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: [email protected]

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