The Skip Podcast

#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. Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookShreyas Doshi: LinkedIn | Twitter | Website 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!—-----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-

#4: Equity, stock options, and other compensation; a complex topic that has essentially limitless negotiable options. We are going to be walking through the basics to lay a foundation and then we will break down the most common mistakes that people make in this area. If you need to know more about offer letters, vesting stocks, and managing exits this episode is for you!Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookLynda Galligan: Goodwin ProfileAnthony McCusker: Goodwin Profile Full Show Notes:[0:00] Welcome to The Skip![2:30] Introducing our guests Anthony McCusker and Lynda Galligan - Attorneys at Goodwin Procter[4:00] Our first example: Startup X offers you an equity package[10:00] What questions do you typically want to make sure that the employee just sort of understands when they're looking at compensation?[12:30] Is the number of shares in the offer important? Balance against the percentage of shares available[16:30] Tax liability when a company has more value on paper than reality[21:30] An 83B election[14:30] Vested options vs unvested options[27:30] Post-termination exercise periods[29:30] Incentive Stock Options or ISOs[37:00] Exploring rainy day scenarios[41:00] You have stock options but the market or company value is going down. What do you do?[43:00] Risks that are specific to private company scenarios[45:00] 409A evaluations[48:00] Important tax stipulations that disallow repricing the same option[49:30] A reminder that none of the conversation today should be regarded as legal advice[50:00] Thank you Anthony McCusker and Lynda Galligan![51:30] Episode summary and wrap up with Nikhyl—-----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

Career transitions are filled with dozens of questions and pitfalls. Join Nikhyl Singhal and four product leaders from the Skip CPO group to discuss the challenges associated with big career decisions. Briana Ings (ClickUp), Anneka Gupta (Rubrik), Shirley Lin (Divvy Homes), and Annie Pearl (Calendly) bring dozens of years of leadership experience to the conversation, as they discuss when to leave (and not) leave your company, how to research the next opportunity, manage the interview process, and successfully interview and land that great next job. Don’t miss their inside tips on what they look for in interviews, common mistakes to avoid, and how they evaluate opportunities.Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | TwitterFollow Anneka Gupta on LinkedInFollow Annie Pearl on LinkedInFollow Brianna Ings on LinkedInFollow Shirley Lin on LinkedIn Full Show Notes:[0:00] Welcome to The Skip![1:30] Introducing our guests Anneka, Annie, Briana, and Shirley![3:30] Shirley Lin describes the company culture differences between Divvy Homes and Airbnb[6:00] The Skip Community for CPOs[8:30] “The head of product or a CPO role, it can be very lonely. You have a lot of pressure on you.”[12:00] Career errors, specifically in times of transitions into and out of roles[13:30] What to do when a company changes dramatically in size and/or in culture[14:30] “It was actually the point where I was frustrated, where I worked through those frustrations and helped solve those problems where I had the greatest growth. Both in terms of my title and getting responsibility, but also just from a personal level and having to figure out a way through those difficult times.”[17:30] Do good companies pass on good people?[21:30] Should you ask for feedback after an interview? Or after getting turned down for a position?[25:30] Pregnancy, life changes, and other times of absence[30:00] There really is no “one size fits all” for every career situation. Every person has a unique and personal journey to creating the career of their dreams[34:00] When looking for a new job, what is the process and where should you look first?[39:00] What does crafting a career framework look like?[45:00] A name with a well-known brand VS. a company that is a great unique fit for you[48:00] “It’s always easier to find a job when you have a job.”[54:00] Factoring in your seniority when thinking about finding a job (and leaving your current job)[1:01:00] Biggest pet peeves NOT to do in an interview![1:06:30] Interviewing and the “take-home” interview[1:13:00] How to decide which of your references to use for your interview and resume[1:15:00] Finding references for the company you are interviewing with or in other words interviewing in reverse.[1:16:30] Wisdom in determining if a company is worth joining or not[1:22:00] “Your boss doesn’t need to be your best friend.” (And respect over friendliness)—-----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. 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

Tech moves fast and is ever evolving. But career worries remain constant and can weigh heavily. In this second Skip podcast, Nikhyl Singhal highlights what he calls “career frequently asked questions”: common concerns people share with him, and how you might approach these concerns to reach the best results for your own professional life. Building a career framework is important, but assessing the complexities branching off of it is vital as well. And he’s hoping you will keep the questions coming! Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | Twitter Full Show Notes:[0:00] Welcome to The Skip![1:00] The concept of “the double jump”[1:30] “If you look through most people's LinkedIn, you'll see there are multiple paragraphs because it'll be “I started in this role and then I went to the second role” and sometimes it's because things weren't working out, but most of the time it's because the company was growing and there was a new need. Companies aren't static, and in fact, if they are, that's probably not the best company to join.”[5:30] “Boring” jobs and the perception of long-tenure VS. short-tenure for a hiring manager[9:00] “Boring roles can be very career additive.”[10:00] “I'm more agnostic to the type of company I'm going to work for in terms of the product, and I'm more trying to make sure that the work I do is career additive, the culture, the people, the values, the speed in which I've seen… that matters a lot.”[15:30] How much time should you dedicate to personal professional development?[16:30] Sometimes, the best value an opportunity will bring you is the people that it connects you with[21:30] Nikhyl’s first startup experience[24:30] The size of the company can often dictate your ability to grow and develop professionally[25:30] Review and conclusion:Consider the double-jump, because the best roles aren’t often available to outsiders.Long tenures at your current company can be good to ensure that you are showing grit and learning.Boring is not a bug, it might be the most career additive.Your professional life should be more than your day job (lower pace might be smart).Meet the people you work with and stay in touch with them.Consider the talent band and ensure you are intentional about where you fit.—-----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. 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

You’re wondering if you should stay in your current role, or maybe you’re stressed about accepting a new one. Well, you’re not alone. In his decade of career coaching, Nikhyl Singhal has often listened to executives wrestle with these dilemmas. And in this first Skip Podcast, he poses five specific questions that he believes can help you create your best path forward and shape your career framework. Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | Twitter Full Show Notes:[0:00] Welcome to The Skip![2:30] “The challenge is that you want a career framework that's very personal to you, and so if your list and everyone else's list is the same, well, then you're not really gonna be able to make that decision around stay VS. go or job one VS. job two”[3:30] Predicament: Job one VS. job two - how to think about different opportunities[4:30] “Retirement is less interesting to people than finding a really satisfying career.”[7:30] The traits of being an exceptional manager vs. the traits of being an exceptional entrepreneur[8:00] Start of the “five career framework principles” section[8:30] First Principle: The story that this opportunity will bring to your next opportunity[11:30] Second Principle: How fast will you find a groove in this new position?[13:30] “Sometimes it's better to find a role, perhaps a little smaller, where you can crush. You feel like yourself in six months; you are seen, people love the work you are doing, and then you get thrust into the next new opportunity. That opportunity might be much more challenging, much more scope, much more opportunity to be a manager, but then you come with confidence. And that second job is where you really do your damage.”[14:30] Third Principle: The growth rate of the company[17:00] Fourth Principle: How will this opportunity add diversity to your portfolio/resume?[19:00] Fifth Principle: Pace of work… Are you looking to work 80 hour weeks, or are you at a stage of life where you need to be allowed a flexible schedule?[20:30] “Nobody loves reducing their free time. But ultimately there are times, and certainly I had these [times], where work was almost my primary focus. [...] And I think that there are times when I try to do things a little bit more in balance, but [I’m referring to] that moment in which you determine, “Hey, for this chapter, this is the space I want the job to take” allows you to then examine the job you are considering in that light.”—-----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. 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

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 has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. And he coaches more than 100 executives, managers, and rising stars in navigating important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life. So subscribe to this podcast to hear from him and other executives as they teach unique career lessons. 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