The Estee Show - Product Management & Business Insights Estee Goldschmidt

Decoding Corporate Jargon and Navigating Workplace Dynamics 
In this episode, David Lifson returns to discuss the complexities and humor found in corporate jargon. The conversation covers the differences between real-world language and corporate speak, the creation of in-groups and out-groups through jargon, and the challenges faced by non-native English speakers. The hosts analyze popular corporate phrases and their hidden meanings, sharing their own experiences and observations.
They also delve into the toxicity of certain workplace cultures, the impact of poor management, and offer insights on how to identify healthy work environments. This engaging discussion provides both comedic relief and valuable advice for navigating corporate communication and dynamics.
00:00 Introduction and Guest Welcome 
00:12 Corporate Speak vs. Real World Language
01:23 Types of Corporate Jargon
02:09 Cultural Implications of Jargon
02:30 Literal Interpretations and Misunderstandings
03:59 Common Corporate Phrases and Their Meanings
04:28 Disagree and Commit
07:04 Digital Transformation and AI
15:40 Executives and Accountability
17:41 Breaking the Cycle of Toxic Work Environments
18:14 Red Flags in Job Offers
18:55 Defining Yourself Beyond Your Resume
19:41 Learning from Career Setbacks
21:29 The Reality of Startup Culture
22:42 Recognizing Toxic Job Descriptions
25:36 Effective Feedback in the Workplace
30:15 Understanding Communication Styles
34:54 The Problem with Bad Managers
35:17 Conclusion and Farewell
 
Bio: David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX.
 
See former episode with David here: https://theesteeshow.com/episodes/episode-24#spotify
 

The episode covers Ali Sipher's experience taking a 7-month career break. She discusses the importance of setting clear goals for the break, such as self-discovery and exploring new directions. Financial planning for 1.5-2x the intended break duration is recommended to avoid undue pressure. The initial months involved decompressing from the fast-paced work mindset and pursuing personal interests like getting certified as a phlebotomist. A major realization was how much time actually exists in a day without the constant urgency of work. The break allowed Ali to rediscover her core identity beyond her job and gain clarity on her values and interests. She advises taking at least 6 months for a true mental reset, and beginning the re-entry process 1-2 months before the intended return date. Overall, an intentional career break can provide invaluable self-awareness and perspective.
Planning for a Career Break Set clear goals for the break - e.g. self-discovery, exploring new interests Financially plan for 1.5-2x the intended duration of the break Determine responsibilities to hand off or cover during the break Embracing the Break Allow time to truly disconnect and decompress initially Pursue personal interests, projects, certifications Expect a mindset shift - days feel longer, less urgency Rediscover your identity beyond work Lessons from the Break You have more time than you think for what's truly important Savor the mental break from constant urgency Gain self-awareness about your core values and interests Decide if/when you want to re-enter the workforce Re-Entering the Workforce Start considering re-entry 1-2 months before intended return Don't wait until burnout to take a career break Plan for a bit more break time than you think you'll need Expect to miss using your brain for problem-solving eventually Key Takeaways Career breaks allow valuable self-discovery and mindset shifts Proper planning (financial, responsibilities, duration) is crucial Be open to the break taking you in an unanticipated direction Decide when you're ready to re-engage based on your goals  
Ali Sipher: Ali Sipher is an accomplished product leader who loves complicated and unglamorous problem spaces (think: supply chain, healthcare, accounting). She’s delivered innovative products, unlocked new revenue streams, and optimized operations in leadership roles at Parsley Health, Walmart, and multiple startups. After taking a six-month career break, Ali started working as a product management consultant. This helped her realize how much she loves owning the day-to-day product work. 

Ali is actively looking for her next full-time role solving complicated and unglamorous problems. Interested in connecting? Reach out: alexandrasipher@gmail.com

 
The Boiling Crisis at Boeing: Unpacking Five Years of Turbulence
 
In this episode, Kathryn and Estee dive into the ongoing crises and challenges confronting Boeing and the airline aviation industry. From crashes, the tragic suicide of a whistleblower to damning congressional hearings, Kathryn, an expert journalist with extensive industry experience, provides a detailed timeline and analysis of the pivotal events since January 2024. The conversation explores multiple Boeing aircraft incidents, including doors flying off mid-flight and wheels falling off upon takeoff, and scrutinizes the cultural and management issues that have plagued Boeing for years, emphasizing the shift from engineering excellence to profit obsession. Kathryn highlights the importance of public pressure on Boeing to enact meaningful changes, advocates for a complete overhaul of Boeing’s management, and urges passengers to vocalize their concerns to legislators and consumer organization.
 
Bio: Kathryn B. Creedy is a veteran aviation journalist and author who has covered every facet of commercial and business aviation.  Kathryn has written for Forbes Online and is the author of Time Flies – The History of SkyWest Airlines. Her byline has appeared in Smithsonian’s Air & Space Magazine and top aviation publications such as Air Transport World, Aviation Week and Space Technology, Flightglobal, Centre for Asia Pacific Aviation and Airline Business. In addition, she has written for BBC Capital, CNN Travel, The Los Angeles Times, AFAR.com. 


Series of incidents: Door flies off Alaska Airlines 737 Max (January 2024) Wheel falls off United Airlines aircraft (March 2024) Whistleblower John Barnett dies by suicide (March 2024) Boeing CEO Dave Calhoun announces retirement (March 2024) Concerns: Potential for more technical issues with Boeing aircraft Shift in Boeing's culture from safety-first to profit-driven Lack of transparency from Boeing regarding safety concerns Effectiveness of FAA oversight Historical Context: 1997 Merger of Boeing and McDonnell Douglas - potential cultural clash 2003 FAA recommendation on 787 Dreamliner battery casing ignored by Boeing (later implemented after incidents) 2018 & 2019 Lion Air & Ethiopian Airlines crashes involving 737 Max - questionable design choices and lack of pilot training on new system (MCAS) Blaming the victims (pilots) for the 737 Max crashes Current Investigations: Department of Justice (DOJ) considering criminal charges against Boeing for the 737 Max crashes FAA investigating Boeing's manufacturing practices Congressional hearings examining Boeing's safety culture Uncertain Future: Impact of investigations on Boeing's leadership and practices Need for stronger FAA oversight and passenger confidence  
 

In this episode of The Estee Show, Itamar Gilad, a former product manager at Google, Microsoft, and IBM, discusses his experiences and insights from his career. Focusing on his new book, 'Evidence Guided, Creating High-Impact Products in the Face of Uncertainty' he introduces the concept of 'evidence-guided' product management, contrasting it with traditional methods that rely heavily on intuition and fixed roadmaps. He emphasizes the importance of gathering and following evidence to make informed decisions, and addresses how his frameworks, including the GIST model and confidence meter, provide practical applications for prioritizing and validating ideas. Through anecdotes and historical examples from industry giants like Apple and Amazon, Gilad elaborates on the role of humility, testing, and iterative development in successful product management. He also shares his thoughts on organizational resistance to change and strategies to foster a more evidence-based, innovative culture. A must-listen for anyone interested in modern product management practices.
Itamar's Bio: Itamar is a coach, author and speaker specializing in evidence-guided product management and product strategy. For over two decades he held senior product management and engineering roles at Google, Microsoft and a number of startups. At Google Itamar worked at YouTube and led parts of Gmail.
Itamar is the author of the book Evidence-Guided: Creating High-Impact Products in the Face of Uncertainty. He also publishes a popular product management newsletter and is the creator of a number of product management methodologies including GIST Framework and The confidence meter.
Itamar is based in Barcelona, Spain. You can find more information on his website: https://itamargilad.com/
00:00 - Introduction and background on Itamar Gilad, author of "Evidence Guided Product Management"
02:20 - Definition of "fake door test" for measuring user interest02:50 - Definition of ICE/RICE prioritization frameworks
03:15 - Definition of OKRs (Objectives and Key Results)
04:00 - Gilad's journey from being a product manager to writing his book
07:40 - Discussing the GIST framework (Goals, Ideas, Steps, Tasks)
10:20 - The importance of humility and not having all the answers as a product manager
12:15 - Examples of successful product launches at Google using evidence-guided approach
15:40 - Proper use of ICE/RICE frameworks and avoiding common pitfalls
19:20 - The role of experimentation and testing ideas before fully building them
22:30 - Leadership's role in embracing ambiguity and disciplined product development
 
 

This podcast episode features an in-depth interview with Alex, a former product manager at Google, now running a business that helps experienced product managers advance their careers. Alex discusses the benefits and challenges of working in product management within the tech industry, emphasizing the value of having top tech company names on one's resume for career opportunities and compensation. He also touches on the cognitive dissonance experienced by product managers, the interviewing process, strategies for job seekers, and the role's requirements at large tech companies. Furthermore, Alex shares personal stories, including starting his YouTube channel and the impact of his advice on others. The conversation also covers topics like strategic ambiguity in tech companies, the importance of organizational and communication skills, and insights into succeeding in product management roles.

Bio: Alex Rechevskiy was a Group PM at Google and has built and run products and product teams of all sizes. He has also coached and mentored hundreds of PMs at all stages of their careers and helped many clients land product roles at top tech companies. Alex writes on LinkedIn, makes videos on YouTube and runs a group coaching program called the Product Career Accelerator for serious tech professionals who want to grow their career and compensation.
Links: 
Product Career Accelerator: group coaching program for getting into your next product role and growing your product skills & career (https://www.alexrechevskiy.com/pca) LinkedIn for daily product management tips (https://www.linkedin.com/in/alexrechevskiy/) YouTube for practical and instructional videos (https://www.youtube.com/@AlexRechevskiy)


00:00 Welcome to the SD Show: A Deep Dive into Product Management
00:27 The Unmatched Benefits of Working in Top Tech
04:39 Alex's Journey: From Google to Guiding Product Managers
04:58 The Realities of Breaking into Product Management Today
05:54 The Genesis of a YouTube Channel for Product Managers
11:02 The Interview Process vs. The Reality of the Job
13:50 Navigating the Complexities of Top Tech Companies
15:47 The Strategic Ambiguity of Monopolistic Tech Giants
19:19 The Culture of Respect at Google
20:09 The Impact of Google's Innovations on Humanity
20:46 The Challenge of Innovation and Risk at Google
23:01 Navigating the Job Market in Big Tech
24:33 Mastering the Job Application Process
31:12 The Interview Process: Strategies for Success
35:58 Preparing for a Product Management Role
38:14 Lightning Round: Personal Insights and Final Thoughts

A Journey from Radio to Product Management and the Essence of Product Thinking
 
The script features an engaging conversation between the host and Brody Clemmer, a former radio host turned product manager, who shares his unique career path from working in radio to eventually finding a passion for product management and mental health. Brody discusses the accidental nature of many peoples' entry into product management, his own experience transitioning through various roles, and the importance of 'product thinking' across all organizational functions. He emphasizes that product thinking focuses on understanding and solving user problems, distinguishing it from product management which requires execution. Further, Brody shares how he implements product thinking in his current role at Koa Health through initiatives like 'product class,' aiming to foster a culture of problem-solving and cross-functional collaboration. The conversation also touches on mentorship versus coaching, the dynamics of therapy and mental health, and concludes with Brody sharing insights on personal fulfillment and career choices.
 
00:00 Welcome to the Show: Brody Clemmer's Unique Journey
01:38 From Radio Host to Product Management: A Career Evolution
02:34 Introducing Product Thinking: Beyond Traditional Management
03:37 Product Thinking vs. Product Management: A Deep Dive
09:30 Implementing Product Thinking in Organizations
15:41 The Impact of Product Thinking on Company Culture
19:20 Mentorship vs. Coaching: Brody's Approach to Personal Development
22:53 Therapy, Mental Health, and Product Thinking
29:26 Lightning Round: Personal Insights and Reflections
 
Tools discussed in episode: Vistaly for consolidating and mapping user feedback
https://www.vistaly.com/
 
Bio:  Brody Clemmer lives in Philadelphia with his fiancé and their son - and is a generalist at heart. For work, he is currently the Lead Product Manager at Koa Health where he was the first US based Product hire, and is focused on the scalability and delivery of Koa’s products, ranging from mental health education to global clinical networks that support employers, payors, and multinational organizations in delivering mental health care for their members. Brody started his career out of high school, after making the decision to not go to university, first working in Radio, then TV Production, then landing at Apple for five years before starting his own business with a guy he met on Twitter. After selling the business at a personal  loss, he found himself as the first product hire for a few “unsexy” companies in unknown industries like Executive Search, Leadership Consulting, corporate Sales Training, and finally making his way into Healthtech startups.