The Beautiful Mess Podcast

John Cutler
  • 5.0 (3)
  • TECHNOLOGY
  • UPDATED WEEKLY

A podcast about how context and nuance impacts our work, how we collaborate, and how we organize. Hosted by John Cutler, author of The Beautify Mess newsletter cutlefish.substack.com

Episodes

  1. 12/01/2025

    TBM 392: When (And How) Tools Matter

    A video post!The Miro board used in the video can be accessed here: https://miro.com/app/board/uXjVJi6NCs8=/?share_link_id=616280785572 (PS: Miro, I’d love another sweatshirt!) This framework explains why tools help in some situations and fail in others by grounding everything in the current state of a behavior. Every important behavior in an organization sits somewhere on a spectrum: it might be purely aspirational, weakly practiced, inconsistent, friction-heavy, fully stable, actively suppressed, or not even clearly defined. Each of these states is held back by different blockers—lack of clarity, lack of skills, lack of time, workflow friction, political risk, or social norms—and each requires a different kind of support. Using a behavior-design lens like COM-B, the idea becomes simple: tools only work when they address the real blocker. Sometimes their job is to scaffold early steps and turn aspiration into practice. Sometimes it is to remove operational drag from a behavior that already exists. Sometimes it is to create shared visibility and reduce political friction. Tools matter, but how they matter depends entirely on the behavioral context they are dropped into. Show Notes (AI Generated) The Core Question When do tools matter, and how do they matter?Answer: It depends entirely on the current state of the behavior you want to see. The Seven Behavior States A. Normal States * Aspirational / Not RealizedOnly talked about. No real practice. * Weakly RealizedPeople agree it matters and occasionally try it, but it gets displaced by urgency and habit. * Partially Realized / InconsistentHappens in pockets. Conflicting interpretations. Local successes that have not scaled. * Mostly Realized but Friction-FilledBehavior is accepted and happening, but it is painful due to workflow friction, manual effort, tool constraints, or time pressure. * Fully Realized / StableConsistent, predictable, routinized. Embedded norms. Change feels risky. Special States * Actively SuppressedCounter-behaviors, incentives, or power dynamics prevent the behavior. * Contested / UndefinedNo shared understanding of what the behavior even is or how it should show up. COM-B Essentials A behavior emerges when people have: * Capability * Psychological: knowledge, mental models, clarity * Physical: skills, practice * Opportunity * Physical: time, tools, workflow space * Social: norms, permission, cues, legitimacy * Motivation * Reflective: beliefs, intentions, identity, political risk * Automatic: habits, impulses, shortcuts Tools can influence any of these. How Tools Help Depends on the Behavior State If the behavior is… Aspirational / Not Realized Primary tool role:Turn aspiration into a repeatable practice. Strategies: * Provide structure and scaffolding * Make early steps easy * Visualize desired state * Reinforce identity and intent Weakly Realized Primary tool role:Lower activation energy and make it harder to forget or skip. Blockers: * Not enough time * Habit competition * Too many steps * Short-term urgency wins over long-term value Strategies: * Reduce steps * Support self-regulation * Nudge and cue the behavior * Make it easy to start Partially Realized / Inconsistent Primary tool role:Create a shared frame without forcing uniformity. Strategies: * Clarify purpose * Help reconcile or visualize different interpretations * Provide minimally viable standardization Mostly Realized but Friction-Filled Primary tool role:Remove operational drag. Blockers: * Workflow friction * Manual coordination * Confusing handoffs * Tool gaps Strategies: * Standardize routines * Streamline workflows * Make bottlenecks visible * Automate repetitive work Fully Realized / Stable Primary tool role:Preserve what works while reducing risk and effort. Blockers: * Risk aversion * Fear of destabilizing the ritual * Manual grind that no one wants to mess with Strategies: * Automate low-value steps * De-risk changes * Protect institutional knowledge Contested / Undefined Primary tool role:Clarify, name, and frame the behavior. Strategies: * Make interpretations explicit * Help teams converge on a definition * Reveal misalignment Actively Suppressed Primary tool role:Shift legitimacy, visibility, and power dynamics. Strategies: * Provide shared visibility * Depoliticize the behavior * Reinforce norms or incentives * Create social proof Tool Change Vectors (How Tools Influence Behavior) Tools can work through different mechanisms depending on the blocker: Influencing Capability * Clarification * Instruction * Cognitive offloading * Guided workflows * Checklists Influencing Opportunity * Automation * Better workflows * Reducing steps * Making time and space Influencing Motivation * Social proof * Legitimacy * Identity cues * Reduced political risk * Reinforcement What This Means for AI AI’s role will differ depending on the behavior state: * In aspirational states: scaffold early steps, provide examples, generate clarity. * In friction-filled states: remove manual overhead, automate stitching, reduce coordination cost. * In stable states: protect quality, ensure consistency, prevent regressions. * In contested states: help surface meaning, definitions, and distinctions. AI is another lever in the COM-B system — not magic, but highly state-dependent. The Core Insight Tools always matter, but they matter in different ways depending on: * Which behavior you’re trying to support * Where that behavior currently sits on the realization spectrum * What is actually blocking it (Capability, Opportunity, Motivation) Getting this right means choosing the right intervention instead of assuming tools “fix” or “don’t fix” things. Get full access to The Beautiful Mess at cutlefish.substack.com/subscribe

    7 min

  2. 06/30/2025

    TBM 365: The Problem With Value Hierarchies (Video)

    I’m experimenting with Substack’s Video feature. I’m not sure how this will look, appear, or even sound, but giving it a go. Below I include an outline of the video: Outline 1. The Familiar Cascade * Many organizations use a hierarchical model: Pillars → Priorities → Initiatives → Epics → Tasks * Timeframes are often assigned at each level (e.g., 3–5 years at the top, sprints at the bottom) * Roles and ownership are mapped accordingly, from executive leadership down to product teams * These models persist because they’re intuitive, visual, and create a sense of order 2. Core Limitations of the Pyramid * Assumes one-way flow of informationThe model suggests strategy flows down, but in reality, critical insights flow up from teams engaging with customers and the market * Outcomes are often missing or impliedThere’s no explicit representation of impact or results, even though that’s what ultimately matters * Ignores time-to-impact variabilitySome tasks can generate impact in a week; some initiatives take years. The model fails to show these lags and feedback loops * Pushes teams into execution rolesAs you move down the pyramid, the framing becomes increasingly prescriptive. Teams are expected to deliver “work” without clear problem framing or strategic ownership * Misrepresents the scope and nature of workHigh-impact short-term efforts may not “fit” in the hierarchy, creating friction. It also disincentivizes small, iterative wins 3. Temporal Scope and Organizational Culture * Comparing two fictional organizations reveals differences: * Org A’s goals are outcome-driven across time horizons (e.g., 1–3 month engagement goals, 3–5 year market positioning) * Org B’s goals are more output-focused and vague at longer horizons * Ownership of goals varies by company—some give product teams ownership up to the one-to-three quarter range, others do not * The same pyramid diagram can reflect entirely different behaviors depending on definitions, ownership, and cultural orientation toward outcomes vs. activity 4. The Need for Multiple Lenses * The pyramid presents a single, strategy-to-task lens, but organizations operate with multiple overlapping views: * Outcome lens – focused on impact and customer results * Work lens – focused on deliverables and execution * Finance lens – focused on costs, forecasting, and ROI * Structure lens – focused on organizational shifts, team structure, and ownership * Each lens has its own rhythm, scope, and patterns of change * These lenses intersect in complex ways that a static pyramid cannot represent 5. Real Work Behaves More Like a Fabric Than a Cascade * Work, strategy, and feedback move in all directions—not just top-down * Many artifacts and processes exist at mid-levels of abstraction, not neatly tiered * A more accurate model is a fabric or network of interconnected items with varying temporal scopes and ownership * Strategic influence can originate anywhere, and changes at any level can ripple across the system 6. Introducing Artifact Types and Their Cadence To support this networked reality, artifacts should be understood in terms of their nature and rhythm: * Anchor Artifacts * Have a defined time horizon (e.g., a 12-month roadmap) * Refreshed on a set cadence (e.g., quarterly planning cycles) * Useful for stability and coordination * Intent Artifacts * Represent bets, goals, OKRs, and strategic initiatives * Tend to evolve as work progresses and understanding deepens * Often nested or linked to other artifacts dynamically * Context Artifacts * Reflect shifting knowledge and environmental signals * Can be volatile (e.g., customer feedback) or stable (e.g., competitive analysis) * Drive updates to other artifact types when significant changes occur 7. The Role of Rituals * Artifacts don’t stand alone—they are reinforced and refreshed through team and organizational rituals * Effective operating systems clarify: * Which artifacts exist * Who owns them * When and how they are updated * How they relate to each other across different lenses and timeframes * Rituals also provide the opportunity to resolve contradictions and adapt to change 8. Final Synthesis * The strategy pyramid is a helpful storytelling tool, especially for presentations or executive alignment * But it is insufficient for designing actual operating models * Effective models recognize: * Multiple lenses (not just one) * Temporal and definitional complexity * The need for dynamic linkages, not static nesting * The interplay of strategy, execution, finance, structure, and learning * Building an effective system means embracing this complexity and supporting it with the right artifacts and rhythms—not oversimplifying it into a cascade Get full access to The Beautiful Mess at cutlefish.substack.com/subscribe

    15 min

  3. 05/26/2024

    Product Coaching with Petra Wille

    On this episode, I'm very honored to welcome Petra Wille. Petra is an experienced product leader, product leadership coach, and author. She has written two books, Strong Product People, A Complete Guide to Developing Great Product Managers, and Strong Product Communities. Community is something Petra is extremely passionate about and very good at. Petra, together with Arne Kittler, organize one of the most thoughtfully curated and run conferences in the world, Product at Heart, in their hometown of Hamburg, Germany. I highly recommend it. And tickets are still available for this fall. Petra and Arne actually had a huge role in my career by inviting me to my first product conference speaking opportunity in 2017 . I returned last year and it was going stronger than ever. In this episode, we focus mostly on coaching. We explore different types of coaching, when coaching is the answer and when it isn't, the role of communities of practice, and boundaries of influence. Of course, I'm rethinking this approach now, but we jumped straight in with a question. Here it goes. Transcript John Cutler: I like to get straight to it. When is coaching a bad idea? I don't want to put you on the spot because I know you're a fan of coaching. But I want you to explain to people when you think it's not the best idea. [00:01:11] Petra Wille: Right into it. I love it. So, a lot of companies use it when they should actually take more time and think about what their people should actually learn more about. And invest in training, capability building, coaching by the product leader itself. So I assume when you say like, when it's coaching a better day, you mean by an external coach, like I am one. So should people actually go to some basic training because what they're missing is know how. They just need to hear some new things. They just need to pick up some new lingo. That's oftentimes what I do in coaching and I'm always like, okay, but that's so basic, read a book, watch that talk, listen to that podcast, go to a training. And then maybe if you've really have a tougher problem to solve, then maybe coaching is something for you. So that was one thing. Reflective training would not be the appropriate format for you. Self learning could be the same thing, right? And then coaching is not a good idea if companies decide that 10 random people from the organization get coaching, and then just the first person that's raising the hand gets the coaching ticket. The coachee needs to allow me to help them and they really need to be invested in the challenge that they're having. And really want to make me understand what their challenge currently is. And then I'm entitled to ask the really helpful questions. So what do you want to be known for? Or what in this particular problem do you want to appear to your colleagues or something like that? The more trickier questions. So people need to be vulnerable at times in a coaching relationship, and if just like random people from random backgrounds gets a coaching ticket with me, then that's oftentimes not so helpful for them. And I have always the feeling that I cannot add the value that I would like to bring to these organizations, if that's what they do. So that's maybe the three situations where I think coaching's not so helpful. [00:03:04] John Cutler: I remember someone telling me recently that at their company, there was an incredible pressure on middle managers to go deep, get in the details, do a better job, essentially in this current climate. And they had actually fired many of the in house coaches. And then they told me that every executive had a leadership coach. And I'm curious your thoughts on that, where it seems like that wasn't quite fair. It seemed like the internal coaches who were trying to help the managers were seen as unnecessary. And meanwhile, it was seen that the leaders were somehow entitled to those coaches, or maybe that it would benefit the company. I know that's a messy question. But maybe what's a generous interpretation of that? And then maybe what's a, you know, what's a less generous interpretation? [00:03:49] Petra Wille: Yeah. So my question, if I hear in house coaches is always what type of coaches are we looking at? Because we're all so familiar with the agile coach concept and a lot of the agile coaches that I've been exposed to and was working with are not kind of coaches by only asking the right question at the right time, right? So they really have their personal take. They always share their personal tech and experience with the teams. That's the shortcut of these agile coaches, right? Ideally they provide the team with options and suggestions, but sometimes they're even telling the teams how to do certain things to speed things up. That's the pressure that the agile coaches are often under. So deliver things faster. But this is rarely something that I see, and I would love to see more of them, is in house product management or product coaches. And it could be all sorts of coaching, right? So if you need more product operations, or now one would call it maybe the product operating model and the transformation coaching towards such a more mature product organization, then that is something that product coaches oftentimes do. I, for example, don't provide executive coaching because it's just a different game. I think you have to have solid executive experience to be an executive coach. And do I have some leadership experience? Yes. But have I been an executive for a long period of my career? Maybe not. But I have been a product person for a long time in my career. So I can help product people and product leadership folks to get better at what they do with the challenges that they currently have. Am I focused on the purely executive part of this whole equation? So not. So it sounds like they have removed some of the people that are doing hands on work with the product teams, maybe the product organization, maybe the product development teams, and have the other side back with executive coaching and now focus more on the execution itself. That's such a different thing to do. Hopefully there's a benefit in that. Hopefully they will see positive impact from that. There's still a ton of stuff that leaders could learn and get better at the executive level, but it's not the same thing then product coaching, product leadership coaching, maybe the agile coaches we're doing. So yeah, I would be interesting to hear how that went. [00:06:10] John Cutler: When you're talking to product leaders that overlap that upper bounds in the hierarchy of the people that you end up coaching, are there any specific tactics that you use? Are there any specific considerations you need when coaching those individuals? [00:06:24] Petra Wille: It always so much depends on their background. So are there already one of us? So are they product people? Then their coaching topics usually are more the ones that the executive coach would have with them, right? So then it's more the storytelling, then it's the providing directional clarity. It's the strategy bit. It's the stakeholder management as in, investors, boards, senior executives. So then it's more these kind of things. You're no longer managing the product. You are now managing your organization to some extent. So your product becomes the product organization itself. And that is a big coaching topic. So it's really, it's this unlearning one thing, your product reflexes, and relearning the product leadership reflexes. So that is maybe the biggest part, if you have former product background. But I have a lot of product leadership coachees that have no former product background. And then it oftentimes is more helping them to understand what actually happens within the teams, the team dynamics that unfold. It can be super simple things like what are the challenges in discovery and delivery? So how does it feel when you are working in such a product delivery or product team, depends on how you call it in your organization, right? But that's, that's an entirely different coaching game. One is more like helping them to develop the empathy that one needs to be a successful product leader when working with product teams and your product organization. And the other oftentimes is more the upper level stakeholder management, I'd say. But these are the evergreen topics. Unlearning reflexes in both situations is one of the big topics I'd say. [00:08:05] John Cutler: When you're first meeting someone that you might potentially coach, there's probably a number of twists in that journey in the beginning where you're trying to understand where they're coming from. I'm curious how you put aside-- or maybe you don't put aside-- your personal biases of the type of environment you want to work in or the way you want to approach leadership and then where that person is coming from. Because I think that's a skill that a lot of great coaches have, but it's hard to understand exactly what's going on there. Are you literally meditating inside? Are you clenching your hands? Are you just telling yourself, stay curious, stay curious? How do you do that? [00:08:46] Petra Wille: I'm a curious person, so that's not the hard part. Some of the thought leaders that all of us are reading and quoting do us a massive favor in describing an ideal scenario. Maybe they're not talking often enough that maybe impossible to reach the super ideal scenario. Especially for one organization at any given point, it is hard to, to be at this ideal scenario. I saw organizations being at an ideal scenario, but with some parts of this organization for a really limited amount of time. And then you have to invest a lot of energy to keep it there, right? So it's not easy. But I think it's good if we have all of these people writing the books and talking about the ideal scenario. And then on the other hand, it is super important to have other people-- and you, for example, for me, fall in that

    34 min

  4. 05/19/2024

    20 Things I've Learned as a Systems (Over) Thinker (Extended Commentary)

    Back in 2022, I wrote a post called 20 Things I've Learned as a Systems (Over) Thinker—”over” was in parentheses—and I've since received so much feedback about that post. I recently re-shared it on LinkedIn and it obviously strikes a chord. And so I thought that for this episode, I would just quickly go through that list, provide a little bit of extra color, and hopefully clarify some things. I'll be back to interviewing guests in the next episode, but I'd just like to experiment with this format and be curious what you think. Here is the list for reference: * Take care of yourself. Your brain is working overtime—all the time. Practice “radical” recovery. * You may spend a lot longer thinking about things than most people. Pace your delivery. * If you go deep first, and then simplify…keep in mind that you don’t need to show all of your work. * Your default description of (almost) any problem will be too threatening/overwhelming. * Do your deepest thinking with co-conspirators (not the people you’re trying to influence). * Informal influence is often not formally recognized. Prepare mentally for this. * The people you’re trying to influence spend 98% of their day overwhelmed by business as usual. * Remember to also do the job you were hired to do (if you don’t you’ll be easier to discount). * Seek “quick wins”, but know that most meaningful things will take a while. * Some things take ages to materialize. It is discontinuous, not continuous. * Make sure to celebrate your wins. They will be few and far between, so savor the moment. * The people who support you in private may not be able to support you in public. Accept that. * Hack existing power structures—it’s much easier than trying to change them. * Consider becoming a formal leader. It’s harder in many ways, but you’ll have more leverage. What’s stopping you? * In lieu of being a formal leader, make sure to partner with people who actually “own” the area of change. * Watch out for imposing your worldview on people. Have you asked about what people care about?. * You’ll need a support network. And not just a venting network. Real support. * “Know when to fold ‘em”. Listen to Kenny Rogers The Gambler. Leave on your own terms. * Don’t confuse being able to sense/see system dynamics, with being about to “control” them. You can’t. * Grapple with your demons, and make sure not to wrap up too much of your identity in change TRANSCRIPT [00:33] Take care of yourself. Your brain is working overtime all the time. Practice radical recovery. I would basically find myself at the end of a multi day effort . I wasn't aware of just how tired I was and just how fried I was. How muddled my thoughts were. And I think part of the reason for that is if you enjoy going deep on things, and if you enjoy picking things apart, and if you enjoy analyzing things, you sometimes don't notice just how much effort that takes and how much bandwidth that takes. And so it was important for me to try to set aside time to just completely disconnect, not jump into another thinking topic, not jump into something else that had high cognitive load, but try to strive for zero cognitive load. One of my favorite things is just watching cartoons with my son. Because I completely disconnect. [01:29] You may spend a lot longer thinking about things and most people. Pace your delivery. So if you've spent many hours going deep on something, you can't walk into a meeting and expect someone in three minutes to follow your thought process. It's just not going to work. You're going to have to pace your delivery to bring someone along on that journey. And if you're good at analyzing things. If you're good at this type of systems thinking or overthinking, you can go so far in a couple hours. You can focus and go so deep. And there's no way you're going to be able to deliver all that information to someone. You have to get really really, really high level and rewind. And be super deliberate about how you deliver that information. [02:17] If you go deep first and then simplify, keep in mind that you don't need to show all of your work. So what I used to notice is that I would keep all of my work and the three bullets. And I would start with the three bullets and say, well, this is where I arrived at. And I felt like it was important because for some reason it's important to me to show how I got there. So instead of just saying, here's the solution, do this. I would say let's try to unpack all the layers of this particular problem and how I arrived at this particular solution. It turns out that that can greatly diminish the impact of the destination that you arrived at. And honestly it can open you up to all sorts of debate. It can open you up to all sorts of questions. And somehow it makes you seem less confident about what you're doing. Now, not that I agree with any of that and I wish it could be different, but realistically you don't need to drag people through the whole mess. [03:17] Your default description of almost any problem will be too threatening or overwhelming. This is something I've had to come to grips with. The default detail that I want to go into on something is just going to seem threatening. And the more I try to sugarcoat it the more weird it sounds also. So this is a tough one to come to grips with, but the important point here is understanding that the depth that you go into on something and the thoughtfulness you try to put into something and the different perspectives you try to discuss can be very threatening. In fact, I used to think that describing something as a systemic issue was in fact less threatening. Because in some ways, by describing it that way you understood that well, there's a lot of contributing factors. There's not one person to blame here. There's a lot going on. And we're going to be able to figure this out. Or so I thought. Realistically, when people hear systemic issue, when you don't point to one specific person or one specific situation and say, that's, what's messed up, it's actually highly threatening. So keep that in mind. [04:24] Do your deepest thinking with co-conspirators not the people you're trying to influence. In an ideal world, at least for me, everything would be co-designed. Everything would be a result of deeply exploring things with everyone involved. And you would arrive at the solutions that everyone believed in. That's not the case, in many situations. You might have other people that you're close with who are willing to go on this deeper journey to understand what the problem is. And I call those co-conspirators in this case. These are fellow system overthinkers who don't mind the ambiguity, who don't mind exploring different paths and then rewinding. Who don't mind dredging up these particular issues and looking at them from different angles. Realistically, if you're trying to influence someone, it might be a good idea to bring them on that journey. But it might actually completely defeat your cause to bring them on that journey. So in that particular situation, if the person you're trying to influence isn't necessarily on that wavelength, and doesn't want to take that journey with you, you don't bring them along that particular journey. And you might be more influential in the long run. [05:36] Informal influence is often not formally recognized. Prepare mentally for this. If you're expecting the same kind of recognition that goes to people with formal influence and formal authority, you'll probably go off track. In fact, I think if you're seeking that, if you're seeking that recognition, if you're seeking to be in the limelight, if you're seeking that kind of gratitude publicly, you will be sorely disappointed. And it will probably send you off track. So you have to prepare mentally for the fact that many of the things you do will influence informally in ways that people might not be able to immediately recognize. You might have a small number of people come up to you and say, you know, I really liked what you did there. Thank you so much. I really appreciate it. But it's not going to be this groundswell thing. You're not going to win the president's club trip to Hawaii or something with your sales team. And as long as you prepare mentally for that, I think you can be in good shape. [06:39] The people you're trying to influence spend 98% of their day overwhelmed by businesses usual. If you're trying to influence senior leaders you need to understand that they are really busy. This seems to be such common sense. But if you imagine that they're going to have any amount of time to go deep or as deep as you've been going on something, and appreciate all the nuances-- if you're expecting that-- you're going to be disappointed. So you need to imagine that you are delivering the message to people who are overwhelmed. Who are under incredibly high cognitive load. Who are not necessarily in the right frame of mind to explore some kind of systemic issue. You have to be prepared for that. Remember, you've set aside a couple hours to go deep on something. You've had all this time to do this focused work on something. This person is getting bombarded by every single person in the company. Back and forth. Everyone has a problem. Everyone is trying to sell them something. Everyone is trying to influence them. Everyone's telling them their version of what's wrong. That's the person you're trying to influence. And so you need to modify how you talk to them accordingly. [07:53] Remember to also do the job you're hired to do. And if you don't, you'll be easier to discount. So you might've been hired in the company to do job a. But upon arriving and because of the way you think you discover all these other problems that are probably deeper problems impacting the ability to do a. And so you go and you try to solve those particular problems. Just be aware that if you don't do the job you are hired to d

    18 min
  5. Sociotechnical Maestros with Gene Kim

    05/12/2024

    Sociotechnical Maestros with Gene Kim

    Today I'm talking to Gene Kim. Over the years Gene's work has had a huge influence on me. From books he authored and co-authored including The Unicorn Project, Phoenix Project, DevOps Handbook, and Accelerate, to his advocacy and community building with the DevOps Enterprise Summit, now called the Enterprise Technology Leadership Summit.  I recently finished reading Gene's latest book Wiring the Winning Organization which he co-wrote with Steven Spear. The themes of slowification, simplification, and amplification have already started to seep into my day-to-day conversations. The book is filled with case studies, but also creative metaphors like Gene and Steven moving a couch, which is where our chat starts. Get full access to The Beautiful Mess at cutlefish.substack.com/subscribe

    31 min
  6. Software Development As Collective Learning With Hazel Weakly

    04/28/2024

    Software Development As Collective Learning With Hazel Weakly

    Back in late February, Tom Kerwin and I wrote a post titled How Capable Leaders Navigate Uncertainty and Ambiguity. The post listed 18 competencies—things like Accept We are Part of the Problem and Blend Diverse Perspectives—along with sample questions you could ask yourself, or someone else, to reflect on each competency. A couple days later, Hazel Weakly shared a deeply introspective post where she used our post as the basis for a personal retrospective. I was completely blown away by the depth and thoughtfulness of the post, as were many others on LinkedIn.  In this episode we talk about Hazel’s journey from individual force multiplier to focusing on collaborative learning and scaling that up. We talk about emergence and systems, developer productivity, architecture as a catalyst for coherent autonomy, migrations, being Done, Done Done, Done Done Done, and how being explicit about values, culture, and collaboration enables more graceful and continuous change. We end by talking about how leaders can’t wait for outcomes to introspect and get feedback (hence Hazel doing that deep dive personal retrospective). Hazel is currently a Principal Platform Architect at Datavent, and serves as a Director on the board of the Haskell Foundation and is known as the Infrastructure Witch of Hachyderm (a popular Mastodon instance). Hope you enjoy the episode, and thanks for your patience as I become a better podcast host. Podcast RSS: Subscribe to The Beautiful Mess Podcast in your favorite podcast platform using this RSS URL: https://api.substack.com/feed/podcast/24711.rss Will Larsen’s post on migrationshttps://lethain.com/migrations/ More info on Stripe’s migration to TypeScripthttps://stripe.com/blog/migrating-to-typescript Cat Hicks (and team)’s Developers Thriving work https://www.pluralsight.com/resource-center/guides/developer-thriving-research-paper Hazel’s retrospective post https://hazelweakly.me/blog/observations-of-leadership-part-one/ Hazel Weakly’s contacts info: LinkedIn: https://www.linkedin.com/in/hazelweakly/ Mastodon: https://hachyderm.io/@hazelweakly Website: https://hazelweakly.me/blog/ Get full access to The Beautiful Mess at cutlefish.substack.com/subscribe

    27 min
  7. Octopus Careers & Throwaway Stickies with Chris Butler

    04/20/2024

    Octopus Careers & Throwaway Stickies with Chris Butler

    Subscribe to The Beautiful Mess Podcast in your favorite podcast platform using this RSS URL: https://api.substack.com/feed/podcast/24711.rss Introduction In today's episode of The Beautiful Mess Podcast, I am talking to Chris Butler. Chris is currently a staff product operations manager at GitHub.During his career, he's worked at companies like Google, Facebook, Cognizant, Kayak, and Waze, as well as founding the Uncertainty Project. Chris embraces the mess like few people I've met. Defying categorization in his career path, inventing models and techniques for collaboration and sense-making, he's well versed in engineering, design and product, and figuring out how to challenge the status quo in big companies. Somehow he manages to be a mad scientist in terms of ways of working, and have a day job. In this episode we talk about being a change agent, introducing new ways of working, embracing a persona external to your day job, and interesting stories about the Google culture and define career categorizations. Enjoy. Transcript [00:00:00] John Cutler: Hi Chris, welcome to the It Depends podcast. How are you doing? [00:01:07] Chris Butler: Good. Thank you for having me. I'm excited to say it depends as many times as possible during this podcast. [00:01:13] John Cutler: You will not be judged for saying it depends in this podcast. [00:01:17] Chris Butler: I have the it depends jar over here that I have to keep putting, you know, a dollar in every single time I say it on other places. So it's, it's good that this is an open space. [00:01:25] John Cutler: And it depends safe space for sure. One thing I wanted to start out with is that typically there's things about our personal experience or how we grew up or maybe the jobs we've had, our personal context, which is our own personal It Depends. When you think about your personal experience, what are some things that stood out that have shaped how you view situations? [00:01:44] Chris Butler: I really hate the question, at a barbecue, "Like, what do you do?" It requires me to simplify down what I am and kind of my experience around what I do down to a place that is you know, maybe not helpful. [00:01:58] In high school I would help teach the C programming course because I was taught by another student and the teachers there didn't know how to do C programming. So I basically taught that course. I was a senior class vice president, but I ran on the anarchist ticket, mostly about how we would get like better pencil machines in the hallways. [00:02:16] And then I was, you know, a team captain on a football team, three time All League, Honorable Mention of my Empire. And I also built red boxes and ran bulletin board systems that were like, Warez Bulletin Boards back in the day. [00:02:30] I try not to require my identity to become one thing. Rather than like a T shaped career or whatever those other things are, like an octopus career. And the reason why I like that is because, you know, the octopus is like a very interesting neural kind of, system where it has one brain, but it also has like brains in all of its arms. [00:02:49] I guess I've just started to allow myself to be more comfortable with having a bunch of different things that maybe unify in certain cases. And I get paid for those things or it's part of my daily job. But I think I've just always followed my interests. [00:03:01] The anarchist kind of thread in my background or the fact that I was building red boxes or doing warez boards kind of says to me a little bit that I also have a problem with doing things within the rules sometimes. I don't think this is fair, right? Like just to be very clear, I don't think this is fair, but I feel like I have a natural distrust for leaders. I realized that there are also people, right. And there was a great post that came out a little while ago that was basically like, you will never fully love your manager no matter what, because of just the way, the way that these systems work. [00:03:29] That's maybe something that has really formed the way I think about all of this stuff and the work that I do on a regular basis is really, it's, it's a lot about how are we pushing back on just the way things are. That's where I would say, you know, I've kind of come from and maybe that's, that's the reason why I am the way I'm today. [00:03:46] John Cutler: I'm curious, when you start a new job do you know you've found your fellow Anarchist, you know, football captain, you know, cause certainly you could run into the football captain in the hall and say, Hey, welcome, welcome to the Anarchy Club, you were in the Anarcy Club too. And they, they might not be too happy with that statement. [00:04:04] John Cutler: How do you know that you found your tribe when you're in a company? [00:04:08] Chris Butler: Joining very large companies is interesting because I guess I see part of what my benefit is to people is building connections between maybe topics that don't make sense together, but also connecting and creating networks within the organization I'm in . [00:04:23] For example, there's a group called Flux and Gale, and it was started by someone internal to Google that was all about people that are model thinkers, system thinkers, like that type of stuff. [00:04:35] You kind of have to pretend to just be a regular person at first. I guess. When you find your other community, it's not because you want to just like be the same as everybody else. It's that you want your thinking challenged in this domain and they have the tools, the terminology, the language and the background to be able to then push you. [00:04:54] I've been doing a lot of stuff with something called design fiction, which is really about this idea of like prototyping some future artifact. And then how do we use that in a bunch of different ways? Like I I've given a talk about like product management is product management, fiction, right? Which like everything we write as product managers is fiction at first. It just happens to be really boring fiction, unfortunately. And so like, how do we do a better job of that? [00:05:15] But me going into like an intranet site and looking up things like design fiction, I started to find groups of people that were, you know, interested in these topic areas. And from there, I'm just have a natural like networking kind of ability that I then just reach out to people and say, Hey, I did this cool thing over here. I think you might be interested in it. [00:05:33] So that's, that's how I ended up like finding those people is really based on topic areas, but it's not always, it's not always possible. The intranet site that runs something like GitHub is different than the intranet sites that were inside of Google. [00:05:45] It's hard, but if you allow for that iterative exploration, you'll find the next person that is like this and, and maybe pushes you in a way that that would be helpful. [00:05:55] John Cutler: I knew you do a fair amount of speaking external to the companies you work at. curious how the desire to express yourself externally from your companies Is that a balancing act for you so that you can balance the need to project that everywhere internally as well. [00:06:10] Chris Butler: It's more of like an escape valve because I think like whenever we're at an organization, there are cultural expectations. There's the Overton window of what is acceptable or not. I've had previous leaders say we're kind of cutesy or like too smart or something like that. I have to try to gauge what is the Overton window for process change inside of this organization, and how do I push them a little bit so I can do more of this stuff? I think I've started to come to the conclusion, and I think a lot of people in the Wardley Mapping community also think about this, is that like, I can't use the terminology, I can't call it this thing anymore. [00:06:42] I was talking to someone at the product ops summit in New York like a month or two ago. And they were an agile coach that had gone into product operations, which feels like a natural progression, honestly, based on the terminology of today. She was saying that if she then tries to do something like hold a retrospective for the team, especially with her current team, they would be like, no, we're not, we don't do that type of thing. We don't get in a room and just like whine at each other about how bad things are. Right. But when she says like, we just had this launch and the launch went well in a lot of ways, but not in all ways, so why don't we get in a room and let's talk about like what went right, what went wrong and what we could do better next time. [00:07:17] I need a place to be able to experiment with these concepts. And so I use the external speaking as a place to do that. Would say that the values that I really care about personally end up being connection, right? Ends up being how do we actually discover new ways of doing things and then how do I personally learn about things. And so that type of drive for me means that these are going to be topic areas where I think they're on the edge of what is acceptability or considered to be normal or regular for these teams. [00:07:44] And that's what drives me is it's that escape valve. [00:07:46] Now, what's cool though, is that like when people that are part of my work come and see me talk about this stuff. They want to do more of it internally. The problem is how do we do it in a way that still allows leaders to kind of feel the culture that they have is appropriate and it's not too much of an assault on that. [00:08:02] So I think that's the, that's the problem I ended up coming up against is that I want to do these things internally. Right. But it's not always going to be considered to be a good thing if I didn't. [00:08:11] John Cutler: don't know if you have any, an example of something within the Wardley Mapping community, for example, that if you went down a rabbit hole, it would b

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A podcast about how context and nuance impacts our work, how we collaborate, and how we organize. Hosted by John Cutler, author of The Beautify Mess newsletter cutlefish.substack.com

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