Coaching for Growth with Diana Stepner (Podcast & Transcript)

“I am a true believer in the power of people. And if you put your people first, even before the product or profit or process, I believe the end result for the customer, for the product, and for the business is better.” - Diana Stepner

Diana Stepner is a Product and Leadership Coach. With over 15 years of international product leadership experience, Diana has led numerous teams at companies such as the Chan Zuckerberg Initiative, Kayak, Pearson, and more.

In this episode we discuss:

• How she went from aspiring fish-store owner with a Marine Biology degree to Product Manager in tech

• How the industry has evolved over the past two decades

• How ensuring all stakeholders feel heard can make a project run a bit smoother

• The advice she gives to clients who are facing burnout 

• The role of AI in product management
  

Transcript has been edited for clarity.

Karen Ko: Hey there. Welcome to Engineer Your Career, a podcast brought to you by WEST, a learning community empowering women technologists through mentorship. Join us as we hear from inspiring women tech leaders who are challenging stereotypes and paving the way for future generations. We hope their career journeys inspire you with new ideas to engineer your career. Let's get started.

Hello, everybody. Welcome to our latest episode of Engineer Your Career. I'm Karen, and I'm excited to introduce our guest, Diana Stepner. Diana is a product coach and product leader who's passionate about creating a strong culture of learning and success. Previously, Diana led product teams at notable companies such as Chan Zuckerberg Initiative, Pearson, Kayak, and Monster, and recently co-founded Product Gold, a product coaching and consulting company. Welcome to the podcast, Diana.

Diana Stepner: Thank you very much. I'm very excited to speak with you today.

Karen: So for our first question, can you please share with us how you got into product management?

Diana: Yeah. Thinking about my career, originally I wanted to run a fish store. I grew up and had a fish tank and a dog, and for some reason, just really thought my career path was going to be aligned to fish, and that led me down the track of marine biology, where I could spend a lot of time with fish. But I learned that you had to count sand particles, and I'm not sure that was something I wanted to do.

So I went into communications, and I was sitting in a class, and we were talking about what we wanted to do after we graduated, and I really wanted to align communications and technology because I grew up in Silicon Valley, and that really started my pursuit of product management.

I went into CRM, which led me to a startup that was doing CRM, that led me to be a partner with engineers who were trying to build an application for marketers. And the marketers just didn't get the technology. And so I went back to school, got a graduate degree in human computer interaction and loved user experience. And so I went into user experience and found that I kept giving my ideas to product managers, and I'm like, why can't I pursue this? And so my next job after that was product management. So it all started with fish and then went into product management.

Karen: Oh man, that's incredible. I wonder at some point, if you'll go full circle and go back to fish after product management.

Diana: That's a very good question.

Karen: So, as someone who's led products for a number of years, 20 years, right? Can you share a little bit about how the industry has evolved over the years?

Diana: Yeah. I think when I started product management, it wasn't really a thing. And so for me, the biggest change has been the emergence of product management as an actual career. Like so many others, I discovered product management. It wasn't something that I knew about or went to school to get a degree in. It was just a way that I could combine my background in business and technology, and understanding of customers.

So yeah, I happened upon it just based on my interests. And starting in London, I just remember the first meetup that I went to with wine, the product, I mean, it was right when it was starting, and it was in a London pub. And thinking about the growth of product management, it aligns nicely with the growth of Mind the Product, because now there are meetups around the world, there are conferences where they fill up huge stadiums, almost. And so that to me has been the biggest shift of seeing product management be something that people kind of just discover to actually being a true discipline that people spend 20 years doing. So it's been amazing to see that change.

Karen: Incredible. And what have you found to be your superpower when it comes to leading product?

Diana: For me, it's putting people first. I am a true believer in the power of people. And if you put your people first, even before the product or profit or process, whatever the approaches that your company is taking, if you put the people first, I believe the end result for the customer, for the product and for the business is better because really considering what motivates your team, where they want to get to, the growth opportunities for them. And so really thinking about the people that are in your team, the people in your organization, I believe leads to a better end result, again, for the customer and product and for the business.

Karen: And I'm curious when it comes to product coaching, if there are any questions that come up often as you're talking to different people that you're working with?

Diana: I think it definitely ebbs and flows based on the time. So right now, I think people are feeling that they're being asked to do more with less. And so there's a lot of folks that are burnt out and wondering, what do I need to do to gain back some of my own time, some of my own energy, brainpower.

And so working with people to help them focus, be able to prioritize, be able to say no to some things, potentially, so that they can have more time for themselves and be able to contribute their entire focus to work as opposed to feeling that they don't have anything more to give. And so that's a lot of what I've been helping people on.

Obviously, in times like this as well, people are wondering, where do I go next? What do I do with my career? How do I advance? And so those are areas I help with people, too.

And a lot of other facets are just what do I want to be next? Product managers, those who really stand out are about learning and collaboration and sharing, and want to be able to be in an environment that allows them to grow and develop too.

Karen: Yeah, absolutely. I think that what you're saying about seeing yourself as a product in some ways and managing your time and your energy and creating boundaries as protecting yourself as the product that you're serving into the world is what I'm kind of hearing as you're talking about how you're working with your clients. Would you say that's the case?

Diana: Yeah, I think that's a really great summary, to be able to look at people as a product, and like any product, it evolves and so to be able to help people better understand what they're motivated by and better understand the impact that they want to have on the world, and that'll change as people gain more experience, but it's something that it often really helps just to have a thought partner that you can talk through what you're thinking about and how you want to get there.

Karen: And what has been the highlight of your career so far?

Diana: For me, it's honestly just working with amazing people. I love it when people from my prior jobs reach out and just say hi or remember stories that we had from work. That, really, to me, is the standout, is that connections to people, the communication, just the updates on their lives. That really motivates me, just simply hearing how people are doing and being able to help in any way I can. That to me is the highlight.

Karen: Love that. Would you say that your past experiences with mentoring others and building those relationships are some of the reasons why you've decided to pivot to coaching?

Diana: Throughout my career, people repeatedly told me I was the only leader they had who truly thought about them, who cared about them as a person, not as something transactional. And I really thought about and helped them develop. I helped them grow and to surpass the potential that they thought they had.

So for me, it was just natural. Why wouldn't someone want to be able to help their teams? I just did that instinctively. And I also had a coach who really constantly inspired me. So, taking all those facets together and looking back over the feedback and the comments I had received throughout my career, I started a course on people-first product leadership, and people reached out afterwards just asking if I could coach them. And so that really inspired me to lean into the feedback I'd received throughout my career and make that transition into coaching.

Karen: I love that. And I often hear from folks that are more junior in their career that they are not as familiar with what coaching is, and the misconception is that coaching is only for the people that are at the executive level or are people managing, but aren't for the people that are more junior, when everyone can benefit from coaching.

Diana: Yeah, I think you said it perfectly. There's so many different types of coaching, and some approaches are for executives, but there are so many other ways that coaching benefits people throughout their career. And so I definitely recommend coaching as you are just in a situation where you want someone to help you realize what's really important to you. And that can be when you're starting your career, that can be later on as well. But coaching, at least from my experience with my coach, has been something that's been helpful from my IC days all the way through leading product teams.

Karen: Yeah, absolutely. And as we were chatting earlier, you mentioned that you really believe in soft skills as something that can be a superpower for others. And I'd love for us to chat a little bit about that.

Diana: Yeah, it goes back to what I was saying about treating people as people, not as transactions. And there are companies where the individuals feel that they're simply just cogs that are getting moved around and put on projects just at a whim. And I think if people, leaders especially, really think about the individuals in their organization as people with desires for growth and learning and advancement, then you get more out of the people by really leaning into what motivates them.

And so I focus on helping people be true to themselves because a lot of times when you're in a working environment, you feel that you need to not be yourself, that you need to turn off aspects of your personality. And I really think individuals have so much potential if they lean into their strengths by being themselves. And that's what I try to focus on. I mean, it's those facets of empathy and understanding and appreciation, and as you said, treating yourself as a product that will continue to evolve as you gain more experiences. But being cognizant of the fact that you're a person and there's things that all people need to be able to reach their best potential, that to me is missing from a lot of organizations,

Karen: Treating people as humans versus just a cog in the wheel that is part of an organization that is nameless. I feel like that is probably one of the more uninspiring things that could happen where you're just, nobody knows who I am, they don't care what my career aspirations are. I'm a nameless number that is working within the organization to help it move forward. And that's all that you are.

And I can see how it would be so much more inspiring to work for a leader who actually is invested in your growth and as a partner in helping you succeed so that you can both succeed together. And I feel like, with soft skills, too, that is probably something that is really important for product managers when it comes to leading without authority.

Diana: Yeah. Yeah, I think you're so right. I mean, whether or not you are an IC or on the manager track, from a product perspective, you're always influencing people. And so that's your cross-functional stakeholders. It may be your design or your technology partners, but you're always working with people and trying to bring them together and trying to get the best out of everybody so that the customers have the most positive experience possible.

And so as a result, as product managers, when you really lean into the empathy and the understanding and the appreciation— and I think listening is one of those key skills that we often overlook when you really think about— and incorporate all of those practices into your work with cross-functional stakeholders who, as you said, you don't lead, but you're influencing, then I feel that teams are more cohesive and more effective.

Karen: Yeah, absolutely. I'm also curious in terms of when you're starting to lean into your role as a leader and needing to be more deliberate, I guess, or intentional, about building that influence across teams, what are some ways in which you've been able to do that successfully in your past organizations?

Diana: Yeah, the first one is really listening. I said active listening, and I'll say it again. And that means truly absorbing what the person is saying and trying to be understanding of their point of view. Because a lot of times in organizations, and it's not for one reason or another, but there are certain teams that feel that they don't have a voice. And as a product manager, you should be able to listen to all stakeholders to be able to ensure that they all feel heard. And that to me is extremely important.

And so there have been so many times where just taking a moment and talking to a stakeholder really opened up the opportunity for better collaboration because oftentimes we're working in groups, a voice that may not be that loud may not be heard. And so just stepping out and being able to have one-on-one conversations with individuals and be able to show that you really have heard them by repeating back what they say, being able to highlight and introduce the context around decisions, and doing so in a way that ensures everyone is at the table, not just the loudest person. I think that really has helped me throughout my career, creating just connection and stronger communities of people that can truly work together effectively.

Karen: I think that one-on-one attention is so crucial, especially for folks who generally don't like to speak up in large groups. And something that I've learned a while back is that there are some personality types that are very anxious about sharing conflicting ideas. And so if they don't mention their idea first and they hear someone else saying a conflicting idea, they're not going to share their idea.

And so I think being able to recognize those individuals and being more supportive in helping them find a voice in the conversation is so key. And I love that you're focused on listening versus speaking and potentially drowning out all of the other voices in the room, but you're really shining a light on all of the other voices to allow them to continue to share and be part of that collaborative process. I really love that.

Diana: Yeah. The way you put it is great. Yeah, you've summarized it perfectly. Thank you.

Karen: Absolutely. So I'm curious, have you had a situation where you are trying to make that new connection with a stakeholder and they're just refusing to be a team player, and they're very, very confident in what they're wanting to do, but it's against what everybody else wants to do? I'm curious how you've navigated those situations.

Diana: Throughout my career, I've worked with very strong individuals, and one situation that comes to mind is a person who was amazingly talented and, like you said, just had very, very strong views about the way things should be done and how we should approach a project.

We had sessions together, talked together, and for whatever reason, she just wasn't feeling that... She wasn't feeling that there were other alternative approaches that were as good as hers. And so I was working with a member of my team, and what we did is we just went through all the messages, all the communications that we'd had with her, we summarized her main points, and we addressed them one-on-one.

So, each item that she brought up, we explained in a written document why we were doing something different, or how we had evaluated the idea, or the aspects that we were taking forward.

And so by showing the detail that we had kept and considered from her, and then showing our thought process about how we evaluated each of the opportunities that she put forward, that we truly put time and consideration into each of the items that she had raised, that changed her whole perspective because she felt, for whatever reason, that we were glossing over some of the pieces that she had raised.

But by putting them out in the open, writing them down, showing line by line the process that we went through, it really helped her to feel heard. So, as you said, some people have different ways that they feel acknowledged. And in that situation, speaking, having those one-on-one conversations wasn't sufficient. She really wanted an asset that she could refer to and visually see that each opportunity she'd put forward had been considered.

Karen: That's so powerful. I feel like, oh man, it's hard to make that time, right, to have those conversations with everyone in advance to understand, how would you like to receive various communication? Do you prefer that one-on-one where we're talking in person? Do you prefer having a verbal conversation about this? Do you prefer to have all of these in writing so that you can see that we're answering your questions line by line? But being able to take the time and energy to recognize the situation going on and then trying a different method to try to be able to create that bridge to cross over and be able to talk to her in a way that she felt heard, I think, can be very difficult. And kudos to you for finding a way to cross that bridge.

Diana: And it's something I've recommended in my coaching as well. And it's one of the facets, again, going back to people-first leadership, we're not all the same. Every person is unique. And so you need to be able to understand the people that you're working with and be able to meet them where they are.

Heidi Williams: Let's take a quick break to hear from our sponsor.

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Heidi: And now back to our discussion.

Karen: Yeah, absolutely. So I'm curious about what other topics often come up in your coaching practice as you've been…you've been coaching for quite a while throughout your career, even though you didn't have the dedicated title of a coach. I'm sure you were still coaching a number of your past team members and also probably across teams and other folks that looked up to you throughout the years. I'm curious if there are other topics that come up often.

Diana: Yeah, it really depends on the time. Right now, it is still, unfortunately, burnout. Again, so many people are being asked to do more with less, and everyone, I think, is still just trying to balance their own mental health and wellness against the demands of an organization. And so that is the one that's top of mind.

That then fuels other things. People are feeling that there's a lack of direction or a lack of motivation, and that comes up quite often in coaching. What do I want to do? What do I want to be? How do I want to get there? Those types of questions come up quite often. And I think it's important because folks are looking for grounding. They want to feel that what they're doing is going to be meaningful for them, for their customers, for their family, for their friends, and trying to evaluate if the path is still right for them. And so those are a lot of the questions that come up in coaching now, just given the environment that we're in.

A couple years ago, the questions were more about product management and how do I build up my skills, and what are some of the expertise or areas I should lean into? But I think after the pandemic, there's been a big shift in regards to just how people feel mentally, physically, emotionally, and right now there's a lot of burnout that's happening.

Karen: Yeah, absolutely. I'm curious as to what tactics or advice you share with folks that are feeling that lack of motivation.

Diana: Yeah. I think a lot of it is trying to understand what success looks like. How do they envision themselves a year from now or even six months from now? Where do they want to be? And so that's often an area that we'll go back to.

Along, what does success look like? It's also trying to understand what do they want to accomplish? And those two aspects of looking at success and what do you want to accomplish often gives a good view into what's important to the person. And then from there, you can get an understanding of what type of areas they really want to dial up or dial down in their lives.

And so you want to be able to explore the pieces that are top of mind for the individual, but also expand on those areas where they feel the most light. And oftentimes, you can see that in people's expressions when they talk about something that they've worked on or some area of vision or value or dream that they're striving for, you can often pick that up. And then you want to be able to expand in those areas that really make them glow and bring them light.

Karen: I love that. It sounds like there's a lot of exploration as to what that success looks like, and then recognizing the areas that bring you joy and energy and the ones that de-energize you.

We talk a lot about that as well, actually in our career accelerators where we have a full workshop on career planning, and we talk about things that people value and how that potentially shows up at their work or doesn't show up at their work or things that motivate them and demotivate them. So I love that you also have that process of exploration with your clients.

And I'm curious for folks that if they've gone through that exploration and they realize that what they're doing right now when it comes to feeling like they're making an impact, that they don't feel connected to their work or the mission of the company, how do they continue forward where they're able to find some kind of meaning for themselves? Or is the recommendation maybe this isn't the right place for you?

Diana: I think it's a really valid question, especially now, and I think there's a lot of opportunities for people to continue to learn at an organization where they're questioning their alignment. And the way that I think about that is to consider the people that you work with. And often there's so much that we can learn from our colleagues. And so even though we may feel that there's a gap between our motivation and the vision or the mission of the company, you'll often find that there's individuals that can help you navigate that. Either because they're going through it as well or because they have insight that could help you just more broadly.

And so I often think about it as, are there knowledge gaps in your own growth, in your strategies or objectives, that you could learn more about through talking with marketing or finance or development or design or sales?

Just thinking about those ways that you could bridge those groups to be able to bring more context to your own work, that can often give you more insight into other areas of the business that you previously didn't have that much knowledge of. And that's extremely valuable, especially for a product manager, given all the cross-functional work we do.

The other ways that I think you can still obtain value from the organization is through just understanding alternative approaches. It's a good or bad with product management that there typically isn't one right answer or one way to do something. And so if you have the opportunity to be able to explore other approaches, Teresa Torres talks about continuous discovery. If you can learn more about alternative ways that you can approach a situation or a problem a customer's facing, that's increasing your knowledge too.

And so that's also really valuable because you're building up more test cases that you can apply other ways or other times in your product career.

And then I also think it's helping people realize there are a lot of successes and celebrations that should be had along the way. So by working with your team, being able to acknowledge those wins along the way often gives us an energy boost that may have been missing for other reasons. And so even though we are all looking towards a goal or an objective or an outcome, along that path, there's steps where you can celebrate, and then often brings a lot of energy back into an individual or to a team.

Karen: Yeah, I love that. So it sounds like there's a combination of figuring out your knowledge gaps and finding ways to continue learning, whether that's within your organization, whether that's from others around you, and within your stakeholders potentially, or people that you're working with, and then being able to celebrate the small wins along the way as well, is what I'm hearing.

Diana: Exactly.

Karen: Okay. And could you tell me a little bit more about, you mentioned Teresa Torres and continuous discovery. Could you tell me a little bit more about that?

Diana: Yeah, so yeah, Teresa Torres wrote the book on continuous discovery. And when you're thinking about your customers, there's often a time that individuals set aside, I will do X number of calls with my customers, and they will happen at this point in time. With the approach that she recommends, it's to always be talking to your customers and always be gaining more insight from them.

And I think that's extremely powerful because the times that we're in, there's always change. And so even though you may have had a conversation with a customer a month ago or a week ago or a year ago, they're going to have new experiences, and that may change how they perceive or want to interact with your product. And so being able to continually, every week, talk to your customers, learn more about them, learn more about why they like your product, why they don't, what they need, what they don't need. All of that insight is really incredible and shouldn't be done just once. It should be an ongoing activity, and that's what she practices.

Karen: Amazing. So, ongoing conversations and staying flexible as things change, I'm hearing from that. I love that. Thank you so much for sharing. And along the lines of looking at being future-forward, I'm curious if you have any thoughts on what the future of product management might look like?

Diana: Yeah, it always makes me think of AI, and it's so much part of our lives today, and I think there are facets of product management that will no longer have to be tackled by a human. They can be tackled by AI in some capacity. I was listening to a podcast where a woman who created an AI bot that could do PRDs, things like that, that's wonderful. Allow AI to take over a lot of the documentation that product managers typically had to do. I think that's brilliant.

Karen: But does the PRD stand for, by the way?

Diana: Oh. Yeah, it'll be like a product requirements document, and typically what you summarize and then work with design and engineering to build into a product over time.

And I really think those types of documentation, AI is amazing. It's summarizing, calling out key themes, especially if you're doing continuous discovery and a lot of exploration. You've got a lot of notes. And so AI is a great way to summarize and call out those themes, but AI cannot replace people.

Humans are fascinating in that we say one thing and then do another. And so you truly need people to be able to speak and understand customers. And so to me, that is where the future of product management is going to become even stronger is being able to really respect and understand and truly try to be human.

Karen: Yeah. I'm hearing AI as a potential assistant for a product manager versus something that will replace product management in the future.

Diana: Yeah, I totally agree. I think it's a great copilot. I think it's a great assistant, as you said, but it can't replace those human-to-human interactions. There's just so many facets to us that you can't get across and effectively interpret through technology. You actually need to speak to people and interact with people to understand what makes them tick.

Karen: Absolutely. I think there's also that understanding of what is being said versus your visual cues that you're seeing, and when they're not aligned, maybe there's something else that's going on that AI might not be able to pick up yet at this point.

Diana: Very true.

Karen: All right. So this has been a super fun conversation so far. I'm curious when it comes to just thinking back through your career, if there are any major highlights that you would be interested in sharing?

Diana: I guess the piece that stands out for me is I lived overseas. I went to London and lived there for 12 years. And so to me, it may not be a career highlight, but it was just a life highlight. It was an adventure. It was going someplace new and learning a new culture. And I was able to work in a lot of different countries around the world. And to me, that's always been extremely valuable because the way we do things in the US or in Silicon Valley isn't the only way that work needs to happen. And so I think having that international, that global perspective really opened my eyes to other ways to do work.

Karen: Incredible. And how did you end up in London in the first place?

Diana: I worked at a startup, and they had engineers in the London office, but no one who really knew about the customer. And so I went over to be that bridge between the engineers and our customers, who are marketers.

Karen: Amazing. And was traveling something that you were very excited about, even prior?

Diana: Oh yeah, definitely. Definitely. Yeah. I've always loved to travel, so for me, it was just a dream come true.

Karen: Amazing. And as we're thinking about what's ahead for you, what are some things that you're excited about that's coming up or would like to share about?

Diana: For me, becoming certified as a coach is what I'm working on right now. Part of the process is you do a hundred hours of coaching, and that's an amazing way just to build up your expertise, be able to help an incredible amount of people. So if folks are interested in coaching, please reach out. Let me know.

I am working towards my a hundred hours to have my ICF International Coaching Federation certification. That's what I'm working towards. So I'd love to be able to connect with people who are listening to the podcast and be able to coach with them.

I also have a newsletter, and you can find a link to that on my LinkedIn. And I'm working with two friends on a book that will come out later this year.

Karen: Amazing. What kind of book? Is it okay to ask?

Diana: Oh, yeah. About product. About product management.

Karen: Very cool. So you're going to be a published author very soon in the future, so very glad that we got you onto the podcast now before you became ultra famous and we wouldn't be able to talk. Amazing. And then if there was one thing that you wished you knew earlier in your career, what kind of advice do you wish you had?

Diana: I think don't be so hard on yourself. Yeah. That would be the thing that I come back to, and that goes hand in hand of having more confidence. If you're hard on yourself, you tend to question yourself, and I think I wish I'd had more confidence in myself as I was starting my career, and wasn't so hard on myself as a result.

Karen: Yeah. How do you encourage that confidence or coax it out of the younger product managers that you're working with right now?

Diana: Yeah, really leaning into what excites them and talking through the why behind that excitement. Because it's typically an area that they feel they feel confident in, for whatever reason. And so being able to dive into that, understand that more, I think, is something that stands out when I talk to people who are just starting their career, because that often could be a clue into what will give them joy and excitement later on.

Karen: Incredible. Well, I know we're coming up at time, so thank you so, so much for this conversation. We talked about so many things with leadership and taking care of people and being people first when it comes to building relationships and influencing across teams, and really even building that relationship with yourself so that you can better understand what motivates you and how to find joy or feel value in what kind of work that you're bringing out into the world. So thank you so much, Diana. This has been such a pleasure.

Diana: Yay. Thank you so much for having me on the podcast. It's been wonderful to speak with you.

Karen: Engineer Your Career is produced by WEST, a learning community that empowers women technologists through mentorship. Special thanks to our audio production team, Heidi Williams, Amanda Beaty, and yours truly, Karen Ko. If you enjoy our work, we encourage you to share this episode with a friend. Want to hear more from Engineer Your Career? Subscribe on your favorite podcasting app. We look forward to having you back for our next episode. Thanks for tuning in.