The Skip Podcast

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. Their situation exemplifies the kind of hard problems that leaders have to solve, and we speak about the traits and strategies required to approach these problems wisely.

Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.

In today's episode, we discuss:

• Why the caller’s difficult scenario could be their greatest opportunity
• How to think about a current role in the context of future goals
• The nature of tough leadership problems
• The value of patience and long tenures
• How to align on performance and timeframe expectations with higher-ups
• Advice for solving contentious problems with multiple stakeholders

Timestamps
[00:00:00] Introduction and context on caller 
[00:02:43] Caller’s question 
[00:06:35] Nikhyl’s initial reaction 
[00:09:11] Could she solve this problem if she wanted to? 
[00:10:48] The relevance of patience/impatience 
[00:12:40] The relationship between tenure and solving hard problems 
[00:15:20] Earning trust as a leader 
[00:16:30] Understanding the company’s expectations and timelines 
[00:18:05] The advice discussed so far 
[00:22:54] Why this matters for future opportunities at startups 
[00:27:10] Advice for approaching this challenging leadership scenario 
[00:31:08] Nikhyl's closing reflections 
[00:33:45] Key links for this podcast

Where to find Nikhyl:

• Twitter
• LinkedIn

Where to find The Skip Podcast:

• Website
• YouTube
• TikTok
• Spotify
• Apple Podcasts

Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons.

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 like this demonstrates how the frameworks are applied in real conversations and possibly helps others with similar situations. Naturally, privacy is paramount, so we’ve anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.

In today's episode, we discuss:

• Strategies for presenting your individual contributor (IC) experience during career advancement interviews.
• How to map the complexities you are solving in your current role into specific phrases that hook a recruiter or a future hiring manager
• Avoiding over selling your experience and landing in a sub-optimal role, focused on org-building vs. product-building
• Exploring how far an IC can travel within a company, and how to ultimately become an executive

Timestamps:

(00:00) Introduction and welcome to the podcast

(00:57) Introducing the format of this episode

(04:08) Context ahead of the coaching call

(06:40) How to frame your experience as an IC when interviewing for the next step in your career.

(08:25) Nikhyl's follow-up questions

(09:11) Why the caller left Microsoft

(11:17) Nikhyl's thoughts and initial reaction to the caller's situation

(12:22) Identifying if you have a product ambiguity or team ambiguity problem

(15:10) Nikhyl's thoughts on how to frame the caller's experience when interviewing

(16:08) Nikhyl's thoughts on the types of companies suitable for the caller

(19:34) How to find suitable companies based on your management experience

(23:13) How to navigate questions around your management experience when your current role is an IC

(28:19) How to navigate people managing anxiety

(29:52) Can ICs build a lasting career?

(33:17) Conversation conclusion and final thoughts

(36:06) Episode conclusion

Where to find Nikhyl:

• Twitter
• LinkedIn

Where to find The Skip Podcast:

• Website
• YouTube
• TikTok
• Spotify
• Apple Podcasts

Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons.

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 newsletter writer, to discuss how established PMs can avoid getting stuck. From pursuing growth over promotion to knowing when to change companies, we discuss a wide range of strategies to help you continue building the career you want based on your individual goals.

Today’s discussion covers:
• Wisdom for mid and late-stage product managers looking to advance their careers
• Why you should focus on growth, not promotion
• Optimizing for company stage instead of company name
• Signs you should leave a company
• The under-discussed trade-offs between compensation and tenure
• Why top companies offer such high compensation

Creator Economy by Peter Yang:
• Nikhyl Singhal (VP Meta): How to Advance Your Product Management Career (Part 1)
• Nikhyl Singhal (VP Meta): How to Advance Your Product Management Career (Part 2)

Referenced in this episode:
• Blog post "Stage of company, not name of company"
• Six Superpowers of Product Managers
• Shadows of your Superpowers (Part 1)
• Shadows of your Superpowers (Part 2)

Timestamps:
(00:00) Introduction
(01:27) Advancing mid or late-stage careers
(04:38) Promotions matter less than you think
(08:36) The different end goals for PM careers
(13:56) How to find the right company to elevate your career
(19:07) The best and worst reasons to change companies
(23:28) The impact of short tenures on someone’s resume
(27:19) Why top companies offer such high compensation
(31:31) The relationship between title and compensation
(34:52) Advice for negotiating compensation
(37:21) The under-discussed tradeoff between compensation and tenure
(39:07) Recapping the "shadows of your superpowers"
(41:55) Nikhyl’s advice for dealing with a common shadow
(47:43) Conclusion

Where to find Peter:
• Twitter
• LinkedIn
• Newsletter

Where to find Nikhyl:
• Twitter
• LinkedIn

Where to find The Skip Podcast:
• Website
• YouTube
• TikTok
• Spotify
• Apple Podcasts

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. In this episode, I answer questions on 3 topics surrounding the complications of mentorship: how to navigate the resources available, how to be coachable, and tips and tricks I’ve learned as a mentor and mentee.

In today’s episode, we discuss:

• Why you shouldn’t conflate success at your company with success in your career
• How and why you should form a “Personal Board of Directors”
• Resources for people who can’t access certain types of mentorship
• How to identify and avoid bad advice
• Actionable tips for becoming more coachable
• Why coaching others improves your ability to be coached

Referenced in this episode:

• Meander: Match your career ambitions with the perfect mentor (Nikhyl is an advisor)
• Shreyas Doshi: links to his content and his courses
• Lenny’s Podcast
• Reforge

Timestamps:
[00:00:00] Intro
[00:01:54] I feel like I’m not doing enough to advance my career, what should I do?
[00:04:34] What if I can’t access mentorship?
[00:06:11] The 4 buckets of people in your network
[00:09:55] The “Personal Board of Directors” framework
[00:12:02] How to connect - not “network” - in 30 mins per week
[00:13:31] How to find people to connect with
[00:15:16] The value of free online content
[00:16:31] The value of communities
[00:18:41] Paid resources
[00:21:24] 2 things to consider when it comes to executive coaches and therapists
[00:24:48] 3 unique strengths of therapy
[00:25:51] The skill of being coachable
[00:26:43] Use specific requests when engaging with potential mentors or coaches
[00:30:33] The courage required to listen to feedback
[00:31:38] How to run an efficient process when being coached
[00:34:55] Why coaching others helps you to be coached
[00:36:42] How do you know if you’re getting good advice?
[00:38:45] Beware of extremists and contrarians
[00:40:04] Beware of copycat coaches
[00:41:12] Coaches must know you and your situation
[00:42:19] My own personal board of directors
[00:46:03] How I think about new requests to be coached by me
[00:47:07] My new idea for a live coaching format
[00:48:21] Conclusion

Where to find Nikhyl:

• Twitter: https://twitter.com/nikhyl
• LinkedIn: https://www.linkedin.com/in/nikhyl/

Where to find The Skip Podcast:

• Website: https://www.skip.show/ 
• YouTube: https://www.youtube.com/@theskippodcast
• TikTok: https://www.tiktok.com/@theskippod
• Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ
• Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202

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 associated mistakes and misconceptions that you should avoid. Whether you’re at a career juncture or are firmly positioned in a role, these rules come with actionable tactics you can implement tomorrow. Ultimately, I believe that following these rules will lead you to a healthier career where you think long-term and control your own outcomes.

Today’s discussion covers 5 rules:

1. Product manage your career like a product

2. Ensure each transition is career additive

3. Who you know will matter as much as what you know

4. Find a strength area and build a superpower around it

5. Bet on yourself

Timestamps:

[00:00:00] Intro

[00:01:33] Overview of the 5 rules

[00:02:00] Rule #1 Product manage your career like a product

[00:05:43] The importance of seeking out feedback

[00:07:13] Rule #2: Ensure each transition is career additive

[00:10:40] The external vs internal realities of a company

[00:13:08] Rule #3 Who you know will matter as much as what you know

[00:15:03] How to build your network authentically

[00:18:38] Rule #4 Find a strength area and build a superpower around it

[00:21:16] The shadows of your superpowers

[00:22:08] Rule #5 Bet on yourself

[00:24:08] Why promotions don’t guarantee you’re advancing

[00:26:11] Conclusion

References

- My Product School talk on the 4 essential product skills: https://productschool.com/product-podcast/pm-to-csuite-by-facebook-vp-of-product/

- My podcast on the shadows of superpowers, part 1: https://www.skip.community/shadows-of-your-superpowers-part-1/

- My podcast on the shadows of superpowers, part 2: https://www.skip.community/shadows-of-superpowers-part-2/

Where to find Nikhyl:

Twitter: https://twitter.com/nikhyl

LinkedIn: https://www.linkedin.com/in/nikhyl/

Where to find The Skip Podcast:

Website: https://www.skip.show/

YouTube: https://www.youtube.com/@theskippodcast

TikTok: https://www.tiktok.com/@theskippod

Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202

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 why the shadow is elusive, common reactions to receiving feedback around it, and actionable advice for addressing the development area. Whether these shadows remind you of yourself or of others - in a personal or professional context - this reflection will help you cast the shadows into the light.

Today’s discussion covers:

• A recap of the “shadows” concept
• Executer who struggles to be a team player (Martin)
• Strong opinions, tightly held (Jackie)
• Team builder who becomes too political (Max)
• Organizational expert who is too hands-off (Jenny)
• Company veteran who struggles to innovate (Evan)
• How you can apply these reflections

Timestamps:
[00:00:00] Recapping the “shadows” concept
[00:02:00] Where to apply these insights in your life
[00:04:38] Example #1: Executer who struggles to be a team player (Martin)
[00:09:31] Advice for Martin
[00:13:07] Example #2: Strong opinions, tightly held (Jackie)
[00:14:18] Advice for Jackie
[00:17:17] Example #3: Team builder who becomes too political (Max)
[00:19:12] Advice for political Max
[00:23:24] Example #4: Organizational expert who is too hands-off (Jenny)
[00:25:06] Advice for Jenny
[00:29:16] Example #5: Company veteran who struggles to innovate (Evan)
[00:33:09] Advice for Evan
[00:36:57] Conclusion

Where to find Nikhyl:
Twitter: https://twitter.com/nikhyl
LinkedIn: https://www.linkedin.com/in/nikhyl/

Where to find The Skip Podcast:
Website: https://www.skip.show/
YouTube: https://www.youtube.com/@theskippodcast
TikTok: https://www.tiktok.com/@theskippod
Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ
Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202

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 limiting to your potential. You may very well be unaware of yours. While shadows are surrounded by complicated personal and workplace dynamics, understanding them is likely one of your best opportunities to unlock the next step in your career.

Today’s discussion covers:

• What shadows are
• The complex dynamics which make them easy to dismiss
• How to identify yours
• 4 reactions people have when their shadows catch up with them
• 10 common examples of shadows
• How to address your shadows and move from acknowledgment to action

Where to find Nikhyl:
Twitter: https://twitter.com/nikhyl
LinkedIn: https://www.linkedin.com/in/nikhyl/
Threads: https://www.threads.net/@nikhylsinghal

Timestamps:
[00:00:24] What’s covered in this episode
[00:02:16] Introducing the shadows of your superpowers
[00:04:00] How this episode is structured
[00:04:40] The unique nature of shadows and why they’re so elusive
[00:07:24] When your shadows catch up with you
[00:08:02] Four reactions people have when their shadows catch up with them
[00:08:07] Reaction #1: Fight
[00:08:22] Reaction #2: Withdraw
[00:08:53] Reaction #3: Ignore the shadow
[00:09:31] Reaction #4: Confront the shadow
[00:10:29] What separates shadows from regular development areas
[00:14:07] 10 common examples of shadows
[00:14:14] Example #1 - The great storyteller
[00:14:51] Example #2 - The collaborator
[00:15:38] Example #3 - The straight shooter
[00:16:36] Example #4 - The process expert
[00:17:32] Example #5 - The idea person
[00:18:18] Example #6 - The wartime individual
[00:19:30] Example #7 - The industry expert
[00:20:44] Example #8 - The hard worker
[00:21:27] Example #9 - The sacrifice
[00:22:39] Example #10 - The future thinkers
[00:23:38] Advice on what to make of all this
[00:26:08] What it takes to address your shadows
[00:29:32] Episode conclusion

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 significance of tackling six ambiguities in product management: product, growth, domain, market, organization, and team. He introduces these distinct skills and types of product managers, each uniquely contributing to the tech landscape. Nikhyl also addresses the often-overlooked organizational complexities and the vital role of team management. Most importantly, he stresses the significance of expertise and specialization over general managerial roles, busting common misconceptions about career growth. Tune in to this invaluable episode for profound insights into career development in the tech industry.

Connect with The Skip

The Skip: Newsletter | Website | LinkedIn CPO Group

Nikhyl Singhal: LinkedIn | Twitter | Facebook
 

Time-codes:

00:00 - Introduction to the Skip podcast and new format focusing on 30-minute coaching sessions.

01:46 - Discussion on the positive transition from manager to individual contributor (IC) and its impact on the tech industry.

02:30 - Introduction of six distinct skills to tackle ambiguities in product management.

04:30 - Leadership and its role in solving bigger, more ambiguous problems.

06:00 - Explanation of the six ambiguities: product, growth, domain, market, organization, and team.

07:57 - Analysis of product crafters, focusing on features and improvements needed for a product to succeed.

09:10 - Detailed description of the role of growth product managers, focusing on data and consistent product growth.

11:57 - Introduction to domain experts who bring specialized knowledge to specific areas.

15:00 - Examination of product managers skilled in navigating market ambiguity.

17:23 - Discussion on the role of internal consultants, strategic thinking, and execution.

18:20 - Emphasis on organizational ambiguity and its significance in delivering complex projects.

20:37 - Analysis of the increasing complexity of the organization with every new feature, product, and product line.

22:56 - Discourse on the importance of team management and executive leadership.

26:18 - Recap of the six skills crucial for product managers.

30:30 - Guidance on using the new language of skills when interviewing for better understanding of candidates.

5 Impactful Concepts:

• Transitioning from a managerial role to an individual contributor can have a positive impact on a tech career.
• Six key skills can help navigate ambiguities in product management, leading to successful project execution.
• There are different types of product managers, each with their unique roles and contributions to the product's success.
• Navigating organizational ambiguity is crucial in delivering complex projects, highlighting the importance of understanding organizational dynamics.
• Specialization in one or two areas, rather than general management, is vital for career growth in tech.

In this episode of The Skip Podcast, host Nikhyl Singhal explains how he helps product managers negotiate compensation. An industry veteran in the tech sector, Nikhyl has worked with 50+ leading executives and dozens of companies to ensure they establish optimal pay packages.  He unpacks the concept of equity in both public and private companies and offers a method for comparing job offers based on annual expected value and potential liquidity events. He then transitions into salary negotiation tactics, cautioning against pushing for the maximum offer and instead recommending a self-valuation approach. Nikhyl explores how companies establish compensation ranges using market data and explains how to compare early-stage, growth-stage and late-stage tech offers. . He later discusses the impact of a candidate's "eliteness" on negotiation power and offers a detailed guide on salary benchmarks in the tech industry. Finally, he concludes with tips on calibrating compensation expectations, hinting at the topic for the next compensation episode: negotiation strategies.

Summary of PM Compensation chart

Previous Skip episodes on compensation:

Tech compensation: Beyond the offer letter

How equity in tech companies works

Explaining Equity and Executive Compensation with Goodwin Procter

Time-codes:

00:54: Nikhyl introduces compensation challenges and equity's role in public and private companies.

02:20: Nikhyl recommends comparing job offers based on the annual expected value and potential for liquidity events.

06:54: He warns about the pitfalls of over-negotiation in job offers.

08:20: Suggests a "price to retain your services" approach to salary discussions.

10:40: Discusses how companies use market data to determine compensation ranges.

11:20: Advises asking about a company's compensation philosophy before discussing specific numbers.

12:20: Highlights how a company's compensation philosophy impacts the quality of people they hire.

13:37: Talks about the significance of a candidate's "eliteness" in negotiations and compensation command.

16:07: Discusses salary buckets for product managers in the Bay Area tech industry as a strategy for ensuring fair compensation.

21:16: Details average salaries for various roles in product management, from entry-level to executive positions.

29:32: Shares his method of calibrating compensation expectations based on a candidate's background.

30:34: Explains how he uses market ranges to ensure people are getting the right offer.

33:33: Wraps up the discussion, teasing the next episode on negotiation strategies.

Get ready for an engaging episode of the Skip podcast, where host Nikhyl Singhal dives into the evolving world of startups, head of product roles, and the fascinating field of product management. Discover how the head of product role has transformed in response to growth and hypergrowth dynamics, gain insights into the current market shifts and challenges, and explore the diverse career paths available, including joining healthy growth companies, considering number two roles, or even founding your own startup. Whether you're a product management professional, an executive, or simply curious about the dynamic landscape of the tech industry, this episode offers valuable perspectives and guidance that will inspire and empower you on your career journey.

Connect with The Skip

The Skip: Newsletter | Website | LinkedIn CPO Group

Nikhyl Singhal: LinkedIn | Twitter | Facebook

Full Show-notes:

0:00 Introduction and setting the focus on the changing role of the Head of Product.

3:10 Discussing the critical nature of the Head of Product role in hyper-growth companies.

6:15 Explaining the shift from hyper growth to sustainability and its impact on the Head of Product role.

8:17 Candid observations on the current Head of Product market.

9:37 Offering guidance to those seeking top roles.

11:43 Discussing the current state of companies and CEOs.

13:08 Emphasizing the opportunities in healthy growth companies.

16:00 Discussing the benefits of a number two role in a company.

19:00 Sharing wisdom about shifting between startup companies and big tech roles.

21:00 Discussing the challenges of big tech roles.

22:00 Addressing the dilemma faced by Heads of Product. 

23:36 Discussing the appeal of post-product market roles.

25:32 Suggesting considerations for choosing roles at different quality companies.

28:16 Addressing objections to starting a company.

30:58 Sharing insights on finding a partner for a startup.

31:57 Challenging the notion that startup work is harder than big company work.

32:56 Providing advice for executives considering founding a startup.

39:46 Discussing the changing job market and considering alternative career paths.