The Beautiful Mess Podcast John Cutler

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

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.

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.


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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/


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cutlefish.substack.com

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.