
75 segments available
John Cutler writes the popular and beloved product newsletter The Beautiful Mess. For many years, he was a Product Evangelist at Amplitude, where he ended up meeting and working with a large number of product teams around the world. Through this role, he gained unique insight into how the best product teams operate. In today’s episode, John reflects on leaving his role at Amplitude and explains the attributes that the top 1% of product teams share and the varying ways that companies achieve these core elements. We go deep into some of his favorite frameworks and discuss the best way to apply these frameworks to your work. We also unpack skills like product sense and product mindset, and what he’s planning in his new role at Toast. — Find the full transcript here: https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing — Thank you to our wonderful sponsors for supporting this podcast: • Merge—A single API to add hundreds of integrations into your app: http://merge.dev/lenny • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny — Where to find John Cutler: • Twitter: https://twitter.com/johncutlefish • LinkedIn: https://www.linkedin.com/in/johnpcutler/ • Newsletter: https://cutlefish.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Referenced: • Amplitude: https://amplitude.com/ • The North Star Playbook: https://info.amplitude.com/north-star-playbook • Craig Daniel on LinkedIn: https://www.linkedin.com/in/craigmdaniel/ • Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 • AppFolio: https://www.appfolio.com/ • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • The Culture Map: Breaking Through the Invisible Boundaries of Global Business: https://www.amazon.com/Culture-Map-Breaking-Invisible-Boundaries/dp/1610392507 • Innovation Labs: https://innovationlabs.com/ • BEES: https://mybeesapp.com/ • Marty Cagan on Lenny’s Podcast: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan#details • Sooner Safer Happier: Antipatterns and Patterns for Business Agility: https://www.amazon.com/Sooner-Safer-Happier-Patterns-Antipatterns/dp/1942788916 • Teresa Torres on LinkedIn: https://www.linkedin.com/in/teresatorres/ • Andrew Huberman on Instagram: https://www.instagram.com/hubermanlab/?hl=en • TBM 49/52: Pyramid of Leadership Self/Other Awareness: https://cutlefish.substack.com/p/tbm-4952-pyramid-of-leadership-selfother • ChatGPT: https://chat.openai.com/chat • How to Measure Anything: Finding the Value of Intangibles in Business: https://www.amazon.com/How-Measure-Anything-Intangibles-Business-ebook/dp/B00INUYS2U • Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 • User Story Mapping: Discover the Whole Story, Build the Right Product: https://www.amazon.com/User-Story-Mapping-Discover-Product/dp/B08TZGKKF2 • Build with Maggie Crowley podcast: https://podcasts.apple.com/us/podcast/build-with-maggie-crowley/id1445050691 • One Knight in Product podcast: https://www.oneknightinproduct.com/index.html#page-top • Sunny Bunnies on Netflix: https://www.netflix.com/title/81286920 • Booba on Netflix: https://www.netflix.com/title/81011059 • Toast: https://pos.toasttab.com/ • Drift: https://www.drift.com/ — In this episode, we cover: (00:00) What is a product evangelist? John’s unique role at Amplitude (05:50) John’s reflections and feelings on leaving Amplitude (17:28) What John’s doing next (18:52) John’s newsletter: The Beautiful Mess (27:49) What do the top 1% of product teams have in common? (40:08) Different ways companies are successful, and why anyone can improve (45:55) Investing in people vs. investing in processes (49:59) Global company cultures: the individualist vs. the collectivist (55:55) Why it’s hard to make changes in large companies (58:49) How to view frameworks (1:01:02) The spectrum of performance (1:05:27) Examples of high-performing people who work outside of Silicon Valley (1:09:02) The skill of product management (1:11:35) The value of learning a bit about everything (1:13:46) Why do people often underestimate the loops available at their company (1:16:20) Chronic vs. acute issues at companies (1:18:07) Product sense and product mindset (1:22:38) John’s writing process and what he plans on writing about next (1:31:56) Lightning Round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
John Cutler emphasizes the importance of introspection for leaders, urging them to understand their beliefs and those of their teams. He discusses how self-awareness shapes authentic leadership and the ability to embrace diverse perspectives, setting the foundation for effective team dynamics.
"let's say you're a founder and you're trying to decide should I invest more on processes or should I invest more in people the first thing is introspection what do you believe in really what do you be..."
John Cutler shares insights from his unique role as a Product Evangelist at Amplitude, where he worked closely with numerous product teams. He describes his responsibilities, including coaching, workshops, and advocating for effective product practices, highlighting the value of expertise in product management.
"starts with self-awareness and then that's like that's how people form their authentic leadership Vibe and then they Flex a little bit and then they Embrace other perspectives welcome to Lenny's podca..."
Cutler reflects on the mission of Amplitude to become a trusted expert in product analytics. He discusses how his role involved not just promoting the product but also elevating the broader product community through workshops and personalized coaching, fostering a culture of learning.
"you to hear it with that I bring you John Cutler after a short word from our wonderful sponsors this episode is brought to you by merge every product manager knows the pain of slowing product velocity..."
In this segment, John Cutler elaborates on the extensive workshops and one-on-one coaching sessions he conducted during his tenure at Amplitude. He shares impressive numbers, indicating the scale of his influence on product teams and the importance of hands-on learning in product management.
"customers for free this episode is brought to you by EPO EPO is a Next Generation a b testing platform built by Airbnb alums for modern growth teams companies like netlify contentful and Cameo rely on..."
Cutler discusses the collaborative effort behind creating the North Star Playbook at Amplitude. He emphasizes that successful frameworks are the result of teamwork and iterative processes, rather than mere marketing strategies, showcasing the depth of expertise within the company.
"your experiment velocity John Cutler welcome to the podcast yeah thanks for having me Lenny I kind of know you as John Cutler I feel weird to call you just John do you find that to be true and also do..."
John Cutler reflects on the challenges faced during his time at Amplitude, particularly during the pandemic. He shares personal anecdotes about the emotional weight of supporting teams in crisis and the unique experiences that shaped his perspective on product management.
"that would have been pretty cool to be John Cutler the DJ I wrote songs and you know played you know rock music and stuff not not like a house DJ so okay this could be the next phase of your career wh..."
In this segment, Cutler expresses gratitude for the diverse experiences he gained while working with various product teams across industries. He highlights how these interactions enriched his understanding of product management and the importance of adaptability in different contexts.
"product teams and product managers unlike anything else I've seen or any other role I've seen before so could you just talk a little bit about this role that you had at amplitude and what it was like ..."
Cutler discusses the concept of community within product management, suggesting that every team member can act as an evangelist. He emphasizes the importance of fostering a supportive environment where knowledge sharing and collaboration thrive, ultimately benefiting the entire organization.
"weird idea could work so I'm really really grateful for that but yeah my official title was product evangelist I don't think that I super fit that role but that was the the title that we had and basic..."
John Cutler shares his emotional journey of leaving Amplitude, expressing gratitude for the relationships built and the experiences gained. He reflects on the challenges and rewards of his role, emphasizing the profound impact it had on his career and personal growth.
"sessions I I had these things called Product therapy sessions when I would just wake up in the morning and just kind of soak in whatever problem people were having for the day and I I did meet you kno..."
John Cutler discusses the collaborative effort behind creating impactful content at Amplitude. He emphasizes that valuable resources are the result of extensive testing, iteration, and teamwork, rather than spontaneous creation. This segment highlights the importance of a dedicated team in developing cornerstone pieces of content that resonate with users.
"with customers around retention and engagement then we had a PM and a great content writer archana zero in and kind of like make it palatable then we did Arc for it so it didn't just magically appear ..."
In this segment, John reflects on his emotional journey after leaving Amplitude. He expresses gratitude for the diverse experiences he had while working with various teams, from startups to established companies. John shares how the pandemic impacted his role and the challenges he faced, providing insight into the emotional weight of transitioning from a significant position.
"how does it feel to have left amplitude at this point imagine you're going through some roller coaster with motions oh geez um well the immense amount of gratitude definitely mentioned that uh wonderf..."
John elaborates on the heavy responsibilities he felt while working at Amplitude, especially during the pandemic. He describes the emotional toll of supporting teams facing crises and the intense workload that came with his role. This segment underscores the challenges product managers face in high-pressure environments and the importance of resilience.
"expertise and amplitude not necessarily me so I didn't get to dictate a lot of times the conversation it's like [ __ ] I'm not doing a very good job here like this person thinks in a very different wa..."
John shares insights from his experiences with various companies during his time at Amplitude. He highlights the differences in company cultures, particularly the passion and curiosity he observed in teams from different regions, such as India. This segment emphasizes the value of diverse perspectives in product management and the lessons learned from engaging with different teams.
"you know key lessons we could probably go into later when we're doing it you know one you're talking to a bunch of different companies and achieving the almost similar results in like very very differ..."
In this segment, John discusses his upcoming role at Toast and his desire to focus on helping a single company grow. He reflects on his experiences at Amplitude and expresses excitement about returning to a more vertical SaaS environment. This transition represents a shift in his career, aiming to apply his expertise in a more concentrated manner.
"just the passion and curiosity there was not one jaded person in the room like there was not one person like been there done that you know when's the performance review cycle ending or anything like t..."
John explains the philosophy behind his newsletter, 'The Beautiful Mess,' and why he embraces complexity and messiness in his writing. He reflects on the feedback he received regarding the lack of concrete advice in his content and discusses the importance of exploring the nuances of product management rather than providing oversimplified solutions.
"shift you touched on so many topics that I want to dig further into and you also talked about where you're heading next which I was going to ask so that's great thank you for covering all that by the ..."
In this segment, John delves into the challenges of providing actionable product advice in a complex landscape. He critiques the common perspectives in product management that focus on individualism and meritocracy, advocating for a more nuanced understanding of team dynamics and the context in which advice is applied.
"like that I actually and you noticed I asked on Twitter what I should ask you you have a lot of fans on Twitter and there's a ton of questions and one actually got pretty spicy and I want to touch tou..."
John shares his fascination with counterintuitive dynamics within product teams. He discusses how teams often overload themselves with work despite knowing that less is more effective. This segment highlights the complexities of human behavior in professional settings and the need for deeper exploration of team dynamics.
"end of this year I put this post out to people saying hey here are things I'm grappling with like the actionability of the content that I put out there diversity of product advice it's important to me..."
John emphasizes the significance of context in product management advice. He critiques the tendency for advice to be context-free and discusses how this can lead to ineffective outcomes. This segment advocates for a more contextual approach to product management that considers the unique circumstances of each team and organization.
"individualistic we can be when it comes to how we think about teams should be set up and stuff and then I think the third thing I realized was that it was very uh often very context free and I mean th..."
In this segment, John introduces the concept of complex adaptive systems in product management. He explains how teams operate within interconnected environments and the implications of this for product strategy. This discussion sets the stage for understanding the intricate dynamics that influence product development.
"basically the people rise to the top they try the hardest they work the hardest the best in companies employ them there's top tier companies there's second-tier companies so there's this very like hie..."
John discusses the phenomenon of high work in progress within teams, exploring why intelligent and capable individuals often take on excessive workloads. He reflects on the paradox of knowing that less is more yet still succumbing to the pressure of doing more. This segment highlights the psychological aspects of productivity in product management.
"broader system called the Bay Area that's in this broader system called California that's in this broader system called Deep In States you know your team is like in a team of many many teams in your c..."
John shares his thoughts on the balance between complexity and actionable advice in product management. He discusses the tension between oversimplification and the need to hold certain variables constant to derive value. This segment emphasizes the importance of nuanced thinking in providing effective product management guidance.
"passionate people in their personal lives and on their teams just like load themselves with up with work what are they optimizing about you know so that'd be like one example counter news so if the ot..."
In this closing segment, John reflects on the spectrum of product management advice, acknowledging the diversity of perspectives and the challenges of providing universally applicable solutions. He emphasizes the need for flexibility in thinking and the importance of understanding the unique contexts of different teams.
"of people who can produce that kind of content realistically and interestingly enough like I probably in my doodling in post I probably given Frameworks to do that I just don't think too much about it..."
Cutler introduces the Reverse Antichrine Principle, which suggests that while dysfunctional companies share common traits, high-performing teams can vary significantly in their approaches. He reflects on his experiences with product teams and the importance of identifying anti-patterns versus high-level principles.
"shifting a little bit coming back to just the bigger picture of John Cutler you've had more exposure I think to product teams and product managers more than like you're definitely in the top one perce..."
In this segment, Cutler explores how high-performing product teams make better decisions faster. He outlines the necessary components for effective decision-making, including diverse perspectives, information analysis, and clear goals, while also acknowledging the challenges in achieving this.
"it kind of makes me hard um to answer the question so you know a great example here is great product leadership like we need great product leaders but you made enough product leaders and you see that ..."
Cutler contrasts different methods companies use to make decisions, from rigorous processes to collaborative approaches. He highlights that successful companies can thrive under various decision-making frameworks, including top-down leadership, and discusses the implications for product managers.
"interesting right you're like oh you're saying you need information to make decisions it's kind of not very satisfying to do that right but then if you think about three companies let's say think thre..."
Cutler emphasizes the importance of coherence between a company's structure and its strategy for high performance. He discusses how startups often have fluid structures that must evolve as they grow, and how misalignment can hinder even the best teams.
"different way but then I'll just take like a couple principles so I just wanted to get that out of the way that like every one of these I mentioned could be achieved in a couple different ways so the ..."
In this segment, Cutler discusses the principle of 'strong opinions, loosely held' as a key trait of high-performing teams. He explains how teams can maintain firm beliefs while remaining flexible and open to new information, which is crucial for navigating the complexities of product development.
"be stubborn about some things that they were doing even when it didn't make sense in the short term right and then they would do that so I think that that's like another thing I think related to that ..."
Cutler reflects on the belief in the power of products and how this mindset influences decision-making and strategy. He shares insights on how successful companies cultivate a culture that values product quality and customer connection, drawing from his experiences at Amplitude.
"I have a couple more in depth like that like definitely the leadership is coherent so that's like you know walking the walk talking The Talk and I think this is one of the most fascinating ones becaus..."
Cutler addresses the critical question of how much hiring impacts a team's performance. He discusses the limits of having talented individuals without coherent leadership and structure, and explores whether teams can be transformed into high-performing units through strategic hiring and cultural alignment.
"right stop learning it you know I'll use the example of a company I mentioned this company AppFolio here in Santa Barbara but Klaus and John founded that company it's just a gem of a company it's an a..."
John reflects on the importance of hiring the right people versus establishing effective processes in creating high-performing teams. He acknowledges the challenges of leadership and the impact of team dynamics on success. This segment dives into whether a team can be transformed into a high-performing unit and the complexities involved in such changes.
"okay so we know there's a limit on one side of this particular problem right and we know on the other side of the problem is like if no one's done this before who knows because how many startups were ..."
Cutler shares insights on the biases that can affect perceptions of team performance. He discusses the balance between individual skills and environmental factors, emphasizing the need for introspection in leadership. This segment encourages leaders to challenge their assumptions about what drives success in product teams.
"too so four or five years ago I would have said well personal skills nothing it's all the environment there's people on Twitter do this all the time they're like bad management kills everything you kn..."
John introduces the concept that high performance is not a fixed state but a continuum. He explains how teams can experience fluctuations in performance and the importance of maintaining a growth mindset. This segment highlights the dynamic nature of success in product management.
"benefit from like challenging their uh they're maybe their their happy place me included I like that and do those things it's like it's an optimistic perspective basically anyone can change anyone can..."
In this segment, John discusses how external market conditions can influence a company's performance. He reflects on the misconception that success is solely due to leadership, emphasizing that market dynamics play a significant role. This insight is crucial for understanding the broader context of product team success.
"again and you know we feel those lows so that's kind of how I think about that particular thing this episode is brought to you by vanta helping you streamline your security compliance to accelerate gr..."
Cutler explores the complexities of leadership within organizations, noting that even effective leaders face constraints from structural and market factors. He discusses the limitations of the 'great man theory' and the multifaceted nature of success in product teams. This segment encourages a nuanced view of leadership effectiveness.
"the Enterprise proving security is essential sock 2 can either open the door for bigger and better deals or it can put your business on hold if you don't have a sock 2 there's a good chance you won't ..."
John shares observations on cultural differences in product teams across various countries. He contrasts individualistic and collectivist approaches, highlighting how these cultural frameworks shape team dynamics and collaboration. This segment provides valuable insights for leaders managing diverse teams.
"latter and I think that's that's why I called the damn thing the Beautiful Mess because I think that everyone we all have confirmation bias you know we'll point to that company and say I mean let's le..."
In this segment, John emphasizes the significance of self-awareness for leaders in product management. He discusses how understanding one's beliefs and values can guide effective leadership and team dynamics. This insight is essential for fostering a coherent and productive work environment.
"little bit outdated and then they were putting them in a competitively bad situation it's even that situation you can like idolize that particular leader for doing it but there's many things that coul..."
Cutler reflects on specific moments of high performance within teams, emphasizing the importance of individual contributions and collective effort. He shares anecdotes that illustrate how teams can thrive even in challenging environments, reinforcing the idea that success is often a collaborative endeavor.
"what do you believe in really and not just what do I believe in that you think the whole rest of the world like not like I think the rules of the world are that blank happens it's like what do you bel..."
John discusses the unique challenges faced by large organizations in maintaining high performance. He highlights the need for strong leadership and a supportive culture to navigate these complexities. This segment provides insights into sustaining success in larger, more bureaucratic environments.
"and people are great there are people that have an outsized effect in particular companies a great example there is like people forget that for example leaders or CEOs also have a lot of formal struct..."
John Cutler discusses the cultural differences between product teams in various countries, highlighting the contrast between individualistic and collectivist approaches. He reflects on how these cultural dynamics influence team collaboration and project management, emphasizing the importance of understanding these differences for effective teamwork.
"day and there's a group of people in this room who are extremely well-meaning and you know what the impact of their work might not even be seen in their tenure at that company these larger companies m..."
Cutler elaborates on the individualist mindset prevalent in some tech environments, where personal ambition can overshadow team collaboration. He contrasts this with more collectivist cultures that prioritize team goals and consensus, illustrating how these differing mindsets affect product development and team dynamics.
"that's one and you pick up about that a lot when you go to different places I mean in the United States but you know you'll find the situation where you've got this one engineering manager and they ar..."
In this segment, Cutler addresses the challenges faced by larger companies undergoing transformation. He discusses the inertia that can hinder change and the importance of adapting advice from Silicon Valley to fit the unique contexts of these organizations, emphasizing the need for tailored approaches to product management.
"an extreme example but then you compare that to other parts of the world it's like much more consensus driven the team perceives itself as a team having a team goal they have like a team objective and..."
Cutler shares insights on how companies can effectively adapt frameworks for product management during transformation. He stresses that frameworks should be viewed as tools for learning and improvement rather than rigid rules, encouraging teams to innovate and customize their approaches based on their specific challenges.
"internet and books newsletters like ours is geared towards Silicon Valley type Tech startups and in reality most VMS don't work at companies like that a lot of them are going through Transformations t..."
Cutler reflects on the complexities faced by large enterprises, particularly those with established structures and processes. He discusses the challenges of innovation within these organizations and the importance of recognizing the unique dynamics that influence their ability to adapt and thrive in a changing market.
"could avoid but then there's also just structural things that are just part of the part of the game to do that so you know like they'll be in situations where maybe none of the executives have shipped..."
In this segment, Cutler emphasizes the diversity of company performance, challenging the binary view of high-performing versus low-performing organizations. He highlights examples of companies that may not fit the typical Silicon Valley mold yet are successfully navigating their own paths, showcasing the variety of approaches to product management.
"and I think that the other thing that comes up with that is that most of those companies need to think of Frameworks appropriately like they'll read about these particular Frameworks or what particula..."
Cutler encourages product managers to learn from a wide range of product teams beyond Silicon Valley. He shares insights on the value of understanding different contexts and approaches, advocating for a broader perspective that includes successful practices from various industries and regions.
"lot of the big ride share and food delivery conglomerates are figuring out they're like oh this is a lot harder than we thought like when you're dealing with moving people around and Logistics and thi..."
Cutler discusses the often-overlooked factors of luck and inertia in the success of high-performing teams. He urges listeners to acknowledge these elements while also recognizing the potential for change within larger organizations, promoting a balanced view of success in product management.
"and that the people in the big companies or these not these companies that believe that's not the way that they can do that actually overestimate the kind of like systemic drag in their organization a..."
In this segment, Cutler highlights the importance of celebrating unconventional success stories in product management. He shares examples of companies that may not be in the spotlight but are achieving remarkable results, encouraging product managers to seek inspiration from diverse sources.
"company in Australia like you meet these companies you know what their revenue is literally like 50 startups they are not doing bad they are not doing bad and you know what they're actually doing inte..."
Cutler concludes by emphasizing the value of learning from a wide array of companies, including those that may not fit the traditional tech startup narrative. He encourages product managers to explore various industries and approaches, fostering a mindset of continuous learning and adaptation.
"game this is not like a slouch company but it's really hard for them to do that or you know at amplitude we'd have a lot of like not old fintech but not newest fintech companies they're printing money..."
John Cutler shares insights about John Smart, an influential figure in organizational transformation. He discusses Smart's humble approach and the complexity of problems he has tackled, emphasizing the importance of learning from leaders who have successfully navigated change in traditional companies.
"action item to like yeah list a couple of these put in the show and I'll give you an example of like one one guy and his name is John smart and he wrote this book called better singer say for happier ..."
Cutler highlights the significance of universal techniques in product thinking, referencing Teresa Torres and her methods like the Opportunity Solution Tree. He stresses that these frameworks are accessible to all product teams, regardless of their company's maturity, and can enhance product discovery processes.
"there's the people like Teresa Torres and others that have come up with a technique that is universal like you can like you can teach an element of product thinking with her techniques or this opportu..."
In this segment, Cutler reflects on the abundance of information available to product managers today. He emphasizes the need for continuous learning and the value of just-in-time knowledge acquisition, suggesting that individuals should focus on learning relevant skills as they arise in their careers.
"when you think of just like here's here's advice I have to share yeah I think um kind of going back to the Reps thing I think that there's this fire hose of amazing information that's out there and li..."
Cutler explains the data-informed product loop, detailing the steps necessary for effective product management. He discusses the importance of strategy, qualitative models, measurement, and the need to circulate learnings back into the product development process to ensure continuous improvement.
"um but I think that you need to keep in mind that this like this is a skill and skill is knowledge times practice mediated by your environment the habits you form and the motivation that you have into..."
Cutler advises product managers on how to navigate constraints within their companies. He encourages them to document their processes and assumptions, even in rigid environments, to maintain a proactive approach and build a portfolio of their contributions over time.
"example you need a strategy without that nothing is possible but you could have an amazing strategy and you don't deploy it with the right models no one can prioritize it we could do all that right bu..."
In this segment, Cutler discusses the importance of maintaining an optimistic outlook in product management, even when faced with challenges. He emphasizes that high-performing companies are not immune to dysfunction and that proactive efforts can lead to significant improvements.
"is don't feel like you need to read everything coming across your place yeah it's instead wait for the moment when you need that thing like I'm working at SEO right now cool I saved that thing about S..."
Cutler introduces the concept of chronic versus acute challenges within organizations. He explains how companies that address chronic issues can better handle acute stressors, highlighting the importance of intentional responses to crises like the pandemic.
"that there is a especially if you're starting out there is a definite value of almost seeing the 501 level courses or hearing that like genius lecture like when you're in college as a freshman I remem..."
Cutler encourages product managers to take ownership of their roles and to document their experiences. He stresses the importance of not allowing external circumstances to define their capabilities and urges them to actively seek opportunities for growth and improvement.
"just at least document like what was the so even if like someone from on high says build X you can at least say you know what uh selected option is X what would the one pager look like if x was one of..."
Cutler discusses the concept of product sense and its significance in product management. He emphasizes the need to unpack this skill into teachable competencies, advocating for a deeper understanding of systems thinking and decision-making in uncertain environments.
"shoulders and say I worked at a [ __ ] up because I worked in a messed up company it's all good yeah well yeah so you I worked in a messed up company it was all [ __ ] you you're not really honoring y..."
In this segment, Cutler highlights the importance of diverse perspectives in leadership. He advocates for showcasing relatable role models in the product management space, emphasizing the need for leaders who can connect with the challenges faced by their teams.
"Company where you just constantly changing it's also very chaotic and things are just breaking all the time and there's people too who just assume it's just has to be that way I I would say that one m..."
John Cutler discusses the critical distinction between 'can' and 'should' mindsets in product management. He emphasizes the importance of moving beyond mere pragmatism ('can we do this?') to a more strategic approach ('should we do this?'). This segment highlights how understanding these mindsets can enhance decision-making and foster a more innovative product environment.
"into things that could be taught and that's going to certainly be part of my role at toast right like the last thing I want to do is be like you have a product mindset or you don't a great example I w..."
In this segment, John Cutler reflects on the need for relatable role models in product leadership. He shares insights on how diverse perspectives and mental models can empower individuals in their careers. John emphasizes the importance of showcasing leaders who resonate with various challenges, rather than just the well-known figures in tech, to inspire others in their journeys.
"that I'm excited about um to do that and yeah I've got like yeah there's a bunch of other things you know like the diverse perspectives uh diverse mental models um maybe working with someone like you ..."
John Cutler opens up about his passion for writing and how he manages to balance it with a full-time job. He shares personal anecdotes about late-night writing sessions and the challenges of producing content while respecting workplace confidentiality. This segment offers practical advice for aspiring writers on how to maintain creativity amidst professional responsibilities.
"so I think that that's one thing I want to like work on in the next year to make sure that people have role models and not the people talking like me but like actual you know maybe I could be a role m..."
Cutler discusses the importance of embracing complexity in leadership and decision-making. He introduces the 'Pyramid of Leadership Self-Awareness' model, which illustrates the journey from ignorance to a nuanced understanding of diverse perspectives. This segment encourages leaders to recognize the value of different viewpoints and how they can lead to innovative solutions.
"to hope to do is maybe um be more deliberate about like trying to provide at least some maybe some mental models for dealing with the mess I mean there's things like that out there there's this thing ..."
In this segment, John Cutler shares his strategy for leveraging his extensive past content to create actionable insights for his audience. He discusses the potential of compiling his previous writings, frameworks, and talks into a cohesive guide that can help others navigate complex product challenges. This approach aims to provide clarity and actionable advice to those seeking guidance in their product journeys.
"the crap that I have I think it's like 700 800 posts maybe nine like there's I had this whole blog beforehand that I did it and then I have these hundreds of images with these Frameworks and then it's..."
John Cutler emphasizes the significance of qualitative data in product management. He reflects on his experiences at Amplitude and the common pitfalls of overcomplicating analytics implementations. This segment advocates for a more straightforward approach to data collection, encouraging teams to focus on actionable insights rather than exhaustive metrics.
"different ways amazing I imagine you might rename your newsletter the Beautiful Mess slightly less messy yeah jam and toast the jam and toast decision uh the the delicious yeah there we go uh also as ..."
In this engaging lightning round, John Cutler answers rapid-fire questions about his favorite books and recommendations for product professionals. He shares insights on essential readings that can enhance understanding of measurement and performance in product management, providing listeners with valuable resources to further their knowledge.
"partially under the under the guise that that I'm talking to so many teams so therefore it's never about amplitude absolutely not I think the one thing that I would change like I I don't think that ma..."
John Cutler kicks off the lightning round with a series of rapid-fire questions. He sets the stage for an engaging discussion, inviting spontaneous responses and insights from his experiences in product management.
"tip you're gonna get a lot of DMs with that we've reached our very exciting lightning round I've got five questions for you I'm just gonna go through them whatever comes to mind fire away are you read..."
John shares his top book recommendations for product professionals, highlighting 'How to Measure Anything' by Douglas Hubbard. He emphasizes the importance of understanding metrics in the context of reducing uncertainty and making informed decisions in product management.
"what are two or three books that you recommended most to other people yeah this one was pretty easy because they are fairly similar uh lately so I really like the book how to measure anything finding ..."
John discusses the book 'Accelerate' by Nicole Forsgren and Gene Kim, which explores the factors contributing to high performance in technology organizations. He highlights the importance of structured research and actionable insights for improving development practices.
"you need to make and we never have like people are like product is like science it's really like an art it's it's like a game that's being played out you never have complete information to do it so I ..."
John praises Jeff Patton's book on user story mapping, explaining how it simplifies the process of visualizing customer journeys. He reflects on its lasting impact on teams and how it fosters a deeper understanding of product management.
"amazing book because you can just literally put the stuff into motion about improving your uh development practices and things you're doing and then I think probably the last one man I just love this ..."
John shares his favorite podcasts, including Maggie Crowley's past episodes and Jason Knight's show. He expresses a preference for revisiting older episodes that feature insightful guests and discussions relevant to product management.
"three that come to mind Taylor suggestions I love I love answers that have books I've never heard of that seem really amazing so you check the checkbox there thank you next question favorite other pod..."
In a light-hearted moment, John talks about his favorite children's shows, 'Sunny Bunnies' and 'Booba.' He humorously acknowledges the challenges of finding adult content while parenting, sharing relatable insights for families.
"other than the one you're currently on I'm in like a voice you know I got a four-year-old I don't really spend a lot of time because I I'm this sort of like I'm such a lightweight it's like I'll do kn..."
John reveals his favorite interview question that assesses self-awareness in candidates. He explains how asking candidates to consider how a colleague would describe their actions can provide deeper insights into their teamwork and problem-solving abilities.
"something to learn two more questions favorite interview question that you like to ask folks oh so so one that I like to do is I do like the behavioral questions like tell me about stuff but then I'll..."
John shares a practical lesson learned from parenting: the importance of keeping kids fed to ensure better behavior. He humorously relates this to product management, emphasizing the need for basic care to maintain productivity.
"final question you mentioned you have kids what's the best lesson someone touched you about raising kids it's a challenge every day I just think they operate better when they are fed the kid as a prod..."
As the episode wraps up, John Cutler shares how listeners can connect with him on social media and expresses his desire for recommendations on guest speakers. He reflects on his journey and the excitement of his new role.
"right yeah you got it John and I feel comfortable calling you John and I feel like I just got to know you you're just like a John now um we hit our goal of I think it's going to be the longest episode..."
The episode concludes with John and Lenny reflecting on the insights shared throughout the conversation. They encourage listeners to subscribe and engage with the podcast, emphasizing the value of the discussions for product professionals.
"something that I can work on Amazing John thank you so much for doing this I'm really excited for this new adventure that you're on and I'm excited to maybe follow up maybe in a couple years of just l..."