The Janel Wellborn Hypothesis: Teams Should Celebrate Learning Fast, Not Failing Fast

In this episode of the Product Science Podcast, we cover Janel’s journey into product working at large retailers like the Gap & Macy’s, transitioning from waterfall to agile. We also cover how to iterate behavioral changes in an organization, and how to embrace quick failed experiments to help build the right products.

The Janel Wellborn Hypothesis: Teams Should Celebrate Learning Fast, Not Failing Fast

Janel embeds herself within a clients' organizations to transform their culture by shifting mindsets at all levels, helping them make many small changes in their product practices that have big impacts on their ability to meet their customer needs & deliver measurable business value.

In this episode of the Product Science Podcast, we cover Janel’s journey into product working at large retailers like the Gap & Macy’s, transitioning from waterfall to agile. We also cover how to iterate behavioral changes in an organization, and how to embrace quick failed experiments to help build the right products.

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Questions We Explore in This Episode

How did Janel get involved in product? How did computer programming classes prepare Janel for a career in product? What were precursors to the field of product before it was a separate discipline? How were pre-agile and pre-product businesses exploring technology to optimize their enterprises? How did the Gap update its entire e-commerce platform and ecosystem. How did the Gap decide updating their entire e-commerce was worth the cost to revenue? How did early product practices develop from within waterfall? How did the Gap transition into agile? What were some of the early product practices that transitioned into agile standards? How did the Gap predict it would recover from its losses after overhauling their e-commerce platform? How was a data driven strategy crucial to the Gap’s growth? How do you scale your business operation while keeping multiple unique brands? How much overlap is there in the day to day operations of many brands? How did the Gap respond to iterative delivery under agile vs waterfall?

How did Janel start to practice product at Macy’s? How did Macy’s train employees to become product managers? Why are product principles applicable to all disciplines? How can you teach product principles? How can product managers validate new ideas? Why is critical thinking core to being a product manager? How can data be used to change a stake holder’s opinion? Why are product managers sometimes seen as an obstacle for stake holders? Why are product managers a means of applying check and balances to an organization? How can lean practices help you run faster experiments? How can lean practices reduce an experiment from taking years to giving results in only days? Why is it efficient to teach lean practices to pockets of teams? Why can adjusting to lean principles be hard for organizations to adopt? How can you use data to encourage a business to adopt lean principles?

How can you iterate behavioral change? How do you avoid creating lean and agile silos when training teams? How can engineers be more engaged with customers? How can engaging engineers in problem solving help incentivize engineers and develop better solutions? How can you build empathy within teams and engage more with customers? What are example of how teams can engage with customers in a variety of ways? How do small changes to an organization become large scale transitions over time? How can an organization embrace failures as lessons? What are the trade offs of training product managers internally versus finding new hires? What skills does anyone interested in becoming a product manager need? What roles does humility play in being a product manager?

Why can’t a product manager become an expert in all aspects of a business? How can product managers view stake holders as experts in a given field? How can product managers build relationships with stake holders so they come with problems to solve rather than requirements to build? How can stake holders be encouraged to view product managers as thought partners to help drive solutions? How does technology’s role differ between retailers and traditional product lead businesses? How can agile practices fit into a business’s operation cycles? What aspects of retail operations limit agile practices?

How is product management built on building relationships? How can product principles be applied to engineering and social disciplines? How does experimentation when building software differ from experimentation in a retail market? How do material and operation costs affect agile and product practices? How do product managers leverage relationships strategically? How valuable is word of mouth marketing for product managers? How do you know if consulting in product is a good fit for you? What is the value of coaching for product managers? How important is portfolio planning towards a company’s business strategy? How does a company’s values differ between different environments? How can you empower product teams to be solutions driven more than requirements driven? How is product at the center of a company’s strategy?

Quotes From This Episode

You can change processes. You can change out team members. You can have tools. But we always forget that behavior change is the most powerful one. Incentivize and reward that kind of behavior when you see it.
If this team did an experiment and it totally failed, and it was a waste, but guess what? It was only a waste of a week, not a year and a half. We're not celebrating the failure. We celebrate that we got that learning quickly.
You want to shift the conversation from an emotional one, where a stakeholder's super tied to their idea, into a more logical one. Are there other ways to address this problem and what are the pros and cons of doing each of those?


Holly: This week, on the Product Science Podcast, I'm excited to share a conversation with Janel Wellborn. Janel is a product coach at Peerless Partners, where she embeds herself within clients' organizations to transform their culture by shifting mindsets at all levels, helping them make many small changes in their product practices that have big impacts on their ability to meet their customer needs and deliver measurable business value. Welcome, Janel.

Janel Wellborn: Thank you. Thanks for having me.

Holly: I'm so excited to have you here. So, let's begin at the beginning. How did you get into product?

Janel Wellborn: Well, I am old school. I'm old. So, when I got into product there wasn't so much product. Right out of undergrad, I went into big five consulting and what was Price Waterhouse at the time, and it was actually a pretty cool program where they took folks with all these different majors, so you could have been a philosophy major, computer science, marketing, English, whatever, and brought us to this place in what we affectionately called [Trampa 00:01:16], Florida, but Tampa. And there, we all came together and learned how to code in Cobol. That's giving you an indicator of the old schoolness, right?

Holly: Wow.

Janel Wellborn: There's little hints of Java, but yeah, Cobol. That happened. And at the time we were kind of like, "Why are we doing this?" Right? And at the end of the day, the intent was for us to be able to understand critical thinking and problem finding, and problem solving is at the core of a lot of what we're doing for our clients at the time. And they also wanted us to know enough about technology. I like to think it's enough to be dangerous. Not enough, but enough about technology in order to kind of call BS if needed, right? About complicating things and being able to kind of step back and see the big picture. So, that was a blast. And I left that training program and worked a bunch of huge clients like American airlines, BMW, Proctor & Gamble, things like that, all across different industries, and was really doing product, but it wasn't called that. It was like, "How can we leverage technology to do more, better, faster, or to have a better experience for our customers?" Right? Internally and externally. So, we were designing experiences. We were defining requirements at the time, which is a word that's like a dirty word to me now, but back then I embraced it, when I didn't know any better. And yeah, had a blast doing that. And then one of my last clients while I was there was the Gap, actually. And the Gap had this president, Toby, who was what I consider a freaking genius, because he somehow convinced the board, "I need a bunch of money, like tens of millions, to redo every system for eCommerce and mobile app and all the supporting ones. Our order management system, our call center system, our product catalog, everything you can you think of. I need a bunch of money, and also I'm going to be in the red for a few years while I basically throw everything away and build it new." And somehow convinced the board to be like, "Okay, let's do that." And so, they brought us in, and consultants to help with that. So, we redesigned all of the customer experiences, as well as the associate experiences and all the processes and all the systems and everything, just from soup to nuts, which was great. An excellent experience. But at the end of it, I was kind of like, "If we leave, my team, myself and my team, we are doing product. We are doing this for them. This is not like a picture. This is more of a video. We're going to have to change this and enhance it and optimize this in the future, and there's going to be a gaping hole when this engagement ends and we leave."

Holly: Yeah.

Janel Wellborn: So, I accept an offer to stay there and build out, with some of the folks who came from other parts of the business who weren't in product, but came from the other parts, for us to build out the organization. The product team and the product practices, which was great.

Holly: Oh, awesome. Tell me more about what were the product practices at that time? What did it look like to redesign from the ground up?

Janel Wellborn: Yeah. There was a lot of big old documents. Requirements documents, right?

Holly: Uh-huh (affirmative). Yep.

Janel Wellborn: Where we tried to capture everything kind of all at once. And part of it was thought like, well, it's a migration, so can't we just make it do what it currently does, right, but in the new platform? But then we also went to seize the opportunity to make it better. So, there was a lot of good core practices, like customer research, and using quant and qual data, and shadowing in the call center or in store operations or in the fulfillment center. Things like that. So, a lot of the core practices were there, but we were just not super nimble at the time, I would say. It was a lot more traditional waterfall, obviously. At that point, we were kind of just dipping our toe into the agile world of thinking about build, measure, learn, experiment, and things like that. But the core practices were definitely there at that point.

Holly: Yeah. That's awesome. And how did the re-imagining of their whole platform and ecosystem end up working out?

Janel Wellborn: Great. I think in the chart that Toby had shown when he asked for the money and the space, he was like, "We're going to be negative for let's call it five years, and then I'm going to come back and be really, really positive. More than we have been."

Holly: Yeah.

Janel Wellborn: And actually, it took us three years instead of five, and we were much higher even in the black than he had anticipated.

Holly: Oh, that's fantastic.

Janel Wellborn: So, it worked really, really well, and it had great results. That's why I say he's kind of a genius. Somehow he convinced them and delivered on what we were going after. And it's rare. I've never seen that ever again, where you can actually convince, "Hey, we're going to have to pause on the new features, the new functionality, and the new changes, the new capabilities that you need, and I just need to go dark and lights out for a little while, right? In order to throw this away and start over." Most often, I'm working with huge companies and they don't have that luxury. That's the only time I've ever seen that be able to happen, to just say, "Let's just do this right, and let's do it as fast as we can and as well as we can while not being distracted."

Holly: Yeah. That's fascinating. Do you have any idea sort of what were the dynamics at play that made it possible for that to come about there?

Janel Wellborn: I think it's interesting, because the Gap, like a lot of large retailers that have multiple brands, was convinced that Banana Republic is super, super different from Old Navy, which is super, super different from the Gap. And so, they had kind of been born out of that, and we had a lot of very different things, and we just were wasting a lot of time and money with doing things three times, right? As opposed to, could we have 80% of this be similar? Like eCommerce is eCommerce, right? Mobile is mobile. And at the end of the day, the way you answer a call and serve your customer and the way that you fulfill a package and all of that is pretty core. The funnel that the customer goes through and their mental model and consideration set. But then certainly there are elements of the brand that are different and whatnot, but that doesn't need to be 90% of it, and we could get a lot more scale. So, it was kind of a short term pain for long-term gain kind of play that he teed up, and I think it was definitely the right move. And especially from a business strategy point of view, because we were, at the time, planning to and gearing up to an acquisition of Athleta, which was another brand that was going to be totally different style, and we wanted to really leverage the masses of Old Navy and Gap and Banana Republic, the traffic and the eyeballs, to expose to this smaller but fiercely loyal brand that we were going to be bringing up. And then also we were launching Piper Lime, which doesn't exist anymore, but was a totally different model as well, where we had a vertical versus horizontal, meaning having products from all kinds of different brands, rather than just our own brands. And so, I think knowing that we had that stuff coming up from a strategy point of view, it was like, "We kind of need to get our shit in order here right now, in order to be able to be nimble and make those things happen."

Holly: Yeah. That's awesome. I'm really glad to hear a story where it worked so well.

Janel Wellborn: Yeah. Yeah. It was fun. I think our first play into actually iterative delivery was really when we did universality and we said, "Let's put these brands together." If you go to the tab and you go to, but you would see Banana Republic tab, you would see Old Navy, and you could see everyone's eyes. The board was like, "Oh my God, you're going to need another several millions and millions of dollars and another three years." And we were like, "No, no, no. This time we're going to try to do this iteratively, slice by slice." There are lots of things that we could do, and we did. They weren't totally sure, but we did, and it was a blast to be able to do that. And after I was there for quite a long time, like seven years, then someone who I'd worked with back at PW, who also worked at the Gap with me, went and became the CTO at Macy's. And he was like, "Holy smokes, I'm here and I need to do amazing things, but it's kind of a garbage in, garbage out situation, right? Technology can only do so much of what's coming in for us. The build is not the right stuff and we don't have great product practices around that. And you've seen this movie before. Any chance you want to come over here and help?" So, I did, and got the chance to work with another group of really smart and amazing people, and build that product org. But that was really different, because we took a bunch of people from the business, and people who were more like business analysts, and my mission was to turn them into product managers. Database, decision making, user at the center, slicing, iterative, and dabbling more into, I'd say, gradual instead of... Not waterfall, not agile, but somewhere on the spectrum.

Holly: Something in between.

Janel Wellborn: Yeah, exactly.

Holly: At least you're more on the spectrum of agile.

Janel Wellborn: Right, right. Exactly.

Holly: How did you endeavor to take those people and make them into product managers?

Janel Wellborn: My curriculum to this day, both the things that I have done subsequently and I'm currently doing, has evolved so much. It is my product, right? And it's constantly evolving. But I think at the core, there's probably some key principles that are the same examples that I'm giving, the same stories that I'm telling, and it's really about trying to get them to think in a different way. We're not taking requirements. And that might be a great idea, but is there a better idea? And that's one of the critical thinking components that I was trying to weave in. We don't want to evaluate an idea when a stakeholder comes, and this person might be six levels above you, especially in a huge organization like Macy's, right? They're a senior vice president who's been there forever and there are 10 levels between you, and they come in and they're like, "We need to go and build XYZ. And don't worry, I've already started the RFP process with this third party vendor who's going to sign up for it. We've already found the product. It's going to be great." And you're like, "What you're saying seems logical. Okay. Seems like a good idea." And then we execute. That's kind of the old business, the analyst type of approach, right?

Holly: Yes.

Janel Wellborn: So, I was trying to teach them a different way of like, let's turn that around and use phrases like, "Okay. So, what's the bad thing that happens if we never launch that thing?" And then they're like, "Oh, well then, the sky will fall in this way." And what's the amazing stuff we can expect if we were to launch it tomorrow, because I'm a total rockstar? "Oh, well then we can blah, blah, blah." And it's just a Jedi mind trick way of getting at what's the actual problem we're trying to solve or the opportunity we're trying to seize? And being able to frame it as a hypothesis and then saying, "Okay." Then the product manager can demonstrate empathy and say, "So, what you're really trying to do is decrease the burden on the customer when there's an issue with their order. Because right now it's a pain in the backside. They have to navigate the IVR, wait on hold, talk to someone, get disconnected, get transferred, redo it again. Oh, that is horrible. And you want to decrease that burden." "Yes, exactly." And now all of a sudden we're on the same team, because we're trying to solve the same problem. Right? Great. And this tool, this thing, this third party thing that you're suggesting and will sign away in ink, is an option for doing that, right?" "Yeah, exactly." "Okay, cool. Let me go away and do the voodoo that I do and see, with my team and with data and with critical thinking and all of that." Rather than just evaluating like, "Yes, that's a good idea." Is it the best idea? And then come back, and are there other ways to address this problem or this opportunity, and what are the pros and cons of doing each of those? So, what I'm telling them, it's not like rocket science. I think it's what we're all doing organically in product, right? But it's more putting it into practice in a tool and in a framework that's repeatable, and it's more like a mindset shift. And then you can go back and say, "So, remember you wanted to decrease the burden on the customers when there's an issue with their order?" "Yes." "Great. And one of the options was this tool thing right here." "Yeah." "Well, we went through and looked at several other options, and this one actually, we could deliver halftime market. Or this one right here is going to take about the same, but it won't have an ongoing licensing cost. Or this one right here is actually going to kill two birds with one stone and also address this other problem that's over here." And it's really hard to argue with that, right? In the sense that you shift the conversation from an emotional one, where a stakeholder's super tied to my idea and this deal I'm making or what I had going on, into a more logical one. Like really, the only way you can argue with that is you seem like a five year old holding onto your toy, right?

Holly: Yeah.

Janel Wellborn: They're not going to want to do that. So, it's like, shift it from emotional into logic. So, that's one example of we have a tool in an artifact we use for it. But for me, it was much more about the mindset and arming them to feel comfortable, challenging people who have hot sports opinions, who are at a very senior level and are smart and good at what they do and may very well have a good idea, but not necessarily the best one.

Holly: That's awesome. I think you almost make it sound easy, but I know it's actually really, really hard.

Janel Wellborn: Yeah. You know what? It's funny that you say that, because people say all the time to me during some of my training or coaching sessions, they're like, "I kind of feel like an idiot because what you said sounds so obvious and so logical, but why are we not doing that?" Right?

Holly: Yeah.

Janel Wellborn: And it's not rocket science. I'm not a genius over here coming up with some magic panacea. Right? It's just, you have to simplify it in a way and know, from an empathy point of view, what might be the blockers, so that you can arm someone proactively to kind of address those. So, that's what I did there, which was a blast. And the other thing I did there, other than building the product org and teaching the rest of the org how to interact with it, because this was a world, very traditionally happens a lot, where stakeholders are used to not having a middleman. They're like, "I need this and here's an engineer. Go build this." And they're like, "Okay." You have these product managers in here-

Holly: Right.

Janel Wellborn: ... and I'm used to go through them and they're going to decide and blah, blah. So, there's a lot of... I call it like, I can build the most amazing fish, product managers, not that they're stinky and scaly and wet or whatever, but the fish. But if the fish tank that they're swimming in, if they are salt water fish and the fish tank is fresh water-

Holly: Not going to work.

Janel Wellborn: It's not pretty what happens. Let's say that, right?

Holly: Yeah.

Janel Wellborn: So, no, no. And so a lot of time working on that fish tank. And I think that was a problem with my earliest. I valued it and instinctively knew about it, but I didn't necessarily quite know the sweet spot of just how important those checks and balances with stakeholders were, which is something that came later. And I will say that the last thing that happened at Macy's that I love, in product, was we tried to adopt lean practices into this large, old school, retailer, which cannot get more old school. In New York, offices on the 20th floor in Harold Square and whatnot, and still wearing suits every day and whatnot. And the principles of lean, right? Eliminating waste and experimenting and valuing the whole and all of that type of thing. So, I spent a lot of time with a couple of my peers. We each had different functional ownership and sphere of control, with us coming back and experimenting in our ways of working, and launching these little baby lean labs that we brainwashed to work in a totally different way, where we're like, "You're going to launch something in four days, and you're not launching it unless you can measure it, because if you can't measure it, you haven't learned anything. And if you haven't learned anything, then we're wasting our time." Which is a very different thing than saying, "We're going to go through a big process and estimate something from the time it's an idea, right? Until the time we actually get it funded, get it kicked off, get working on it in sort of a iterative way, ultimately launch it, and then find out that, ugh, that didn't really work." That could be three years.

Holly: Right.

Janel Wellborn: And our goal was to shorten that cycle. And we did it in a smart way, because we asked for just a little bit of money that no one would even notice in such a big portfolio, and said, "Can we just try this?" And did it, and something that was meant to take about three years and was estimated at 2.9, $4 million, we delivered in a couple of months for like $300,000.

Holly: Wow.

Janel Wellborn: So, you can imagine that later, folks are like, "Oh, we want more of those."

Holly: Of course. I should think so.

Janel Wellborn: Yeah. But it didn't apply to everything, but we ultimately ended up scaling that to like, 20 of those. And for me, it was more like, again, can we get people from regular teams working this way, then go back to their teams and have this mindset and this way of working spread like a positive cancer? I need a better analogy, but spread it in a good way, like that. And that was really fun. It was a great adventure, and it was really hard thinking of the fish tank. I remember I pitched this with my partners. We asked for the funding. We got the clearance and said, "We're going to do weird stuff. We're going to work differently. It's probably going to smell weird. People are going to get stressed out. Just be ready for it." They're like, "It's okay. We believe in your mission and the spirit of what you're doing. You have our protection. Go forth and multiply." And then I remember we did this really quick change on the home page one day, and we saw actually a 66% lift in the click through rate to our wishlist, which was great. Our data, our hypothesis was validated. It was working. And I got a call in my office, and you can read on the caller ID, and it was our president. And he was like, "Janel, did you all just launch something on the home page?" And I was like, "Yeah, last night. Isn't that great? And wait til we tell you the results." And he's like, "We don't really do that. We all look at the homepage, every piece of it, every Monday." Because it's a very value driven organization, right? So, every piece of real estate is incredibly critical, and there's all this logic going through. And I'm went, "Well, the fact that we have 20 people sitting in a room looking at every pixel is one problem, but we're not going to solve that right now."

Holly: Right.

Janel Wellborn: "The second one is, I thought you wanted to move faster. I thought you wanted data driven decisions. I thought you wanted to experiment. Blah, blah, blah." "You are right." I'm like, "It will be uncomfortable. We have rollback code if we somehow crash the homepage, and it's going to be okay. But actually, the results are really good and it's working."

Holly: Yeah.

Janel Wellborn: And he was like, "You're right. You're right. This is what we signed up for. So, carry on."

Holly: That's awesome. How did expanding it go? Because I know a lot of times in the enterprise, people set up like a lean lab or an incubation or an innovation center, and sometimes they never get out of their own fishbowl. How did you tackle that?

Janel Wellborn: Yeah, that's a really good question, because part of it, I think, we learned, we debated a lot, is this a separate thing over here? And we didn't love the sound of that, because then there's drama associated with that. Internal politics. And it doesn't really change and move the needle on the big stuff, right? It's just, you're limited in your impact and scope and capacity and all of that. So, we debated that a lot, and we very intentionally decided to do a rotational program, where we funded this team, this lab, initially for the little bit of money we asked for, just to fly under the radar, so people wouldn't be bugging us about just how off we were going on doing things very differently. But we set it, you're there for three months, for a quarter. And then we're going to send you back into the fish tank, into your regular team, and we're bringing in a new batch of folks. And then we would brainwash them, and then they would drink the Koolaid and be so excited about working this way, and then rinse and repeat for the rest of the year. So, that was one of the ways, because then they'd go back and take some of the practices around things they did that were wasteful. Do we really need to do that? I mean, a very simple thing is standup. The morning standup that they were doing. Usually they were saying, in traditional agile sense, "Here's what I'm working on, and here's where..." If they're... "I'm blocked on anything." Right? Do you really need to spend time going around a room of 10 people saying what you're working on when we have a board right there that makes it obvious, because your name is up there on the card? How about we just save that time for aha moments? Like, "Hey, we made an assumption three days ago. Dug into the code, found out that was crazy talk. Never going to work like that. So, now we need a plan B." That's meaningful and helpful and can take five minutes. Right? I mean, that's a very subtle and simple thing, but there were tons and tons of those every single day that we were doing. Or a lot of times product managers would frankly come in with more like requirements. Like, "I wrote a story and this is what you need to build." And they focused on what you need to build. Engineers are like, "Okay, cool." And let's say we pushed them to say, "Could we get this thing out the door by Thursday?" I guarantee not many of them are in there like, "Sure, I'll stay late and do it."

Holly: Right.

Janel Wellborn: Because they're not even motivated, right? Versus building empathy around, here's a problem that we have to solve with a real use case, and letting them engage. Things that we all do normally now, and we know our good practices, like having the engineers have contact with our customers as well, or our users and so forth. But having a hypothesis and framing it with humility. Like, "I think this is what's going to happen, but I'm not totally sure. And it's really important that we don't throw that analytics tag scope overboard and cut that story, because I don't know and I want to measure it and see if I'm right, so we should keep doing it or not." So, getting them to build and breathe and lean into that kind of stuff was great. And it was awesome, because on Monday morning in our kickoff for the week, I've never seen so many engineers who are like, "So? So? Did we move the needle to conversion increase? Did it happen?" Just so excited and really feeling motivated, and we got way more creative solutions and energy and all of that out of them, because they felt like they were really tackling something real, rather than just coding X, Y, Z. Which again, sounds simple, sounds obvious, but how do you do that in an everyday practice, and just make it part of what we expect as the way that we work as a product manager? Right?

Holly: Isn't it amazing how such seemingly small change of adding a few statements to what you're saying to get that goal across, to share the reason why, to build the empathy, has such a big impact on what the whole team can do?

Janel Wellborn: Yeah, you're right. Absolutely. And you can think of that in the context... Oftentimes, I'll have product leaders who are like, "Team's just not really customer centric. We're talking the talk, but we're not walking the walk, and I really need to do a better job of getting the customer at the center. Do you have any recommendations? Can you do some training?" I can. Sure. But I can tell you something you could do for free and you don't need my time for, which is the next time that you have a one-on-one, presuming you have a one-on-one with each of them every week, right? You're checking in.

Holly: Yeah.

Janel Wellborn: Rather than going through the status of their projects or whatever fire drill's going on or whatever, just say, "Hey, what did you learn from your customers this last week?"

Holly: Yeah.

Janel Wellborn: Just that simple statement. And they might be like, "Doh," the first time. Like, "Well, I haven't talked to them per se, but..." You know.

Holly: Yeah.

Janel Wellborn: But you can bet your bottom dollar, the next week when you show up and you ask that question, they're going to say, "Oh, well, I actually stopped to talk to someone, or I did a listening session in the call center, or I asked the dude at Starbucks, tell me a story about the last time you made a return. Was it painful or easy? Let me hear about it." Right? So, it's just a subtle behavior change that we can do. The language you use, how we spend our time together, how we frame things up, to your point, absolutely makes a huge like ripple effect. So, to go back to your earlier point, that's an example of, we would do those things that were so obvious and felt so good that when we sent them back into the world, they were pushing and they were evangelists for that, and it was organically spreading, which is great. And there were a lot of other tactics that we did, but I think to me, that's the biggest one, is just do little small shifts that don't feel insurmountable, don't feel hard to adopt and adapt into your day to day, and then see the goodness that comes from it. That's the way you get people to internalize it and change their behavior. Right? You can change processes. You can change everyone. You can have tools. But we always forget the behavior change is the most powerful one. And that's that human connection, right? That, show me what matters to you. Incentivize and reward that kind of behavior when you see it, right? Things like, we would go to our town hall and be like, "Hey, this team did this experiment and it totally failed, and it was a waste, but guess what? It was only a waste of a week, not a year and a half, which is how we normally roll." Right?

Holly: Yes.

Janel Wellborn: And that was great. We're not celebrating the failure, because I hate that. Fail fast, like we want to fail. No, we celebrate that we got that learning in a quicker part. So, that was my time there. And then I left and went back to consulting. So, I had spent like 15 years back in industry, two huge retailers, and was like, "Okay, I think I need to try to apply a lot of this goodness that I've been honing in more context." And I leaned a lot on my relationships when I was at the Gap and Macy's, with my engineering partners and my program partners and strategy and finance and all that to drive a lot of this change. And I wanted to, frankly, challenge myself and see if I could still do that same kind of thing with elevating product practices and thinking in a place where I didn't get to lean on those relationships, and so I could scale that goodness. And I ended up in South America, which is fascinating and random, but not. I speak fluent in Spanish, but applying a lot of this outside of retail. A little bit of retail, but also in airlines and banking and other industries, and it was a really interesting time because they were behind us in sort of the digital evolution, and so it was a question of, do we build or do we buy product managers? Do we go and import and get them, or do we just try to build them from scratch from folks in the business who we think have the right mindset and whatnot? And I spent a lot of time doing that with my clients, identifying talent. People who I thought we could build into amazing product managers, and then doing training and in context coaching with them. Dabbling in the fish tank, to make sure they had the space to do all the goodness that they could. And I remember once, one of my clients who is a dear friend to this day, we were interviewing for these core product positions. So, I was like, "We'll just interview them. We'll get together at the end of the week and decide what we think about them." Right? Okay, great. We come back together. He's like, "I think Susie and Bob are the best. Whatever. These people." And I was like, "Huh, okay." He's like, "You don't. You hate it. You hate them." And I'm like, "I don't hate them. I just don't think they're the best." And he's like, "What?" And I told two totally different names. And then we did it again the next week and came back, and still, we were totally not on the same page with what... And he's like, "Okay, what am I doing wrong?" It's not that you're doing anything wrong. It's that we're looking for very different things, right? Especially because we're building, not buying, these product folks, because of the state of the market and where we're at. You're looking for people who know travel and have experienced an expertise in the travel industry. I don't give a flying flute where they come from. I'm looking for someone who can develop a point of view and defend that point of view, but isn't so tied to it. It's a strong point of view based in data, very articulate, very logical, they're exposing their logic, but it's also weakly held, in that they're open to more information and shifting it as they go. And so, we're looking just for totally different things. I can teach them these things. This, not so much, right? And that's more natural. And these things they can lean on their business stakeholders for, right? And this, not so much. That's what they need to have subject matter expertise in. It's been really fun applying it in different areas. It's kept me growing. And I would say, one of my latest things that I'm doing is awesome, because I went over to the dark side. I did a residency where I went in and led a product team for nine months, in order to find where the bodies are buried, start elevating the product practices, and then ultimately hire who should be in that role.

Holly: Yes. Yeah.

Janel Wellborn: And then afterward, when my work was done, or so I thought, my main stakeholder, the president from the business side was like, "Hey, not so fast. Where are you going? I want you to keep doing what you're doing, but on this side of the house, with us and the business."

Holly: Oh, interesting.

Janel Wellborn: And that has been amazing, because I already innately had empathy, and felt that business stakeholders, well, they could either be the biggest pain in a product manager's backside, or they can be the biggest asset. And most product managers think of them as the biggest pain in their ass, because they're the people who are like, "When, when, when, when, when? And I need this, this, this, and this." And so, they're often painful. But the reality is, I think that we need them, and the power in co-creating some of what we're doing, like, are we focused on the right problems and opportunities? And over time, you build trust and credibility with them, so that they don't come to you with solutions all the time. They come to you with problems, and trust you to be a thought partner, right? And they're prioritizing problems and opportunities in that sense. So, it's been really great for the past year or so, to be having that lens also on both sides, and it's helped me evolve my product practices, my tactics, my ways of thinking, in what's the ideal engagement model between product and business stakeholders.

Holly: So, what has it evolved to? What's an example of a thing that has changed about your thinking?

Janel Wellborn: I, like most good product managers, have a healthy ego, and I think that I used to feel like, yeah, just back off, and let us do our thing, right? Like, this is what we are here for. And I still do believe I'm the biggest advocate for product in the planet, but I also really believe in checks and balances. That they're thinking about things in ways that were not. They're running a business, and they are closer to certain things that we can't... I don't think a product major should be an expert in all the operations of business, right? You can't. It's a math problem, frankly. You're going to be mediocre at 10 aspects of the business, and they're going to be a rock star at one aspect of it, right? So, they're meant to be leveraged in that way and partners. And so, I think that manifests a lot in the way that we engage them throughout the planning as well as delivery cycle, right? So many times I see product managers go in, and my teams have done this before too, where we talk with the stakeholders in the beginning, and we're like, okay, we're going to build this circle. And then we go away, and then we come back and we're like, "Ta da." And they're like, "Ah, what the hell just happened? That's a square. Where did the right angles come from?" And then we expect them to just adopt it and support it when we move on to the next shiny sexy thing there. Right? But are we actually building something that this business can support? Too many times I've seen where a product manager will throw a use case overboard and they're like, "Oh, that doesn't matter." Actually, it does. It represents 33% of what's happening within the market over here, right? Or, "Oh, we'll just pilot it in this category." It doesn't even help us there, but this one over here is screaming for love. It's whatever it is. So, there's just a lot of... I think the humility. It's helped with that. Being humble that I have subject matter expertise, but so do they, and treating them as one of my biggest assets and my team's assets, rather than this constant... And frankly, that time part, which is the biggest pain in product's backside, is what stakeholder's always asking: "When, when, when, when are we going to have it?" And the reality is that it matters. So much of what we launch... And again, I'm coming from a very different perspective than traditional, where the technology is your product. I'm talking about large organizations where technology is just an enabler for their strategy. So, a big retailer, for example, and what we do with the web or mobile experience, or how associates use it in the store, in the call center. Things like that. But so much of what we need to do has a big old boatload of work to be done on operational readiness and business readiness.

Holly: So much.

Janel Wellborn: And when things are kind of like, "Yeah, you'll get it when you get it, man," that's what I call hippy agile. It's like, 'Yeah, it's good times. Don't sweat it. Don't worry. It's coming when it comes." And they're like, "Yeah, but no. I actually have to sign a contract. I actually have to hire 100 people for that new fulfillment center. I actually have to get inventory in there. Am I buying summer inventory? Am I buying fall? I don't want to take a hit on my margin." So, there's real decisions and real work to be done, and we have to kind of be in lockstep with that, rather than just circle and squaring it.

Holly: Yeah. This resonates so much with me. I've been working with some clients recently that have a lot of that sort of like, "Well, I'm the products manager. I figured out the strategy. I figured out what we need to build, and can't they just go sell it?" And it's like, "Well, there's a whole lot more partnership needed. Even if you did listen to them and listen to the market and come up with the right strategy, you still can't just throw it over the wall and be like, 'Have fun with it.'"

Janel Wellborn: Good luck with that. Totally, totally. You're absolutely right. And it happens a lot. And one thing that's interesting is in the past three years, I've started teaching at UC Berkeley at Cal, which is what I want to do when I retire, is I want to teach. And I do teach. I teach all the time with my clients, but this is a little bit different, right? And all masters of engineering students have to take two business classes. They're in this amazing world class masters of engineering program. They're going to go into leadership positions in these organizations, and they need to have a little bit of business acumen and how to navigate the org. So, one of the classes that they take with me is product management, and I tweak it from an engineering point of view. And another one is about implicit leadership and org influence. So, how do you rally people around your idea or tell a story? All those. Same things that are quarter of a product manager, but frankly, everyone else needs to know as well.

Holly: Yes.

Janel Wellborn: And so, I think that has never become so clear to me, what you were just speaking about, and it's really hammered it home for me, because I've had to take what I do traditionally in digital of a large organization, the digital part of a large organization, and adapt it. My students are building a machine that's going to clean up oil spills more efficiently, or biomedical device that's going to be in hospital that detects diabetes earlier, so that you reduce the likelihood of going blind, right? Or a rover on Mars that's testing the viability of air quality and whatnot. So, these things that have to go into building and manufacturing and hundreds of millions of dollars and lots of legal and environmental and social types of impacts around it, where this is like the tail wagging the dog in this case. Product is not driving this bus. Right?

Holly: Right.

Janel Wellborn: We are not driving the bus. So, being able to apply these same practices and mindset and that empathy in that context has been a blast, because I'm learning, I think, more than I'm teaching, frankly, which is awesome, and my idea of a good time. It's very interesting, because I've always said that to my teams, that hey, it's not just us. There's a lot of work that has to go into getting this out, other than just coding this stuff, right, and designing it. Right? But in here, I've seen that be magnified even more.

Holly: Yeah, that's incredible. I actually went to school for a chemical engineering, and so my early career was working in environmental, and everything was physical. It's so much harder to do the work on physical atoms than it is to do it on bits and bites. It's just slower. It's more expensive. It takes more space. There's all these things that just have very different manifestations, and to me it was one of the big pulls to come over to software was just like, "Wow, it's so fast. It's so comparatively light."

Janel Wellborn: Totally. And they have to remind me of that when I'll give them examples or coach them into doing stuff. They're like, "If you do that on the web or mobile or in software that's within an organization or wherever, that's great. But if I do that, I've just wasted $23 million." I've had to kind of adapt, adopt and apply it in a new context. It's very true. So, it's very different, I think, when the tech is your product, versus when technology is an enabler for it.

Holly: Yeah. Yeah, absolutely. So, you've talked about teaching, you've talked about consulting and coaching. Has the last number of years all been independent, or do you have other people you work with?

Janel Wellborn: Yeah. Right when I left Macy's and went back into the consulting world, I went with a partner. Someone who I just love, who'd been a mentor for a very long time, who owned a consulting practice, but it was largely technology. And he had 2000 people, engineers and architects and whatnot, employed at Macy's and Gap and other places. And he was like, "If you ever want to come back to the consulting gig, I'd really love you to come help me build my product practice and UX practice and whatnot." And I was like, "Yeah, yeah." And that's sort of how that South America thing actually happened. And so, I spent a lot of time going from zero to 200 people on three different continents and five different time zones, and building up this team really quickly. And I just realized I was spending so much of my time worrying about billable rates and who's where and on the bench and the sales pipeline, and I had far less capacity than I wanted for actually digging in with my clients and solving and helping and being connected with the product teams themselves. So, I gracefully exited and was like, "I hope that helped." And he's like, "Yes." "And it's yours. Take it back, and so now you have this. Merry Christmas, Feliz Navidad, whatever." And to this day, we're still working together a lot. It's great, because I decided at that point very consciously to shift to saying, "I want to be small but mighty." And instead, at least for a while, I want to focus on more of my capacity, rolling up my sleeves and working, and less of it worrying about the rest of that stuff. And as a result, I will surround myself with trusted partners who have sweet spots that I don't. The ying to my yang. I am the first person to say, "Yeah, I could do that for you. I could probably help you with that, but you could probably get someone cheaper or faster or more available or more whatever." Right? I'm pretty picky about, is it something that gets me out of bed in the morning, which I really like? And my brand is very important to me. I've never spent a dollar on marketing, because it's just people I've worked with who are like... you know. And then they go somewhere else, or they know someone who's having a similar problem that I helped them with, and they're asking, "Can you help with that?" So, that's kind of the route where I've taken the past few years now, is surrounding myself with yings to my yangs, so that I don't have to say, "Sorry, good luck with that. I can't help you," with any of my clients or potential ones. But instead I can say, "Yeah, probably I'm not your girl for that one, but here's somebody who I trust would be able to help you with that. Because I know enough to be dangerous and I could wing it, and I'm pretty smart and have a good learning curve, but doesn't seem like the best use of your money or time." Right? Or just because I'm busy or whatever it might be. So, it's been great, because I am able to really dig in. But yeah, it's been good to be able to do that. As with anybody, and I know you can relate, the more independent we are, the harder it is to scale, and you just want to spread the goodness as much as possible, and you want a bunch of mini mes, and yet it's like short term pain, long-term gain. You can invest the energy in doing that, but then it's an opportunity cost, I think, at the end of the day.

Holly: Yes. Yeah. We all have to decide what's right for ourselves, in terms of how we want to be spending our time and what that looks like.

Janel Wellborn: Yeah, absolutely. So, I have people who were students of mine in my training and coaching curriculum in these big organizations, who now have moved on to different roles, often more senior, and they're running product teams, and we do in context... We call it personal training. You have a personal trainer for your real physical muscles. Why not for your career, right? And then they're like, "I still think of your Janelisms, and the messages and the key core concepts and the practices and the tools still stay with me, and I would love for you to help me transition into this new role." So, I love being able to keep capacity to do that with those folks one-on-one, because most of the time I'm spending it with groups who then have access one-on-one, of course, or leaders one-on-one. But it's nice to like see people at different stages of their career, and trying to apply the same like product mindset to different problems, right? And in different environments as well.

Holly: Yeah, absolutely. It's really fun working with people at different stages of their career. So, I think we're almost out of time, but I did want to ask you, you've built a lot of product organizations. What is a key learning that you wish you'd had sooner?

Janel Wellborn: Good question. I think, frankly, because of the organizations I've built have all been large organizations within large organizations, right? One of the things I see most of my clients and everyone struggle with is how we do portfolio planning. How we decide what to invest in. And oftentimes, we are spending 150 million a year. And so, it's not insignificant, right? That's a lot, and hundreds of teams to keep busy. And I think that's been the single most painful part for product teams, and I wish I had known earlier a lot of things around balance. I feel like so many organizations, there's a spectrum and it's like a pendulum, and they start in one place and then like, woo, go all the way to the other. And I spend a lot of my energy trying to bring them back into the middle. Only I feel kind of like an a-hole doing it, because it took me a while to get there too, and I was going with them sometimes in those pendulums. So, I mean, a great example is empowered. Like, "Oh, we're going to have these empowered teams." Well, empowered doesn't mean that everyone decides everything about everything. That's not actually the definition of empowered, right? Or, prioritizing problems versus opportunities, or balancing push and pull. Sometimes our business stakeholders are going to know exactly what they need, and we just need to figure out how to build it for them, and not argue with that. But also other times, we need them to not give us a solution, and just give us a problem, and we'll figure it out and iterate the best way to deliver against that or move the needle on that metric. So, it used to be very output based. Success looks like you delivered X on Y date for Z dollars. And then we swing over to this outcome place with OKRs and this more like, "Oh, we'll see what we get." Neither of those work, right? And being able to come a little bit where you're balancing both of those, I think for me, that's a really big part of it, is that. And how much upfront planning we do, because you need to know the date of when you're launching a new fulfillment center, right?

Holly: Right.

Janel Wellborn: Versus no, I don't know. Let's leave space to be nimble and react and see what's happening outside or inside. Right? So, to me, that's probably the number one thing, is I have a lot of scars on my back from too far this way, too far that way. I feel like I've gotten to a really good sweet spot, and I'm seeing the results with my clients, which is great. But I kind of feel bad. Why didn't I get there earlier? And we could have been faster and had even better results earlier.

Holly: I mean, everything looks like the obvious thing in hindsight. Right?

Janel Wellborn: Of course.

Holly: Once it makes sense, it makes so much sense, and then you're like, "Why? Why did it take me this long?" Exactly.

Janel Wellborn: Yeah. Yeah. Yeah. Of course. Yeah. So, balance in the context of how we optimize our ROI on our spend, at the end of the day. Because product generally is stuck in the middle of it. It could be that we don't have a good strategy, we don't have a cohesive strategy, and you just have 20 stakeholders with totally different siloed needs, all coming thinking theirs is the most important, and product's supposed to decide what's better for the business, right? And that's over indexing, right? Or it could be in the, "No, you don't give us requirements. We'll tell you what we'll build." Or the opposite. We just take requirements. So, it's the whole thing around, I think, balancing across probably four or five of those aspects.

Holly: Yes. So, it's all about balance. I like it.

Janel Wellborn: Yes. Very Zen. Very Zen.

Holly: Yes. Zen and the art of Janel's product management.

Janel Wellborn: Yeah. I don't think that's words that... Said no one ever. Yeah. Zen and Janel are not usually in the same sentence. Not so much. Yeah.

Holly: Yeah. Fair, fair. Where can people find you if they want to learn more?

Janel Wellborn: LinkedIn, definitely. I aspire to have a more active Twitter presence, but I'm a work in progress, just like my products. But I think LinkedIn is probably the best. I used to have a HSO, hot sports opinion of the week, where it was things I would be seeing and I would frame it up, and I'm going to bring that back, because I took a bit of a hiatus. So, I think that's probably the best one.

Holly: All right. Sounds great. So, look for you on LinkedIn. Awesome. Well, thank you so much, Janel. It's been such a pleasure to talk to you.

Janel Wellborn: Thank you, Holly. Thanks so much for having me.

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