The Estee Show - Product Management & Business Insights

Mastering the Art of Reference Checks: Deep Dives and Honest Insights with Alison In this episode, Alison delves into the intricacies of conducting reference checks, sharing her personal experiences and methodology for obtaining the most valuable insights. The conversation explores the importance of in-depth questions, how to detect sincerity versus bias, and the role of reference checks in the hiring process. Alison also shares practical tips on navigating backchanneling, dealing with potential red flags, and using silence effectively in conversations. Additionally, she touches on her side business focused on health and wellness for high achievers. This episode is packed with actionable advice for hiring managers looking to enhance their interview process and set new hires up for success.   00:00 Welcome and Introduction 00:05 The Art of Reference Calls 00:24 Deep Dive into Reference Checks 01:17 Evaluating Reference Feedback 02:04 Setting Up for Success 03:50 Identifying Red Flags 04:27 Backchanneling Insights 04:57 Cultural Context and References 06:40 Effective Reference Questions 19:23 Handling Biased References 24:10 Importance of Reference Checks 27:51 Backchanneling Strategies 30:40 Understanding Weaknesses in Interviews 31:27 Evaluating Growth Mindset and Self-Awareness 32:13 The Importance of Culture Fit 33:28 Real-Life Examples of Improvement Opportunities 38:31 The Power of Silence in Conversations 42:19 The Role of Reference Checks 54:23 Red Flags in Hiring Decisions 59:04 Balancing High Achievement with Health 01:01:52 Final Thoughts and Key Takeaways   Bio: Allison is a founder, fractional CPO, and product advisor, who's worked at LinkedIn, Oscar Health, and various early stage startups.  She's built and led high performing product teams, and coached other product leaders uplevel in their career and navigate the uncertainties in the job. Allison is passionate about women's health and has also developed a support program for high achieving women struggling with their relationship with food, exercise, and irregular periods. Allison's company: https://www.theallymethod.com/  

Transforming Tech Careers: The Rise of Fractional Work with Ben Erez In this episode, we explore the revolutionary concept of 'fractional work' and its impact on career trajectories in the tech industry. Our guest, Ben Erez, shares his experience transitioning from a full-time product manager to embracing fractional work. He discusses his roles with Continuum, benefits of fractional engagements, types of fractional roles such as advisory and interim positions, and strategies for building a successful career in this field. The conversation also highlights balancing personal and professional life, especially as a parent, the value of maintaining a diversified portfolio, and the importance of pursuing work that energizes and excites you. 00:00 Introduction to Fractional Work 00:20 Personal Background and Initial Exposure to Fractional Work 01:02 Understanding Fractional Work 01:43 Real-World Experiences with Fractional Work 05:24 Financial Viability of Fractional Work 07:24 Advisory Roles in Fractional Work 16:25 Interim Roles and Their Challenges 28:28 Part-Time Product Management 30:58 Balancing Fractional Engagements 31:23 Challenges of Context Switching 33:01 Choosing the Right Tribe 35:00 The Owner's Mindset 36:54 PM and Interview Coaching 46:22 Navigating Parenthood and Work 51:16 Building a Fractional Career 58:31 Final Thoughts on Career Fulfillment   Bio:  Ben is a fractional product leader, interview coach, podcast host and newsletter author. He has been a 1st PM at 3 startups, and also worked for large companies including Meta. Ben is frank and insightful, and full of practical tips for anyone interested in fractional leadership.

Navigating Product Management Through the Lens of Political Strategy   In this bonus episode of the Estee show, David Lifson, a seasoned Chief Product Officer, joins the conversation to extract lessons from the recent presidential debate from June 27th, 2024. The discussion focuses on how product managers can learn from high-stakes political scenarios, touching on themes such as the importance of hypothesis-based thinking, planning for contingencies, managing expectations, and the necessity of effective communication. They also discuss leadership qualities, the need for adaptive strategy, and the value of surrounding oneself with diverse viewpoints. Lifson provides actionable insights for product managers on aligning strategy with execution and the critical role of messaging in achieving organizational goals.   00:00 Introduction and Guest Introduction 00:28 Analyzing the Presidential Debate 01:17 Hypothesis-Based Thinking in Politics 02:06 Lessons from the Debate: Execution vs. Strategy 05:50 The Importance of Setting Expectations 08:48 Leadership and Adaptability 10:55 Surrounding Yourself with the Right People 22:04 Effective Communication and Messaging 28:18 Final Thoughts and Takeaways   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.

Gaurav Discusses the Power of Napkin Math for Product Management In this episode, Gaurav Hardikar, VP of Product at HomeLight, talks about his journey through the real estate and startup scenes at companies like Zillow, Trulia, and now Homelight. He dives into the concept of 'Napkin Math' for Product Managers, advocating for quick and efficient decision-making over extensive financial modeling. Gaurav explains how this approach informs product prioritization and testing hypotheses swiftly. He also discusses his course on Maven, which aims to equip PMs with actionable growth strategies. Throughout the conversation, Gaurav emphasizes the importance of continuous learning and adapting new approaches within various business processes. 00:00 Introduction and Background 01:53 The Concept of Envelope Math 03:46 Practical Applications of Napkin Math 05:46 Failing Forward and Iterative Testing 06:25 Prioritizing Features and Roadmapping 12:17 Training and Mentoring Product Managers 15:19 Integrating AI in Business Processes 19:33 Collaboration with Engineering Teams 29:10 Course and Educational Initiatives 32:34 Lightning Round and Final Thoughts Bio:  Gaurav is a Product Executive with over 10 years of experience building digital products. He started at Trulia and Zillow Group with a reach of 50MM+ monthly users, grew an established mobile commerce app (Shopkick), and helped take Brilliant Smart Home 0 to 1 across SaaS, embedded hardware, and mobile app platforms. He's currently VP of Product, Consumer at HomeLight where he owns Product, Ops, and Growth.  Gaurav’s course - https://maven.com/insider-growth/pm-impact Link to Gaurav’s original post that inspired this conversation: https://www.linkedin.com/posts/ghardikar_as-a-product-manager-using-data-in-every-activity-7206363910474506242-BFxr

Creating Quality Products: A Candid Conversation with Toma on Design and Product Management In this episode, Estee converses with Toma, the first designer guest on the show, about the integral relationship between design and product management. They reflect on how they connected through a humorously truthful LinkedIn post that Toma put up about the dilution of design quality during product development. The discussion delves into the challenges of aligning different stakeholders' priorities, the importance of shared values in achieving extraordinary outcomes, and the pitfalls of compromising on quality for fast metrics. Toma talks about the significance of maintaining high-quality standards and the impact of values-driven decision-making in organizations like Apple and Microsoft. The conversation also touches on the detrimental effects of MVP culture and how true product management focuses on creating excellent products rather than just checking boxes. The episode concludes with a lightning round exploring Toma's views on design podcasts, his admiration for Steve Jobs, and key takeaways for product managers to prioritize quality and fight for the product. 00:00 Welcome and Introduction 00:24 The Designer's LinkedIn Post 02:44 The Importance of Aligned Values 04:54 Design in Tech Companies 08:34 Quality vs. Metrics 10:20 The MVP Debate 19:22 Top-Down Quality Culture 22:22 The Power of Value-Driven Decisions 23:13 The Problem with Compromising Quality 24:10 Top-Down vs. Bottom-Up Culture 25:18 The Importance of Using Your Own Products 26:40 The Role of Product Managers vs. Project Managers 31:06 Creating a Strong Product-Design Partnership 33:59 Evaluating Quality in Popular Apps 37:45 Lightning Round: Insights and Inspirations About Toma: Toma’s journey to becoming a designer was unexpected. Originally from Australia, he studied law and business before life took a turn in 2006, leading him to Italy. There, he moved his first pixel and wrote his first line of code. Since then, Toma has brought his design expertise to tech companies across multiple continents, focusing on product and organizational strategy and design. Now based in Amsterdam, he is a Design Director at the European hospitality unicorn MEWS, where his teams spearhead the creation of outstanding guest experiences. Link to the image that inspired this episode: https://www.linkedin.com/posts/activity-7188806639368462337-QDrv?utm_source=share&utm_medium=member_desktop  

Leveraging AI in Product Management with Rachel: Insights Beyond the Basics Rachel, an experienced AI product manager, shares her journey from electrical engineering to working at esteemed companies like Microsoft, Facebook, and Instagram. She discusses her career transition, the rise of AI, and the essential paper 'Attention Is All You Need.' Rachel dives deep into practical applications of AI for product managers, emphasizing productivity, personalization, and real-world examples like Spotify and e-commerce. She also explores the future of product management and engineering roles amidst AI advancements, providing valuable insights and advice for professionals in the field. Referenced in the episode:  1. Article about Shein: https://www.linkedin.com/pulse/how-data-science-artificial-intelligence-helped-shein-keep/ 2. Air Canada forced to honor refund policy invented by AI chatbot: https://indianexpress.com/article/technology/tech-news-technology/air-canada-ai-chatbot-9170822/ 00:00 Introduction and Welcome 00:04 Rachel's Career Journey 01:21 Impact of AI in Product Management 01:49 Deep Dive into LLMs and AI Technologies 06:26 AI for Productivity and Personal Use 18:21 AI in Professional Settings 31:33 Future of Product Management and AI 35:48 Personal Insights and Hobbies 38:57 Final Thoughts and Farewell Rachel's Bio:  Rachel started her path to product management as an Engineer in the semiconductors industry. Prior to that, she was a Digital Marketing and Product Specialist at Fiverr, where she was one of the first members of the team to focus on marketing and product research. As a strategy consultant at BCG, she focused on private equity and operations. Rachel joined YouNow as a Product Manager where she focused on broadcaster experience and internal tools, and joined DataDog to lead monitors and alerting product. Rachel holds an MBA from Columbia and a BSC in Electrical Engineering from Tel Aviv University.

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