The Skip Podcast

Latest Episodes:

4 secrets of career-boosting companies Aug 29, 2024

Show notes

Not all successful companies can supercharge your career. And not all companies that struggle are bad for your career. How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture. Whether you're job hunting or evaluating your current role, these insights will help you identify environments that truly foster career growth.

–

We also discuss:

Strong signals of a supercharged company
Why shipping velocity is crucial
Learning opportunities at immature companies
Looking for companies with strong talent
What makes an excellent development culture

–

Referenced:

Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=913s
Greatest hits on career advice with Peter Yang: https://www.youtube.com/watch?v=-BcCHEXAVVk
Is my next job at a startup or big tech?: https://www.youtube.com/watch?v=MiELOo4_XGg&t=9s
Should I join or leave an ex-hypergrowth company: https://www.youtube.com/watch?v=5-rr1cYYfEU
Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-c
Stage of Company: A career unlock: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s

–

Where to find Nikhyl:

Find The Skip:

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: nikhyl@skip.community

–

Timestamps

(00:00) Episode Teaser: How to 10x your career

(01:10) Introducing the framework

(03:41) The caller’s question

(05:00) 1: Speed and execution

(08:43) 2: Market position

(11:47) 3: Quality of talent

(15:27) 4: Development culture

(20:22) How to get in touch

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

Navigating careers while expecting Aug 21, 2024

Show notes

In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior role post-maternity leave, or seek opportunities elsewhere.

–

We also discuss:

Maximizing career potential without sacrificing family
Reframing career decisions in the context of long-term growth
How to have it all, just not at once
The value of wartime leadership experience
Overcoming job search anxiety

–

Referenced:

Avoiding burnout for high achievers

–

Where to find Nikhyl:

–

Find The Skip:

–

Timestamps

(00:07) Applying my career framework to the caller’s case

(02:13) Caller context

(02:52) Why one option is a “no-brainer”

(03:58) The value of wartime leadership experience

(07:43) Why you won’t regret choosing family > career

(09:53) The wisdom in “playing it safe”

(11:11) Key takeaways

(11:44) How to get in touch

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

Stage of company: a career unlock Jul 30, 2024

Show notes

Many product managers focus on brand names or job titles, overlooking a crucial factor: company growth stage.

This episode reveals how a company's phase - from startup to market leader - shapes your work and career path. We explore the four key growth stages, how product management evolves, and how to align your strengths with the right stage.

Featuring insights from seasoned product leaders, learn to identify your ideal company stage and navigate transitions. This episode is your guide to making strategic career moves in product management by leveraging the often-overlooked power of company growth stages.

We also discuss:

The 4 stages of company growth: drunken walk, product market fit, hypergrowth, and established market leader
How PM roles evolve across stages
Matching your skills to each stage
Intentionally choosing your company stage
The value of diverse stage experience for successful PMs
Strategies to gain multi-stage experience

Referenced:

Stage of company, not name of company: https://theskip.substack.com/p/stage-of-company-not-name-of-company
Shadows of your superpowers (Part 1): https://www.youtube.com/watch?v=XZbjvymjabA&t=912s
Shadows of your superpowers (Part 2): https://www.youtube.com/watch?v=lcdb5enbDLE

Where to find Nikhyl:

Find The Skip:

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.

Timestamps

(00:00) Intentionally choosing your company stage (episode teaser)

(01:25) The importance of company stage

(02:47) 3 common questions from PMs

(05:383) The link between PM and company stages

(07:48) The 4 company stages

(13:45) What’s unique about early-stage PMs

(15:24) How PM evolves when there’s customer traction

(18:00) Product management at a hypergrowth company

(21:50) One example of what changes between the first three stages

(24:49) PM at an established leader

(30:04) How to know which stage is right for you

(37:03) Spotting when it’s time for something new

(38:36) Choose your stage of company wisely

(41:38) Why top product people have multi-stage experience

(43:28) How to get in touch

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 art of building your personal brand Jul 10, 2024

Show notes

Personal branding is a crucial yet often misunderstood aspect of career development. Many professionals mistake personal brand for self-promotion or social media showmanship.

This episode debunks these myths and reveals the true power of strategic personal branding. Featuring insights from two tech executives, Annie Pearl of Microsoft and Iska Saric of Meta, we pull back the curtain on how industry leaders craft and wield their personal brands to open doors, land dream roles, and shape their legacies.

The episode provides actionable strategies to build an authentic and compelling brand that catapults your career forward.

We also discuss:

The critical distinction between reputation and brand
Why you don’t need to become an influencer
The power of ‘peak roles’ in accelerating your career
Tailoring your brand story to specific audiences
Strategies for expanding your professional network
Navigating gender dynamics in personal branding
The 30-minute per week method to brand-building

Referenced:

Annie Pearl, CVP at Microsoft: https://www.linkedin.com/in/anniepearl/
Iska Saric, VP of Communications at Meta: https://www.linkedin.com/in/iska-saric-97210212/
Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=1078s

Where to find Nikhyl:

Find The Skip:

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.

Timestamps

(00:00) Episode format

(02:14) Why brand matters

(04:47) Building a brand ≠ becoming an influence

(08:14) Reputation versus brand

(10:28) How to establish a reputation

(13:55) Leveraging professional connections

(18:08) The role that will transform your career

(24:12) Crafting and communicating your brand

(30:09) The "30-minute per week" method

(30:49) Navigating

(35:36) Key takeaways from this episode

(35:56) How to get in touch

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

Battling job search anxiety Jun 20, 2024

Show notes

Navigating job transitions in today's competitive tech landscape is difficult. Many people get stuck between roles, and an extended job search can dent your confidence. You might doubt your past achievements, question your current skills, and worry about what's next.

In today’s episode, we tackle job hunting in today’s tough market. I share insights from a real coaching session with a design leader who's struggling after being out of work for a few months.

The episode is packed with concrete tools, useful tips, and proven strategies to help you navigate a job transition.

–

We also discuss:

The mindset needed when in between jobs
Rebuilding your confidence from the ground up
The role of grit and hustle in an extended job search
How to run an effective job search
Making the most of your time between jobs
Transforming your mental, physical, and social game

–

Referenced:

–

Where to find Nikhyl:

–

Find The Skip:

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.

–

Timestamps

(00:00) Episode teaser

(01:45) Navigating a job transition

(04:34) The caller’s crisis of confidence

(10:22) Nikhyl’s advice

(16:24) Several strategies for effective job searches

(17:53) Pro Tip 1: Set realistic expectations

(21:41) Pro Tip 2: Work on yourself

(28:04) Pro Tip 3: Treat your craft like an athlete

(30:40) Pro Tip 4: Don’t cut your search short

(34:50) Pro Tip 5: Run the process with grit and hustle

(41:33) Pro Tip 6: Take advantage of the US calendar

(43:55) Pro Tip 7: Don’t try to find the ‘perfect role’

(47:55) Pro Tip 8: Bet on yourself

(48:59) Key takeaways from this episode

(51:02) How to get in touch

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

Avoiding burnout for high achievers May 28, 2024

Show notes

Around 10-20% of my coaching calls tackle burnout. Despite being a deeply personal experience, burnout frequently affects high achievers, who often don't have the time to develop effective coping strategies.

In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set healthy boundaries, and cultivate a resilient mindset.

–

In today's episode, we discuss:

Why burnout is a deeply personal experience
Insights on burnout from real-world examples
Why burnout is a side effect of success
Adopting a long-term career view
The importance of finding a hobby
Avoiding low-energy work

–

Referenced:

Balancing Work and Life: Insights from Nikhyl and the Skip CPO group

–

Where to find Nikhyl:

–

Find The Skip:

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter/X.

–

Timestamps

(00:00) Why you resent your company

(01:35) People experience burnout differently

(04:52) Today’s episode format

(05:36) The mindset needed to enforce boundaries

(07:25) Observation 1: High performing companies will always push their best people

(11:45) Observation 2: Family planning will require you to rework the timing of your career plan

(17:23) Observation 3: Ambitious, overworked people will eventually resent their job

(23:21) Pro tip 1: Changing your mindset toward burnout

(24:58) Pro tip 2: Finding a hobby forces joy on your calendar

(29:00) Pro tip 3: Recognizing what drives low energy at work

(31:04) Key takeaways from this episode

(32:39) How to get in touch

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

Crafting a compelling career story May 14, 2024

Show notes

After a three-month hiatus, The Skip returns with exciting news: April marked my departure from Meta, and I'm now fully focused on The Skip.

Though leaving was a difficult choice, the decision highlighted something important: effectively telling your career story matters more than ever in today’s job market. Companies are concerned that some people may have been spectators to growth rather than contributors. Or worse yet, compelling successes at work are ignored or misunderstood due to an articulation skill gap.

In today's episode, learn to craft a compelling two-minute career story you can use for interviews, personal assessments, networking events, and LinkedIn. Good stories ensure clarity, showcasing your achievements and authenticity. We dissect a typical PM career story and walk through how to make it compelling.

—

In today's episode we discuss the 6 steps of career storytelling:

Describe the project
Define your role
Frame the challenge
Outline what you built and why
Highlight what worked and what didn’t
Conclude

—

Referenced:

Where to find Nikhyl:

Find The Skip:

—

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.

—

Timestamps

(00:00) Why your career story is more important than ever

(01:25) Leaving Meta

(04:09) Episode format

(11:38) The case study

(15:04) The 6 steps

(16:44) Step 1: Project context

(16:40) Nikhyl’s commentary

(18:09) Step 2: Role context

(18:43) Nikhyl’s commentary

(21:12) Step 3: Frame the challenge

(22:15) Nikhyl’s commentary

(25:14) Step 4: What you built and why

(25:19) Implementing step 4

(32:05) Step 5: What worked and what didn’t

(31:58) Nikhyl’s commentary

(37:08) Step 6: Conclusion

(37:30) Nikhyl’s commentary

(38:39) Key takeaways from today’s episode

(39:42) How to work on your career story with Nikhyl

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

Shedding perceptions: Moving from lone wolf to team player Feb 11, 2024

Show notes

In my fourth live coaching session, this caller felt like they had earned an unfair reputation as someone who struggles with collaboration in the workplace. The caller wanted guidance on transforming past perceptions into a new reality.

The caller reveals both their superpower and its shadow. They are an opinionated product manager, blessed with exceptional taste and intuition. However, these traits also lead them to resist compromise. We confront the caller’s shadow, and explore frameworks and strategies essential for effective collaboration.

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:

How to shed poor perceptions in the workplace
Navigating organizational power dynamics
The up/down/across model of collaboration
When and how to compromise
Why 0 to 1 doesn’t exist in big tech
How to use the founder mindset in a large org

—

Timestamps:

(00:00) Introduction

(01:56) Caller context

(05:02) Caller’s reputation as a “rebel leader”

(07:11) How can I change people’s perception of me?

(08:37) Nikhyl’s response

(12:05) What the caller wants to avoid

(13:09) Nikhyl outlines two choices

(15:12) Should I optimize for short or long-term career wins?

[00:15:41] Nikhyl’s advice on risk and reward

(17:38) Should I leave big tech and become a founder?

(19:25) Nikhyl’s notes on compromise

(20:57) Should I play organizational Game of Thrones?

(21:45) Nikhyl’s recommendation

(25:39) Key takeaways from today’s episode

(33:03) Key links for this podcast

—

Where to find Nikhyl:

—

Where to find The Skip Podcast:

—

Don't forget to subscribe to The Skip to hear Nikhyl teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.

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

Is my next job at a startup or big tech? Jan 21, 2024

Show notes

In my third episode of live coaching sessions, this caller was feeling dissatisfied with their narrow scope of role and lack of cultural fit in their current company.

The caller wanted guidance on what their next role should be, given their personal situation and professional ambition. Their situation captures a difficult choice facing many superstars: seeking a sizable impact rarely found outside of startups, while also craving the compensation only late-stage companies can afford. We discuss the frameworks and strategies required to approach this career choice 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:

Aligning the stage of company to your specific situation
Compensation expectations
Risk tolerance in making career moves
The risks and benefits of joining big tech
Why top product executives do tour duties at big companies
How to break a big tech tenure into two roles
Why some big tech projects are more data-driven than others
Why experienced managers should consider IC roles

—

Where to find Nikhyl:

Where to find The Skip Podcast:

—
Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
—
Timestamps:
[00:00:00] Introduction and caller context
[00:02:17] Caller’s question
[00:07:40] Nikhyl’s follow-up questions
[00:10:15] Matching the stage of company to the caller’s situation
[00:11:03] Nikhyl’s recommendation
[00:16:56] Should I join a big tech company?
[00:18:03] Nikhyl’s response
[00:22:08] How do big tech product teams operate?
[00:22:55] Nikhyl’s response
[00:25:58] Why managers should consider IC roles at late-stage companies
[00:29:44] Key takeaways from today’s episode
[00:32:27] Key links for this podcast

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

Coaching grit, patience & tenure Jan 07, 2024

Show notes

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:

Where to find The Skip Podcast:

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

Our TOPPODCAST Picks

Follow Us

Stay Connected

Related Podcasts

Links

Stay Connected