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Pulling from the Features in the Attic

Myles Grote, Co-Founder & Chief Product Officer, Upper HandTyler Hill, Chief Design Officer, Upper Hand

When it comes to digital products, it’s common to see major shifts from brand to software. This week highlights a company who has done both.

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Anna: Christian, you're gonna love this episode.

Christian: Oh yeah?

Anna: Today we're joined by Myles Grote and Tyler Hill from Upper Hand. Upper Hand is a sports automation software that's revolutionizing the way coaches, trainers, and sports management professionals conduct business. Miles Grote is the co-founder and Chief Product Officer, who's been with Upper Hand since 2013 when it was called Book A Coach, and Tyler Hill is the Chief Design Officer, who's lead creative strategy for brand, UX, and visual design, since 2016.

Christian: Oh, okay. Now I know why you said I'm gonna enjoy this. Chief Design Officer has been like, my dream title, my whole career.

Anna: You literally have that title right now.

Christian: Oh, yeah. I didn't really think about that. I make people call me that, but I need to update my LinkedIn profile.

Anna: Sir Chief Design Officer.

Christian: Oh, that sounds even better.

Anna: Maybe you'll get a plaque, someday.

Christian: That would be nice.

Anna: The conversation we had with these guys was so much fun. For one, they've completely transformed their original brand, Book A Coach, to what is now Upper Hand.

Myles Grote: We built an MVP version of the product. It just didn't really work well. The biggest problem was that, and I think this is a common issue with marketplaces, is you spend a lot of money to go out and get one side of the equation, and then you spend a lot of money to go out and get the other side of the equation, and the transactions that occur are really what has to cover the cost of both ends of that particular marketplace equation, and if you don't get people coming back and using the product over and over again, that equation breaks down pretty quickly.

Christian: Yeah, Myles knew they needed to leave the coaching brand behind and start fresh. They had to find a better product market fit, so they tracked data meticulously. Not only that, but they conducted customer discovery so they could figure out exactly what the pivot needed to be.

Myles Grote: We started to basically talk about scrapping the whole business model of the marketplace, and pivoting toward more of, like, a automation tool for the more established sports businesses. Not the one-off coaches.

Anna: So, I think you loved doing this episode.

Christian: Totally.

Anna: Not just because of the product conversation we had with Myles.

Christian: Which was great.

Anna: Very great, but because we got to dive really deep into design with Tyler.

Christian: Which I could talk about for hours.

Anna: So, let's start with that. Let's start with Tyler sharing with us what he has to consider from a design perspective.

Tyler Hill: We're a pretty robust software offering, so from the design side we have to look at, "Does adding this flexibility in our software add complexity?" And, "Does one user experience interrupt another?" Right? Because it's not your typical linear path. We have to meet a lot of different customers' needs without stepping on the toes of another.

Tyler Hill: We've had to balance that a lot, even, with new features. Right? So, this feature's great for A, B, and C customer. It works perfectly for them, but if we introduce this, is this gonna disrupt the user experience for the other customer that can care less about this feature?

Tyler Hill: So, those are some of the things that we think through on the design side.

Christian: How do you determine that?

Tyler Hill: It really starts at a high level. When we look at a feature, it's typically, "If we introduce this feature, what other aspects of the software does this touch? Does this change the client profile view? Does this add additional UI to reporting?" Right?

Tyler Hill: So, we have to, instead of designing a user experience kind of in a isolated environment, we kind of pull back and look at the software as a whole. "If we do this, what other features are gonna be affected by it?"

Christian: The secondary effects about it.

Tyler Hill: Exactly. And do they have to be affected by it, or do we need to design another whole user flow?

Christian: Do you ever have to say no? Like, do you ever do an exercise like that, and say, "This is too impactful, and the value's not high enough."

Tyler Hill: Yeah, we've said no.

Myles Grote: So, my first inclination's always to go to the customer and talk to them, but the one thing I know about customers is that they know what they want, but they don't know, a lot of times, the best way to achieve it, and so there's, I always call it, like, the third dimension. The third layer, and you've gotta peel back the layers with the customer, talking to them one on one, a lot of times, to find what the true problem is and to really connect the dots.

Myles Grote: 'Cause some of the customer feedback I get from the success team, which is no fault to them, it's just, you know, we have a young team and they haven't talked to customers in a SAS environment for that long, but the one thing I get from them is, like, it's always a very surface-level. "They wanna do this," and there's no, "they wanna do this, because this."

Myles Grote: And a lot of times, you find it's just the product just doesn't do this thing three steps down the road very well, and if we did that really well, they wouldn't even need this. So, that's one thing that we commonly find.

Myles Grote: If you ask 'em how you do it today, a lot of times the conversation will eventually go back to the way that you're doing it today is probably, like, it might be the best way. A lot of times, it's the best way to do it. You're just trying to get us to really stretch to build you this custom feature.

Myles Grote: But, you know, look: we track it. Like, if they ask for it, even if we think that they're being unrealistic, we still track it, and if a lot of customers start asking for it, I mean, isn't that what great products do? They figure out how to solve complex problems, and so it's not like we steer away from the hard stuff. It's just, we gotta get a decent amount of people asking for it before we start considering building it.

Tyler Hill: And some of those issues stem from, I'll call it, UXPTSD. They've been so ruined by bad user experience in another app that they want the same experience in a better app.

Christian: I think a lot of times designers have a way of doing it, but forget about the communication part. It's like you may know it's a better way of doing things, but people don't always know that it's a better way, and sometimes there's a certain amount of trust involved. So, you mentioned walkthroughs. When you design a new feature, when you think it's going to be something new, is that typically how you handle it?

Christian: You design walkthroughs, and-

Tyler Hill: So, typically, we'll push an email a couple weeks before the features out, to our larger customers. We'll let them know what's coming so they can be on the lookout, but typically we don't like to surprise our user base too much. Right? But it has to be explained. "Here's why we're doing things better." As we build the software, we're trying to intentionally focus on better communication within the app, so we don't have jarring experiences.

Tyler Hill: We have power users, right? Some of them have workarounds that they use in the software, so that user education is crucial. I like to think of our software, and the industry that it's in. People typically, they shouldn't want to stay in the software, because they have a game to run, or they have money to collect, or people to train. Right? So typically when I'm designing, or we're talking through user experience, we try to keep it as lean as possible.

Tyler Hill: 'Cause you have things to do, right? We're not a software. We're your quote-unquote doing the business in the software. No, you're getting out there. You're running the camps, and you're doing the training, so we're trying to create a user experience that's less obtrusive as possible.

Anna: You know, in research, we always look for workarounds. It's one of the best opportunities for product improvements, or a way to make people more efficient, but you kind of mentioned it as just par for the course that people make workarounds. So, tell me a little bit more about that.

Tyler Hill: Earlier on in the product's life, there were a lot more workarounds than there needed to be. I'll be kinda candid here. There were workarounds that even the product side didn't know about, but the positive side with the workarounds that we discovered were they let us know the needs that were unmet on the customer side.

Christian: At least from the outside, it seems like you've had a lot of impact on Upper Hand, so I'd like to dig into a little more. When you made that transition from Book A Coach to Upper Hand and started instilling design, how did you carve out your space to actually do what you wanted to do, and how did that interaction work out with Myles and other people on the product team?

Tyler Hill: I've been conditioned to design under pressure, so I attended the Illinois Institute of Art in Schaumburg, probably three of the most brutal design years I've ever had that I loved. Great instructors, cutthroat deadlines, cutthroat critique. It trained me to take a beating and appreciate it. Produce quickly, take, no feedback quickly, no emotion involved, and just have ... I think, at the end of the day, when the success of the product is your motive, you don't really get emotional as a designer when somebody says, "This isn't working."

Tyler Hill: Because you're part of the team, right? The success of the company, let's be honest, it's your check, at the end of the day. Right? So there's no feelings attached to it, and there's also a piece that, as a designer, you always wanna be gleaning, you always wanna be getting better, and coming in at the ground level, where there's no screens, there's no user flow, that's the best place to learn.

Tyler Hill: It's this mad dash, right? In the startup environment, where you are discovering valuable features. Right? You're writing user stories, you're getting designs out there, you're getting minimal feedback, because it needs to work so everybody can eat. You're getting, you know, customer data. You're seeing customers thrive in their businesses. You're getting hoo-rah one day, and, "Fix this or I'll leave," the next day.

Tyler Hill: You know, and you're juggling all these things, so for the two years that I've been with Upper Hand, it's been, you know, "Let's get these features out. Man, this is incredible. Wow, this adds value." Now that the software's matured and become complex, where we have multiple user flows kinda interacting with each other, now it's like, "Let's zoom out."

Tyler Hill: Now that we've put everything in the attic 'cause we didn't know where to put it in the house, let's look at this thing as a whole, take the customer feedback we have, take their clients' feedback, and really look at the product with fresh eyes. You know? And say, "If we were to do this from scratch, what would we do different now that we know what works?" And I think that has to happen, really, every year and a half or two years or so.

Tyler Hill: You know, and I'm beginning to see it in the industry, now, lately, where there's these really critical overhauls in product.

Anna: That metaphor you said of, like, everything's in the attic, and now you have to bring it out into the house. So, how do you go about that process?

Myles Grote: We have, like, a client drawer, where it used to just be events. Right? That's all that was in there? And it's this little drawer that pops out whenever you click on a contact, and we started to notice, by looking. We use FullStory, too, which is like, you can watch full sessions of users interactions.

Tyler Hill: Shout out to FullStory.

Myles Grote: Yeah, FullStory's sweet.

Tyler Hill: Send us some shirts.

Myles Grote: I don't know what I'd do without them, today.

Tyler Hill: If you're listening.

Myles Grote: We'd watch these sessions, and you start to see, like, to his point about we stuffed things in the attic, didn't really know where it should go. We thought it should go here, and then you watch the sessions, and you're like, "Wow, we were way off on that." And I think, like, transactions is an example of that. We housed all the transactions for, on the event level, within our application, and we started to see they would just click on the contact and see all the transactions on the contact level versus on the event level.

Myles Grote: And so, we see people going from the calendar, all the way to the event, to mark a transaction as paid, and then back to the calendar. So, you start to notice that things are just out of place within the app, and consolidating that into what should be the flow based on what the user's behavior is is probably a concrete example of that coming into play.

Tyler Hill: It's funny, because, sometimes when we're designing these interactions, sometimes we depend on future interactions to guide the current design process, which we've had to be careful of. It may be that something works the way it should because of something that we would introduce in the future, but we really can't afford to do that, so it's difficult, as a designer, because you're always in the future for the most part, you know, and Myles has done a great job with just keeping everybody in the present.

Tyler Hill: But it's easy to say, "Oh, this'll be solved, because we're gonna introduce ... " but that doesn't exist yet, so it's like, "What can we do to make the user experience great now and not lean on future features to improve something that we're pushing live this week?"

Christian: I wanna dig into where you're at today, and how it might be tied to the rebirth you were talking about, now. So, Upper Hand's starting to get a little bit more into facilities, and what does that mean for product? What does that mean for design? You know, where are you at in that process, as a product team?

Myles Grote: The product, you know, we've gone from just purely probably a software to talking with a lot of software-enabled hardware the devices, so the product has changed a lot, the user type has changed a lot, and therefore the needs of the customers have changed a lot. So, we're, right now, we're continuing to iterate. You know, I have weekly calls with this large customer to make sure that we're ... and not just the owner of the franchise, you know, the guy sitting at corporate.

Myles Grote: But all the individual owners, and you know, the front desk people, and we have a person from our CS staff, our head of CS, Danielle, who's traveling around the US, going to all these different locations, and meeting with front desk staff, and implementing them, and you know, she's giving me feedback.

Myles Grote: So, we're very much drinking from a fire hose right now, in terms of getting feedback from these brick and mortar customers, but I think it's going well, and I think we were prepared for it because we got out there a lot before. We literally took the entire product team, engineers and everything, to a couple of the locations, early on this summer.

Myles Grote: A lot of times, I think a handful of those situations, was the first time that some of our engineers ever stepped into a sports facility of that time, so I think it was like, literally pulling the veil off. As soon as they walked in, and it was a great learning experience for everyone.

Anna: Did you already have product there that they were watching ... ?

Myles Grote: No. We were observing.

Anna: It was just kind of, "What is it like?"

Myles Grote: Yep. We were observing. We were watching them use our competitor, that we were displacing, and just asking them questions like, "What'd you just do there? Is that a cumbersome process?" And, you know, we'd talk to the high school front desk staff and tell them to tell us what's the most frustrating part about your job, you know, with the software.

Myles Grote: So, we learned a lot of just getting out beyond our walls and understanding what the problems were before we actually went and started building them, and I think that was a critical piece, 'cause we were talking through it at Starbucks, like, "Man, we pushed a lot this summer, and I'm surprised it went as well as it did." But, you know, you start to play black some of the things you did to proactively get ahead of the building process, and I think that that forward investment of time definitely paid off.

Myles Grote: 'Cause, a lot of times, it was hard for me to pull our entire product team and engineering team away from their computers. That's valuable time. You know, that's lines of code, that's features that aren't going, those couple of days that you do that. But I think it was ... it paid dividends, and it continues to.

Anna: What benefits did they get out of that? Why did you take the whole team on the field?

Myles Grote: Just learning the customer, I think, and seeing ... there's just something to be said about seeing something in real time. I forget who it was. There was a large company. I think it may have been QuickBooks, at one point, that literally took their engineers and put them on the support desk, and at that point they started to learn and started to iterate on fixing bugs, 'cause they realized how buggy their product was.

Myles Grote: But, so, I think there's a lot to be said, just sticking them in that experience, and letting them watch and observe.

Christian: And so, from there, I don't know if this is tied to what you were talking about earlier, Tyler, the new rebirth of Upper Hand. So, you went out to the field. Did you come back and start designing new concepts before going to build

Tyler Hill: So, having the engineers there really kind of aligned a lot of the different UX conversations we were having before. Another crucial part, I think, about having them in the field was they're so behind the desk and in the code, for them to see people enjoy the software that they built, and to tell them to their face this is amazing, they just perform better when they come back to the office.

Christian: Is this starting to help sales? Like, the new stuff that you designed now.

Myles Grote: I think sales has gone kind of through a little bit of a rebirth. It's been one of the biggest challenges, honestly. We've talked about it internally with the product team, with our board. It's like, when the product team really starts clicking, and you continue to invest in additional engineers, one of the problems that we've had is keeping the rest of the company up to speed on the new features, and, really, how to sell them and communicate them.

Myles Grote: Because you kinda forget that, a lot of times, I find myself forgetting, that they're not ... I mean, they're talking to customers all the time, so a lot of times they'll get it, you know, and they'll be like ... they've been asking for it, and you build it, and they just hit the ground running.

Myles Grote: But, then, there are a lot of user experience upgrades that you do that it's not quote-unquote a sellable feature, but if they understand it well enough to what it used to be, or what it's like on a different competitor, then when they go into those sales meetings they can communicate that effectively and make it a big selling point for the product.

Anna: So, what does better product mean to you?

Myles Grote: I think, for me, better product now versus what it was like 10, or 15, or 20 years ago, I feel like it's just everything ... product is so customer driven now, I think if you can deliver a product that strikes a great balance between customer needs and innovation, I think that's a better product.

Tyler Hill: Better product, to me, is a product that lasts. A better product speaks to longevity. It's the relationship that the human being has to technology, that they feel they can't live without. That's a better product.

Christian: That was Myles Grote and Tyler Hill from Upper Hand. If you're interested in seeing what we talked about in action, head on over to You can also connect with the guys on LinkedIn, and Tyler says you can check him out at

Anna: This is the part of the show where we take what we learned from Myles and Tyler and really break it down, kinda dive in deep, and pull out the things that we thought were really interesting, and to do that, we're joined by Jon Moore. He's a lead Product Designer here at Innovatemap.

Anna: So, Jon, you and I worked on a product, specifically, that was really beautifully designed, nobody had any beefs with the UI, but the high level organization was a problem. People couldn't find things, they didn't know where things were, and it really was that, as these features got added in, they were kind of just put wherever they fit.

Anna: No real kind of rhyme or reason, and when we did the research, we found that people were just cognitively thinking about the product in a different way, so we recommended a redesign that was more workflow oriented. So, how do you take something like that, and then think through ... ? Again, like, how do you put those pieces all back together?

Jon Moore: It really just depends on how you want to organize your product and how you want your users to use the product. A great example I can think of is, like, Wal-Mart versus Ikea. Both wildly popular. I'm sure you've heard of them before.

Anna: I am somewhat familiar.

Christian: Wal-Mart?

Jon Moore: Wal-Mart. Yeah.

Christian: I'll have to write that down and check them out.

Jon Moore: So, very popular, in similar spaces in that both businesses offer hundreds of thousands of products, but they do it in a very different way, and the experience of a shopper going through a Wal-Mart is very different than the experience of a shopper going through Ikea. If you're going through Wal-Mart, everything's very organized into categories, and it's organized into aisles and shelves that'll help you find the products that you're looking for.

Jon Moore: Ikea, on the other hand, is very workflow driven, and they wanna take you through a specific experience of shopping through their store. So, they'll start with showing you examples of bedrooms that have been built and designed using their products, and then you'll kind of weave your way throughout the store, and they'll eventually take you to the products that they wanna sell individually.

Jon Moore: So, you can pick up the glassware, you can pick up the lamp that you saw earlier, and it's all tied into that workflow and that story that they wanna take you through. So, neither is right, and neither is necessarily wrong, but they're very two distinct ways that they have chosen to organize and sell their products to create an experience for their end users.

Anna: That's a really good point. I think, like, the Wal-Mart model is, I go in, I'm very goal ... I have one thing I need to get. Hopefully more than one. It's a lot, to get into a Wal-Mart, but you know, I go in, I get it, I'm out, and Ikea is very much an experience.

Jon Moore: You can't really go to Ikea just for a single item. You would go to a Wal-Mart, or a Target, or one of these other superstores, but Ikea has set it up so that they want to take you through this particular workflow because they know that, along the way, you're gonna find things that you didn't intend on buying, and you know, products can be set up the same way.

Anna: How do you balance a really rigid design, like Ikea? You have to ... I mean, you can go into, again, like you said, to the accessories and get what you want. But they have a very flow-focused, you kinda have to go through their flow, otherwise you get lost and scared, versus the Wal-Mart, which is a very generic design. It's really easy to get to that one thing. How do you balance something where it's so rigid you're changing behavior, versus being too generic that it doesn't mean anything?

Jon Moore: I think it's like an exercise in granularity, because there are certain products out there that you can use literally for anything that you want to. So, can use Dropbox to organize your video production studio, and you can use it to share files with clients. You can also use Dropbox for your personal documents and photos that you ... so, like, it's such an open, generic product that they leave it up to the users to kind of decide how they wanna use it.

Jon Moore: On the other end of the spectrum, there are products that are so rigid that, if you don't wanna use it the way that they tell you it ought to be used, then it may not be the right product for you, and that is a decision that they've made at a business level, and they've said, "This is the audience that we wanna pursue." And they do it in a very strict way. They're not going to compromise their products to make it more generic so that people can kind of be, and not in a negative sense, but, wish-washy about the way that they use the product, and get the things done that they need to get done.

Christian: This is, I think, a great discussion, and it's reminding me of another thing that they talked about, which is not just the workflow, but the workaround. So, it's not just that there's a lot of features in the Upper Hand product, but, a lot of their users, when they try to introduce new features, have created workarounds in the product. So, one of the things that Tyler was talking about is this sort of delicacy you have to take when you're designing a new feature to be careful of the workarounds people have already created.

Christian: I'd love to hear your thoughts on that, too, as well, on how you balance what's a workaround you build around, or what's a workaround where you say, "I'm sorry you had to work around that. Here's a better way of doing it."

Jon Moore: Workarounds are design gold, because it is pretty much straight up validation that this is the way that a user wants to use the product, and the way that it's been designed today isn't meeting that, and so you can look at the workaround and you can see, almost exactly, how they expect that product to work. So, I love watching and experiencing a user pursuing a workaround, because it's a lens into the way that they wish things were, and so it may not be perfect, their workaround, to directly inspire a feature.

Jon Moore: And you just literally change it to support that workaround, but it can definitely hint at a better way to solve the problem that they're looking to solve, and I think a lot of workarounds can really stem from different people who maybe weren't the original, intended audience for the particular product to use, and now a new audience is using the product, and, with a new audience comes new assumptions, new expectations.

Jon Moore: And so, if new types of users that you really didn't expect to have are coming into the product, you might start to see more workarounds, and that's not necessarily a bad thing. I think it's an opportunity for you to step back and say, "Do we want to make our product more generic so that we can expand into more audiences, or more personas, or target more users, or do we wanna let them continue with their workarounds, but we're not gonna bend over backwards to try and change the way that the product works fundamentally just so that we can accommodate those new users?"

Jon Moore: So, there's no right or wrong way to do it, but it is an opportunity to step back and say, "This is a change that we wanna make fundamentally to the way that the product works?"

Anna: One really good example of this that I've noticed is, I don't know if you guys remember, at the beginning of the year, Chipotle had the ... I forget what they called 'em.

Christian: The health bowls?

Anna: Health bowls, yeah. Something like that, where, basically, they took all their ingredients and repackaged them into the Whole30 Bowl, or the Paleo Bowl, or the Keto Bowl. So, people who are on these very specific diets were going to Chipotle and only getting really specific things, because you know, you're on the Whole30, you can't have any sugars, the only meat you can have is carnitas, and so, basically, they took these workarounds and allowed people, but you could only order online.

Anna: You couldn't walk into Chipotle. I mean, maybe, if they knew what you were talking about, you could get the Keto Bowl, but you could only order these online. So, that was one way they took basically a workaround and packaged it. They didn't change the product, but they just packaged it.

Jon Moore: Yeah, no, I think that's a really great example because Chipotle was basically just embracing what people were coming into their stores to purchase anyway, but, to your point, it's fascinating that they didn't change anything. They don't actually have any new ingredients at all. They didn't have to change the menus. All they did, it was just an exercise in packaging up their product a little bit differently than before, and it's absolutely genius.

Jon Moore: I think it fueled an entire marketing campaign around health-conscious eaters, you know, these people who were coming in with lists of ingredients on their phone, and building these very specific bowls, so they said, "You know what? That's a great idea." And they spun it. Another kind of digital example of a company that did this was Spotify.

Jon Moore: So, Spotify is an example of a very open product where you could kinda use it however you want to. You can use it to just listen to individual tracks. You can find albums, you can build playlists, and what they did was they took an opportunity with regards to packaging to really inspire users as to different ways that they could use Spotify to fit into their lives, and they did it around playlists.

Jon Moore: There was a really fun campaign that came out 2018 and 2017 around these playlists, and they would go out, and they would look at user generated playlists that people were creating, and blow them up on these massive billboards, and they would be very oddly specific playlists for things like, "I just broke up with my girlfriend, and here's a playlist that I made."

Jon Moore: Or, "I'm celebrating Grandma's 102nd birthday, and here's a playlist that we made of all of her favorite tunes from decades passed." And they were basically just packaging up their music in all kinds of different ways to inspire users different ways that they could use Spotify to fit into their lives, and I think it's a really awesome way that they didn't have to create any new features.

Anna: So, Spotify's a good example of where they saw workarounds, but they actually integrated it into the product, because they found that people were creating these very specific, Grandma's 102nd Birthday, you know, but then they brought in the browse feature of Spotify where you can browse curated playlists based on your mood, and I think that's become one of the biggest values of Spotify, is, "I don't have to create my own, 'I'm working,' playlist."

Anna: It's like they have, like, 50 ambient noise playlists that I can choose from. I think it's genius.

Jon Moore: Yeah, it's definitely a differentiator for them.

Anna: Thanks so much for listening to the show this week. If you haven't, yet, be sure to subscribe, rate, and review this podcast. Until then, visit, and subscribe to learn how you could take your product to the next level. As always, we're curious: what does better product mean to you? Hit us up on Twitter, @innovatemap, or shoot us an email at

Christian: I'm Christian.

Anna: And I'm Anna, and you've been listening to Better Product.

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