Teaching Alliance on LinkedIn: https://www.linkedin.com/company/cityteachingalliance/
More about City Teaching Alliance: https://cityteachingalliance.org/
City Teaching Alliance on LinkedIn: https://www.linkedin.com/company/cityteachingalliance/
Connect with Mike: https://www.linkedin.com/in/mmsc/
Stronger Consulting: https://strongerconsulting.com
Start a podcast that matters: http://podcastsmatter.com
Stay strong.