November 1, 2022

Living the Product Mindset with Jessica Hall & David DeWolf

Episode 188 of The Innovation Engine podcast.

This podcast is part of the Masters of Innovation.

Learn more about this series and join the community.

In this special episode of The Innovation Engine, we’re joined by Jessica Hall, VP of Design at CoStar Group, alongside Founder and former President and CEO of 3Pillar, David DeWolf. Three years ago we spoke with Jess and David about their book, The Product Mindset: Succeed in the Digital Economy by Changing the Way Your Organization Thinks.

Now that the book has been out in the wild for several years, we take a look at what they’ve both learned, how Jessica’s perspective has changed since she’s moved from being a consultant at 3Pillar to working in-house at CoStar Group, and what they would change or add to the book today.

Listen to the Episode

Tune in to the entire conversation to hear our discussion with Jess and David and learn more about how Jessica introduced the concepts of The Product Mindset to her work at CoStar Group, what Jessica and David have both learned in the three years since publishing, and the bonus chapter they wish they could write.

What is The Product Mindset?

The Product Mindset breaks down digital products by describing three characteristics that make them distinctly different from other types of software. It also defines three principles for thinking about your digital product that allow you to make the right decisions surrounding your product and give you the greatest odds of making it a success.

The three characteristics of a digital product:

  1. Digital products have to be self-funded.
    A digital product that is able to drive the growth and revenue of a business and engage with customers exists to provide value between the business and the customer. It must create its own value chain, not just optimize the value of an existing product on the market.
  2. Digital products need to be chosen by the customer.
    Many types of software are mandated for employees or come “standard-issue” from IT. But a product has to be useful enough that it is chosen and adopted by users and customers, which means it has to be good enough that people want to pay for it.
  3. Digital products are never done.
    The expectation of customers in the digital age is that a product is always improving. A digital product should be evolving and providing new value throughout its lifecycle, which makes it fundamentally different from other types of software.

The three guiding principles of The Product Mindset

  1. Minimize time to value.
    If you are driving and self-funding your own product, you want to be taking small bets. You want to be releasing early and you want to be releasing often, minimizing the time it takes to build something, put it out, and derive value from it—both economic value and feedback.
  2. Build to actual needs.
    What is the problem or pain point your customer is dealing with? You need to provide value to them to drive adoption and usage.
  3. Excel at change.
    If a product is always evolving, you need to be ready for constant change. Your customer expects it, and you should expect it as well.

These three principles are critical to the success of any digital product, and complement the three characteristics of digital products.

Lessons Learned Living the Product Mindset

One key thing Jess has learned about putting The Product Mindset into practice is that it can be more challenging to do within an organization than it was from the outside. As a consultant, you have the benefit of distance from the organization and the expectation that you’re going to make an impact quickly.

Once you’re working within a company, which has its own culture and operations, there’s an expectation that you’ll pick up an oar and start paddling. This change has required Jess to shift how she approaches decision-making. She places less of a focus on convening all the right people and building consensus through influence and more of a focus on giving direction along with justification for her decisions.

The main example she gives is the one big bet she placed that helped galvanize her team and bring Design and Engineering closer together: a design system called Cosmos. The design system gave both teams a standard set of design features that should be applied throughout the entire CoStar Group ecosystem of products, freeing both teams up to focus on higher-value product considerations.

Episode Highlights:

  • [01:46] Jess discusses her role at CoStar Group, a new addition to the S&P 500 that provides a number of data-related digital products to customers mostly in commercial real estate
  • [08:35] David shares the three characteristics of a digital product and the three guiding principles of success that make up The Product Mindset
  • [12:24] How Jess’ personal experience with The Product Mindset at CoStar Group has shifted her perspective on putting The Product Mindset into practice
  • [21:10] Changing the conversation from what are we doing? to why are we doing it?
  • [27:28] Connecting the dots between a digital product and the company’s success
  • [29:31] The continual decision-making process
  • [44:07] Leveraging insight to see behind what is being said


About The Innovation Engine

Since 2014, 3Pillar has published The Innovation Engine, a podcast that sees a wide range of innovation experts come on to discuss topics that include technology, leadership, and company culture. You can download and subscribe to The Innovation Engine on Apple Podcasts. You can also tune in via the podcast’s home on Spotify to listen online, via Android or iOS, or on any device supporting a mobile browser.


Scott Varho: [00:00:03] This is The Innovation Engine Podcast from 3Pillar Global, your home for conversations with industry leaders on all things digital transformation and innovation.

Welcome back to The Innovation Engine Podcast. I’m Scott Varho, 3Pillar’s chief evangelist and your host. We have a special episode for you today as I’m joined by Jessica Hall, VP of Design at CoStar Group, alongside 3Pillar’s CEO, David DeWolf.

I get to talk to them about living The Product Mindset. David and Jess are co-authors of a book called The Product Mindset: Succeed in The Digital Economy By Changing The Way Your Organization Thinks.

For this episode, we’ll cover what Jess has learned from putting The Product Mindset into practice at CoStar Group, what Jess and David have learned about The Product Mindset in three years since the book was published, and much more.

Jess and David, welcome to The Innovation Engine or probably better said, welcome back to The Innovation Engine.

David DeWolf: [0:00:55] It’s great to be here. Thanks for having us.

Jessica Hall: [0:00:57] Yeah, thanks for having us.

Scott Varho: [0:00:59] So, Jess, let’s start with this. What have you been up to during the two years at CoStar Group? And congratulations, by the way. I see that CoStar Group just got accepted into the S&P 500.

Jessica Hall: [0:01:10] Yeah, just last month, we got that notice. That was pretty exciting. So, when I was at 3Pillar, we were many times Inc. 5000 and S&P 500 so it’s kind of neat to have the experience of being in both organizations.

I did a really weird thing in October of 2020. I told my parents that I was going into commercial real estate in the middle of the pandemic. So, totally huge asset class, definitely getting decimated by commercial real estate. So, let’s go there. That sounds like a really good idea.

Scott Varho: [0:01:42] That sounds like – it sounds your kind of challenge.

David DeWolf: [0:01:44] That sounds like – yes, isn’t it? Yeah, it really does.

Scott Varho: [0:01:46] Yeah, that totally works.

Jessica Hall: [0:01:46] Yeah. And so, what really drew me to the organization, is one of the things is I’ve been in DC Tech my entire career, but I never heard of CoStar Group. And I imagine a lot of folks haven’t but chances are you’ve used a CoStar Group branded product.

So, CoStar Group started over 30 years ago with our Founder and CEO Andy Florence and he had an option to buy a commercial property, but he’s trying to figure out if there’s a good deal. And right now, we think oh my gosh, there’s so much information about how we buy everything.

If you want to buy a car, if you want to buy a used car, shout out to our good friends Carfax. If you want to buy a house, if you want to buy, you know headphones and there’s a million reviews, so much information is out there in the world about how these things are and how they’re performing and what’s going on with prices.

Well, back then that didn’t happen in commercial real estate. You didn’t know who’s in the building. You didn’t know what they were paying. You didn’t know what’s happening in the area. And so, it’s this entirely transparent, you know, opaque marketplace where nobody knows what’s going on. And then a bunch of people have their own researchers calling, trying to get that information.

And what CoStar Group really did is democratize that information by being – having this centralized research team that would go out and collect this and then make it available to all the brokers. It makes the market more transparent and makes it more efficient, more fair. And that really enables everybody who’s acting in that marketplace to be more successful. And that’s the cornerstone of CoStar.

So, whether or not you’re trying to lease a building, you’re trying to buy or sell a building, chances are you are going to touch our data. But also, if you’re going to rent a building, use or if you’re going to buy a house using or you’re going to – you’re a residential real estate agent using Homesnap to interact with their customers.

So, really, we sit at the nexus of all that, connecting to people to information and an opportunity. I thought what an interesting place to go to, to use data to connect people with insight to help them make decisions. So, I know you all have bought houses and so multiply that by about 10, and that’s the kind of complexity and the kind of dollar amounts we’re talking about when you’re doing a commercial real estate transaction.

So, you really want to know your data and information, and really provide that to folks. So, the good news is we don’t actually do the buying and selling, we just help people with the information part, which whether the market is going up or down, we’re still good.

Scott Varho: [0:04:11] The information is valuable both directions.

Jessica Hall: [0:04:14] No matter what you’re doing, you need data.

Scott Varho: [0:04:16] So, pushing a little bit more into what you’ve been doing at CoStar Group, specifically during your last couple of years there.

Jessica Hall: [0:04:22] Yeah. So, it’s a pretty familiar story, right? You have organizations that grow through acquisition, and you have a product that’s been around for a while. What is that likely going to enable? You know, what’s going to happen there is we’re going to have an experience that’s really fractured where you’re going to have a lot of different product areas. And well, it sort of works this way in this product area and you sort of works that way on this product area and it sort of does this other thing. And you have a bunch of teams that aren’t necessarily talking to each other.

And so, my remit was really to come into the organization and say, okay, let’s try to carry a more cohesive experience. Let’s start up a design system. Let’s start having more design reviews. Let’s not start, you know, having different product leaders doing their own thing in areas of the product, but let’s pull it all together.

And that’s been the journey that we’ve been on. A couple of detours to work on some of our other brands, so mostly work in the commercial real estate area, but occasionally got to spend some time with the folks at and

And there is a big launch of and we’re really excited to see what that’s going to do in the future. But for the most part, it’s really been about trying to get to understand this experience. How do we make it more cohesive? And we’re also launching a bunch of new products. We’ve launched a new product for commercial lenders to use our data. We’ve launched a product for people in the hospitality industry that’s coming out this, pretty soon.

So, if you want to know how your hotels are performing, we – that benchmarking product is moving to Costa Rico system. And then we’ve got some new products coming to help different people look at prospecting and decision making. So, lots of new product development, as well as trying to make a cohesive, more internationalized, more consistent product.

Scott Varho: [0:06:07] Jess, such a Fascinating example of a perfect company for the digital economy, right? It’s all about information. It’s all about commercializing and democratizing this data and finding new ways to leverage this information rich environment in new ways to serve clients and their needs.

You talked about the M&A and how it’s driving some complexity in the need for your role. What about the legacy of the business? Has it always been a digital business? Or if you look back, is there some element of digital transformation as well that’s taking place?

Jessica Hall: [0:06:41] The core business as I understand it, because I wasn’t there three years ago, it started digitally native.

Scott Varho: [0:06:47] That’s amazing.

Jessica Hall: [0:06:48] Like pretty basic. And like I think Andy actually wrote the first version in his dorm room at Princeton and really started from a digitally native company. Now, they’re in a couple of acquisitions. And one specifically that I know about, they did start with mostly delivering in Excel.

And I think anybody in B2B product management will tell you where there is an Excel that runs a business, there is an opportunity. And so, that particular one was being delivered via Excel. But you know, as I understand it, the core product really grow up being digitally native.

And I don’t – you know, it did replace books. It’s like back in the day and I think there were kind of these, as I understand it, this kind of printed bounded books that would go around and the brokers would buy in order to get information. But, you know, it’s not tremendously useful.

Now, maybe back then, the commercial real estate sector was more stable, but what we’ve seen in the last two years is we have regular reports from our economists. And those graphs that they’re putting out every week, they’re pretty squiggly. A lot is changing really quickly.

And so, those old ways of doing things, or I also think the buyer has changed where maybe in the past you would have, you know, if you were working with an agent – I’m sure David you’ve worked with plenty of agents if you, you know, rent and gotten real estate over the years like leasing things, that you’re like, okay, they pretty much know what’s going on.

Now, you’re like, yeah, okay. Data, yeah, okay. Can I see the data? And like what’s going on with the – what’s, you know what’s up, what’s down, where are the people across the street playing? You’re expecting that because I think that’s changed. And that’s where I think, you know, CoStar came along at a good moment to be like we’re already doing this and then the expectations have only just fueled the business.

Scott Varho: [0:08:42] Yeah, it’s – that is a great example of a digital – a data rich, digitally native play in the economy. And so, David, I want to ask you as you think about this, you know The Product Mindset is a way of thinking about products that you’ve been espousing for years. And you know that, you know, my first interaction with The Product Mindset was actually a workshop that Jess taught or lead with Lindsey Clipping, and I’m a huge believer.

But for listeners who haven’t read the book or aren’t familiar with it, what’s the short version of What The Product Mindset is?

David DeWolf: [0:09:15] Yeah. Well, The Product Mindset breaks down digital products and really describes first and foremost three characteristics that make digital products different from other types of software, okay. And then, on top of those three characteristics, it says if you want to honor those and have a successful product, here are three principles for thinking that allow you to make trade off decisions, judgment calls in the moment as you’re executing to optimize towards having a thriving successful product, okay.

So, those three characteristics are first and foremost if you think about a software product, that is something that is driving the revenue and the growth of a business and engaging with their customers, it’s a product. It is what is being transacted to drive value between the business and the consumer or the business and the business customer that they have.

And so, a digital product must self-fund. It’s got to create its own value chain, not just optimize the value chain of an existing product in the market. And that’s fundamentally different than other types of software.

The second thing about a product is that a product has to be chosen. It has to be something that others say hey, I need to, I want to use that, other types of software running an IT closet or is mandated to employees, right. A product has to be so useful, has to be so delightful, has to be so XYZ that it’s chosen and adopted by users and customers. Typically, not just users, but people that will pay for it to use it.

And then finally, the other reality of product in this digital economy is that digital products are just never done. The expectations of those users, is that they’re always evolving, they’re always changing, they’re always providing new value. And that again is fundamentally different from other types of software.

And so, those are the three characteristics that sit at the base of The Product Mindset and say if you’re building a digital product, if you want to be successful first and foremost, you have to embrace these realities. And then secondly, once you embrace those realities, here’s three hints, here’s three guiding principles for how you and your teams should think.

Number one, minimize time to value, right. If you’re driving in self-funding, your own product, you want to be taking small bets, you want to be releasing early and you want to be releasing often. And minimizing the time it takes to build something, put it out and derive value from it. Hopefully, economic value.

But there’s also free conditions to economic value, right. Before somebody pays for it, will they actually use it, right? Getting that feedback, right. Feedback is a currency of value. But ultimately, that economic values, what you’re looking to minimize the time to value for.

The second thing, then, is if a product has to be chosen, you need to build two actual needs. So, what is the problem, the pain point that the customer is dealing with. What is the value you are driving to them to drive that adoption and that usage? And then finally, if a product is always evolving, you need to excel at change. And so those three principles are so critical and in chlorine and complementary to those characteristics of the product.

Scott Varho: [0:12:37] Yeah, absolutely. And it’s interesting, you know, Jess, you as co-author with David on that book, I’m curious to hear from you how your thoughts on The Product Mindset have evolved in your work at CoStar Group, you know, versus being on the outside, right, looking in on these companies? How has that evolved in your journey there?

Jessica Hall: [0:12:59] So, when I knew this was what we were going to talk about, I started to write it and I have nine themes and a double-sided sheet of paper.

Scott Varho: [0:13:07] So, you’ve had a couple of Bahamas?

Jessica Hall: [0:13:09] A couple of Bahamas, I’m sure David will be shocked to learn that early on I was entirely too aggressive.

Scott Varho: [0:13:18] Neither of us are shocked.

David DeWolf: [0:13:21] Part for the growth.

Scott Varho: [0:13:22] I think I remember I should take a walk with you in between 3Pillar and CoStar Group talking about that.

Jessica Hall: [0:13:26] Yes, yes. Actually, I do recommend this, if you can get a little time in between jobs, it’s a good thing to do. And Scott and I went night, the Billy Goat Trail, which is on the Potomac River, and you do a lot of like scrambling over rocks and stuff.

So, we had this very long conversation, we’re doing this. And Scott was like, in classic Scott Fashion, say, you know, take your time, understand what the landscape is, what are the players, and really be thoughtful and take your – and like good, that sounds great because I never do that. And we had this whole plan that we completed on our multi-mile hike in Great Falls. And then three hours in, I got asked to make a decision.

Scott Varho: [0:14:08] You threw all that away.

Jessica Hall: [0:14:10] With – I think I had a grand total and Scott who might have complained for a very long time about onboarding, I got 45 minutes. That was it, 45 minutes about [inaudible].

And so, it was very clear. It’s like oh, wow, okay, everyone needs me to make a decision. Great. So instantly, I did fall back to the consultant model which is I can’t make a decision. I can convene the right people and like put them through a process to make a decision. So, it was useful that I had that.

But I think you know, as you’re going through the benefit of being in a company like 3Pillar is that you get a wide view of what’s happening in the world. You get to see how you take an idea like The Product Mindset and apply it in lots of different organizations and different industries and different stages of life cycle. And it gives you a lot of interesting patterns.

And then you arrive in an organization and you’re no longer inside, you got to get in that boat and pick up an org and grow. A lot of times when people in organizations come in from the outside, they’re kind of well, you guys this and you guys that. And we actually had someone joined our team and we made him put money into the happy hour jar every time he called us you. Like no, no, there’s no you. It’s we, it’s us. And so –

Scott Varho: [0:15:24] Welcome to the party.

Jessica Hall: [0:15:25] Welcome to the party. And I think it’s also, one of the tricks in any organization is that you can have – one of the first lessons was listen, you know, they don’t necessarily know what The Product Mindset is. They’re not necessarily going to learn all the ins and outs of it. This is not an organization where everyone is deeply steeped and lean and agile and design thinking in all these methodologies. It’s not really core, it’s not what the culture was.

So, the first thing was like, okay, I got to meet them where they are, which is I’m going to focus on a smaller amount of things. So initially, I was like here’s 20 things I want to change in all these. This is like, okay, we’re going to start with this one thing. It’s like we’re just going to have regular conversations about design.

And in those regular conversations, the first thing you need to tell me is why the heck we’re doing this. So, you just start with what need is this. And so, I never said, oh there’s this principle, solve for me. It’s like hey, so why are we doing this?

Scott Varho: [0:16:20] It’s a great small way to start to bring that into the conversation.

Jessica Hall: [0:16:23] Really simple.

Scott Varho: [0:16:24] Yeah.

Jessica Hall: [0:16:24] Why are we doing this? Okay. Who is it serving? Great. How do you know? And then just trying to say like because one thing I think where people come in from the outside, a lot of consoles will come in and say here is the holy grail, here’s the whole thing, here is the whole.

And invariably, when I would teach people about The Product Mindset, they would say, oh, how do I put this into play in my organization? Like well, there really is this smart – it’s the smallest possible thing which really came with. So, what are you hoping this is going to accomplish? I think a lot of times I try not to ask people why. I think it puts them in a very defensive position, you know. If my kid makes a mess and, you know, in the kitchen, I was like why did you do that? So why?

Scott Varho: [0:17:12] That doesn’t get you a good response.

Jessica Hall: [0:17:12] No, no, no. I think everybody gets put when you say why is that. Almost everyone gets put back in that thing where one of their parents is mad at them. So, what are we doing here? What’s this all about? How do we know this is going to work?

And so, if you just start with like asking someone a couple questions and kind of letting them go, it’s like, well, there’s this thing, would you like to try it? There’s this idea, would you like to, you know, try this thing? And I think – well, one thing about me that is uncommon is that, well, I had read a book and people had read it and – I wrote a book, sorry. And I did a TEDx Talk, and people had watched it. So, it’s really weird. Whenever I go places, people know things about me. And so, I came in and so people already kind of knew a little bit about what I was about.

And then initially I was like we’re going to do design sprints. Like oh man, that was wrong. Okay, we’re not going to do – we’re not ready for design sprints. We’re not going to do this. But I’m just going to start asking questions. I’m just going to say, okay, we can do that design work but why don’t we have this conversation first? Have you written this down?

And so, just trying to take some time and just getting people to think a little bit differently. That was one of the big changes and reset and just finding a place to place a big bet. Like I could probably only place one really big bet in the organization because I was really given the mandate to fix the experience and make it consistently. My big bet was on the design system.

And so, the first thing I had to do is tell my product manager like, right, I’m reducing capacity for design by 25 percent because we’re going to build a design system. And then I had to go sweet talk engineering to give me some resources. And so, you know, the first thing was like I – if I could do this –

Scott Varho: [0:19:01] Which of course you were successful at?

Jessica Hall: [0:19:07] Kind of, mostly and –

Scott Varho: [0:19:09] We’ve seen your work and magic here, so yes. That’s awesome.

Jessica Hall: [0:19:13] And so we were able to like say I’m going to pull this – I’m not going to change everything but I need to make this one bet, I’m going to bet on the design system. I pulled out the designers to see the most engaged in that conversation. I found the engineers through like notes and correct some of them appeared to say hey, I’m going to do this, this is a big deal.

And so just working the network, found the right engineers, found the right designers. Meanwhile we were all remote at this point. We are back in the office now and we have been for a while. But so pull everybody together and say we’re going to do this thing, here’s the plan, this is my big bet, I will put whatever needs to, and make this happen. And then talk to whoever I need to.

So, I spent a lot of time focusing on one big bet which was launching that, and we call it our design system Cosmos because you have to name them. I don’t know why.

Scott Varho: [0:20:02] It’s branding.

Jessica Hall: [0:20:03] IBM has Carbon. Salesforce has Lightning. Spotify has gone through about three design systems. Our friends at had a design system Mortar. And so, the person I put in project, she’s like I don’t want to sign it, it’s not really thing. Should I name it? I’m like name it.

And then she comes back about 20 minutes later, and she says Cosmos. Okay, tell me more, I’m very excited about this. And she said “Well, we’re CoStar and there’s a star and a cosmos is a well ordered whole universe”. I’m like, okay, we got a star theme. We got a name that talks about where – she’s super excited about this that I want to feel. So, it’s like boom, it’s Cosmos. We are going to launch Cosmos. This is it.

And someone said, oh this, it’s like no, we’re talking about Cosmos. And so, you start being the language police like really quickly. And so, we laid that out. We got, you know, pulled it together, hook and crook, cut it down significantly from what we wanted. We got that launched.

That’s kind of like the first pancake. You know, when you make the first pancake, it’s not quite what you needed, but hey we got the first pancake. So like then we got to adjust that and like figure out how we grew it. But that was really the place of I’m going to make one really big bet and it’s going to be on that. And then a smaller bet was about how do I start to change behavior in the organization?

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Scott Varho: [0:22:01] So, before you go to your small bed, go back to the big bet because you talked about how you got it done. You talked about the what or what it was, but why? If you had one big bet, why was it that was the bet you chose? How did you come to that decision?

Jessica Hall: [0:22:17] Because that was what they hired me to do. That was the number one project on the top of the mind of our CEO. That was the one thing that he wanted, and if I could give him that, then it opened up the possibilities for a lot of other things. So, if we could start saying we’re going to make some really big progress on there, we’re going to stand these things up, that was going to unlock.

It was about unlocking things. It was about unlocking, you know, establishing trust that we could do things. It was about having something that was going to reduce the amount of time we had to spend on little like changes. Because you have a design system, it speeds up the design process.

We had a very – when I arrived, engineers and designers didn’t really talk to each other. Everything flowed through product. So, it was a way to build the relationship with engineering. So, like we’re building a partnership with engineering, we’re addressing the key strategic priority for our CEO.

And meanwhile, because you’re doing the design system, you have a nook or crook of the product. You’re going to learn the product. But I’ll say two years later, there are still things [inaudible] product. To call it a product is silly. It’s actually a –

Scott Varho: Yes, it’s an ecosystem of products.

Jessica Hall: [0:23:25] It’s a whole ecosystem of products.

Scott Varho: [0:23:25] Right.

Jessica Hall: [0:23:26] So, it’s a lot of different things. So, it was kind of like this one thing gives me a lot of opportunity to make progress, and so that’s why I put all my chips on it.

Scott Varho: [0:23:35] But it’s also – you know, to your earlier point, it’s also a systemic bet because design, not just the words design system, but even in terms of culture and conversation, right, it elevates the conversation. We’re no longer talking about, oh, what’s the RGB code for the call to action button? We’re now talking about what’s the psychology of the user? What are high stakes transactions in the software? What are, right, like you’re able to move the conversation up a notch towards the why? Why are we doing this? What is the impact we’re hoping to have? And then get into the psychology of it. It moves you in that direction as well. Have you experienced that at CoStar? Is that –

Jessica Hall: [0:24:13] It’s definitely been helpful because we don’t have to talk about what the button colors are.

Scott Varho: [0:24:17] Right.

Jessica Hall: [0:24:18] Like those are the button colors. There’s – and they have rules. So, it’s like that – it changes the conversation, and it also enables – I’m just fortunate to have not only do I have a great team, but I also have a great group of engineers who really are committed to this and lean into it. And they are so persnickety, it’s delightful.

And that just enabled us to kind of get the people who are really focused on that together and focus on that. And then other folks got to start to focus on, yeah, well, what’s – then we can start talking about okay, well, what’s the flow and what are the different pieces and why is this different here?

And then we can start to change the conversation a little bit. It has been harder than I thought it was. It has taken longer than I thought it was. They can work controlling than I thought it would take. But I think, you know, I think that’s one of the things you know when you come into an organization as a consultant or someone in the organization, well the 3Pillar, that – the meter is running, right, minutes. Most people will give a full-time employee awhile to get on board. Not me.

But well, I guess you had minutes and so you had to just get in there and go. And here it’s like well we’ve actually got to, you know, whatever we do, we’re responsible for it and we have to be able to maintain and grow and scale it. And we have to do it in a way that we don’t scorch the earth like we are getting stronger on the other side of that.

Scott Varho: [0:25:40] Right.

Jessica Hall: [0:25:41] And so, that was definitely figuring through how much change can I actively push in at once was a little bit tricky because, you know, that’s not what I’m just changing. Like HR is doing some stuff and other teams are doing some stuff and all of that changes trying to funnel through the same place.

Well, I got to figure which one am I going to try and put through and I got to be willing to, you know, go on it for a while because it’s just not going to happen. I can’t just say, here’s the thing, and it happens. It never course out that way.

Scott Varho: [0:26:14] Right, right. Well, it’s kind of interesting to note that a lot of our 3Pillar teams have been very sticky with our clients and which gives us that opportunity to build trust to see it through our, you know, our hands are dirty in it, we’re with you on that journey. You know, while you a lot of times were sent in as a, you know, as a consultant and you’ve got minutes, a lot of our teams get years to help our clients get better at product development and applying The Product Mindset in their context, which is really – it’s a fabulous opportunity. But it also raises the stakes, right? Like it’s – you’re sticking around with those results. You don’t get to just give great advice and walk away.

Jessica Hall: [0:26:54] Yeah. I never – to be fair, I never said like oh, I’m out. I always – when I’m – here’s the trick of being a consultant, the answer is already there. The answer is already there. The problem is no one’s listened to it. The people in the organization probably know what happened. They probably have a good sense, but for whatever reason, the right things aren’t getting – the right people aren’t connecting with the right information, have the right ideas.

And what we have to do is slip that out so they have a – either they don’t know what they’re doing which is nine times out of the ten of the problem. It’s like I can’t tell you how many times I walked around organizations as a consultant. The first thing I do every time was like so what are we doing? What are the big priorities for the next three months?

And people are like uh or they would start laughing at me. That definitely happened. Or they would say like, here’s some gobbledy strategy gobbledygook. I’m like do you know what that means? Really. And or it be like CEO says. It’s like, all right, okay.

Problem number one, nobody knows what they’re doing. And so, all the time when I said, what’s my big bet? Cosmos. What’s my top priority? Cosmos. What’s the main thing I’m doing? Cosmos. Like this is it. This is the one thing that’s on the top of the list. Now, we’re going to service, we’re going to do other stuff, but I was like super clear about what our priorities were and make sure that every product manager when I said, oh yeah, we’re not going to work on this thing right now, it’s because of what and what the benefit was.

Scott Varho: [0:28:20] So with that, I think that – I mean that’s a perfect segue into this question, which is how do you align Cosmos then with organizational outcomes? Because it’s just a design system. And while it has all these, you know good bits and parts, how does this make CoStar Group more successful as an organization? I think connecting those dots has to be a part of your why, why Cosmos?

Jessica Hall: [0:28:43] So, what is that, you know – with any legacy product, any organization that it’s really hard to change things. So anything you can do – when you and I have had this conversation, you made me read that accelerate book. It was so hard.

Scott Varho: [0:28:56] It was so boring but so good.

Jessica Hall: [0:28:57] Oh, God, it’s so good. And so –

David DeWolf: [0:29:00] So boring but so good.

Scott Varho: [0:29:03] Oh yeah, you would love it.

Jessica Hall: [0:29:02] So here’s the thing. Nobody ever comes into an organization and gets the fancy job or the kudos for saying what I’m actually going to do is I’m going to make everything run better. But what nine times out of organizations, especially legacy organizations need is they need things to run better. They – the reason why they have no way, it doesn’t – everything is hard, everything takes a really long time, whether you have to deploy and it takes a long time or you have to test or you have to make decisions or you have to make designs.

The thing in so many organizations is they have no time to do excellent stuff or really about – because just doing the basic stuff is so hard. So, all you’re going to do is say you know what, I’m just going to speed this sucker up. We’re going to have less conversations about minutiae. We’re going to have easier times putting things together, and we’re going to make it easier for our engineers to be able to deliver things were in clients.

If all we do is speed the process up and we can put more through it, we have a better chance of being successful. And can I put that against the OKR? Maybe. But I know if I can make things flow more easily through the process and I can focus the conversations on the ones that we need to have, I have a better chance of making a KP. So, it’s not – it’s one of those times where you have to say like, yeah, I can’t exactly measure this, but that’s what we should do.

Scott Varho: [0:30:23] You know, I’m struck. I just listened to a podcast from IDO, not to plug another podcast, but I was just listening to a podcast on strategy and strategy activation. And I’m struck by thinking about your design system, plus the questions that you ask, and how those two things work in tandem.

One without the other isn’t necessarily as valuable, right. But if you can create the design system which drains the minutiae conversations and it creates space for the higher level conversations, and then you’re injecting the right questions at the right time, you’re forcing the conversation up as you’re creating the space for that conversation. Does that feel right?

Jessica Hall: [0:31:02] Yeah. Well, that sounds really terrific and very logical. In reality, slower.

Scott Varho: [0:31:12] So talk about that because I mean that to me this is an obvious one punch. Cosmos.

Jessica Hall: [0:31:16] Yeah, yeah, yeah. It sounds awesome, right?

Scott Varho: [0:31:18] I’m in. Yeah.

Jessica Hall: [0:31:19] I probably wrote something that told somebody to do that very same thing. So fun fact. You can get mad at people for not doing the things that you expect them to do, but you probably shouldn’t. And I might have done that, I guess. It’s like hey, into an organization, I think one of the tricky things in organization, so is that one, a lot of value and it makes total sense if you spend any time looking at this stuff, is put in this organization on subject matter expertise. And gosh, you really do need them. You really do. I’ve learned a lot about –

Scott Varho: [0:31:56] It’s a complex market.

Jessica Hall: [0:31:57] – triple net leases and 1031 exchanges, and what ADR is. And not only do I need to know one area of the business, I need to know all the areas of the business. So, a lot of emphasis put on that understanding of the data and the industry. Not as much expertise and focus has been put on the craft and you know, Scott’s just like super happy about this right now.

Scott Varho: [0:32:21] Pushing that button.

Jessica Hall: [0:32:22] Not as much emphasis was put on the craft of product management and design. So, it wasn’t exactly like a process. There weren’t artifacts, you know, templates and things. And so, it was like, yeah, do the thing and they’re like I did this. It’s like, oh wow, that’s not what I want at all. And so, I was like, okay.

So, one of the things in that is like yes, we can start to advance the conversation. But at some point, I’m like I got – I’ve legit written – this is the checklist that you need for me to begin design. And these are the things I have to have. And we’re not going to start without it.

Scott Varho: [0:32:53] What kinds of things are on that checklist?

Jessica Hall: [0:32:56] You and I would call it product definition. So, it’s like who’s it for? Why are we doing it? What are we trying to accomplish? Where is it going to sit in the product? What are the major features that you need to release?

And you need to – a lot of people just talk a lot about what those are. And that’s great to have that, but I needed a more concrete format, but I wasn’t getting it. And so, there was this moment of like well, I can keep asking for something. I can be like can I just have this? Can I have this thing? And can you give it to me in this way? Once I have it, then we can get started.

And, you know, just starting to have that kind of like this is how – these are terms of engagement. These are the ways that we’re going to gage and just start to really funnel that in so that we can have the conversation that I wanted to have. Instead of the conversation was I want to do, these are the things that I want to do. And I’m like no.

So that was the conversation I kept having and like well this isn’t working. So, now I have to get clear on here’s what I need and here’s what we’re trying to accomplish. If you don’t give me this, like I’m not going to – there’s not a lot I could do for you.

Scott Varho: [0:33:58] Right. But I – so, I’m going to push a little bit on that because Cosmos, you talked about how that that is going to make the organization run faster?

Jessica Hall: [0:34:05] Yeah.

Scott Varho: [0:34:06] And that’s oftentimes what’s needed. You also injected these questions like you know the why. And then you used upstream thinking just to cite another book that we both read at the same time. You know, Upstream by the Heath Brothers, right?

Jessica Hall: [0:34:19] Yes. Well, it’s one of them. I think it’s Dan Heath.

Scott Varho: [0:34:23] Okay. So, we talked a lot about Upstream, you know, back when we were working together and here you are doing that, right. Like you’re also, you’re saying, okay, well like I can make the engine run faster and keep producing guesses. And then you can tell me why it’s wrong or I can go upstream and say, why don’t you give me a clearer picture of what you want? And then as we’re going faster, we’re also more likely to be closer to the target.

Jessica Hall: [0:34:44] Yeah. And then it was less pranky. I was like why aren’t you doing what I want? Oh right, you don’t know what I want, right. I should probably tell you what I want. And that was definitely something that we had to do. Along, we’re going the lines of you’re both effects on me with Scott and more systems thinking because that was something like Scott has pushed me out of.

The one that I think David will like was, you know, I started as an 18-year-old designer, working my way through school. That’s how I worked. I worked at a museum in D.C., and I worked – I went to school. And then I stepped – stayed at the museum. So, when I was 18 and I was an intern, I could never tell him – it’s like I’m an intern. I was like, no, I’m the – I’m designing this thing.

And so, I spent so much of the years of my career influencing that I got really – I was like that’s what I do, I convince people. And I got to sell it and I got to get you on board. And then I came here to 3Pillar and I was – which is a whole another story. But like I had to go into clients, and I had to work with the other people, and I had to influence and influence. And I was always trying to sell something.

All of a sudden, I stared down something where I’m like, oh right, I need to decide.

Scott Varho: [0:35:57] Authority.

Jessica Hall: [0:35:58] I am so deeply uncomfortable.

David DeWolf: [0:36:01] Interesting.

Jessica Hall: [0:36:02] I am so uncomfortable with authority.

Scott Varho: [0:36:04] Well, it’s interesting because most people think they covet authority when they’re tired of working through influence, but you’ve gotten very comfortable with influences.

Jessica Hall: [0:36:10] Well, that was my gem, right. That’s what I did. I didn’t learn how to use authorities. All the sudden, it’s like you have authority and I hired you to do the thing and I hired you sometimes be a dictator. And I was like deeply uncomfortable with that because I’m an influencer, I’m a team player, I’m a collaborator. And all of a sudden, it’s like wow, I have to be like yeah, we’re not doing that. We’re just not – it’s so uncomfortable.

Scott Varho: [0:36:34] How did that impact your leadership style?

Jessica Hall: [0:36:36] So, one is just trying to say reflecting a little bit on when did – when I was with clients who wouldn’t make decisions and their whole organization was screaming, just decide. Just decide. I’m like, right, I’m that person now. So, you’re going to reflect on that and say like I remember what it was like for the team and where someone just got to make a call because otherwise, we’re not going to get anything done.

David DeWolf: [0:36:59] And you can oftentimes live with a bad decision more than no decision because –

Scott Varho: [0:37:04] You can recover from a bad decision.

David DeWolf: [0:37:05] Right. You can pivot off of that. Okay, now we know that’s wrong, we can – but leaving the organization without one is tough.

Jessica Hall: [0:37:11] Yeah. And so, it was kind of realizing, oh wait, this is what I’m doing like. Like these – we’re already swirling and I’m making this far worse because I’m trying – I’m not making the decision. And so, what I would end up doing is make a decision and then try and explain my decision and get everybody okay with it, which would make things go on for longer.

And then I got to the point where I would say, okay, heard what everybody has to say, this is what we’re doing. And then I have to start counting in my head. Like this is it? One, two, three, don’t say anything, don’t soften your position, don’t back down. Just do the thing.

Scott Varho: [0:37:46] Don’t caveat.

Jessica Hall: [0:37:46] Don’t caveat. Don’t stop, don’t change. It’s like hold it, hold it. Listen, if we have some data this is not right, I’m happy to revisit this but go.

David DeWolf: [0:37:55] But based on the information we have right now, this is the best possible decision that I think we can make, and we’re going with that. That’s the burden of leadership.

Scott Varho: [0:38:04] Good for you, yeah.

Jessica Hall: [0:38:06] It’s so weird.

David DeWolf: [0:38:07] I don’t know anybody who has that challenge.

Jessica Hall: [0:38:08] Yeah.

Scott Varho: [0:38:10] David.

Jessica Hall: [0:38:11] Well, one is you can outsource some of that, right. Like you can offload that. If you’re doing a good job with having a design system, having design principles, having objectives, some of that decision making, you can outsource. So, one of the investments I’m continuing to make like that was version one of those nice being done anywhere close, right.

So, we need to continue to invest in the systems and the things that allow people to make good decisions without having to come to me. I don’t want to make every decision here. I don’t want to have to do that. But if I don’t have things in place to people make the – and we’re talking about day-to-day decisions. Does this arrow have a drop down, you know, is that a dash or a button on this or a circle on this placard?

I don’t want to make that decision, but I need a system in place for my team to make a good decision. You know, I’m like, you know, I’m trying to think of something. So, like I need to make those decisions where I have to make the gut check, but I also have to invest and so that the decisions are getting made at the right level.

Scott Varho: [0:39:10] And the tricky part about that is that even that delegation and empowerment itself requires a decision because it requires the abstract decision of creating the framework so that other people can make good decisions, right, and deciding who are you delegating it to. Are you creating clarity around who gets to make the decision? Are you creating the parameters so that they’re comfortable making that decision, right. So many aspects fall into that, that it is a continual decisionmaking process of how do you continually improve.

Jessica Hall: [0:39:46] So, David yeah, we got to write about this chapter because that’s what we didn’t put in.

Scott Varho: [0:39:51] On decision making?

David DeWolf: [0:39:52] Yeah.

Jessica Hall: [0:39:53] Yes. Well, we missed. I think it’s funny because we did a bonus chapter around the time the pandemic happened. And it was all about we need to get better at communicating intent and objectives. And I think that the one thing that the, you know, Covid stuff and the great resignation and a lot of these other things we’re seeing is that decision making and how you equip people to make decisions is broken in a lot of companies.

So, like people are like – so, the only thing they have now to feel good about the progress we’re making is that a butt is in a seat typing, right. And then you don’t know. And so, what I think in a lot of organizations is that ability to know, think about where is that organization – where should that decision be made, and have we equipped those people with the ability to make that decision, and the people above them and the people above them.

That’s a huge missing piece. Like I saw that in so many clients and heck, I have perpetrated that on my own team in the last two years. And I think that is a piece of understanding like how do you create that architecture of decision making and all the pieces and parts and necessary for that to flow through. Otherwise, all those decisions have to come back to you.

And so, you know, that’s going to grind the gears intentionally. Everything is going to take a while because now we have to come back to me to make a decision about, you know, does that open in a new tab or is it a modal? Or is that a dash? Or isn’t it – that’s not the right decision.

And so, if that’s happening and you’re involved in those, like the question has to think who’s the right person to make that decision and how do I equip them to make that decision? Or if they’re making decisions you really don’t like, well, something’s wrong.

Scott Varho: [0:41:40] There’s another decision you have to make.

Jessica Hall: [0:41:40] There’s another decision you have to make. And I think that’s – I think there’s a couple things maybe – I don’t know if they’re in The Product Mindset, but I think there are some things missing and that one is really grinding the gears right now because so many organizations are kind of relying on, you know, without necessarily being co-located physically in the same space, like you’re doing a lot of things, so there’s a lot less structure and then people are waiting. They’re not quite sure.

And some of that’s because they’re afraid, right, and they’re worried about. But I think there’s a lot of decision making. How do we make decisions? And I remember being on a client where I can remember the slide clear as day. I’m like every decision is the decision that is raising to an altitude of the C-Suite. And maybe, maybe 20 percent of these should be C-Suite decisions, but they’re all coming up here.

And so, you know, trying to work through with that particular team of how do we drive those decisions down. And the problem is they’re like, hey, make decisions and the team would make – of course, they’re going to make a decision that you don’t want because you didn’t give them any guardrails. And then, oh, I don’t like that decision. Bam, smack the hand, they won’t make another decision again. The whole gear start grinding.

Scott Varho: [0:42:54] Right. Right. Well, you know the ability to distribute decision making is usually a function of how far you’re willing you have trust. And I think that one of the ways of building trust is also putting if you assume positive intent and you give them the tools and resources and exposure that they need that make wise decisions, then you can start to think about an ecosystem that runs healthier.

But if you just yoyo decision making, right, like it’s like I expect you to make decisions, oops, you made the wrong one, no more, then you’re never going to get to that high functioning distribution of trust and decision making.

Jessica Hall: [0:43:29] Yeah. One of the best mentors that I had and I for many years have taught skiing and my ski school director used to say, you know, you got to teach – you have – one of the ways you would say is you got to help teach people how to think. And so, we’d say, well, when I’m in this situation, here’s what I like to do. And oh well, you know, you would watch you teach a lesson and say, well, you know what you could do is this other thing.

And so, like you’re starting to talk through why did it make it? So, I had a bunch of interns this summer. Super fun. I had three design interns. We also had some product interns and like a data person on the floor. And so, like all these intern’s comments is like okay, we would start doing this and I look over them like looking at me, I’m like right, okay, here’s what I saw and here’s why I said to do this, and here’s what I’m hoping is going to be.

And so, it’s like it forced me to be much more explicit about like here’s what I’m doing. And that, for me, going back to the authority thing is like I’m explaining my judgment. I’m not opening the door for you to like for us to relitigate. We’re not relitigating this thing. I’m just helping you understand it.

And like, you know, if I’m wrong, which happens, we’ll change it but I think it is, you know, those types of things I’ve got to make my decision making process a lot more transparent and open. So, these other folks can now start, and I need the tools, and then they can start making decision. And again, that makes things flow easily because they’re not waiting for me.

Scott Varho: [0:44:59] Well, one – I have a proposal. I’m actually curious to get both of your thoughts on this because I do have a proposal for another chapter of the book.

David DeWolf: [0:45:05] Well, here we go.

Scott Varho: [0:45:07] This will be fun. And sorry, I know I’m way off script here. But one of the things that I learned from you, Jess, was the importance of UX research and how important it is to mind for the insights that ultimately can make the difference between a great product, mediocre product, or what that just doesn’t make it.

And one of the things that got me thinking about organizationally is how often, you know, the strategy is the CEO said, right, and how many organizations I’ve been in that have been like that. And then the ability to actually take insights into the organization, and this builds on some like concepts that we talked about around Bob Moesta in demand side selling. What if I could tell the company as a product leader, tell the company things they don’t know about their own customers or users?

And then this is where that minimize time to value, start the learning process, be engaged with real customers, with these pain points and start the learning. It’s not going to happen, you know, you can’t – I mean you can do some learning before you start building, but you ultimately have to have real contact and try to actually solve these problems in real ways.

And so, I wonder if another addendum to The Product Mindset is in excelling at change and minimizing time to value and understanding need more deeply. And as a product – and also we talked about things like product like growth and things like that, like taking the product team and repositioning in the organization from an executor of orders to a source of insight and even a source of how to better support customers that lead customers to use your product for its intended purpose.

David DeWolf: [0:46:37] One of the things I love about the way you ask that question is use the word insight. So often we talk about gathering intelligence from the market in terms of feedback, and I think the word insight implies seeing inside something at a deeper level than what is just said.

And one of the struggles that I really have with the big, big, big push for, you know, customer research and the voice of the customer, and all this is that people want to go just collect what is said and then pass it on like it’s a direction. And innovation doesn’t actually happen that way, right.

Innovation happens from those deep insights of getting to the bottom of what’s actually going on, what the real pain point is, what the real need is, and then using intuition and using problem solving techniques in order to take that insight and actually solve the need in a new and different way. And I think there’s a real skill set there that we have to be careful when we talk about going and listening to the voice of the customer, not just to ping pong back and forth of they said this, they said that.

And it’s the exact opposite of the ivory tower. We don’t want an ivory tower either, right. Innovation doesn’t come from just barking orders from on high either, right. And it is that art in the middle that you’re talking about that I think is just so powerful.

Jessica Hall: [0:48:07] Yeah. I need to say I believe in it because I’ve been in so many cases where I’m like this is what we’re going to do. And like, no, that didn’t work. But I hate to say that I think a lot of companies are sharpening their pencils. And I think a lot of companies are explaining some of the research functions. And I think they’re going to suffer for that.

In part, I think is there’s a fuse or one I think to David’s point they’re not seeing the value is because they’re getting the raw materials and not the actionable intelligence. In some cases, I think there’s a translation layer missing between hey, we went out and talked to customers and we did really quality research. Now, how do I put that into action such that we can get value out of it? That’s missing.

And I remember going many rounds with our UX research team here, which is like you have to give me a message I can sell because this isn’t it. And so, we got to fast, flexible and focus. And I still remember it, two years later, that’s the kind of research we do. That’s the kind of value we create. And so we really had to hammer in on how are we going to get to a place where we can get customers something that they really value.

So, I think some organizations are sharpening their pencils and look, you know, because they’re not quite sure where things are going, and they’re going to go through. And I think that organizations that haven’t quite figured out how to, what that translation layer is and how you get actionable intelligence, I’m afraid that’s going to get cut and that’s going to hurt a lot of organizations, because they’re going to fall back on with – in the absence of that research, what do you end up doing is what does the powerful person think? And they’re not always right.

David DeWolf: [0:49:42] That’s right.

Jessica Hall: [0:49:43] Sometimes they are. I mean sometimes they aren’t.

Scott Varho: [0:49:45] But even into David’s point too and I think it’s so important to realize that the customer doesn’t know what the product looks like, what the solution to their problem looks like necessarily. They oftentimes can talk a lot about what they don’t like, they can talk about what they want, what they wish for, and they might even try to use feature language to describe that. But if you get into their why, then you open up the aperture for innovation because they can’t imagine all the possible ways that problem could be solved.

David DeWolf: [0:50:11] Yeah. The really simple analogy that I love to always point to on this is like if you just really dumb it down. If Henry Ford went out and asked customers for feedback, right.

Jessica Hall: [0:50:22] Got to get Henry Ford.

David DeWolf: [0:50:22] It was on a faster horse. I want a faster horse. I want a faster horse.

Scott Varho: [0:50:26] Right.

David DeWolf: [0:50:26] And the automobile never would come about, right.

Scott Varho: [0:50:29] That’s right.

David DeWolf: [0:50:30] And it takes, yes, there is a customer feedback of going and looking at what does the everyday man or woman need in terms of transportation and understanding why they’re asking for the faster horse, and all of the ramifications of that, that can absolutely fuel a better car. No doubt about it. But yeah, can’t just, you know, pair it.

Scott Varho: [0:50:51] You can’t user feedback your way to something brand new, a new category.

David DeWolf: [0:50:54] Exactly. Exactly.

Jessica Hall: [0:50:55] So, okay, this is what I call getting Henry Ford’d because someone’s going to pop up this Henry Ford quote. Sorry, I don’t work for him anymore. Not like I wouldn’t have when I did. Okay. So, here’s the thing. There is – HBR published a great article about this a while ago. There’s no evidence that Henry Ford ever said that. But if you go back and think –

Scott Varho: [0:51:14] But it’s still right.

Jessica Hall: [0:51:15] Right. Kind of. So, when the Model T came out, what Henry Ford realized is that people had a problem is that they wanted to go and experience the outdoors and get around and they wanted a reliable mode of transportation that didn’t poop a lot and that didn’t kick you and potentially kill you.

And so, you know, yes, if he had asked what they needed, but it was – it’s kind of – I think that is surface level understanding. And that’s where we get into promises like, you know, and Steve Jobs saying, there’s a version of a Steve Jobs quote because everybody wants to quote Steve Jobs, which are not, by the way.

But I think what – if you go a little bit deeper, you can kind of understand what were people really trying to achieve, and I think Bob messed this work and so demand side selling is not about sales. I love that book. I recommend it to everybody. It’s not about sales, it’s a jobs to be done book.

Scott Varho: [0:52:04] Yeah.

Jessica Hall: [0:52:04] And so, it’s really about how can you get below the surface level stuff of I want this, I want that to like what are we really trying to do here and what’s motivating you and what’s limiting you?

David DeWolf: [0:52:15] What’s the point of struggle? What’s the point of awareness that I want a product to solve this need for me? Yeah.

Jessica Hall: [0:52:21] And that’s where people are – and that’s the thing where people are going. You’ve got to go to that slightly deeper place to get a fuller understanding. And that’s where the insight lies and most people aren’t doing that.

David DeWolf: [0:52:31] And that’s where we use the word insight, not feedbacks.

Scott Varho: [0:52:34] That’s right. Well, data is not insight, right.

David DeWolf: [0:52:38] That’s right.

Scott Varho: [0:52:37] Data is data. And we have to look at that data in order to drive hypothesis which then get us to insights. Interesting. All right.

So, Jess, we – I know we could talk all day and have, in several occasions. But I’d love to close that with a quick speed round, a couple of speed round questions. Are you ready?

Jessica Hall: [0:52:59] Yeah.

Scott Varho: [0:53:00] All right. Where are you more comfortable, in front of a white board trying to hone in on a bihag, a big hairy goal or shredding some fresh powder on the slopes in Vermont?

Jessica Hall: [0:53:10] You say that like I can’t do both at the same time. I can’t do the white part.

Scott Varho: [0:53:14] I know too well that you can.

Jessica Hall: [0:53:16] Yes. Well, so you skid down and then you discuss ideas on the chair lift up.

David DeWolf: [0:53:24] So, you’re just not going to choose, huh?

Jessica Hall: [0:53:25] No.

David DeWolf: [0:53:27] Okay.

Scott Varho: [0:53:28] All right. Avoided the question. Number two. It has been a while since The Product Mindset came out. Have you had the itch to write another book?

Jessica Hall: [0:53:38] So, I’m currently working on a little bit of a nerdy research project, but which I’ll tell you about a second and I do have an idea for another book that I – like I have time. So, the research project I’m kind of interested in is so many times I’ve been the first leader in my function in an organization. In fact, I think almost every leadership role I’ve ever taken I was the first whatever in the company I was in.

And I think that there is something pretty broken about how we launch leaders. A lot of times, this is about on boarding. So, onboarding is about understanding how the organization functions today and how you fit in. And when you’re the first leader of your kind that is there to do something that is different and help grow the company, you don’t need – you thought about onboarding, it’s not about fitting in, it’s about preparing the road to be something different.

And so, I have this notion like I don’t think we need to onboard new leaders. I think we need a different mindset shift and that’s towards how we launch leaders. Like we launch a product, and we think about the goals, and we know that this has to be a cross functional effort. And so, I’m kind of talking to some folks and playing around with that idea.

And if I ever get the chance to write a book again, the one I think I’d want to write is like would be called the turnaround job, because I think a lot of people talk about how do you get out of the garage or how do you scale up or – but how do you turn around a ship.

Like that’s something – like the product is not working and the business is kind of broken. And like there’s a lot of people who tell you how, but not a lot of people will tell you like what actually happened to the people in that situation, how do they actually do it in real life. And I’d love to do that at some point. But I don’t know when in the heck I’m going to have a time.

Scott Varho: [0:55:22] Well, that – I mean you and I’ve joked often that, you know, if both of us encountered a building on fire, you would run into it, and I would stand outside wondering why it’s on fire which is a perfect –

David DeWolf: [0:55:34] So true. So true for both of you.

Scott Varho: [0:55:37] And she’s up there and, you know, babies are coming out the windows and, you know, and I’m still like, oh, I don’t understand why is it on fire? It’s so –

David DeWolf: [0:55:42] So, here’s the question. What would I do?

Scott Varho: [0:55:45] I don’t know. What would you do?

Jessica Hall: [0:55:46] Martial the troops.

Scott Varho: [0:55:47] Yeah. Yeah.

David DeWolf: [0:55:47] Yeah, that’s true.

Jessica Hall: [0:55:50] And prioritize – my favorite things about David, you’re like David, three things, priorities now, and he will – he doesn’t hesitate. He’s like one, two, three, boom.

Scott Varho: [0:55:57] No, he always. It’s always three too, it’s amazing.

Jessica Hall: [0:56:00] It’s always three. Yes.

Scott Varho: [0:56:01] Well, Jess, thank you so much. This has obviously been enjoy. It’s always good to see you and great to hear these new insights from your journey at CoStar Group. And we look forward to more of them as you progress.

David DeWolf: [0:56:12] Thanks for joining us. It’s so much fun.

Jessica Hall: [0:56:13] Thanks a lot.

Scott Varho: [0:56:15] This has been an episode of The Innovation Engine, a podcast from 3Pillar Global. 3Pillar is a digital product development and innovation company that helps companies compete and win in the digital economy. To learn more about 3Pillar Global and how we can help you, please visit our website at

Lastly, remember to give us a rating and leave a review on your podcast player of choice. If you have any feedback or guest suggestions, send them over to Thanks for listening and see you next time.