The Examined Life

Should you be weird and manipulative at work? [Jenny Wood]

Mar 27, 2025

Join Jenny Wood, a former Google executive and author, as she shares her unconventional journey through workplace dynamics. She discusses the fine line between authentic boldness and calculated self-promotion, revealing the necessity of overcoming fears of judgment. Practical tips range from mastering the 'Monday MiniFesto' to fostering genuine connections in professional settings. Jenny's insights on striking a balance between assertiveness and ethical behavior highlight that success doesn't mean being manipulative—it's about embracing your true potential.

48:49

Creator website

Episode guests

Jenny Wood

AI Summary

AI Chapters

Episode notes

Podcast summary created with Snipd AI

Quick takeaways

Navigating corporate life successfully often requires understanding workplace politics to leverage relationships for career growth and mentorship.

Effective communication is vital for career advancement, with concise, impactful exchanges significantly enhancing how ideas are perceived.

Challenging unspoken corporate rules and embracing boldness allows individuals to assert themselves and promote personal growth in their careers.

Deep dives

Career Progression Insights

The discussion highlights the importance of being proactive in managing one’s career, using specific techniques that improve visibility and influence within an organization. One notable example includes observing behavioral cues during interviews, such as noticing an interviewer's eye movement when they are losing interest. Recognizing this cue allows candidates to adjust their responses accordingly, ultimately increasing their chances of success. This practical advice reflects a realistic approach to navigating corporate life effectively.

Intro

1min

Navigating Work and Family: Boldness in the Workplace

4min

Navigating Professional Relationships with Confidence

24min

Navigating the Fine Line Between Self-Advocacy and Manipulation

3min

Navigating White Lies in Parenting

4min

Navigating Confidence in the Workplace

9min

Overcoming Fear to Unlock Professional Growth

3min

What happens when career advancement requires you to be manipulative, bossy, and a bit reckless? Jenny Wood's meteoric rise at Google reveals that success often demands breaking unspoken rules. From strategically meeting your boss's boss to mastering the Monday MiniFesto, Jenny shares how walking the line between authentic boldness and calculated self-promotion propelled her career. But beneath these tactics lies a deeper truth – it's not about becoming cutthroat, but about pushing past the fear of judgment that keeps most people playing small. [Episode 95]

Jenny Wood is a former Google Executive, author and entrepreneur.

Learn more about Jenny:

• Website: https://itsjennywood.com/

• LinkedIn: https://www.linkedin.com/in/jennyilles

• X/Twitter: https://x.com/itsjennywood?lang=en

• Instagram: https://www.instagram.com/itsjennywood/

—-

JOIN OUR GROUP COACHING COHORTS:

Are you looking to ask deep, introspective and provocative questions about your own life (with Khe and likeminded peers)

⁠⁠⁠⁠⁠Apply today⁠⁠⁠⁠⁠

—-

BECOME A RADREADER: