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The Skip podcast

Latest episodes

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7 snips
Mar 26, 2025 • 1h 5min

Super Shadows | When Strengths Limit Growth

This discussion dives into the concept of 'Super Shadows'—the hidden challenges that come with strong abilities and how they can stall career growth. The hosts tackle the struggle of feeling stuck in a rapidly changing work environment and emphasize the importance of self-advocacy and seeking feedback. Listeners learn how to adapt their strengths while recognizing the areas needing growth. Practical strategies are shared to help professionals overcome stagnation and unlock their true potential.
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39 snips
Feb 27, 2025 • 50min

Should you Stay or Go? A 5-factor framework for career-defining decisions

Explore the dilemma of whether to stay in a declining job or pursue new opportunities. This insightful discussion introduces a 5-factor framework to evaluate your career choices, focusing on compensation, skills, lifestyle, and potential for success. Timing your decisions and maintaining a personal narrative can enhance your job application process. Balancing personal well-being against career ambitions is essential. Gain practical strategies for assessing job satisfaction and understanding your true value in the job market!
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39 snips
Jan 30, 2025 • 56min

The Insider's Guide to Tech Compensation, Negotiation, and Career Growth

This discussion dives into the art of negotiating tech compensation with practical strategies. Listeners can learn how to evaluate multiple job offers and the critical elements of compensation packages, including salary and equity. The hosts emphasize the pitfalls of chasing high compensation early and the importance of aligning roles with personal strengths. Insights into bonuses and how they impact overall earnings are provided, alongside tactics for discussing salary expectations without revealing too much too soon.
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81 snips
Jan 10, 2025 • 58min

The Widening Tech Career Divide: Big vs Small Tech

Carly Malatskey, an engineer-turned-investor and host of 'She Leads,' dives deep into the tech job landscape. She explores the crucial choice between big tech, small tech, or launching your own startup. With AI reshaping opportunities, Carly highlights the differences in career paths, particularly the evolving roles in product management and engineering. She also emphasizes the importance of self-reflection for aspiring founders and the skills needed to thrive in today's market, making it a must-listen for anyone navigating the tech career divide.
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43 snips
Nov 18, 2024 • 1h 6min

Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)

In this engaging discussion, Shreyas Doshi, a product leader turned founder with experience at Stripe, Twitter, and Google, shares valuable insights on the journey from employment to entrepreneurship. He highlights the key traits that successful founders possess, such as thriving in ambiguity and embracing personal motivations. Shreyas challenges the mainstream belief that venture-backed startups are the only path to success and offers strategies for avoiding burnout. Listeners will discover the importance of niche markets and enhancing product sense for startup success.
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38 snips
Nov 1, 2024 • 22min

Live from Lenny's Summit | Career advice highlights

Explore innovative ideas on rethinking retirement and the importance of power years versus foundational years. Discover how to leverage career stories to enhance your personal brand and reputation. Unpack strategies to conquer burnout and build a supportive network. Delve into essential questions every leader should ponder for career growth, and understand how a product manager can navigate the complexities of job searches and professional identity. Each insight aims to redefine career pathways and elevate success.
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87 snips
Sep 20, 2024 • 54min

Mastering your 30 second resume

Discover how to elevate your career story in just 30 seconds! Learn common storytelling pitfalls and effective techniques to captivate your audience. Through live workshops, you’ll hear real transformations of career narratives from everyday professionals. Uncover the art of balancing brevity while showcasing your unique value. Plus, get tips on adapting your story for different audiences. This engaging conversation promises to equip you with the skills to craft a compelling introduction that hooks listeners immediately.
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38 snips
Sep 10, 2024 • 1h 16min

Founder Mode, done right | Shreyas Doshi (ex-Stripe, Twitter, Google, Yahoo)

Shreyas Doshi, a product and leadership expert with a background at Stripe, Twitter, Google, and Yahoo, dives into the intriguing concept of 'Founder Mode.' He explores how this mindset is crucial for early-stage entrepreneurs, emphasizing its role beyond just a title. The discussion highlights the balance between detail and delegation, the power of self-awareness, and the importance of strong opinions in product development. Shreyas shares operational insights and offers practical strategies for navigating the challenges of leadership in tech.
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13 snips
Aug 29, 2024 • 21min

4 secrets of career-boosting companies

Discover how to spot companies that can turbocharge your career! Uncover the four essential traits of successful organizations: rapid execution, strong market positioning, high-quality talent, and a thriving development culture. Learn why shipping velocity matters and how to identify meaningful learning opportunities. This insightful discussion equips you with the knowledge to assess your current role or navigate your job hunt, ensuring you find an environment that truly fosters your career growth.
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Aug 21, 2024 • 12min

Navigating careers while expecting

In this enlightening chat, a pregnant Product Executive grapples with career choices amid her impending motherhood. She shares her dilemmas about staying in a senior role versus seeking new opportunities, emphasizing the emotional tug-of-war many face. The conversation dives into overcoming job search anxiety, balancing career ambitions with family priorities, and the importance of long-term growth. It offers fresh perspectives on how to navigate professional life while ensuring personal well-being, all seasoned with candid insights on wartime leadership.

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