Leadership Lessons: Spotting the Good, the Bad, and Forgiving Yourself as a Work-in-Progress with Leslie Miley

Technically Speaking with Harrison Wheeler

Join us on an insightful journey with Leslie Miley, a tech industry veteran and advisor to the CTO of Microsoft. In this episode, we explore topics of leadership, courage, representation, and the unique perspective of an introverted business influencer. Leslie shares his remarkable career path, spanning from diverse experiences of privilege to marginalization, providing valuable insights into the tech industry. Discover how he hacked his way to success and gain thought-provoking perspectives on leadership, oppression, and navigating marginalization in the tech world. Don't miss this engaging conversation with Leslie Miley, where we challenge conventional norms and explore the untold stories of the tech industry.

About the Guest:

Leslie Miley (he/him), The Complicated Man Who Risks his neck for non-binary peeps, trans folk, women and men, currently works as a Partner Technical Advisor to Microsoft CTO.

Empathy, self-awareness, and coffee are three of the things he's trying to get better at. He has extensive experience building, motivating, and managing globally-distributed teams with different cultural backgrounds. He's an expert at designing and implementing development best practices to manage geographically-distributed teams.

An amazing technologist who worked as the 1st CTO at The Obama Foundation, he also held leadership roles at Google, Slack, Twitter, and Apple. He also invests in a number of start-up companies around the world.

Connect with Leslie Miley:

Twitter: https://twitter.com/shaft

Linkedin: https://www.linkedin.com/in/lesliehm/

Medium: https://shaft.medium.com/

Timestamps

(01:03) - How Leslie's engineering background helped him keep up with his physical activities, maintain his fitness level, and track his progress during the pandemic

(04:34) - Icebreaker: The groundbreaking intro song he would play upon entering an arena or walking onstage

(06:05) - Icebreaker: The subject he would instantly become an expert in if he’s given a chance and how he’d use it to solve problems

(07:54) - Icebreaker: His current obsession: How to inspire leaders to be courageous; and why he thinks voter suppression contributed to Roe v. Wade getting overturned

(09:46) - Voter suppression, lack of representation, how leaders use their current position as a stepping stone to higher office instead of serving their people, and what they should focus on instead

(13:13) - Why the public sector lacks experts in technology

(15:10) - Taking the cue from Dave Chappelle about the need for grace and space to grow and the importance of acknowledging that people can change

(17:00) - Hacking systems and access as a hallmark of his career, and charging his own adventure and career in tech as a person of color

(22:25) - The experiences that almost made him quit his tech job, the two reasons why he chose to stay, and the constant battle between changing the world vs. trying to survive through tech

(24:54) - How tech jobs are transformational for women and people of color, why it’s okay for white people to quit tech, and what reverse friends and family round means in meeting BIPOC hierarchy of needs

(27:41) - What it means to be a leader (how to pick good model leaders and how to spot the a*****e ones), and the challenges he faced in his leadership journey and transformation

(31:53) - His inspiration for his leadership style and why he took a step back from leadership roles

(33:19) - Working through trauma by forgiving himself and accepting he's a work-in-progress, the difficulties in being an authentic human...
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