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The Skip podcast

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35 snips
Jan 16, 2023 • 1h 26min

Discussing career transitions with Heads of Products from Calendly, ClickUp, Divvy Homes, and Rubrik

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.
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34 snips
Jan 16, 2023 • 29min

Career FAQ with Nikhyl Singhal

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.
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29 snips
Jan 16, 2023 • 26min

Crafting a career framework with Nikhyl Singhal

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.
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Jan 9, 2023 • 5min

The Skip podcast trailer

The Skip Podcast, hosted by Nikhyl Singhal, offers career advice to tech professionals. It emphasizes making good career decisions, improving skills, and understanding success. Listeners will learn about avoiding career mistakes, receiving practical advice, and hearing from top industry leaders.

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