Storytelling in Product Management and Design | Jessica Hall

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Jessica Hall, design and product leader, discusses communication between designers and product managers, storytelling techniques, and the importance of AI in design and product management.

Jessica is a design and product leader who assists companies in understanding customers, focusing efforts, and driving business results. She authored “The Product Mindset: Succeed in the Digital Economy by Changing the Way Your Organization Thinks,” a book that guides leaders in building thriving product teams through a bold, innovative approach to product development focused on shared outlooks that drive focus, speed, experimentation, and innovation.

Takeaways

• Functional tension between design and engineering is crucial for effective collaboration.
• Clear alignment on goals and priorities is essential for a successful partnership between design, product, and engineering.
• Leadership plays a critical role in fostering a collaborative and respectful environment.
• Storytelling is a powerful tool for conveying product strategy, organizational change, and career progression.
• Storytelling is a crucial skill for product managers and designers to effectively communicate the value and purpose of their products.
• Product managers need to be adaptable and embrace change in the face of evolving technologies like AI.
• Developing a growth mindset is essential for product managers to continuously learn and stay relevant in a rapidly changing industry.
• Effective communication and the ability to have difficult conversations are key skills for product managers to navigate the workplace successfully.

Connect with Jessica

• Website: https://www.hallwaystudio.com/ 
• LinkedIn: https://www.linkedin.com/in/jessicashall/
• X: https://x.com/JessHallway 

Connect with Vit

• Website: https://vitlyoshin.com/ 
• LinkedIn: https://www.linkedin.com/in/vit-lyoshin/ 
• X: https://twitter.com/vitlyoshin 
• Other: https://linktr.ee/vitlyoshin 

Timestamps

00:00 Introduction

04:02 Communication Between Designers and Product Managers

11:51 Handling Different Opinions Between Product Managers and Designers

18:45 Storytelling Techniques in Product Management

22:40 Types of Storytelling

32:18 Crafting a Career Story for Advancement

35:11 Storytelling for Multiple Products, Personas, and Markets

36:44 Storytelling in Content Creation

40:15 Fractional Leadership Trend

42:27 Adapting to the Age of AI

51:10 Prepare Yourself for AI Revolution

56:45 Advice from Jessica Hall

Transcript (Edited by Vit Lyoshin for better readability)

Vit Lyoshin (00:01.834)

Hello everybody, welcome back to the Vit Lyoshin podcast. Today’s guest is Jessica Hall. She’s a design and product leader, coach, speaker, and also co-author of the book, Product Mindset. Welcome, Jessica. Nice to have you here.

Jessica Hall (00:16.705)

Thank you so much for inviting me.

Vit Lyoshin (00:19.498)

I invited you today to talk about a couple of things. Communication between designers and product managers, some storytelling techniques, and maybe we can also touch a little bit on AI and how it helps designers and product managers.

Before we jump in, could you share a little bit about your background and journey and the work that you do?

Jessica Hall (00:42.401)

Yeah, I have kind of an interesting, you know, path that I’ve been on and one that I don’t know is possible today. I was always interested in technology and interested in computers and I was always interested in art and I wasn’t necessarily a particularly good artist. I could not draw you in a way that perhaps you would recognize or anything.

But I liked doing it and I liked playing with technology. But I was really hoping I was going to be a journalist for the Washington Post. That was the dream. So I went to work at a museum of news that at the time was in Roslyn, Virginia, but eventually moved to downtown DC. And my job was to get in at 6 and print out physical front pages from all over the world. And then post them and then beyond that I could do what anyone wanted me to.

I learned how to program satellites and use television cameras and do graphic design and set design and write code and really discovered graphic design as a possibility of a career. Beyond that, I got into animation, then interaction design, then web and mobile.

And, you know, along the way I got sick of being told, make this thing pretty that I didn’t think was a good idea. So that’s how I’ve gone into product. And so really I’ve spent a lot of time going back and forth between product and design. You know, I’ve worked a lot with ML engineers over the years on some data science projects or some data analytics products. And then I’ve gotten really interested in AI strategy and helping companies and people think through how we need to adjust to some of these new developments in AI.

Vit Lyoshin (02:33.674)

I see. That’s pretty cool how you start in one place and then you end up in a different place. It kind of leads you in a way.

Jessica Hall (02:44.225)

Yeah, I’d love to say I had a plan. I did not.

Vit Lyoshin (02:49.77)

So let’s start with some of the best practices for communication between designers and product managers.

Jessica Hall (03:01.857)

It is something that has been around for a long time and it’s always been an issue. And there’s a concept in sports. So we’re coming up on the Olympics, right? And we’re going to see tremendous athletes from all over the world who are going to do all sorts of things. But one of the things they need to be able to have is agility, the ability to kind of respond quickly and jump around. The way that works in the body is something called functional tension.

There’s these two things that are kind of holding and twisting and releasing together and working together in concert that create that agility in an athlete. And so as someone who’s coached a lot of people in sports and grew up playing sports, I always think that a certain amount of tension is good. Is that tension functional? Is the tension being that design is able to think of big ideas and advance the experience without running over-engineering or that engineering is able to create things that are performant and predictable and they’re able to keep their velocity up without running over-engineering.

And when that works and there’s respect for both crafts and the value that they bring, I consider that really functional tension. What isn’t good is then when we have a lot of dysfunctional tension, we have silos and we have people not necessarily working together.

And sometimes product managers can be a part of the solution there. And sometimes product managers actually can make the situation a lot worse. So I like to think about not just design and engineering, but design and engineering and product as kind of what we like to say, you know, the proverbial three-legged stool, which oddly enough, I cannot get DALL-E to make a three-legged stool. It can only do four.

But really thinking about how these three crafts and these three folks work together is super important. And I found over the years, there are a couple of things that make a big difference. The first of them comes from one of my favorite organizational psychologists, because I’m the kind of nerd that actually has one of those, and his name is Richard Hackman. And he did a lot of really formative work on teams. And I’ll never forget, he says, though there be many choices in our collective endeavor, the choice of mountain is not among them. Which is to say that when you get a group of people to work together as a team, it needs to be super clear what mountain they’re climbing, and what thing they are trying to achieve.

And when that is not clear, you’re going to see more silos, you’re going to see more bickering, you’re going to see it’s taking longer to make decisions, particularly about prioritization and estimation. You’re going to see that things are going to, the gears are going to grind.

In fact, when I was a consultant going into organizations, the first thing I would ask everybody, the highest person I could find, the lowest person in the organization I could find or the newest, what are we doing for the next three months? The top three priorities. And the answer was important, but not as important as the way they answered.

So if someone came in and I’d say like, hey, what are the priorities? And they would be like, well, I don’t know, the big boss wants this and I guess we’re doing this other thing. Or they would jargon me with something they kind of thought they should say. That was the right answer, but didn’t exactly make sense and connect with them. And some people would laugh. That’s cute. You think we know what our priorities are and we can actually keep with them for three months? That’s hilarious.

So it tells you a lot about where the clarity in the organization is. And with that clarity, now we can start working together. So that doesn’t exist. We can have trust circles and we can fix our agile processes. We can do all other things, but without that clarity, we’re not gonna have a great relationship. So that starts.

The next thing I think is super important is that the heads of design, product, and engineering need to know how to go into a room and have it out. And when they emerge from that room, emerge arm in arm.

I think my oldest daughter was maybe three the first time she went and asked her dad for something. And I was in the kitchen doing dishes and then she came into the kitchen to ask me and I said, but your dad just said no. So what I like to say is nobody gets the mommy daddy us. Nobody gets to, you know, like if we are working as a, if the leaders are together, just like if mom and dad or mom and mom or dad and dad are all working together, well, if the top unit is working, the rest of the organization works.

I have seen so many organizations where the people underneath are trying so hard and they’re building relationships and they’re going out of their way to make it work. But they are really being hampered by the fact that the top of the organization doesn’t get along. And I have a couple of fun little tricks to tell if that’s happening.

One is healthy teams, say we? Unhealthy teams talk about functional. They’ll say product wants this, design wants this, engineering wants that. So if they’re saying we, that’s usually a good sign that they’re aligned. If the leaders do not refer to each other by name, they usually don’t like each other.

Usually, they think they’re being cute, but like I can tell pretty fast. Like, yeah, you don’t like them. I got it. That’s fine. We need to fix that. That’s a problem. So I’m not saying they have to be a buddy buddy, but there has to be some certain level of respect and again, functional tension between groups, or that’s going to be really hard.

If we have the clarity of purpose, if we have leaders who are committed to working together and winning together, it’s nice if their incentive structure incentivizes them to be cooperative, then it really comes down to let’s talk about our practices and our individual relationships. Are we building strong relationships and enabling strong relationships across the team? Are our practices working for us?

I think a lot of people, in the way they work, they get kind of stuck into it. This is how we do it, or this is the way, this is the way so and so, big fancy pants, thought leader thinks we should do it. So we should do it that way. And there is no, right? And nobody is going to come like an otter and say, I’m sorry, you’re not doing blah, blah, blah, agile practice. That’s super important. Like that is not a thing. So I think it’s important every quarter or as things feel like they’re not working, figure out how to make it work.

Because azure organization involves a different type of people around the team. As you’re now even starting to think about, a lot of typical agile private development processes are not conducive for machine learning projects. They’re not conducive for generative AI projects. Like this is a different way of thinking. And so I think it’s super important that we always keep the door open so that we can do things differently.

The goal is to figure out what serves the company and the team and the client the best as opposed to what is most adherent to whatever we think our philosophical view of how we make things is. And that’s true with your designer, product manager, or an engineer. They all have their dogma. They all have the things that they cling to. And ultimately, it needs to be about figuring out what works.

Vit Lyoshin (10:39.882)

That makes sense. And then you kind of mentioned a little bit, sometimes there could be conflict, maybe in opinions on what should be done and how should be done. How do you handle that between designers and product managers specifically?

Jessica Hall (10:56.705)

Yeah, I mean, it’s a pretty common occurrence. Again, if we don’t have clarity of purpose, we’re going to have conflict. The other thing is like, if we do not have the voice of the customer in the conversation, then what we’re left with is preferences and interpretations. So the more data or the more, either the qualitative or quantitative, the way we can get the conversation to be richer and more productive is to not make it, this is my preference versus your preference, because that becomes a power.

The other thing, I think a RACI chart is just ridiculously complicated and not a fan, but what I like to think about is focus, which is where do I put my energy? And prominence, which is where should my voice really be listened to? And those two things together are your contribution to the team. So as a designer, your focus is really on understanding the customer and delivering the design solutions. And working with the engineering team to really make sure those can be implemented properly and that they are implemented properly. So that’s your focus.

Your prominence is when we are talking about a design decision. How should this control work? Where should this button be located? How should the sequence of this flow go? Should we create this variant for the design system? That is a question that clearly lies in the prominence of the designer. And what we should do is allow the designer to have that voice in a meaningful way. And not just say, you know, I think it’s important for product managers to set the table for the conversation that you want to have, right? If you think about a table and it’s very formal or it’s very unwelcoming, like you just fit like a, right? What word do I use?

Have it right, greet people, like you don’t feel welcome. So as you want to do is set the table where people feel welcome. They feel like you’re heard. They feel like they’re understanding why they’re there and what we’re trying to accomplish. And then you’re going to get the best answers out of everybody. But I think sometimes product managers are not being served by whos ever.

I don’t know if they’re coming up with it or where they’re getting this from someplace or that bunch of crap that was totally ridiculous behind the lips CEO of the product, which made everybody hate you. Or, at least not like you very much. So I say that the product, like the role of a product manager is to create, to define what we’re doing and why we’re doing it, to prioritize, to make sure we have a line that it is not like, it is too much for one person to say you have all the answers and you make all the decisions and you control all the things, you will burn out. And you will alienate them.

Think about your job is to bring the team together, bring people together, facilitate the conversation. And if you need to get involved and you need to make the call because it needs to be made, great, fine. But see if you can bring people together first and be a convener or enabler or a director of decisions, not the center of all things, because that’s just, it’s way too much for one person to do.

You are not getting the best possible contributions from the engineers and the QA’s and the designers or any other stakeholders for any other parts of the project or that, you know, the data engineers that, you know, whoever on your project, you’re going to get them the more you do to set the context, to set up the conversation, to frame what the stakes are and what the major things that we should be considering are. Then frankly, there’ll be less conflict and less decisions. But there will come a time when a team, they’re spending, they’re stocking. You’re like, listen, if we do this, how freaked out and scared are we about it? We’re about 20%. If we argue this for like three more hours, are we gonna get that much further? No? Okay, let’s go.

Vit Lyoshin (15:00.01)

I really like that. I don’t think I heard this idea before, but we tend to think about product managers as people who can do everything there, right? Especially if they even come in from engineering background, they can even code for us. So it’s like a solo person on the team doing everything.

But I really like this idea of delegating things and delegating decisions, which is most important to design, to engineering. Maybe you have a user researcher on the team, or maybe you have QA or whatever. That way you have more time to actually think about the bigger picture and value and all that other stuff.

Jessica Hall (15:41.025)

I mean, so many product managers, again, they’re getting burnt out. They spend all their time on fire drills and tactical stuff. And they’re like, why can’t I have more time for strategy? That this is a way to, the more you can enable and bring more people together to make solutions, the more you can create space for that. And in a way you’re just putting less work on yourself.

But I would say that is a skill. And it is a skill that you need to develop and the skill that you probably need some feedback from your team and maybe you need some coaching and maybe you need some people to observe you or even to say like create a little fun game when you are out of your lane to just have people go like this on the video call and you know wave their arms around me like yeah you’re in my lane buddy and we all have a laugh and then we move on so there’s lots of different ways but I will say that the skill of setting the table hard for product manager.

The skill of being able to really enable that conversation and get out of being in the middle of everything, also hard. And then, by the way, you’ve got to be able to sequence up all this work into a reasonable set of things that can be working. That is also hard. Those are like three super hard skills that I don’t think anybody comes into product management. You may have a little bit of this, a little bit of that. But those are skills that are tricky to learn and I think they take time to develop. And even if you’re good at them, doesn’t mean you’re going to be great at them all as I can definitely demo on a basis that makes me somewhat embarrassed.

Vit Lyoshin (17:18.293)

Yeah, some people may even feel they’re losing control if they start delegating, if they are used to doing it. So now they have to rely on somebody else and they feel like they’re less. But they can apply their knowledge in other areas. So it’s always a trade-off.

So let’s talk about storytelling techniques and why they are important in the product management world.

Jessica Hall (17:56.321)

Yeah, well, like I said, I wanted to be a journalist and I worked at the museum. And so I have a strong appreciation of story through going to journalism school and then spending a lot of time with people who are great storytellers very early in my career who really taught me a lot about story and the importance. So you know what I said earlier that when teams don’t understand the purpose and the things that are going on there is a lot of friction.

But sometimes you find an organization that really gets it and the way I can usually tell is that I meet that product leader within the first five minutes they’re telling me their story and telling me what the situation was and how these people weren’t being served and where we saw this opportunity and how we are serving these people and what we are enabling them to do and supporting them to do. And how that’s creating value for them and how that’s going to help our business grow.

And when you hear one of these, you’re like, one totally got it. I fully understand that. I can’t tell you how many times people explain to me what they’re doing. They’re like, huh, that sounds great. Yeah. I have no idea. I didn’t get any, something, something, supply chain, something, something blockchain, something, something, I don’t know.

So one, totally get it. Two is you already have a lot of ideas. You’re already listening to them. You’re like, I have ideas. And you remember it. Like you’re at a party or whatever. You’re at the fire pit in the backyard and you’re saying, yeah, I met this guy who’s with company and here’s what they did. And it’s like, so those are really the three things. It’s like, when you think about how these things work, you might think it’s culture and culture is super important.

Google’s product Aristotle, right? Talked about psychological safety as being super important. Very true. But, having a great culture doesn’t necessarily mean that you’re doing the right thing. So it would be successful. And I’m sad to say I’ve seen some organizations with great cultures kind of not be able to achieve their goals. You can also say process. And you can, again, you can have a great process, but what you need to do is be able to really operationalize your strategy. And nothing does that better than story because it is how we learn.

It is how we learn to make decisions. It is how we remember things. And, it is how we process things. It’s how we think about what our values are. And so you are taking, you are using the tool that has effectively served humans since we started. And despite everything else that will happen with AI, in AI you still need to be able to help the AI understand.

You think about a prompt, right? You’re a financial analyst and it’s really important for you to save money. So review this spreadsheet and identify opportunities for me to save money and go do the thing, right? That’s kind of what a prompt is. So in a sense that English is a new programming language, right? You hear a lot of people, I didn’t come up with that. You hear a lot of people do that.

And now, storytelling moves from how do I get a bunch of people to do things to how do I now communicate to machines to do some things too. And so it really is a portable skill. But I think that anyone who’s great at storytelling, a comedian, an actor, someone who does like a solo performance or a writer would tell you that this is not something that you’re fully born with and you’re amazing at and your materials are great like you really got to work at.

Vit Lyoshin (21:45.45)

Yeah, I see.

So there are a few types of storytelling that you mentioned before. Something for product strategy, for process change and for career also.

So let’s talk about the first one, the product strategy, and how, I guess this applies specifically to product managers, and how they can use those techniques to maybe talk about strategy and mission and value and things like that to the team and to the stakeholders.

Jessica Hall (22:26.945)

Yeah, thank you for reminding me that I thought that was a useful thing. So there’s someone named Marshall Gans and he, I believe, is from the Kennedy School of Government at Harvard. And he came up with this thing called public narrative. It was really focused on helping activists or people who are trying to create social change. Because when we think about transformative change, who do you think about?

Someone like Martin Luther King, right? Or Malala or, you know, were just in Ardern and New Zealand or some of these generational leaders who are able to communicate this vision of the future and help go to a place. So that is where the research is really in social movements, but the application can just as easily be business. And he talked about three kinds of stories.

One is the story of self, which is kind of a motivational story about your personal story. I don’t think that’s super useful in business. I mean people get a little too attached to founders and sometimes that doesn’t always scale. And if you don’t have a particularly powerful personal story, which I do not, I do not have these massive barriers in front of me that I overcame during these moments. So I think the story of selves doesn’t have a ton of applications of business.

The next one that really does, particularly in the realm of product, is the story of now, which is what is happening in this moment that is either a dire problem that we need to solve or a wonderful opportunity that we need to take advantage of. So the story of now is really talking about what is happening, why it’s happening, what we want to do about it and what the value of that thing will be.

If you think about it, I think if I can come up with an example, you know, there’s a lot of kids out there struggling with behavioral issues because the COVID pandemic and the kind of weirdness that followed has made it difficult for a lot of children to learn social skills. So that’s a problem, right? That is a story of now where we have all these kids who didn’t quite get the socialization and the exposure that a lot of other kids did at this time. And so now we have this moment that needs a resolution. So what we need to do is figure out how we can help these kids learn these skills.

And then you’re talking about what that initiative, what that program, what that product is, and how it’s going to create that outcome of giving these kids who missed out on those core social skills opportunities. And that’s kind of a story of now. If this is what happened, these are the people who have been impacted, we think these people have something very important to do, think they’ve been underserved, we want to help them, this is how we’re gonna help them.

This is how by helping them that they are going to be effective. And this is how our organization will be successful because what we did, there’s like a lot of ways to, you know, a lot of ways to combine that story. But I think that’s the most effective for a product story. So I usually say I’m talking about a product story and sometimes you need to talk about a change story.

So I was just talking to these people from this organization. They were going from functionally aligned teams to feature teams. And so in the past, they were all aligned kind of individual teams and then the poor product managers were running around between all these individual teams trying to do things that weren’t super effective. So now they want to align to product teams, right? So that becomes a story of us. And us is really about how our values and our goals and how that’s going to change and how that means to be.

The best example I think of this is if you ever look into the work of Francis Fry and Anne Morris. So Francis Fry is a Harvard business professor and Anne Morris is her wife and she is a leadership coach and business builder. And they went to Uber when Uber was having all of its problems and the CEO was out and everyone was very, very upset with them. And so that is like a cultural value transformation that happened to happen inside that business so that people would be excited about working there, but also outside of that business. So people wanted to do business with Uber. And so that’s really about these are what has got, these are the values and norms and the ways of behaviors that have gotten us to the moment we’re in.

This is what the future looks like, and that is no longer serving us. And so this is how we’re going to change. And every organization needs to go through inflection points. Typically that might be at a certain growth number, either revenue growth number or headcount number, or maybe they’re going through some other transformational change. And that’s what we’re going to talk about. Here’s where we come from. And let’s honor that past. Let’s respect that achievement and the people who brought us to that moment. And also realize to get to the next moment, we need to do something different and what that thing is and how we have to go towards that together. And that’s a story of us.

So, those two, I think, are super useful. So for PMs, I think it’s more about the story of now, so you only have to learn how to do one. And then for leaders, it’s being able to tell a story of us, which is about organizational change or change stories, the way I like to say it.

And then the third kind that everybody needs is a career story. So usually if you’re at a networking event or you’re in a first meeting with a hiring manager or you’re just getting coffee with somebody that you’ve been introduced to that might be an interesting connection, they’re gonna ask you the who are you story. And I’m sad to say actually I did not give you a great one at the beginning now that I think about it.

But a career story is really about starting with the end, which is to say, what is special about me is that I do this thing, that I have these superpowers, that these are my superpowers. So you actually start with the through line. What is the one thing that connects all your experiences? It expresses to the world what you are uniquely good at and what you are very excited about.

And so that’s your through line. You start with that and then you start to tell the chapters of your story. Right. By the way, this is not Marshall Ganz. This is actually my invention. So maybe it won’t be as good as his because I don’t have a Harvard research team to back me up.

So first, each chapter is about I went to this place, I did these things,  I created these results, and then learned the set of skills. I went to the next place. So you think about through line individual chapters that advance the story.

And then you want to get to, and now here’s where I am in my world. I am looking to go to a place where I can deliver my through line and operate in a certain kind of environment. And if everything is good, what you just described is actually the people you’re talking to. If you get there and they’re like, wow, that is not us. And that is not what we’re about. And that’s not what we have to argue. Right. You can both part ways. Nobody wasted that much time.

But it’s really about bringing in being super clear about what is special and valuable about you because the right company is going to want that. You know, a lot of times when I have, when I am working with people who are newer to the industry and trying to break in, they’re like, I will take any job. I’m like, I got it, man. I was there too. I had literally $20 in my bank account when I was trying to get my first job in the business. And, I was living in my parent’s basement and I didn’t want to do that forever.

But companies want to be wanted and you want to connect. So I think being able to tell a career story is a really positive one, a really useful one because you know you’re going to get the question. And what I also say to people is I’m going to label you or you’re going to label you. I think you would rather be the one who positions yourself.

So you should be thinking about positioning yourself just the way you want to position a product, which is, this is the value that I bring. This is the kind of work I’m really good at. And what you’re trying to do is find people who want that. And that’s not going to be everybody.

Vit Lyoshin (31:30.25)

Yeah, I see. So there is also a component of promotions. Maybe you don’t want to get to a new place or start a new career path, but you just want to jump one level up, for example. Is there basically the same technique that applies for promotions?

Jessica Hall (31:54.177)

Yeah, you know, it’s funny I hadn’t thought of it that way before, but yeah, I think it does. And it’s about the next chapter. So if you think about it, maybe you’ve come into the organization, you’re a new product manager, so you’re new to the craft, and now you’ve been doing it for a while, and you know, you’ve developed some skills, you’ve learned some things, you’ve shipped some product, and now you’re ready for the next opportunity.

And yeah, that would be part of the story is what have I learned? What have I delivered? And what is the next set of values that I have to offer you? So I think you could definitely, you know, I hate to say it, but you know, go in and say, well, I’ve been here for two years. Being promoted is not the most effective way to do it. I think the thing you want to do is go in and make the business case and be able to talk to the value.

I will tell you that there’s something really ridiculous largely in the corporate world I do not understand, which is if they go out to the market, they’ll spend 20% more to get someone who knows nothing about this company instead of just giving the 20% to the person who’s been here with a known quantity, who we have invested in.

And so there is a weird thing. So one thing I would tell you, which is advice my mother always gives me, which is to come in as high as you can. Because once you’re getting in, you’ve set the floor and it can be tricky to get raises once you’re in unless, you know, if the great resignation happens again, which we may never, I’ve never seen one before. And I may never see one in a market like that again. Like you want to try and come in as high as you can because that kind of determines where you go.

I try to bring people in as high as I can, usually. Unless, you know, there’s a point at which I’m like, it definitely was happening like two years ago. I’m like, yeah, I’m not doing that. But in general, I try to do right by people when they’re coming in the door, because I know how hard it can be to get them a raise once they’re there.

Vit Lyoshin (34:04.874)

Yeah, some people, there are many tricks to do that. Well, not tricks, but like strategies to do that. But most people just maybe happy where they are and they’re not really motivated enough. But people who really want to advance, they should probably come up with their story and pitch the story once in a while, every couple of years for a raise, for promotion, for other opportunities and things like that.

Jessica Hall (34:22.465)

Yep, and also, you know, it’s also a great way to learn it, right, and to practice it.

Vit Lyoshin (34:35.018)

Yeah. Another follow-up question I had is for this other strategic story type. So sometimes we have a company, or there may be a company that has maybe serving multiple markets or serving multiple personas or have multiple products. Should this storytelling be applicable for each of those lines or just one in general covering everything?

Jessica Hall (35:01.825)

Yeah, what I would say is they’re probably in the way that you might look at a roadmap and see this is the overall roadmap and then there may be our other smaller road maps that connect up. The story has a story that should be an overall company level story. And there may be individual areas. How does that play out in individual areas? And that should hang together. It should kind of make sense. And if it really doesn’t make sense, you might have a strategic problem.

Vit Lyoshin (35:24.298)

I see.

It may be like splitting by those chapters like in the career story, right? Like this is who we are, this is the value that we bring, but those are the things that how we actually slice it in chunks and serve all these kinds of different markets of people.

Jessica Hall (35:48.609)

Yeah, and once you get good at this, you can craft a story for an individual feature. You can craft a story at the product level, you can have a story at the epic level or the feature level, you can story up to the organization level. So you can put it together. It does, again, this is, you know, I remember watching this film with Jerry Seinfeld, I think it was called Comedian.

You watch him go through the entire documentary and talk to all these other comedians. You realize what a craft that is and how much work it is for comedians to really develop a set and how hard it is and how long it takes. And you start to have an appreciation for that. It feels like they’re just so relaxed and doing their thing, coming up off the cuff. And maybe some of them do that, but it’s so interesting when you peel back the performance layer just how much is going on. They just make it look easy, but it was never easy.

Vit Lyoshin (36:52.81)

Yeah, I actually remember a story of one of the influencer and she was telling it takes her hours and hours almost like a couple of days to create one small like one or two minute video for social media and she gets millions of views but it takes her a lot of effort to actually generate that one little piece of content and when people consume it and watch it on Instagram or TikTok or whatever they feel like it’s just nothing. She’s just messing around and she’s getting a million views. It’s already easy. And then when they go and try it, it’s not that easy. It actually takes a lot of time, a lot of shots, a lot of editing.

Jessica Hall (37:32.429)

I mean, I made videos before, in my previous life, like in making and content is hard. Content is hard. I do think it’s important for particularly product managers. You know, designers have portfolios and story is a big part of the portfolio, right? And use cases and things like that. Product managers need to be good on their feet with story because, or maybe just creating content and putting things out there because we don’t have the same easily accessible set of artifacts from you.

So like I can go through a portfolio and be like, I kind of get a sense of who they are and what they do and how they work. I’m like, great. I want, and I can, I can see that, I can judge that. But with product managers, if you’re putting content out there and doing other things, you’re kind of helping me understand who you are and how you think about your reason. It gives me a taste of what it’d be like to work with you and what your values are and do and what your strengths are.

And that’s the kind of thing where I can say, you know what? I think this person might be really good for us because I’m seeing in them that they’re interested in the kind of problems I have to solve. They work in a way I think is going to be a culture add to our team. Not necessarily you’re just like one person like the other, but like you’re great, like I can see more about you. So I think it’s useful to, you know, have some kind of like, you don’t have to go full on influencer, right? But some sort of presence out there in the marketplace that kind of helps us learn just a little bit more about you and get excited to meet you.

Vit Lyoshin (39:14.193)

Yeah, that makes sense. I think I heard from somebody who helps people to find jobs and things like that. She said people always wonder why I post so much on LinkedIn but then when I get like 10 offers in five days they are always surprised how I do that. People already know her and they can really check out what she’s done and how she does and yeah exactly what you just said.

Jessica Hall (39:41.729)

There is a theory, I heard Adam Grant, the organizational side, that he thinks people are going to more move towards, you know, like gigs and guilds and less, you know, less traditional full-time employment where you will need to rely on your reputation and your relationships and your network because you won’t necessarily have the traditional, you know, nine to five, go to the office job.

Although you can argue to a certain extent that’s eroded already. So maybe, I don’t know. But certainly, yeah. I mean, I don’t think it’s totally outside of the realm of the possible that, you know, I think what we’ve seen in the last couple of years is that a lot of, particularly senior people in product and design are kind of getting to a point where they are mid-career and they have a lot of experience and knowledge. And they’re not necessarily finding the roles that are interesting to them. And they’re starting to go out on their own, either a freelance or fractional or consultants.

It’s enough that I think it’s a trend. I haven’t seen any data. I’ve seen, okay, I take it back. I feel like I went looking and I did find in general, fractional leadership is a trend in the market.

Fractional leadership, I think really started with CFOs because a lot of people wanted, you needed a CFO brain for those times when you really needed that, but you didn’t need it every day. You needed critical decisions. We’re going to do a raise. We’re going to do a sale. And, we’re going to do some major strategic planning. I only really need that person for those big things. I don’t need them to worry about payroll. Right?

Like I can have somebody else worry about payroll. So I think it got started with CFOs and heads of people. And now we’re seeing a lot more fractional leaders. We’re seeing a lot of senior people kind of get disillusioned and move out onto their own. And I don’t know what that’s going to bring. But I think it’s enough that it’s like a trend I’m watching and try to understand how the market is gonna really evolve and what opportunities are for folks in the next five to 10 years.

Vit Lyoshin (41:55.53)

Yeah, that’s interesting to see where it will end up.

Why don’t we switch to AI topics? How do you see AI transforming product managers’ jobs these days?

Jessica Hall (42:18.785)

Yeah, so it was really funny. Today, or at least on the day of recording, is the first day in the keynote of CONFIG, which is the Big Design Conference. And I did not catch the keynote, but I will watch the recording later. And someone came into my office and said, well, I don’t think we’re going to have jobs anymore. So certainly, AI feels like the biggest wave we’ve had in my career.

I, you know, I was around for mobile. I was around for cloud. and now, you know, and the funny thing is like AI has been around since like the sixties, right? Like some of these things are not new, but chatGPT launched what 18 months ago and, and these huge, you know, much bigger compute, much more, data sets available, more talent available.

I think we’re seeing another major wave that is going to transform things probably not as fast as we think it is, probably not as much as we think it is, and some of that transformation will be good and some of that transformation will be bad, and some of that transformation will lead to things that we have no idea how it is.

So I think there’s a cut one to get in there now. Try to do things in your day-to-day job, if you are allowed to, using these tools and use all of them. Because you want to, I am joining the chorus of people. Fei-Fei Li said, AI may not take your job, but someone who knows AI will.

And that sentiment has been, so one is a person who knows how to use AI would be one thing to get started. There’s a ton of great courses on Coursera and they’re all free. There’s a lot of content, a lot of, you can get on some of these tools and you can use these things. You start developing that skillset just for free. Things I think are changing.

One is, interesting enough, I talked about the importance of being able to delegate to provide context to tell a story, right? You are now a manager. Everyone’s a manager. You have a strategist, you have an image creator, you will potentially have a coder, you have a data analyst, you have a researcher, you have a writer, you have an editor, you have a coach. AI can really play all those roles for you. And so you should really be thinking about you as a manager.

What are the capabilities of my team, right? Who should I be giving what work? How should I be giving each person on my team that work? And how do I continue developing those capabilities and maybe subbing in and out players to make sure that my team is the most effective team that I can put together and put towards things. The other thing is I think we’re going to see a lot of roles changing. My assumption is that we’re going to be moving towards a lot more generalist roles and some specialist roles.

So, you know, I, it’s really funny, one of the Agile Manifesto signers and I were having dinner together with some other people and we had a joke and I said, yeah, and I pulled out perplexity and searched him and handed it to him. And he’s like, yeah, I got some of it right. And then we were just chit chatting about something else.

I’m like, yeah, right. It’s a pretty good user story. I gave the most simple prompt ever. And then I handed it to him with a user story on it. Why I was handing this phone continually, I don’t know. But here we are. And very quickly we were getting these user stories out, these other things out. So when I can generate a lot more things and do even if I don’t have the Figma skills or the Jira skills or the coding skills or the whatever skills, I can actually do a lot more.

Then I think there’s more of a need for generalists who can do a lot of things that are pretty omni-capable and know how to use the tools. And some specialists who are more setting up the environments, defining things like doing specialized operations.

So you kind of got to think about, well, which one am I and where can I succeed? And to be flexible about what your role is and be willing to flex it to other areas that maybe today are not your domain, but you want to think about those capabilities. Because I think we’re going to have to also relearn how to work together because we won’t have some of these really defined boundaries. And so we’re going to have to navigate more fluid and more flexible boundaries.

The best thing I say to people is actually, one is you need a mindset that is about, this is opportunity, change is opportunity. I want to take advantage of that opportunity. I’m gonna lean into that opportunity. This is gonna be awkward and I’m gonna get confused and I’m gonna feel dumb and I’m gonna screw things up and I’m still gonna be okay. That you can get through this and you could do it. So if nothing else, you have an adaptable, resilient, opportunity focused mindset, you will be at a better choice place than most people. And as a mom of small children, like that’s what I’m thinking about.

I can’t, there’s a lot of things that you might need to know and I don’t know what they are and I can’t teach you them, but I can try and focus on resilience and I can try and focus on storytelling because people are always the hardest part of any project, right? Like being able to get everybody on board. And so that’s the way I’m kind of thinking about this. I, you know, I think there’s also, you know, a lot around explainability to come. There’s a lot about adoption, thinking about scaffolding and affordance of adoption.

I think, you know, what data strategy and forward looking forward leaning data strategy is interesting. And I’m working on a bunch of concepts with a friend of mine who’s like an ML expert. Maybe that’ll get it out at some point.

And that’s really thinking about what is the difference between product development and AI enabled product development. And we’re thinking about like, what are all the shifts? Right? Like when we think about product developments, like fail fast, work in sprints, do iterations, do iterative and improvements. Well, you can’t do that with AI, but those are bigger, longer term bets that are riskier. Right? And so you need to be able to think about spreading the table, you know, the value of the product team delivers kind of gets to production and then they’re done and they have to go production again to add value.

But when we’re talking about an AI enabled product, once you’re in production, that’s really when you want to get serious work because like now we’ve got to tune and train and adjust them all. And we can be doing that without having to ship like doing whole new production releases. So that’s a bit of a shift there too. You know, the one thing I will say that seems to unite both is that talented people who make things want those things to get out the door.

And they want to get to clients and they want to be valuable. And if they don’t think that’s going to happen, they’re going to go to someplace where that is going to be possible. So that is one thing I think is going to stay together.

So the other thing is the mask got to work, right? Like what you can get out of something needs to, you know, what someone will pay you to do needs to make sense with how much it’s going to cost you. Right now it’s not. Right?

Like setting up a lot of these things is very expensive. And, you know, I remember a couple of years ago, we worked on this cyber security product and they’re like, well, this is how much the fine costs, you know, let’s call it $20,000. Okay. But it costs $200,000 to prevent getting the fine. Well, might as well just pay the fine because that’s cheaper. Right? Like, so the math is still a thing. Okay, what someone wants to pay you for it needs to be more than what it costs you.

Vit Lyoshin (50:50.378)

Yeah, that’s true. I think this is like the next revolution wave, if you will, like starting with the Industrial Revolution and all the rest. It just keeps changing and all the time people are thinking, now we’re going to lose our jobs. But then somebody comes up with a factory and the production grows thousands of times and we still don’t have enough people to staff the factory.

And here we go again with AI and everybody is, we’re gonna lose our jobs. But then you need people who will help run all these machines and run all this stuff, right? still running all these things and then I hear other people saying well, we need to worry about soft skills now because all these AI bots will not change but will supplement their hard skills. They will start doing actual tasks. And people who know soft skills, they will be irreplaceable basically. Maybe to some degree, but not completely. And we will need more of those people.

Who knows where it’s gonna go. But it’s surely interesting to see and the more and more I see in social media and everywhere people are saying, this job is gonna be gone in five years. This job is gonna go soon. Like don’t go to university to acquire these degrees. They will be gone in five years.

So I think it’s scarcity as well.

Jessica Hall (52:13.377)

Yeah, I mean, I don’t know. I think you’re right. I think we don’t know, things are going to change, and there will be things we’ve thought about. There will be a group of people who do get hurt by this because it will come on them too fast before they can change.

If you think about, you know, back in the day, in order to call someone, you would call a switchboard, and then a person would take one cable from one place and pull it out and stick it in somewhere else, right? And that job went away.

There was somebody who used to push the buttons in the elevator and operate the elevator when you got in, which as I understand it, they didn’t actually need the person. It’s just the person they’re pushing the buttons to give you enough confidence that you would actually get in the elevator.

And so there’s definitely going to be a group of folks who are going to, this is going to come at them faster than others. And they will get more heavily disrupted than others. But I think over the arc of these things, if you think about the word processor, we’re like, it’s going to kill the print or we print more stuff or like, email is going to kill this. It’s like, we’ll have to worry.

And you know, like, and humans sure are good at creating busy work for each other, aren’t they? And we don’t know what it’s going to do, which is why I come back to the most important thing you need is a mindset that is focused on learning, resilience, growth and opportunity.

Because no matter what happens that will support you in what that thing is. And you know, it’s funny because people say, well, how do I have your career? Which is like, I don’t know if you want it anyways, but like you can’t have my career. No one can have your career. No one can have anyone. You look up to you. You can not do what they did because what they did was possible in the moment in which they did it.

Product management was not a thing when I started. UX design was not a thing when I started. Product design was not a thing when I started. None of that exists and I found myself in it and I kind of went with it. There will be new jobs created, there will be new opportunities, there will be others, I don’t know what it’s going to look like and like I said, some will be good and some will be bad. The one thing that you can control in all of this is the way you approach it.

But you need to start developing that. If you don’t naturally have that, good news, Carol Dweck and all our research on mindset would tell you that this is absolutely changeable. You can change your mindset. If you think this is not possible, if you think you’re stuck, if you think you’re left behind, if you think you can’t participate, I guarantee you we can shift that mindset. But it’s not gonna shift on its own and it’s not gonna overnight.

And so what we really need to do is get involved. And you know what? We’re so early on this and there’s so much we don’t know. And there’s so many different ways this could go that nobody is locked out. Right. Nobody. People are frozen out of product and design now. But whatever this future is that we’re heading to, nobody’s locked out yet. So the opportunity is there for the people who will lean into the change and lean into the adaptation and get involved and be deeply uncomfortable and embarrassed and feel shitty about the whole thing and find a way to keep going.

Vit Lyoshin (56:13.962)

I totally agree. I think it’s people who are still able to learn and provide value, they still will be there doing great things and people who are not willing to do that, they will have to somehow adjust and, I don’t know, do something else. Do some supporting jobs, I guess.

What would be your final advice for designers and product managers? Maybe something that we didn’t cover yet and you would like to say something to them.

Jessica Hall (56:59.713)

People used to always ask me, like, what’s the biggest mistake people make when they come into the workforce? And I think I’m being inspired by the fact that I was talking to a bunch of interns this week. And what I’ve always said is that you need to look at the organization that you’re in, not the one you thought you were going to get. Because we have a lot of expectations that come from our parents, that come from our teachers, that come from social media, and other kinds of media about this is how things work, and this is how things have to be, and this is how you’re supposed to be, and this is what this all means.

And let me tell you, as somebody who’s been around for a long time, It’s not any of those things. Like it is going to people who are weird and irrational to you at least. And organizations are made up of weird and irrational people and they’re going to do all sorts of other things. So you need to start forgetting about what your expectations are and deal with what’s in front of you and talk about that and be able to have a real conversation about something that isn’t working.

And something where, you know, if you are having friction with the product manager on your team, the conversation you need to have is, I want us to get along. I want us to work together. So how can we do this? How can I be a better partner? Here’s what it would look like for you to be a better partner for me.

That’s the one thing and it’s funny because I’ve been hearing a lot about like, you know, new people, people who are entering the workforce that maybe don’t have the skills. Like you’re going to have a vulnerable conversation. You’re going to have to have a hard conversation. You are going to have to tell somebody that the way they’re doing something with you is not helpful.

Or tell somebody that you’re being micromanaged and there’s got to be some way to see if you can get them to back off. That’s a skill set, right? That is like any skill, it can be coached and it can be developed and it is not easy. And so I think there’s a lot of people who maybe have not been prepared with the best social skills because let me tell you, I still screw this up.

I, you know, it is hard to tell someone. I’m working really hard to get better at setting expectations and to tell people my expectations have not been met and to make sure that you understand that it is your job to meet the expectations and I’m not going to fix everything for you. And that is one piece where I think we can all do some work to make better workplaces if we’re more able to have the conversations that need to be had.

I was always struck by this HR leader I know, because she said, what HR is like is just a steady parade of people coming in your office, like always complaining. And she said the way she thought that was really simple. As soon as you came in and started complaining, she would look at you and say, what did they say when you told them that?

And I was like, I heard this like, wow. She just held in that moment. She’s like, what did they say when you told them that? Right. How are you going to tell them that? I will work with you on how I will not solve your problem for you.

Vit Lyoshin (01:00:48.362)

Yeah, that’s a great one.

Jessica Hall (01:00:50.433)

Whoa, man, and I think in some cases. You know, everyone’s saying it’s a Gen Z thing. Well, I am not a Gen Z and I have challenges with it. And I know boomers who can’t do it either. So I don’t think it’s generational. I think it’s just art. And maybe, you know, social media and screen time has made it harder to develop that skill set. But man, those of us who didn’t have those things struggle too.

But I think that’s the other piece. Like we’re going to navigate a very bumpy world. And that is going to take that and we are going to navigate it with each other. And we’re sure as heck going to need to figure out how to do that.

Vit Lyoshin (01:01:38.378)

This is great advice. Thank you for that.

Jessica Hall (01:01:43.649)

Thank you. I didn’t know I was going full philosophical with this.

Vit Lyoshin (01:01:48.234)

No, that’s great. Thank you very much for your time. It’s been exactly an hour that we’re talking here, so that’s great. And a lot of information from you, a wealth of knowledge. So hopefully we can talk more in the future sometime.

Jessica Hall (01:02:04.609)

Yeah, and thank you for the wonderful questions. Like you took some of these ideas to places where I had not thought about. And that really made for a really fun conversation.

Vit Lyoshin (01:02:14.666)

Okay, well, I tried my best though. Thank you very much. We’ll talk soon. Bye-bye.