#5: Welcome back to the Skip podcast! In this episode, Nikhyl invites Shreyas Doshi to discuss the ever-evolving role that Product managers have in today's business world, finding yourself “stuck” in the ‘middle-stage’ of your career and how making high-quality career decisions is more important than ever. Using more than a decade of experience, Shreyas also describes vastly different experiences in similar roles at similar (or sometimes very different) companies, following your own internal excitement to help guide you in the proper direction, and how to optimally manage the critical transition from an operator role into an advisory role.

Shreyas Doshi has led & scaled products at Stripe, Twitter, Google, and Yahoo in over 15 years as a product manager & PM leader. In this next chapter of his career, he is an advisor for fast-growing startups across the globe and is building out content & courses based on his experience of building successful products & teams across various domains.

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Full Show Notes:

[1:00] Welcome to The Skip!
[2:00] Introducing our guest Shreyas Doshi
[3:00] “Careers are made by not one playbook, but having many playbooks. Every new challenge is not a page out of a previous playbook, but it's a blend of all these different lessons that one's learned.“ - Nikhyl Singhal
[4:00] Sheryas’ experience as PM at Stripe, and redefining the idea of Product Management
[9:00] “Trying to put product management as a role in a spreadsheet with cells and specific rules doesn't quite work in my opinion.” - Shreyas Doshi
[10:00] How different companies and different company cultures impact the role of Product Managers
[14:30] In the 'Act Two’ of your career, how do you best shift to an advisory role?
[20:00] It can be useful to follow the emotional excitement about particular opportunities, and using that to gain momentum that eventually leads you to the right opportunity down the road
[22:30] Quality Questions as a Superpower… The efficacy of your role as an advisor likely depends largely on the quality of the questions you ask.
[24:00] Nudge, nudge: Follow Shreyas on Twitter
[25:00] Sheryas’ sought his own advisors to figure out what’s next, and the answer was building effective courses
[28:00] “My hypothesis was that if I structure this in a unique way and if I treat this course, like I would treat a product and kind of basically just like product manage it, since that I can have the right kind of effect on my users, in this case, my students, then that would be a wonderful kind of experience and hopefully useful for students. And that hypothesis, I would say, has been proven at this point because a lot of people have told me that it substantially changed the way they were thinking about their career.” - Shreyas Doshi
[32:00] Discussing Shreyas’ tweet on success in academics vs. professional life
[36:00] One's career may reach a point where they feel like they are no longer advancing or growing, which is commonly known as career plateauing, and this stage often causes a great deal of frustration
[42:30] The difficulties of going from a large company with many layers of structure to a startup with essentially no multi-domain structure
[44:00] Eric Wienstein’s “High Agency”
[48:00] “Especially as leaders, most of our problems are actually in many ways messaging problems - because we know what the right thing is, and how we got to that conclusion, but there are so many challenges along the way to kind of message it in a way that resonates with everybody.” -Shreyas Doshi
[51:00] It is important to keep in mind that both internal and organizational changes require a significant amount of time
[52:00] For individuals who feel like they are at a standstill in their career, Shreyas offers advice on how to move forward.
[53:00] Be rigorous about your career decisions. Take pride in your career.
[1:00:00] Find Shreyas on Twitter and Linkedin!

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The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.

Join entrepreneur, coach, and Facebook VP Nikhyl Singhal as he offers guidance on navigating important career decisions, management challenges, and personal crossroads. For many, career is one of the most critical parts of identity. Yet most people don’t have a clear sense of how to maximize their current position, evaluate job transitions, or invest in the right long-term skills to optimize their professional life. Unfortunately, if you work at a company, your manager is rarely capable or incentivized to help you develop the necessary skills or to think through transitions. And most self-help books and articles focus on your current role, not on the next one or on any sort of long-term career roadmap.

Nikhyl advises nearly a hundred leaders on their tech careers. Nikhyl is certain, however, there are many others also looking to become more intentional about their career choices – which has led him to produce this podcast. Each edition, Nikhyl will dive into some of the common questions he encounters and give his distinctive insight with the hope of reaching as many people as possible. Though Nikhyl mostly works with tech leaders, he believes the themes apply to anyone looking to shape a fulfilling career.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

How to avoid getting stuck in your career with Shreyas Doshi

The Skip Podcast

How to avoid getting stuck in your career with Shreyas Doshi