The Beautiful Mess
The Beautiful Mess Podcast
Product Coaching with Petra Wille

Product Coaching with Petra Wille


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.


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 bucket of talking about all the messy decisions that one need to make and all the messy situations that one could end up in trying to improve things.

And in coaching, my take is if I can help this product leader and improve the whole work environment of every person in their organization by 5%, I think we already way better than where we started. So this is more or less my ambition. And therefore it's important to be curious about their situation.

I'm more curious about figuring out, okay, what might be most helpful for them and what is a realistic thing to work on. Because even if I see, "Oh my God. Role descriptions are a mess and career ladders not existent and so many things that actually they could work on." But then I figured I have a massive conflict with one of the stakeholders and that is what currently is blocking them, then we're working on that and the rest remains messy and I think that's perfectly fine because this is just how it actually is.

And do I totally love when they go still read the books and watch all the talks that we put out there and listen to these podcasts and get inspired. Yeah. But I oftentimes tell them, "Hey, don't be too overwhelmed, if you go to a conference, you will hear a lot of great things, but take one idea back to your office and just try to implement it and see how it goes and iterate on that." Then you're already ahead of the curve, I'd say, because so many people are so overwhelmed by all the material out there that they're not starting anywhere.

In coaching, my main goal is always to find something that helps them in their situation because they need to do it. I'm not there. I'm just a remote coach. We have our session every other week or something like that. So we need to find something that really resonates with them where they think like, yeah, this is actually something that I could do, that I could implement it, I could try it and I could, I don't know, pull off whatever.

[00:11:29] John Cutler: One thing I liked about the Product at Heart conference was afterwards there was a patio and everyone was at picnic tables and I actually observed a lot of coworkers coaching each other or reaching out to other people, maybe not at their company. And in some way, I know that's not formal coaching, but you could see that people were often balancing curiosity curiosity with the desire to help, with the desire to see what that person wanted out of the situation. Understanding the situation.

When you think about a company and you think about all that informal coaching and informal mentoring, are there tips anyone could use even as an informal coach within their organization to build just a culture of that type of guidance? Or would you suggest that everyone should go to coaching training?

How do you create a culture of that informal coaching? You seem to have done it with your conferences. So like, how do you do it internally?

[00:12:22] Petra Wille: Yeah, so community, that's what the conference does, right? A community for the day in particular. But I think that is something that we highly in the organizations that we work in. We always go to the training, go to the conference, bring in the coach. But this peer coaching is tremendously valuable and should happen more often.

For it to happen, you need to create these moments where it can happen and it was the water cooler, it was the coffee kitchen. This is still a challenge for most of our working environments, right? So, deliberately designed community of practice-- sessions, meetups, and can be super informal gatherings-- and I know it's expensive for some companies to bring everybody in, but every once in a while, I think that would be massively helpful. As you said it, it was the after hour conference and people were still like, yeah, pumped by the stuff that they heard and massively inspired by the speakers. But also inspired by the great company around them. So you want to learn from them. You want to talk to them. So whatever you do, create these moments where people are allowed to share, encouraged to share, able to share, what they're learning.

And then I think one thing is better listening, which sounds boring and so many people are saying this, but for me it really helped once I learned this "listen to understand and not to reply." I think this is the first good thing that coaches should learn and actually leaders as well. If you're in a leadership role, then be curious and ask your question and then listen to understand where the person is coming from. Learn more about the context, why they're saying things that they say, all these kinds of things, and not so much for helping them immediately.

And yeah, at times that is something that I do when I have this kind of, okay, this person is super junior, super early in their career, in their leadership role. So they might need a recommendation now, because otherwise it takes them ages to get to the exact same point. That definitely is something that I sometimes do, but I try to avoid it as much as I can. So giving options is already better to say "Hey, I learned, with all of my clients, some have solved it that way. Some have solved it the other way. There is something in between. What, what sounds like you? What resonates most? Should we unpack one of these scenarios?" So really kind of offering options helps a lot.

And that is something that you could do with your colleagues as well, right? If they share an issue, then be curious. Why is it bothering them so much? Then, by the way, figure out where the energy comes from. Figure out where the energy comes from. So why are they so upset? Why are they kind of in this conflict scenarios all the time? So where's the energy going? Where's, where's the energy wasted, maybe even? And then ask questions around that topic. And that already helps a lot.

And not so much giving advice. That's not usually not so helpful because people, if they have like, ooh yeah, I had this realization, they're so more likely to act on it, than if you give them a recommendation, say like, go read that book. Yeah, sometimes helpful. But if you offer your time and your clever questions to walk them through something, I think that is, yeah, even more valuable, maybe than a recommendation.

[00:15:34] John Cutler: This probably is a more advanced coaching topic, but I think it's probably relatable to many people, but I've been reading a lot where people are advising on emotional regulation. This idea that you have these feelings and having the feelings is okay, but if you can magically detect the feeling before anyone else can notice and before you do anything stupid, you can somehow capture that idea and then do something productive with it...

[00:16:00] Petra Wille: ... and that's the energy thing, right? So if you feel the tension, the energy building, how could you sense that? And how could you then do something with it ideally? Because a lot of people think it's about doing something against it, but, but actually you should do something with the energy, maybe not the thing that you were about to do the last 300 times you were in this situation.

So we find new ways of reacting to it, but we're using the energy, just channeling it somewhere else and doing something with it. And sometimes it's having this harsh conversation with somebody. People can handle way more and tougher conversations than one would think.

That's another thing that we often discuss in coaching, this love it, change it, or leave it and I think people, if they don't love it, they so easy flip to leave it. And I'm always like, "Okay but you, you skipped the changing part. So can we have this tough conversation and see how things turn out!" Because maybe that actually creates something from there. We don't want to burn every relation we get, obviously, but people can usually handle more conflict than we think.

[00:17:02] John Cutler: That is incredible for a couple reasons. One reflection is the idea of not thwarting the energy, but directing it somewhere. So you have control of that energy. It's not a bad thing. You're doing something with it.

And the other idea that jumped out to me about that is the idea that under certain conditions, you can have those difficult conversations. It's rare, but when someone is in a conversation with a lot of people and says, "I'm going to pause for a second, I want to acknowledge that I'm feeling this level of X, Y and Z, it's a little vulnerable to admit that, but that's what I'm feeling right now. I want to dig into this." Although maybe those conditions are rare where you can say that it seems like you can get away with more than you imagine if you set that conversation up correctly. But it does take a lot of courage and it also takes decent delivery at that point.

[00:17:56] Petra Wille: Yeah, but I had several coachees that had great success with especially postponing things when they were in a meeting and they felt like, okay, really anger is building up or a physical reaction. They want to actually postpone it kind of run out of the door of this meeting room, because for whatever reason, some people are really not well in tune with their emotions. So you can sense attention is building up, but you cannot on the spot share with others what the actual problem is.

But the other humans in the room usually are actually perfectly fine when you say like "Hey I'm not comfortable in this conversation right now. I can't tell you why. Can we come back in an hour from now and start again?" or something like that. And it's rare that all the others stare back at you and think like you such a crazy person because everybody of us had been in a similar situation, right?

And it is actually seen as rather professional to have a reaction like that. So instead of just rushing through the meeting, not paying attention to it anymore because you're feeling your emotion and you just can't pay attention to the situation anymore, then I think it is professional to say like, "Hey, I can't process things anymore because I'm not feeling well. It's a weird situation I'm in. Can we just come back in an hour? Or can we have one on one conversations instead of a group discussion?" That sometimes that the group dynamic is a problem in some So all of my coachees then observe that others are doing this as well, really quickly, because it's such a comfortable thing to some extent. If one person, one brave person starts with it.

[00:19:29] John Cutler: There seems to be a lot of popular advice that basically boils down to Improving your agency, improving your ability to control your emotions, improving your ability to impact your situation, believing strongly that you can impact your situation.

And then there's this flip side of that argument, where people stress the environment that you're working in and whether the environment is conducive. And then the other side says, "It shouldn't matter, you can always control your emotions." And the other side says, well, it's the environment. Someone says, well, people created the environment. The other people said, yes, but the environment has an impact. And this sort of swirls and cycles.

When you're coaching people directly who are struggling with that balance or trying to come to some narrative in their mind about how to balance the sort of individual side of it versus the environment, do you have any coaching prompts that you use with people? Or do you take any certain approaches to help people find a balanced perspective in their mind.

[00:20:26] Petra Wille: It really depends on their level, right? If they're still on IC individual contributor level, especially in a coaching relationship, let's assume we have these 10 calls over the course of five months, that's all we got, so we have this bi weekly conversations, and when I was still coaching individual contributors, there's not much a coach could influence on a system level through an individual contributor, right?

So I usually made sure that they understand they have more influence, they, one could think. Sean Russell always, I love when he uses this go positive and go first. That's always the headline that he uses. So whenever you see something not going well, then you still could improve it with your team or in your area, and then just go first. And hopefully other people see that and pick it up.

But that's basically the influence that one got if you're on an individual contributor level. Plus it's the managing up. That is something that I always encourage my coachees to do, because now that I'm working with the product leadership folks, I can tell you there's not enough feedback towards the leadership layer.

So whenever you see something going wrong, then please be vocal about it, talk to your manager, point it out. Share what your concerns are when the system stays as it is, what the problem and negative consequences are for the organization, because that oftentimes is not happening and leadership is not seeing the issues because from where they are, it's invisible to some extent. You see the issues, but you think they see the issues, but never told them. So the managing up part is big if you are on an individual contributor level.

Then once you move one layer up and you kind of product team lead, head of product in a small organization, these kinds of things-- so you're still directly managing the product organization, you may be still doing all the product strategy stuff and all these kinds of things-- then you have a bigger influence on the system.

It's kind of a third, a third, a third, it's always the rule that I try to implement with the people. So people process products. So one third of your time, approximately, what are we building in the future, what are we building right now? What are we shipping right now? So that's kind of the product stuff.

And then the process is, are we building-- and I like this shipyard metaphor that I'm borrowed from Jeff Redfern, former Atlassian. So he uses that shipyard metaphor to say the teams are building the ships and the vessels and the boats. But have we as leaders, thought and really designed the shipyard around it. So that's kind of my process thing.

And then it's the people. So are we having the right people on board? And I think if product leaders try to look at all three dimensions, every once in a while, that already helps a lot.

They should look into this more systemic issues that they get. But still, again, they have not influence on all of these things, so managing up is still a thing. It becomes more meta once you're there. So the topics that you talk about with your senior executives are even more meta than what the individual contributors see.

Then I think there is no excuse once you have a leadership role that it's out of my hands, what should I be doing about it? Then it's on you at least to some extent to form meaningful allyships with your peers, because there are CTOs somewhere and there's a marketing person somewhere and sales lead somewhere. Build this allyships, raise concerns if they're conflicting goals and all these kinds of things. So then it's, then you're not off the hook anymore, I'd say.

[00:23:53] John Cutler: I liked your discussion of managing up. It's funny. Maybe we don't talk about product followership enough...

[00:24:01] Petra Wille: hmm.

[00:24:01] John Cutler: Versus product leadership. And so I'm curious your thoughts on that, where it's not exactly managing up. It might not be managing up directly to the person that you report to, but there are product leaders-- they might be skip levels, they might be other folks in your organization-- and you have to come to grips on some level that you're following their lead and you're following their strategy. And then there are times when you want to try to relay feedback. Is it just too dangerous to try all those skip levels? Or are there ways that you can be a better product follower?

[00:24:30] Petra Wille: Ooh, that is a, I think there are massive cultural differences from country to country and from organization to organization, right? So I work with a lot of Scandinavian clients and their skip level is not a problem. Nobody cares. So if you see something, you point it out to whoever you meet in the elevator first in the morning, right?

Colleagues will never finger point at you because you've done that or something. So that's not weird. In Germany, it's weirder to do these things. So we love our hierarchies, but not in every organization, right? So this is really understand the company culture that you live in, understand some of the cultural backgrounds of the people that you're working with, because even if the company might be a German one, the diversity cultural wise might be massive, right?

So understand the cultural backgrounds, understand what others think is appropriate as well. I think that's the first thing that you would need to do to start all of these.

[00:25:25] John Cutler: Have you noticed why in certain cultures there seems to be an aversion about talking about how you work? It's sort of seen as too process oriented or talking about working is somehow seen as not working?

I'm curious one, if you've seen that, but two, how do you maybe coach leaders that it could be okay to talk about how you're working, that it's not some sign that people are just twiddling their thumbs or getting too theoretical about things?

[00:25:52] Petra Wille: Some companies love their frameworks, their tools, their processes. They're super obsessed with it and then it's too much of these conversations. Where others have too few of these conversations and now always just so focused on the output, so to say. And to me, this is weird because the whole Agile thing was all about reflecting every once in a while, pausing, have your retrospective. And that is for improving your ways of working. The retrospective is not just drinking tea together and chillaxing the hell out of the last two weeks. Right? So it is actually about improving your ways of working every iteration basically. And I don't know where things went sideways here, but why are we not doing this in product as well? And I know a lot of organizations do. But that should be a common practice. If we learned one thing, rituals and rhythm are super helpful in an organization. So why not putting rituals and rhythm to all your product work, at least to some extent. And it does not need to be a weekly, how do we do product meet up? That's definitely not something that I would recommend. Longer cycles is what we're looking for. But still we want to do this every once in a while.

I hope, always hope, that product people have this kind of balancing this forces between what is valuable and what is just a waste of time. If you don't do it, it's not cool. If you do too much of it, that's not cool. So you need to strike the balance somewhere in between. And that depends on the situation of your company, maturity of your product organization, maturity of your product people. If you need to run the show with fifteen junior product people, then hopefully you have more of these sessions. If you have super experienced product veterans, then maybe not so important an occasional coffee, does it?

So it is really tricky to strike that balance, but I would love more product leaders to at least think about and deliberately decide where do we draw the line in the sand? So how much community do we need? How much change do we need? What is healthy? And answering your question from a different angle, by the way, part of my leadership coaching is always to help leaders understand that time to think, or actually thinking things through, is part of their work now.

It should have been part of their product management work. Oftentimes they just managed to get by without it, but when you're in a leadership role, you need to create that strategy and therefore you need to stroll the city and think about random things, get your inspiration from some somewhere. And that does not happen when you're in your small cubicle or home office, even worse.

So. Product management is a science, yes, but it's also an art. So treat yourself like an artist and allow yourself a bit of time to just think things through, let your mind wander. This is part of being a creative human being, and you need to be such a creative human being if you're in a product leadership role.

[00:28:50] John Cutler: I had more questions, but I think that might be an amazing place to end because that was a, a nice mic drop. We had discussed this before, but, you mentioned that there was a number of things that no one asks you. And so maybe to finish it off, what's that one thing that no one asks you that you are a super nerd about that you would go on forever. You're just waiting for a chance. And then we'll use that as the hint for our next podcast. So like on the next podcast, we'll discuss your super nerd out thing that I didn't ask you about.

[00:29:18] Petra Wille: So you've been to a conference last year, right? And Arne and I are really, so we both nerds about this providing directional clarity is one key part of product management. And the other thing that we had is theme around it. So three speakers were delivering a talk on that particular topic is how to make time for yourself to think things through. Because I think that's the prerequisite for any providing directional clarity to your team.

First, you have to block yourself some time and think things through, and then you are able, after you sort some things, and you have mental models that actually work with everybody, and you have a story that you can tell, then you can provide that direction of clarity for your team. That's super important.

So I could geek out about this. How to create yourself the time to think things through all day.

[00:30:08] John Cutler: Well, we'll stop now to give the listener time to think things through. So maybe pretend that the podcast went for another five minutes. I'll insert silence for the next five minutes. Okay.

[00:30:17] Petra Wille: White noise would, would do white noise.

[00:30:20] John Cutler: I'll add five minutes of silent white noise at the end of this for you to meditate.

[00:30:24] Petra Wille: And the question, the question for the meditation is what do you want to do differently?

[00:30:30] John Cutler: There you go. Okay. Well, thank you so much, Petra. Um,

[00:30:35] Petra Wille: That was fun.

[00:30:35] John Cutler: I guess I'm supposed to ask where people are supposed to find you, but you're so ubiquitous

in the product community ...that they will find you. Are you sold out of Product at Heart yet for this year.

[00:30:45] Petra Wille: No, we still have some tickets left. It's in September this year, so it's not in June. So we have some tickets left. So come visit us in Hamburg in September. Should be lovely.

[00:30:56] John Cutler: Yeah. Hamburg in September. It's wonderful. Okay. Thank you so much. And yeah, we'll chat soon.

[00:31:00] Petra Wille: You're welcome.

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The Beautiful Mess
The Beautiful Mess Podcast
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