Colleen Bashar, Guidewire Software

·58 min·5 clips

A colleague pointed out Colleen showed up as a different person in executive meetings, prompting her to get a coach.

The episode begins with host Sue Rocco introducing Colleen Bashar, who joins from Raleigh, North Carolina. Colleen shares her background growing up in western New York, first in a Rochester suburb and later in a small town. She describes her mother as her rock, a single mom who continuously advanced her education, modeling self-investment. Colleen opens up about her father, a pulmonary specialist, and how his divorce and new family led her to feel unworthy, affecting her self-esteem. She chose biomedical engineering in college partly to impress him, acknowledging this drove her early career. Colleen recounts a pivotal moment four years ago when a female colleague noticed she acted differently in executive meetings versus with her team, prompting her to seek coaching to understand why. She explains how this led to her embracing authenticity and developing a leadership philosophy she calls 'raw leadership,' which focuses on creating safe environments, vulnerability, and allowing teams to handle personal chaos. Sue asks about her role as Chief of Staff to the CEO and whether the CEO supports this approach; Colleen notes it's new and a learning process. A listener question from Dusty Wofford asks how Colleen landed her seat at the table; Colleen emphasizes the power of mentors, advising women not to hesitate to reach out. She discusses facing challenges as a woman in male-dominated industries, recalling her MBA class had only nine women, and stresses focusing on adding value rather than gender. Colleen talks about being a mother of two boys, her concerns about social media's impact on children, and the importance of teaching emotional intelligence. She shares the best advice she ever received from a mentor: to never stop investing in herself, which she applied after a five-year break when her kids were young. The episode includes breaks with ads and a Lifestyle Watch segment featuring Jackie O'Malley, founder of Project Mindful, discussing mindfulness, but the main interview focuses on Colleen's personal and professional journey.

As heard by us

A grounded look at moving from sales into operations and how that shift changes work.

The piece stays centered on a move from sales into operations, and that focus gives it a clear workplace lens. It treats hybrid work as a real productivity model for companies, while still leaving room for the idea that its value can differ from person to person.

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Why you'd press play

For when you want a calm look at a sales-to-operations shift inside a software company.

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