Episodes
Feb. 27, 2025
Should you Stay or Go? A 5-factor framework for career-defining decisions
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisio…
Jan. 30, 2025
The Insider's Guide to Tech Compensation, Negotiation, and Career Growth
We dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking to understand tech compensation …
Jan. 10, 2025
The Widening Tech Career Divide: Big vs Small Tech
In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor who is now a founder, and podcast host. We dive into one of the most important career questions in tech today: Should you work in big tech or small tech, or found your own company?
Nov. 18, 2024
Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)
I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders.
Nov. 1, 2024
Live from Lenny's Summit | Career advice highlights
Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months.
Sept. 20, 2024
Mastering your 30 second resume
This episode focuses on crafting a captivating 30-second introduction to your career story that engages listeners and enhances your professional profile. We've taken a unique approach by inviting Skip community members to submit their career stories for a live workshop. You'll hear real examples of…
Sept. 10, 2024
Founder Mode, done right | Shreyas Doshi (ex-Stripe, Twitter, Google, Yahoo)
In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders.
Aug. 29, 2024
4 Secrets of Career-Boosting Companies
How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture.
Aug. 21, 2024
Navigating Careers While Expecting
In this "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma.
July 30, 2024
Stage of company: a career unlock
Many product managers focus on brand names or job titles, overlooking a crucial factor: company growth stage. This episode reveals how a company's phase - from startup to market leader - shapes your work and career path.
July 10, 2024
The art of building your personal brand
Personal branding is a crucial yet often misunderstood aspect of career development. Many professionals mistake personal brand for self-promotion or social media showmanship. This episode debunks these myths and reveals the true power of strategic personal branding. Featuring insights from two tech…
June 20, 2024
Battling job search anxiety
In today’s episode, we tackle job hunting in today’s tough market. I share insights from a real coaching session with a design leader who's struggling after being out of work for a few months. The episode is packed with concrete tools, useful tips, and proven strategies to help you navigate a job t…
May 28, 2024
Avoiding burnout for high achievers
Around 10-20% of my coaching calls tackle burnout. In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set healthy boundaries, and cultivate a resilient mindset.
May 14, 2024
Crafting a compelling career story
In today's episode, learn to craft a compelling two-minute career story you can use for interviews, personal assessments, networking events, and LinkedIn. Good stories ensure clarity, showcasing your achievements and authenticity. We dissect a typical PM career story and walk through how to make it…
Feb. 11, 2024
Shedding perceptions: Moving from lone wolf to team player
In my fourth live coaching session, this caller felt like they had earned an unfair reputation as someone who struggles with collaboration in the workplace. The caller wanted guidance on transforming past perceptions into a new reality.
Jan. 21, 2024
Is my next job at a startup or big tech?
In my third episode of live coaching sessions, this caller was feeling dissatisfied with their narrow scope of role and lack of cultural fit in their current company. The caller wanted guidance on what their next role should be, given their personal situation and professional ambition.
Their si…
Jan. 7, 2024
Coaching grit, patience & tenure
This is my second episode experimenting with live coaching sessions. The format is my attempt to scale insights on common queries and themes I’m often asked about by listeners.
This caller was looking for guidance after finding that a role they joined 4 months ago was not what they expected. The…
Dec. 11, 2023
Are you short changing your career by not managing people?
Welcome back to The Skip; this episode is a little bit special as I’m experimenting with a new format: live coaching sessions. This idea came from the realization that the coaching queries I receive from listeners often have common themes.
My hope is that recording and sharing a coaching call li…
Oct. 1, 2023
Greatest hits on career advice with Peter Yang (Roblox, ex-Reddit)
Much of the career advice out there is for aspiring PMs. But what about those who have one foot on the ladder and are looking to climb the next rung? This episode is about advancing mid to late-stage product management careers. I'm joined by Peter Yang, Product Lead at Roblox, and product newslette…
Sept. 10, 2023
How to find a great Mentor
This episode is about mentorship. Mentorship is a powerful personal development tool that naturally attracts ambitious people. However, it can be a complicated tool to maximize. Mentorship comes in many forms, with varying degrees of accessibility, quality, and suitability for a given individual. I…
Aug. 13, 2023
5 rules that will unlock your Product Management career
Today’s episode breaks down my 5 rules for optimizing the most important product in your professional life: your career. These rules synthesize some of the key takeaways from all of my other content about product management and career growth. I break down why each rule matters, and outline some ass…
July 30, 2023
Shadows of Superpowers (Part 2)
Today’s episode is the second part, and deeper analysis, on “the shadows of your superpowers”. These are a type of development areas that are associated with your greatest strengths. I use example personas to detail 5 common shadows I’ve noticed across my career and coaching. For each, I breakdown …
July 16, 2023
Shadows of your Superpowers (Part 1)
Today’s episode breaks down the shadows of your superpowers. These are a type of development area that is associated with your greatest strengths, and these apply to people inside and outside of tech. Shadows are one of the most elusive areas of self-development, and therefore one of the most limit…
June 19, 2023
Six Superpowers for Product Managers
In this episode of The Skip podcast, Nikhyl Singhal presents an enlightening discourse aimed at aiding tech industry professionals in their career growth. Through a new 30-minute coaching format, Nikhyl explores the transitions between managerial and individual contributor roles, emphasizing the si…