The Skip podcast
Discussing career transitions with Heads of Products from Calendly, ClickUp, Divvy Homes, and Rubrik
Episode guests
Podcast summary created with Snipd AI
Quick takeaways
- Consider the impact on career trajectory, including mission, growth opportunities, and team dynamics when making a career transition.
- Set expectations with potential employers, negotiate leave terms, and prioritize attributes for your next role.
- When evaluating job opportunities, assess the manager's fit with your goals and values, and consider the company's financial health and growth potential.
- Prepare for interviews by telling compelling stories, demonstrating curiosity about the company, and addressing potential weaknesses.
Deep dives
Finding the Right Career Transition
When considering a career transition, it is important to assess the impact it will have on your career trajectory. Factors such as meaningful mission, growth opportunities, and team dynamics should be considered. It is also crucial to set expectations with potential employers, negotiate leave terms, and prioritize the attributes you want in your next role. While conventional wisdom suggests staying in a role during a transition, it is essential to evaluate the potential growth and learning opportunities that a new opportunity can provide. Family support and a supportive network are key in navigating career transitions, especially when balancing family responsibilities.
Starting a Job Search
When beginning a job search, it is advisable to start broad to get a sense of available opportunities. Connecting with friends, ex-colleagues, and industry contacts can provide valuable insights and referrals. Building awareness of your job search through networking, engaging with venture capital networks or recruiters, and leveraging connections with previous managers can create opportunities. It is essential to narrow down your search criteria based on career progression, company stage, or other relevant factors to effectively manage your search.
Responding to Inbound Opportunities
Inbound opportunities, such as blind emails, LinkedIn messages, or recruiter contacts, can be valuable depending on the context. It is advisable to respond to opportunities that align with your criteria or come from reputable companies. However, it is essential to research the company, evaluate job fit, and consider factors like role, compensation, and culture before deciding to pursue further conversations.
Allocating Time and Managing the Job Search
Managing a job search while currently employed can be challenging. Allocating time and effort to the search is necessary, but it can be done strategically. Evaluating and clarifying your search criteria, narrowing down opportunities quickly, and focusing on high-priority conversations can help manage time effectively. Networking and leveraging existing connections can also streamline the search process, ensuring that valuable time is spent on meaningful opportunities.
Choosing the Right Opportunity: Evaluating Manager, Financials, and Turn
When considering job opportunities, it is crucial to assess the manager and their fit with your goals and values. A good manager can determine success and growth in a role. Additionally, understanding the financial health and growth potential of the company is vital. Learning about customer churn and why customers are leaving can provide insights into the company's future prospects. Back-channeling with previous role holders can shed light on their experiences and reasons for leaving. This information can help make an informed decision when choosing between multiple offers.
Preparation and Interview Tips: Stories, Curiosity, and Self-awareness
Preparing for interviews involves the ability to tell compelling stories that showcase different skills and experiences. Building a repertoire of anecdotes and being able to adapt them to different questions can make a candidate stand out. Demonstrating curiosity about the company, its culture, and strategy through well-researched questions can also leave a positive impression. Additionally, being self-aware and proactively addressing potential weaknesses or areas for improvement can show a willingness to learn and grow. Mock interviews and practicing concise responses are helpful in preparing for interviews.
Taking Time for an Effective Job Search: Full Commitment and Tank Level
Embarking on a job search requires a full commitment and an understanding of the time and energy it demands. It is important to assess whether one has the necessary motivation and energy to dedicate to the process alongside their current job. If the tank is already empty or the job search is not energizing, it may be necessary to leave the current role to provide the necessary space and focus for the job search. Assessing one's readiness and understanding the time commitment can lead to a more effective job search.
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.
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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)
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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.
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