Success on Your Terms: Redefining Leadership and Joy with Jossie Haines
Thu Feb 05 2026
Imagine working your entire life for a retirement you never reach. Engineering leader, Jossie Haines, shares how a family tragedy transformed her perspective on ambition, burnout, and the urgent need for human-centric leadership in the age of AI.
After reaching the heights of Silicon Valley as a VP of Engineering and working on iconic products like Siri, Jossie realized that the traditional "up and to the right" career path often leads to burnout rather than fulfillment.
She discusses the systemic reasons why 50% of women leave tech by age 35, how to leverage AI as a leadership tool rather than a replacement for human judgment, and why true success must be defined on your own terms.
3 Key Takeaways:
(1) The "Next Step" Philosophy: Avoid the paralysis of trying to map out a massive goal from A to Z. Focus exclusively on the immediate next step—whether it's a phone call or a brainstorm—to gain clarity without the overwhelm.
(2) Inclusion is a Product Feature: Diverse teams aren't just a metric; they build better tech. Jossie highlights how a lack of diverse testers can lead to products (like voice assistants) that fail to recognize women's voices or various accents.
(3) AI is a Change Management Challenge: Integrating AI into a team isn't just about the software; it’s a leadership task. Success with AI requires human oversight to determine what "good" looks like and to ensure it solves the right problems.
Connect with Jossie Haines on LinkedIn - https://www.linkedin.com/in/jossiemann/
Check out her website - https://JossieHaines.com to learn about her upcoming workshops and coaching programs.
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Imagine working your entire life for a retirement you never reach. Engineering leader, Jossie Haines, shares how a family tragedy transformed her perspective on ambition, burnout, and the urgent need for human-centric leadership in the age of AI. After reaching the heights of Silicon Valley as a VP of Engineering and working on iconic products like Siri, Jossie realized that the traditional "up and to the right" career path often leads to burnout rather than fulfillment. She discusses the systemic reasons why 50% of women leave tech by age 35, how to leverage AI as a leadership tool rather than a replacement for human judgment, and why true success must be defined on your own terms. 3 Key Takeaways: (1) The "Next Step" Philosophy: Avoid the paralysis of trying to map out a massive goal from A to Z. Focus exclusively on the immediate next step—whether it's a phone call or a brainstorm—to gain clarity without the overwhelm. (2) Inclusion is a Product Feature: Diverse teams aren't just a metric; they build better tech. Jossie highlights how a lack of diverse testers can lead to products (like voice assistants) that fail to recognize women's voices or various accents. (3) AI is a Change Management Challenge: Integrating AI into a team isn't just about the software; it’s a leadership task. Success with AI requires human oversight to determine what "good" looks like and to ensure it solves the right problems. Connect with Jossie Haines on LinkedIn - https://www.linkedin.com/in/jossiemann/ Check out her website - https://JossieHaines.com to learn about her upcoming workshops and coaching programs.