[On Demand] Product Management Webinar: Agile and Leadership

Janna Bastow: [00:00:00] Hello, everybody. And welcome to this product expert fireside that we are running here at ProdPad. This is a series of webinars that we run. And so if you take a look back at ProdPad.com/webinars, you’ll find a big list of all the ones that we’ve run in the past. Basically, Month on month for four years now.

So we’ve had all sorts of interesting experts coming along and that’s what this really is a chance to bring in amazing experts from the wider product management world and to have a chat about interesting insights that they’ve collected from their experiences over there. There’s a real focus on the content and the learning and the sharing.

So today is going to be recorded and you will have a chance to ask questions. So drop them into the chat or into the Q and A and every time we do this, we always bring in an expert who’s here to share their experience. And, today we’re joined by Stephanie Ockerman, who is joining us from Costa Rica.

We’re gonna be talking about how her surfing practice has informed her insights about product [00:01:00] management and things like business agility and leadership as well. So yeah, it should be a really interesting session. Wondering if anybody here is also a surfer. Or into similar sorts of sports.

I always love talking to product people about what they do on the side to keep them entertained. And in the meantime, before we kick off and do a full intro I want to tell you a little bit about ProdPad and what we’re building here. As a lot of you probably know myself, my co and my co-founder Simon, we’re both product people ourselves when we needed a.

It’s a tool to do our own job, and it just didn’t exist. And so what we’ve created is ProdPad, and it’s now being used by thousands of teams around the world. And basically, ProdPad is a tool that basically creates a single source of truth for all the product decisions that you make in a day to day.

It helps your team stay agile, helps your team stay focused on the problems that are there to be solved. The goals that you are aligning around, and making sure that you’re thinking in an experimentation-led way. [00:02:00] So it’s a tool that you can try for free. We have a free trial you can jump in. And we even have a sandbox mode that you can access.

And basically the Sandbox mode is preloaded with example data, like roadmaps, if you want to see a Now-Next-Later roadmap, and OKRs in conjunction and how they all play together. You can jump into the sandbox, play around, even move things around, and get a sense as to how it’s going to work for you. And our team is made up of product people, right?

It was founded by two product people. Myself and Simon were originally founders of Mind the Product, a big community of product people as well. And we’ve surrounded ourselves with product minds and that’s what you get when you reach out to us here at ProdPad. So if you have any feedback or want to talk about how it fits your use case, reach out and we’ll hook you up with a demo of your own.

One last thing that I want to mention is what we’ve been working on. So some of you might have already been trying this out and have seen how this can work for you. But we’ve built what we’re calling the Prodpad CoPilot. It’s an AI agent and AI [00:03:00] assistant that lives within ProdPad and helps you do a number of different things, right?

So it knows all of what’s in your vision and your goals and you know what your road map is made up of and what you’ve tried and what you haven’t tried. It knows what your customers have asked for. It knows all the ideas in your backlog. And so you can use it. You can use it as a sidekick, you can ask it things like Hey, can you help build out this product vision?

Or can you tell me if this roadmap is aligned with his vision? Or can you summarize everything that so and so has said, and then tell me if there’s anything on the roadmap that I should give them heads up about. So lots of different use cases would love to hear if anybody here has any particular use cases that they’d like to see with it or that they are using with it as well.

I’m always crazy to find out how people are using new AI tech as it’s out in front of them. With that in mind, I’m going to jump over and do an intro to Stephanie. Stephanie Ackerman is joining us today here from Costa Rica but she’s a business agility specialist. She.

Is [00:04:00] a scrum. org professional scrum trainer and the coauthor of mastering professional scrum. And so for more than 15 years, she’s helped customers across retail, insurance, government, banking, tech. They’ve all, she’s helped them all embrace agility and navigate their complex challenges. What makes Stephanie truly stand out?

Why I wanted to invite her here today is that she connects surfing to leadership, just as surfers read the ocean and adapt to changing waves, great leaders learn to stay resilient and respond quickly in unpredictable environments. And she runs workshops and through these workshops Stephanie shares these ocean inspired lessons and she helps leaders and teams become more flexible and innovative.

So with that in mind, I want to say a big welcome and hello to Stephanie. Hi, thanks so much for having me. Of course. Thanks so much for joining. Great to great to have you here. So we’d love to hear a little bit about your background. What have I filled us in, tell us a little bit about where you’ve come from in the world of Agile.

[00:05:00] And also, what keeps you busy on the surfing side. Yeah. 

Stephanie Ockerman: So I, I always like to mention that I did start my career in traditional I. T. project management actually came right out of college into an internship program. And when you come out of college, you actually don’t know anything in terms of what you think you do, right? It’s like I have some skills, but I don’t really know how to actually get things done in an organization or how they get things done. It’s a lot of what you have to learn. And so I did come from that traditional I. T. project management, very waterfall, very process heavy documentation oriented.

And I was pretty good at it. I’m a very organized person. But what was interesting about that is because I, you don’t normally go into that. It’s because I was an intern that I was introduced to project management much sooner. I really had to take a facilitative approach because I didn’t know anything and I couldn’t pretend to be like, Oh, I’ve done this before.

And this [00:06:00] is how it should work. So I think that really helped me enter that with a different lens and different perspective. After I got my certification, my PMP moved on to larger program management or release planning and large scale enterprise releases and various things and went into consulting after that.

It’s Oh, if I’m going to be good at this, I really need more experience, different industries, different types of projects. And then at some point, like I realized wow, I’m really good at this. And everybody’s yeah, you do a good job. But what that turned into was me being very stressed out and overworked.

And I had this Like struggle with there was always this pressure I felt whether it was explicitly said or not to like, try to just force things and get people to work overtime when they were being pulled in different directions and all of these things and I had Spent so much time, like what I called my days of playing with spreadsheets, like updating this plan and this plan and, filling out change management documents, because, of course, things are always changing [00:07:00] and but I didn’t know anything different.

And 1 day I was with a client and we were struggling with all the things that people typically struggle with, but it was like an extra stressful situation. And I was talking to a colleague about, Hey, like we’re consultants. So we’re still energized and we want to help and we can help them.

And he mentioned scrum and agility and gave me a five to 10 minute, like overview. And I was like, wait, what did this exist? This is how I’ve always wanted to work. It’s what I was naturally trying to do. And so at that point, I really just shifted my career. And, we actually got approval to do a pilot and kind of went from there.

And fast forward and, working, as a professional scrum trainer, like really enjoying as an entrepreneur, getting to work with different clients. And when I started to realize at that point was, we can teach this theory and we can teach the practices and we can teach the processes.

But what I’m noticing is that people still struggle to actually change the [00:08:00] way they’re actually, they’re approaching these frameworks, these processes, these practices, right? We’re still bringing. a predictive plan driven mindset and to how we’re using these tools. And so then there’s this friction that happens, right?

There’s this resistance and we’re like, why aren’t we getting the benefits? And it’s we’re not getting the benefits because we’re not really doing it, but it’s not just that, right? And so what I realized is Oh, like this is more than just knowing processes and tools and frameworks.

Like we really need to grow who we are and how we’re showing up. And that’s at all levels of the organization, right? We all need to grow our leadership skills. We need to truly nurture the human side. It’s the people right who are using the process who are improving and evolving the processes. It’s the people who are ultimately getting value from our work, too.

And I’m a process nerd. I can speak out about processes and tools and things like that all day. But I realized that we need to bring that human aspect in and [00:09:00] that’s where it’s really helping with the team dynamics, effective self management and leadership. So now I take the 3 pieces of business agility, self managing teams and leadership, and that’s where you get sustainable results and true alignment starts happening in those spaces. There’s, there’s an overlap of a Venn diagram is what I think of and then the other fast forward I’ll give you is that a few years back I call it my gift of the pandemic. I was led to. Escape, essentially.

And, I really needed something and I had been to this place in Costa Rica where I did my vacation, like I’d been several times actually, but, then I would go back to where I’m from, Ohio, and not surf. And then I’d go back for vacation oh, this is beautiful, the ocean.

being surrounded by the jungle, the peacefulness, and this idea of surfing. And so something in me told me at the end of 2020, I [00:10:00] was like, I need to go there. And I need to feel different. And something tells me surfing is the thing I need to do. And so I spent 10 weeks there. Doing what I call becoming a real surfer where, you know, like I’m independent, like I can go out on my own.

I can stay, I know my limits. I know how to practice in a way that ‘s like reflexivity where I’m actually aware and like being able to make changes and adapt and go out and feel like I can be independent and improve and stay safe. And that was like a big unlock for me, because I’m like, Oh, this is what I’ve been learning for years about what leadership is about, right?

This idea and also then connecting it to agility and this idea of emergent solutions. I’m like, the ocean is a natural emergent system, and when we’re trying to catch a wave, it’s literally like the exact things that we talk about, where all of these variables are coming together to impact how that wave forms and the energy of that wave.

And I [00:11:00] have to be very present and in my body and sensing and responding. And then you don’t really learn to catch waves by catching waves. You learn to catch waves by failing to catch waves. That’s the majority of what you’re doing. But it’s like you get knowledge every single time. And so that’s like my history with those key points of where I came from.

My agility journey and what led me to where I’m at today. And now, like I, in addition to running professional scrum training, doing coaching engagements with clients to help them with that Venn diagram of business agility, self managing teams and growing leadership, in any and all levels of the organization.

In addition to those things that I call my traditional business I’ve started running Leadership surf camps in Costa Rica, where we’re leveraging, we’re learning, we’re leveraging, learning to surf as a tool to really embody it. Because that’s the type of thing [00:12:00] that it’s so different from learning in a classroom and I understand the theory and that most people do understand the theory of agility and they believe in it. They’re like, yes, that’s why we need to take this approach because things are complex and there’s a lot of variables that we can’t control them and things change.

But then it’s still hard. And so it’s that idea of embodiment and how the ocean gives us that experience. And then when we have that experience, you still have to work at it. I’m not saying it’s magic, 

but 

it gives you something to like, really like anchoring back into when you’re out in the world, applying this idea to how you’re managing products, how you’re leading in an organization and how you’re working within your team.

Oh, that’s 

Janna Bastow: amazing. It’s such a great story and actually really inspiring in many ways. I was talking to a friend of mine yesterday who is a product manager. Now product leaders moved up through the ranks over the years and I was looking to step aside to go do something in the world of or reskilling in the world of yoga, [00:13:00] for example, I was like, and one of the things she said really stuck with me.

She said my self care is more important than my career. You’re welcome. That prioritizing one over the other and I was like, that’s really cool. But at the same time, what you seem to have done is combined the two into something that actually empowers you on both fronts. So I absolutely love to see that.

Yeah, absolutely. 

Stephanie Ockerman: And, just that idea of recognizing that we are not our job, and the idea of we’re actually better at our job when we are taking care of ourselves is it’s. It’s strange how often we don’t think about it. And I would even argue that even I still have to be intentional, right?

Because there’s just, we’ve been programmed, right? We’ve got all of these ingrained beliefs that have been handed to us by the systems and culture that we’ve grown up in, right? Whether it’s from our family system, whether it’s from our education systems, our workplace cultures, just like how we think about.

Productivity culture and like how that’s, it’s just [00:14:00] more, or, busyness as a badge of honor. And we don’t recognize that a lot of one, a lot of the best ideas come when you just have space like with nothing, or it’s not even just like a new idea that you have, but just more like.

And unlock if you’ve been dealing with the thing, you’ve been spinning on it and unsure. And then you go for a walk and you’re taking care of yourself and, all of that self care piece, you go out for a walk. I go out into the ocean for a surf session and I come back and I’ll have and, I’ll be like, this is the answer to that thing.

I wasn’t, it was a dilemma I was having, I wasn’t sure which way to go and I’ll come back and I’ll, it’ll just have. Almost dropped into my brain. 

Yeah, 

absolutely. I think it happens through my body. It’s happening because I’m in my body and I’m not forcing it and trying to like it.

And which ultimately becomes overthinking. It’s not really just thinking about it. It’s overthinking about it 

Janna Bastow: And that’s magic. It’s the ability to clear your mind [00:15:00] and focus on something that’s, outside the usual box that we often put ourselves in, I’m friends with another product person who is an avid knitter and was talking about what what she’s learned about the product development process in terms of, drafting and Creating things, drafting patterns and creating things from them and how that relates to what we do in product management it got me into knitting as well.

So I do that but, I always love talking to people about what they do on the side and how it informs them. And, for this, it’s given you a really unique lens into how we work and why companies work the way they do. Tell me a little bit about how you equate the two.

You talk about this emerging system. What are you seeing in companies and how do you get people to think about that and how they react to it? 

Stephanie Ockerman: Yeah it’s very interesting because even with very different types of companies whether it’s like a small startup to large multinationals, it doesn’t even matter that, different industries.

The same patterns still show up and they may look different, but when you start to see it then you’re like, okay, this is the plan. This is [00:16:00] our fear of uncertainty. This is our worry about getting it wrong. This is our need. To guarantee something and the reality, that’s really just not reality and I understand it.

But so the, so what I’m seeing is this whole idea of emergence as we talk about it, right? Like us, if you go to a more agile training, especially if you’re learning about the basics, they’ll talk about the best solutions emerging, from self managing teams and this idea of being responsive to change and that.

We’re not, it’s not about just planning. We need to actually deliver something in order to have value. And then we inspect and adapt. We use all that language. We talk about empiricism. We talk about emergence, but I don’t think we really know what it means beyond the theory. And part of that is because there isn’t like a 10 step.

Process right to do these 10 things and this is your answer. And of course, it’s hard. I just like to normalize that. Of course, it’s hard. 

And then you get into the actual many people [00:17:00] trying to work together. And it becomes harder. And then there’s different goals we’re moving towards.

And this idea of emergence, I think. Is something it’s something I talk about when I hear from clients we want to standardize our agile processes 

and, 

We need all the teams using Jira the same way and we need our roadmaps to look the same way and, before and it’s getting to the what’s the why of that?

And ultimately the answer is usually. Something around I need to be able to say this and this and, it’ll definitely be true or it’s just, but there is like a general yeah, I do need to be able to communicate to our customers, right? We do need to be able to understand our progress.

But there’s a different way to do that when you don’t have this guaranteed 10 step process and this is how it looks for everyone. And I think by talking about this idea of emergence most people, even if they haven’t surfed, they’ve seen [00:18:00] a surfer. Maybe they do have experience in the ocean, playing in the waves, and it’s like they can connect to that idea of oh yeah I understand like that, that feeling of the energy.

The energy of the wave. And that’s what’s happening in your organization. And so as I’m going to not give you the truth, like I’m not an expert in the physics of how waves form. I’ve read some books, but I couldn’t repeat them to you. 

Janna Bastow: But you don’t need to be in order to react to, shoot, I’m in the shallows here and a wave is about to hit me.

You learn to embrace yourself and play with it. And you don’t know when it’s going to happen, but you just got to keep a lookout, right? 

Stephanie Ockerman: And so it’s that idea of you can kind of sense from your experience of Oh, yeah, I get that’s happening and because I felt it in my body before I, I believe it more 

and 

I like, I trust more in this idea of emergence where there’s all of these things happening, right?

To create the formation of a way that’s like chaos turns into order to truly form a wave. [00:19:00] And as that wave is coming, I think. As a surfer, you’re using all of your senses, right? Like you are, you’re looking, you’re observing, right? So in our organization, we’re noticing what’s happening in the market.

We’re looking at what our product teams have been delivering, iteratively and what the value is. We’re looking at that customer data, we’re looking at all of this information and I can see the wave. I can see the height of it. I can get a sense of the force of the wave, like the power of the wave and how quick it might be breaking.

And then I, but I have to just go for that wave, right? And I have to hope I’m in the right spot and I start paddling at the right time. And then I have to paddle to get enough energy to get into the wave and truly make the drop into the wave. Without being too far ahead of it where it’s going to break on top of me so all of these things are happening and I can’t just think my way into that wave, right?

I can know all the theory and trust me, you got to know the theory, you have to understand [00:20:00] how these pieces, do impact your ability to catch a wave, but you’re not going to it’s not a puzzle that you’re putting together a formula and it’s only as you start to try it. Okay. And you might miss that wave.

And it’s okay. And in my brain, I’m like, okay, what happened? Okay. I noticed it broke faster than I thought it would. Okay. New information, right? New information that I can play with, but nothing guarantees the next wave is going to look exactly like that. There’s usually slight variations.

So it’s this idea that you’re trying something right. Talking about experimentation so you’re treating each wave as an experiment and you’re bringing in new information. You’re also looking at, oh, this one does look a little different. So I’m going to move a little bit further from the peak because it looks a little bigger and, that’s how you think about it.

And the other thing, the other piece I’ll add, though, is if as that wave is coming at me, I’m in my head freaking out about the wave coming at me or just like upset because I haven’t caught a wave yet, [00:21:00] I’m not going to catch that wave because I’m in a reactive state. 

Janna Bastow: It’s a really good way of putting it.

And this concept of being more experimentation led I think whenever I talk to individuals, they’re always like, yeah, I get it. I understand why I need to try out something and then see if it works or not, and then learn from there. But there’s always this resistance.

In the company to give the time and the space to do what a product manager carves out their time and their ability to do and how do they get to the point where they’re not afraid of failing? Cause it’s not just that they’re going to get tumbled around.

It’s that it’s, is it putting their career on the line? Maybe not, but it’s certainly creating tension within their workspace. 

Stephanie Ockerman: Yeah, absolutely. And, I, again, like I’ll, I come to the ocean for this as well. And I fully understand that if my job is on the line, if I’m worried that this is a failure, that’s going to affect my career, of course, there’s more on the line.

But the reality is, when you start to get into leadership, like the actual theory and practices of leadership, if you look at [00:22:00] very different schools, they all teach the same thing. They might use different language, 

but 

this idea of creative versus reactive leadership. I like to talk about it that way.

So like with creative leadership, you’re open, curious, committed to learning. And if you’re in a reactive state, you’re close, defensive and more committed to getting it right or being right. And so the idea is I want to notice if the worry I’m having or the, it’s really coming from a place of fear, feeling something’s a threat.

That’s how our lizard brain works, like it’s helping us but it doesn’t know the difference between the tiger versus what the dynamics of work and, 

Janna Bastow: exactly that, like dealing 

Stephanie Ockerman: with conflict. Yeah, so it’s like, when we start to cultivate this idea of understanding what it means to be present, and then starting to reflect on like, how, knowing how our reactivity shows up like in our body or like the thoughts that we have around it.

Then we can catch it and we can ask ourselves and be more intentional around. Am I really [00:23:00] assessing the situation in the right way? And sometimes it’s helpful to have that conversation with others to gain some perspective. And then at the end of the day, it’s always our choice of what we feel is worth risking.

I know when I first started my career and agility, I was very like, yeah, you should be willing to be fired. That’s, some of the scrum master’s job or, might mean you have to have difficult conversations and maybe we’ll get fired. And then as I became a more aware and mature person realizing that I am in a different position than other people and we all have, we all make our own choices about what our risk tolerance is and I’ll have our own experiences too. If we’ve been burned before we carry that with us. I never, I don’t judge we all make our choices. The question is can you make the choice of, I’m going to take this risk, right?

Or I’m not going to take this risk, but here’s how I’m still going to show up in integrity and try to learn and experiment and try to be [00:24:00] able to adapt if we need to. So it’s like when we ground ourselves, get presents. We can have a more meaningful understanding of the situation and ourselves in that situation.

We can get input from others if it’s supportive, but then we can make that take responsibility for that choice. And also know that no choice is the only choice, right? Something’s going to happen and then the next wave is going to come and then, and then you’re going to make a new choice.

And then do I want to go for this wave? I don’t know. This one seems bigger. Like, how do I reduce the risk? And there’s lots of options but we don’t always see those options when we’re in that state of worry, reactivity. 

Janna Bastow: Yeah, that’s a really good point. I know a lot of product people almost sit in paralysis over which decisions to make.

Have you ever heard that whole thing that I think Bezos originally came up with? They certainly popularized it, the idea between, type one decisions and type. Two decisions, one being reversible decisions, the other [00:25:00] being irreversible decisions and pointing out that actually most decisions are irreversible, so you can make them and without absolutely sinking in the ship, you can undo them.

Whereas some things are irreversible decisions, like if you decide to lay off a whole team or sell the company or do something like that, a lot of times the stuff we do actually is less, not impactful, but less permanent than we often think. 

Stephanie Ockerman: Yeah, absolutely. I love that framing.

Like again, like we can use tools like that to put us back into like our presence in our body and like using our full body intelligence versus spinning on things unnecessarily. And the other thing that you just made me think of is this idea that. We’re not doing it alone as product managers, as product leaders.

So it’s like developing your skills to facilitate conversation and like that helps others be involved because let’s take advantage of the, the collective intelligence, the wisdom of the team. And I’m [00:26:00] not saying put it to a vote necessarily. I’m not saying abdicate your responsibility, but this idea of if You want to see more perspectives.

You want to tap in to the team and the decision might at the end of the day be on you. But I think a lot of times we isolate ourselves and feel like we gotta do it alone. 

Janna Bastow: And that’s ultimately the job of the product manager, right? If you boil it all down to what we’re doing, it’s we’re making decisions about the direction that the company is going, the direction that they, the product is being taken and you’re making use of the company resources.

But you’re not doing so ideally, you’re not doing so, from a corner looking out and saying, yeah, this is what we’re going to do. And moving pawns around you’re in the middle of it, right? You’re surrounding yourselves with these people in your team, right?

So you become the conduit for insights to come through. You’ve got people in the marketing team telling you what’s going on over there. You’ve got people on the dev team telling you what’s, what new tech is possible and what you can do now. You’ve got your customer stakeholders and your job is not.

to have all the answers, right? Your job is not to just lay out [00:27:00] something and say, go do it. Your job is to actually, more than anything, collect this information and ask the best questions, pull this stuff out of people so that you’ve got this wider view as to what the big picture is and therefore making more informed decisions and hopefully more defensible decisions.

Stephanie Ockerman: Yeah. And, we’ve been talking a little bit about this concept and I just want to name it the idea of timing. So I don’t want to be stuck in analysis paralysis, and wait too long to make a decision. But I also don’t want to be reckless. I just got to go.

And we, I think we tend to be in a culture of urgency, false urgency. I think some of that we just got to do something we got to do something and it’s that can be irresponsible because we do also need to be intentional and there’s a patience, I think, and there’s this idea of sensing timing too.

It’s hard to talk about because it’s intuitive, right? It’s as you’re talking about that we’re getting all this information from different sources. We’re sensing what’s happening in the wider market, which is even [00:28:00] harder to get a sense of. And, I think there’s something about us, there’s a trusting in our ability to sense the timing and there’s so I’ll bring it back to serving.

Of course there’s this idea that, like. When you decide to go for the wave so let’s say it’s a, it’s a big wave and I’m a little bit afraid of it, but if I hesitate, I’ll tell you what the wipe out is going to be way worse. If I hesitate versus if I commit fully okay, I’m going, I might fall, but I’m actually going to commit.

I 

Janna Bastow: Mean, is that a little bit like, when we build these kind of crap MVPs and put them out there and hope that it solves the problem being like we didn’t fully make it, but we made this half assed version. And now it turns out no one likes it. So is that because we didn’t finish it?

Or is it because it wasn’t the right thing to do? Yeah. There’s that 

Stephanie Ockerman: hesitation, right? Yeah. Whereas if I’m really going for it and I’m really like, if from a surfing perspective, if I’m truly in my body and I can [00:29:00] sense what’s happening, I’m going to learn from that wipe out. And I’m also, and I’m going to learn okay, here’s what I need to do differently next time.

Or, you know what, that is not the type of way that I should ever go for. 

Yeah, 

and I’ve had those two. And there’s also the idea of being too slow. And this I think comes when we’re trying to get it right and perfect and we’re overthinking it. And we get stuck in that like analysis paralysis. I need to build more 

to make 

sure that it’s successful.

And I equate that to the idea of like you, you wait too long. To start paddling and then the wave just the energy of the wave just goes over you because you haven’t gotten enough speed to match the wave. 

And 

So there’s the hesitation side of it and then there’s the panic, I didn’t fully commit and I panicked at the end.

Janna Bastow: Yeah, no, absolutely. And you know what? This sort of reminds me of what I’ve heard. I think it was Des Drainer was talking about standing still not actually getting things out. If you’re going at a slower pace your competitors are going faster and faster. And it means that your handle [00:30:00] on the product market fit is going to be slipping because the market is moving forward, their expectations are changing, and so there’s this sense that there is a sense of urgency that you’ve got to keep moving, you’ve got to keep going but you’re absolutely right in that you’ve got to get the timing right so that you aren’t putting the wrong stuff out the door and, making haphazard guesses that aren’t impactful.

Stephanie Ockerman: Yeah. I equate it to the idea of frequency of your practice, right? It’s what we’re talking about more is like we’re learning something. We’re doing something and learning, right? We’re not just sitting out there waiting for the perfect way, right? Like we’re trying some things.

We’re learning more about, oh, I sense today, like there’s a little more current happening. That means I need to paddle a little harder to get into a wave, right? So it’s that idea. I think more like the frequency. It’s like putting in the reps so that we’re getting new information in and we’re practicing.

So yeah, it’s this I we, and then the other piece I would say is know where it’s coming from. Am I just sitting out here? Because I’m just [00:31:00] being patient and I’m observing and I’m present and I’m having, I’m getting information and I feel good or am I sitting out here because I’m worried about something I’m, I’m afraid of missing the wave.

I’m upset because these people are catching waves and I’m not catching waves. So again I really love this idea of creative versus reactive leadership. And I come back to it frequently because to me, it’s like kind of that always like that foundational piece of our own personal leadership and how we’re showing up and that always is going to have an impact on the decisions we make, it’s going to have an impact on all the people that we work with.

If we’re coming in and in a reactive state into a meeting and we’re panicking. About what our competitors are doing like that energy is contagious, right? Like it rubs off. And we can think about how we’re showing up and that just alone, just dropping into your body will give you a sense of.

Wait, where am I coming from right now? Am I in a creative state or am I in a reactive state? And then you can, and then you start to practice finding ways to shift yourself. And it doesn’t [00:32:00] mean you suddenly have an answer to your question, but now you’re in the state that it is possible to observe. It is possible to sense new information.

And you’re not coming from a place of worry or fear of getting it wrong or anything like that. You’re coming at it with a true let’s run an experiment. And like, how do we mitigate risk? Okay. This is too big of a risk. Okay. Let’s talk about how we make it a smaller risk experiment. How do we get, that’s too big of an experiment.

We can’t go that long without feedback. Okay what can we do to mitigate going too long without feedback? And so it just helps us have those conversations instead of conversations that are about, but this feature has to be in this release or, if we don’t meet this date, it’s like those conversations.

It’s information that may or may not be useful. But there’s a different conversation we want to have to utilize that information more effectively. 

Janna Bastow: Yeah, absolutely. And, the reality is that many of us won’t have access to warm water and waves to go get [00:33:00] out there and start a surf practice.

But, what are ways that people can get themselves in the mindset to be this creative leader type persona that you talk about? 

Stephanie Ockerman: Yeah. I do think that it can be helpful to actually try to put yourself into an experience, like a memory of an experience of waves. Even if you don’t live by the ocean now trying to put yourself into the memory of that experience, and even sometimes playing wave music, or watching a surfer on a video, and just noticing a really good surfer is often like you see them dancing with the waves, right?

Like they’re creating with the wave they’re creating with the natural energy that is emerging as they ride the face of the wave. And so I really do encourage people to like, try to get yourself into that. Even by watching a video, if you can or tapping into a memory of the feeling of the energy of the way.

It’s 

Janna Bastow: almost like a meditative state where you’re making use of your, listen to your body and your senses. Yeah. 

Stephanie Ockerman: Yeah. And then we [00:34:00] can even tell ourselves things like I’m committed to being out here, like I’m a surfer. Like I’m committed to that. And what would a surfer do?

And I actually put together a guide called leaders ride the waves, a guide to navigating uncertainty and complexity, because I wanted to give people a way to think about what they would do, what are these surf lessons, right? Like these surf lessons for leadership and business agility.

And then what would it look like for me to start to practice this? So I will share that. It’s a free download. You can also get some beautiful photos to get you in the vibes of waves in the ocean. And some maybe warmer weather than you have right now. I’ll go ahead and drop that in the chat right now and send it out after as well.

Everyone 

Janna Bastow: will get a copy of that in the email that we’re sending it afterwards. So you’ll have access to that. And it sounds like a really great resource. 

Stephanie Ockerman: Yeah. And so there’s, I bring in some context like how this relates. So it’s like making sure we understand the relationship to leadership, business [00:35:00] agility, why we struggle and then bringing in what are these core leadership concepts that help me really connect in and get to presence and start to trust myself. There’s this idea that we also have to start trusting our own decision making, and then also remembering that. I’m going to use it as the surfing metaphor, but we don’t learn to surf by catching waves.

We learn to surf by failing to catch waves. And so it’s really getting yourself into that mode of running experiments, right? I’m out here trying things, but I have to be intentional in how I design that experiment. And this is where you can get into some really useful practices, right? What is good experiment design?

What are good measures, right? Like, how do we take something big and break it in and, to risk based experiments, right? So we can leverage our tools to help us think in this idea of a surfer catching waves. But we have to be like approaching it that way. To be able to see those possibilities and to be able to work with our team and [00:36:00] facilitate these ideas coming to the surface of Oh, here’s an experiment actually that we could try if this is the thing we’re trying to learn.

And being able to unlock those conversations for people. And in the guide, I’ve had more surf lessons than I, we’re doing like the in person leadership surf camp experience in Costa Rica. But I’ve included three of the surf lessons, some of which we’ve already talked about here.

And then how you can actually put them into practice like in the day to day. 

Janna Bastow: Oh, fantastic. And you mentioned trust and it brought to mind a conversation that I was having yesterday around how product managers need to trust their gut or trust their hunches, right? And there was a bit of debate about what is a hunch?

What do we mean by that? How can you just trust you got over the data, for example. But it’s not necessarily about trusting it over data. If you have data that’s proving you’re wrong, then that’s probably where you should be listening. What does a product manager gut feel?

Because you have a gut feel because you’ve exposed yourself to all the different elements, right? You’ve been through releases that have [00:37:00] gone wrong. You’ve fallen off a whole bunch of waves. Yeah. Yeah. You’ve tried to experiment and it’s blown up in your face enough times that you go, ah, this time we’re not going to do that.

And that gut feel is often this almost innate sense, innate feeling, but actually it’s been informed by your entire life’s experiences. And oftentimes it’s not just from stuff that you’ve done in the workplace, it’s your entire. World sense of, what, and that goes into your gut feel, I was saying a junior person, a junior product manager, you wouldn’t trust their gut as much as somebody who’s senior, who’s battle is hardened and weathered and has seen all the different things.

I saw all the different ways it could go wrong because they’re saying, actually, this is what we might need to do. And this is what might need to change if we’re going into this particular approach. Yeah. But it brings to mind somebody who is in that situation.

The state of learning is gathering these experiments, sorry, these experiences, which later on go and inform how they approach this experimentation, agile mindset. Yeah, 

Stephanie Ockerman: absolutely. Like intuitive wisdom, right? Like we’re learning all about their [00:38:00] experience and we might not even be able to fully explain why our gut is saying it, but it’s like in us. And I, I think we really don’t emphasize that enough in leadership and if you do go out and deep dive into leadership bodies work and institutes like they are talking about your inner leader and this idea of trusting yourself and not in part of that is. Not trusting that you’re always going to get it right.

It’s trusting that you are tapping into some intuitive wisdom. You’re sensing something that’s happening out here around us, and you don’t necessarily know how to say exactly what that wave is going to do, but just something tells you should go for it and how to do it or not go for it and wait for the one that’s coming right behind it.

When I’m out surfing with people who have 20 years of surfing experience, it’s truly amazing. Like I’ll still do coaching sessions, like periodically every several months just to keep improving and starting and having that challenge of an expert pushing me [00:39:00] to improve and also pointing out where I maybe have developed some bad habits and helping to correct those.

And it’s amazing how they can read the ocean and they know when waves are coming and I’m like looking, I’m like, I don’t see, I don’t see it. And I didn’t grow up. 20 years 

Janna Bastow: of experience, right? 

Stephanie Ockerman: And it’s also, I didn’t grow up around an ocean either. So it’s I wasn’t even watching waves form really for, except for maybe a vacation here and there.

Until a few years ago, and so I still very much see myself as an advanced beginner still in my mind. Yeah, I’m probably intermediate really, but it’s I’m going to be intermediate and there’s 8, 000 levels of intermediate, 

Janna Bastow: And yet in the agile world or the product management world, what you have is a wealth of experience, right?

What I loved is that you said you started off in the waterfall world, getting your PMP. I did the same thing, actually. And on paper, you look at it going, why doesn’t waterfall work, right? It looks like it should do. It’s nice and orderly. It’s got that checklist that people love.

Once you actually see it the other way and you [00:40:00] start getting into the motion of it, you realize, Oh, wow, yeah, this is way less energy intensive and we can do way more with the resources we have, but also time to take that experience to go like, Oh, we tried it that way. And this is actually what went wrong when we did it.

Stephanie Ockerman: Yeah. And I think of it as like really tapping into the co-creation possibilities, like when we really. That’s when we’re going to have the most innovative solutions, or we’re going to realize that we can deliver this value for half the cost if we do it this way. And that might even be preferred, right?

Like we can have those things emerge when we’re co-creating with, not just the team, but co-creating with what’s happening around us and what’s changing around us. 

Janna Bastow: Yeah. Absolutely. No, the thing is I definitely see how individuals start, changing this mindset, but what about somebody who’s, just joined a company that doesn’t have this mindset or, recognizes they need this mindset and is surrounded by a bunch of people who just want a checklist, just want to budget things out, just want to know when everything’s going to be [00:41:00] done.

And what does somebody, what does an individual do to make that change? 

Stephanie Ockerman: Yeah. So individuals in that situation, like you really got to work on your own leadership, like your own ability to like the creative reactive, like to me, that’s your number one tool, because you want to notice, right?

You want to be aware of what’s happening so that you can think I see what’s happening. They want guarantees, like they want, a yes, no Okay. Perfect outcome. What is the best conversation I can create here? And you can really only tap into that aspect of how you can impact what’s happening in that room when you are not in a reactive state yourself, 

right?

And so you get smart. You get your start to notice like, okay, I’m curious. What do we think our customers are going to be able to do? What value are they going to get from this next release? I just want to ask, have we talked about that yet? So we can shift conversations, from outputs to outcomes. We can shift conversations that are like, we have to meet [00:42:00] the date. We have to meet the date for things like let’s talk about what happens if we don’t meet that date or okay, if the date. So if the dates are really important, and we know why. Let’s talk about how we can take some of these nice to haves and move them to a future, move them lower in our product backlog and move them to a future release and or maybe get more information from our customers and ask them if you could only have this or this, which would you choose?

So there’s lots of ways to create that conversation that’s really moving us towards the value that we’re trying to create, the impact we’re trying to create, and like in a, I think of it as like you’re interrupting magical thinking in a way that is, I think, useful and respectful and not quite like confrontational.

It’s just like, how do I help people have better conversations? And shift us towards talking about things that are actually helping everybody understand the complexity more and helping us, helping [00:43:00] me a lot of times as the product person makes decisions, right? How do I get the information I need to make decisions, knowing that my job is not going to make every stakeholder happy, like that’s not my job.

And that’s very rare. That we do that. But it’s like, how do I create transparency to what is happening? How do I get the information I need to help me make better decisions and help ensure everybody else is seeing these things differently as well? 

Janna Bastow: Yeah, absolutely. And actually I think we have time for one more question because I know that you had a a hard stop at the top of the hour, but one of the things that’s a reality in the agile world, and I’m not sure whether there’s anything like this in the surfing world, but once you’re actually done something, you’ve finished a release, you’ve got something out there teams should take the practice of doing the retro, the retroactive meeting, right?

So how can somebody best reflect on what they’re doing as a team and make sure that they’re learning from it. 

Stephanie Ockerman: Yeah, I do think if we’re talking team level building in some form of [00:44:00] regular cadence for reflecting, and I think it’s helpful to have what you want to bring in from, you want to kind of prepare for that too.

I think I see a lot of we have a retro, and it’s really not deep, right? It’s very surfaced. Hey, do we need to improve anything? Yeah, everything was pretty good. There was this one thing like, okay, we can do that next time. And I think it’s more of like a real, like you want to put time and effort into it.

You want to come with data because there may be things you don’t know and you can’t see until you start looking at data, right? So if we’re thinking about, flow of value in our process. That’s what they are, what is the data we want to look at if we think about actual value measures, right?

What are those key value areas that we need to look at to assess? Because it’s usually the trends that matter, right? That tells you something. So I do, I. Fully believe in the concept of retrospectives. I just think we need to be more intentional about how we do them and [00:45:00] be also data driven but not but still creating space for the human aspect right of our work because it has an impact.

And so we want to be talking about that. 

Janna Bastow: Yeah, and you touched on something there, which is about the process itself, right? A good retro should be about making sure that it’s not just about, the surface level, did we like how this particular feature has turned out and that sort of thing, but it’s more about, how is the process, what could we learn more about how we approached this along the way and improve for next time we go in.

Stephanie Ockerman: Yeah, and I think you’ve inspired an idea for me of what would be a surfing inspired retrospective format? What would be some of the questions that we could ask ourselves to think about, like, how are we sensing and responding? Like, where are we? Where do we tend to like, panic when the waves come or who’s pushing who’s around us, right?

That’s creating chaos in the sea. 

Janna Bastow: Amazing. I love it. Perhaps a follow up to the guide that you’ve created already. Yeah. So on that note, I want to give you a [00:46:00] chance to just share a little bit more about how people might find you and follow up on some of the stuff you’re talking 

Stephanie Ockerman: about. Yeah, absolutely. The best place to find me is my website, agilesocks.com. And if you want to download the leaders ride the waves, the free guide I’ve created is agilesocks.com/Prodpad, and you can just download that. And I’d love to hear, I’d love to hear feedback on, I’d love to hear what’s resonating and how you’re using it. In your day to day you can also sign up for my newsletter, it’s called leaders ride the waves.

So if you’re looking for something that’s a little, both practical and inspirational and a little creative and different and when you can also find me on LinkedIn. 

Janna Bastow: So fantastic. All right, cool. We’ll absolutely see there. And just to wrap up, Oh, we’ve got the guide here, so I put it here in front of everybody.

I’ve got a slide on it, which is wonderful. And just as a heads up. For everybody. There’s more to come on this. Save this date. It’s going to be March 27th and it’s going to be a guide on how to run a product launch, a GTM guide for product [00:47:00] managers. So if anybody’s got impending launches or has messed up the previous launches and wants to talk about it, come along and you’ll be talking to our product experts here.

And finally, just to wrap up, make sure that anybody who wants to have a chance to take a look at Prodpad themselves, this is a tool that actually helps you keep that agile edge, right? Make sure that the work that you’re doing is very experimentation led, that you’re asking the questions: what are our target outcomes?

What did we actually get out of this? And what have we learned along the way? Prodpad is a space to help you keep on track with that process and make sure the stuff you’re building is actually truly valuable. Start a trial for free, go hit up a demo at Prodpad.com/demo or try out the sandbox Prodpad.

com slash sandbox, where you can jump in, play around and see how it would fit your own processes. So on that note I want to say a big thank you, Stephanie, for coming along and sharing your insights. It has been both really insightful and a lot of fun to chat about. Yeah, 

Stephanie Ockerman: Thank you. Thanks for letting me geek out on surfing and agility.[00:48:00] 

Janna Bastow: Absolutely. And thank you everybody for joining today and hope to see you here next time. Bye for now.