Small But Mighty, with Ridwell Co-founder Aliya Marder

Ep 14

Aug 23, 2023 • 40 min
Aliya Marder, Co-Founder of Ridwell, joins us to share what she’s learned about the people-service mindset for product work, the demands of running a startup with a real-world footprint, the power of a higher mission for rallying a company, doing more with a smaller team, the pathologies of product backlogs, strategic communication past 150 employees, and the challenge of delegating for detail-oriented leaders.

Allen: Welcome to It Shipped That Way, where we talk to product leaders about the lessons they’ve learned, helping build great products and teams. I’m Allen Pike. Today’s interview is with Aliya Marder. Aliya is co-founder of Ridwell, a startup that does home pickup of items for recycling and reuse, that in five years has grown to over 200 employees operating in seven states. Welcome, Aliya.

Aliya: Thank you so much, Allen. It’s really fun to be here.

Allen: I really appreciated seeing your keen product thinking at work while we were working on the Ridwell app project together early last year, so I’m excited to dig in to conversations specifically about that rather than just two minutes here or there in between Zoom calls or at the beginnings or ends of some other conversation.

Aliya: That was a very fun project and it’s been really fun to see all of our members loving the app. I think I pulled data on it and we had 35,000 active members, so that’s awesome.

Allen: Awesome. That’s a pretty healthy percentage of the user base. Sometimes you’ll have pitches where a company will say, “Well, I think we should have an app,” and I’ll be like, “Well, what percentage of your people are going to actually install an app?” And I don’t know if it’s public, how many members you have total, but my sense is that it’s a pretty healthy fraction of the user base.

Aliya: It is over goal. My goal was at least a quarter of the user base. So we’re doing better than that, which is great.

Allen: Awesome. And we got one of my favorite testimonials of any team we’ve worked with. We got to quote you saying, “The app is really fucking nice.”

Aliya: It is. Well, I mean, I am biased, but that’s how I feel.

Allen: Of course. But if you were to put it that way, it made our team pretty excited. Before we get into the product conversations and how you think about that stuff and some of the things that you’ve learned leading product teams and leading products for years, as you have, how would you summarize your story so far in a soundbite podcast?

Aliya: Yeah, so I got my start in startups in San Francisco, and fell into really a focus around consumer products in the early stages, kind of the MVP product market fit. Before that, I was in the restaurant and service industry, and I think bringing that people service mentality really served my transition into product and design. Because it was always about how you make people happy and how you help them solve a problem and how you make their experience delightful. And that’s what really drove me and brings me excitement in my day-to-day work. And so gravitated towards consumer products, things that bring people together, things that solve problems. But always really focused on the individual user and the individual person, what their motivations are, what their values are, and how you help them on their journey to do whatever they want to do. Now, in my case, it’s live a more sustainable life. And so it’s been really fun. I like what I do every day. That part’s amazing and I work with brilliant people.

Allen: That’s a lucky place to be. Unlike a lot of funded startups, you mentioned you were in the startup scene in San Francisco, which is many people’s origin. San Francisco has a tendency to be like that. Unlike a lot of funded startups, Ridwell has a business model that’s rooted in the real world. We’ve got real goods need to be picked up by real vans with real drivers and recycled at real facilities. What has been the kind of interesting surprises or lessons from you going from the digital-only world where you spend a bunch of time to the real world?

Aliya: Go to the real world. Yeah, it’s funny. I remember we were talking with an investor who said, “Man, you guys started a hard business.” It was like, “Thank you.” So to be fair, I’ve done a few real world startups. One was food delivery for offices. Another was tools for field service technicians who took big truck fulls of $80,000 of inventory out to gas stations to see why their pumps weren’t working. But this is new just in its volume and its logistics. I think real world, there’s a lot of upside. There’s a lot of very tangible impact that you can see on a near daily basis. When I worked in purely digital, my first job was in mobile gaming. And there’s something less fun, less meaningful about closing your computer for me and then all of your work kind of disappears. It’s like, well, it’s all in the ether. It’s like in Willy Wonka, it’s all in the bits in the sky. Having a very physical footprint in our business definitely makes things… It complicates stuff. It means we have warehouses, it means we have vans, it means we have very real physical inventory, but it also means we have very real physical impact. I can go out and see the number of pounds of plastic that we brought in from people’s homes that was going to go to the landfill and is now going to our recycler. Or I could see the… They’re called gaylords, they’re these giant cardboard boxes of corks or kitchenware that are being recycled or taken to our nonprofit partner to help refugees who are relocating to various new areas in the country. So it has a lot of meaning to it, but it definitely complicates stuff. I think there’s value when it comes to building camaraderie and building meaning within the team. And what we’re working towards has this purpose that just is very visible in a way that was hard to replicate when you’re just working on digital products. And I think the meaning that you can have in customers’ lives is different. Like our members, this is a behavior change, which makes it harder, but it’s also something that is very physical in their life and it has a presence. And we have our bags that hang in people’s kitchens and we get pictures about, “Oh, here’s how I hang up my bags.” “Well, I do it this way and here’s where I put it.” And that impact we have on both sides, front of the house, back of the house, is really fun.

Allen: Yeah, it’s interesting. I hadn’t thought about that as a product. Obviously, when we’re thinking about our product, it’s easy to just think about the digital services, especially those us in primary digital businesses to think about, “Okay, they’re our website or our app.” But the product and the ability for your product to spread awareness from person to person can go as far as, okay, there’s a physical box on my porch where people put their recyclables, or a bag in my kitchen. And then someone says, “Oh, what’s that?” I’m like, “Oh, it’s Ridwell.” I hadn’t thought about that as an interesting, I don’t know if viral is the right word for it, but an awareness loop.

Aliya: I would be a little misleading if I say we didn’t think about that a little bit when we designed the bins, that they would be sitting on people’s porches. And we didn’t want them to look like just another trashcan. We wanted them to look like something that was simple, streamlined, fits in with your life, but also be visible. It’s something that people have on their porches in Seattle and Portland and Minneapolis and Denver, and when you walk down the street, you can see, “Oh, there’s a Ridwell bin, and there’s a Ridwell bin.” And that really helps that feeling of it’s a whole community doing small things together that’s going to have a real impact. Which it’s interesting because you bring up another point kind of on the side, which is product at Ridwell goes beyond just digital product. We think a lot about the service design and the physical product and the design of the bins and the bags, which means we’re probably trying to do too much with too few people. We can get to that later.

Allen: Welcome to startups.

Aliya: Yeah, exactly. But there’s a fun part of the diversity of the product and design problems we’re trying to solve. And I think that’s been exciting for people who came from more digital backgrounds, people who came from Amazon or people who came from other digital startups where it’s tighter constraint.

Allen: Often folks doing design at a startup, if they’re working on something that has physical element to it, it’s because they’re maybe doing the yearly T-shirt.

Aliya: Yeah, exactly. You get your swag store. Or there’s a whole nother arm of the business that’s hardware design, something like that.

Allen: Right. So there’s a bunch of interesting threads I could pick up on that. But the one that I think I’m going to pull on first is this one about the impact and the motivation to the team when you have something that’s having this real world consequence of what you’re doing. And so you talked about having previously worked in a mobile gaming company and now you’re physically bringing sustainability and recycling stuff in the real world, which is a huge gap in terms of… Most startups call themselves mission-driven. Oh, yeah, yeah. I’m sure the mobile gaming company claims to have a mission of bringing joy to people, or whatever. But Ridwell being about sustainability, reducing waste, it makes for a more obvious mission. Not to say all these other startups don’t have missions, but a mission that’s potentially going to help the entire species. How have you found that’s changed your ability to… Or how you think about how you build your team, how you might build your product. Has it made some things easier, the ability to rally the team to be able to do certain things that might maybe not have been feasible if you weren’t on such a clear mission?

Aliya: I think the thing, to your point, is every company has a broad vision and usually that vision is in some way altruistic, whether it’s bringing people together over food or doing good while having fun, whatever it happens to be. The nice thing about having our mission be part of our daily life is that decisions are a little bit easier and the focus is a little bit easier. We’re able to make faster prioritization decisions because often they very easily ladder up to what that vision is. So the more members we have, the more pounds we save from the landfill. And it’s a very direct line from growth to diversion. Similarly, the quality of the partners that we can find and that we can partner with, as we find ones that reduce or reuse over recycling, all of those types of decisions become clearer because our mission is deeply ingrained in the daily work of our team. I personally feel motivated to come into work for many reasons, but I think it does help with getting through the hard days where it’s like, “Yeah, today we spent six hours in Jira, and it was brutal. But hey, we also did 6,000 pickups and that’s 12,000 pounds that’s not going to the landfill or to the incinerator.” It’s almost like immediate gratification. On a hard day, you can still look outside and see what you accomplished or what you’re part of. And really, I want that for both our company, our employees to feel that way, and also our members. You’re one of many doing one of many solutions for this bigger problem of climate change and building a brighter future. So I guess in summary, there’s the clarification of purpose and priority, which is very helpful. There’s the motivation side that both help get work done on a regular basis. Because the work means something bigger than just ourselves.

Allen: Have you found that it’s made a difference in terms of your ability to recruit people? Because I talk to a lot of people out there, talented people that work in some Bay Area company, FAANG or whatever. I ask them, what are they going to do next when they leave? And they’re like, “I’d like to make some difference on the environment, or the world.” And then often I think, I scratch my head and I’m like, “Hmm, what percentage of jobs available to you can offer that?” And you can actually offer that.

Aliya: It’s absolutely a value add for recruiting, for our pipeline. For me personally, I think there’s also making sure that people are still excited about where we are as a business, though. We are still a startup pushing for growth and success as a business, because being a sustainable business means that we can have a bigger impact on what our mission is. And so I want people to be inspired by both the challenge of what Ridwell is and the mission that we’re trying to solve. Because I think if you only resonate with one of those things, there’s just a lot of work we have to do with limited resources. And so that part can be tough.

Allen: So if someone just comes in imagining, “Oh, we’re on a mission, so it’s just going to be this playground of unicorns.”

Aliya: Kind of, yeah. I think most folks I talk to, I wouldn’t say come in with necessarily that mentality. But there are real business trade-offs that we’re making regularly, and I want people along for both parts of that journey. Because it is a startup journey and it’s a mission journey.

Allen: I guess that is the flip of this. Some decisions get easier when you’re mission-centric, but I imagine, and tell me how true this is, that some people who are maybe not in the co-founder level of the company might have an idea of, “Okay, well, if our mission is to reduce waste,” then they might not necessarily see the full end-to-end chain of results and they may get hyper-focused on one minor thing. When at the end of the day, if you’re a startup, if you don’t meet sustainability… There’s sustainability of the planet, but then there’s also startups need to make more money than they spend eventually, otherwise they stop existing. That’s the nature of capitalism in our world, that you have to keep existing in order to keep making the world a better place. Is that ever hard or is that something that you’ve learned how to socialize on the team?

Aliya: It’s both. And maybe another podcast we could dedicate to my personal beliefs on capitalism. But it has been a balancing act of communicating our strategy for growth, sustainability and our mission, and how those three things play together, and how they reinforce each other. I think a struggle has been that we can’t be for every mission. Because we’re a mission-driven company, that doesn’t mean we are every mission driven, if that makes sense. We have to focus on our specific mission, which right now is reducing waste, building a less wasteful future. And if we get too distracted by other missions and visions, we won’t be able to execute on that core mission. That is what and why Ridwell is here. It’s easy to get focused on one area or another, whether it’s, “Hey, we really want to drive the reusable circular economy,” or really-

Allen: Right. It would be nice if nothing had to be recycled, everything was reused. That would be nice.

Aliya: That would be wonderful. Or, we’re going to solve the plastics problem. Or, we are going to partner with every single CBG company out there to make sure that everything they package is compostable or recyclable or reusable. And we’ve had to pick and choose our battles, for sure. And I think we have a vision of laddering up, if that makes sense. We have a bottoms up strategy when it comes to how we tackle this problem of waste, starting with consumer behavior change and moving up the chain to companies, to government, to how can we help even on the legislation side? But all of that takes the grassroots community of people believing that this is a change we can make together. And we want to do that by moving us towards that behavior change in small, approachable, aspirational, imperfect ways. I think there’s historically been a very all or nothing approach. I mean, the movement’s even called zero waste, so it’s an all or nothing approach to living sustainably. And one of my big beliefs is that small actions add up. And there’s a lovely quote, “We need millions of people doing things imperfectly, not a few people doing things perfectly.” And I see Ridwell as one of many imperfect solutions to this problem that people can start chipping away at together.

Allen: Yeah, I love it. So shifting back to… As much as I find all of this stuff fascinating, and could probably talk to you about it for an hour, or more, this is a product leadership podcast. And so in service of that goal, you’ve been building these products, the physical goods, the physical parts of that we talked a little bit about. There’s also the website and the mobile app which we were talking about. You mentioned briefly that you have this very small product team to make all of this happen, both on the design and the engineering side, which is something that I appreciated working with you on this app project, seeing how much your team was able to execute on and at the level of caliber for how small the team is, which is a little bit of a famous thing. A lot of people end up wishing, “Oh man, I wish I could have 100-person product team. Then we would get so much more done.” And then they lament five years later, and they’re like, “Oh God, what have I done? We’re so much slower than we used to be.” So I have two questions to you on this small product team thing. One is how much of that is an intentional thing in order to keep that sort of lean focus versus just the constraints of being a startup, you always have to do more with less? And then second, how do you think of making the most out of a small product team?

Aliya: Those are meaty. So, one, thank you. I am very proud of the team that we have here, the small but mighty group of folks. Some of it is the natural constraints of a startup environment, where we have limited resources. I want to be very conscientious about how we spend our resources in a way that is both sustainable but sustainable in the long run, I think. We’ve seen a lot of the pain that comes from businesses hiring unsustainably, and we’ve been really fortunate that we haven’t had to go through significant layoffs or anything like that. And so part of that is living, one could say, stingily, but I would rather say within the constraints of our business. That has kept our team small. However, many would say we are underresourced. Our team is very small. And we’re trying to serve, if you want to count it, six or seven different product lines across the needs of our business with four to five engineers and a handful of other folks playing multiple roles. But I think what it has done is caused us to be very intentional about who we hire. Because the environment is both very exciting, it’s very high ownership, it’s high paced, but it can be difficult. And so we’ve had to be very, very deliberate about who we bring on that team. And so it’s been this interesting balance of both, yes, we have constraints as a business, but also because of those constraints, we are selective and deliberate about the types of people who will succeed on the team. When you have to wear multiple hats, when you have to get excitement out of that level of ownership, there’s pretty tight camaraderie. When you only work with four or five people regularly, got to get along, got to work together, got to learn from each other and work fast. And so I think the reinforcing of those things together has caused kind of a virtuous cycle of strength in the team, ability to get things done well, habits of knowledge sharing and teaching and mentorship that is almost circular. So it’s let us be really high performant while staying small. And yes, we should probably hire.

Allen: But I mean, that’s the famous thing about a product team – and this is probably true for all teams, but I’m just familiar with product teams – is that if you don’t feel a little bit underresourced, and if you don’t feel a little bit like, “Oh man, we should probably hire,” then you’re probably too big and you’re probably being wasteful. Maybe that’s just a story that resource constained leaders tell ourselves.

Aliya: It’s like, no, we’re doing great, because this discomfort’s what it’s supposed to be.

Allen: But I mean, I don’t know. I know you’ve worked at various places, different companies and sizes that you’ve probably seen an overhired team and some of the pathologies that can come into that. Bureaucracy for the sake of it and all that kind of stuff that tends to happen.

Aliya: Yeah. Process gets harder and slower. Communication lines get harder and slower. And I think it’s even harder now, post-COVID, when many teams are hybrid and just working through the different speed of communication. When you’re over Zoom and doing things async and doing things via Slack and it just adds different challenges. And I think those challenges are exponential as your team grows, which is tough.

Allen: Yeah, I recently wrote a short article called Do Something So We Can Change It, which is one of my quotes I like to encourage the team. It’s like, instead of just spending so much time on a decision that we could change later, let’s do something, see how it is, learn from that action. And the number one comment on it someone posted to Hacker News today. And the number one comment was someone saying, “Well, I like the idea of that, but in practice, you do something and then there’s 18 layers of bureaucracy and then you can’t change the printer cable because of this and this and this. And so you have to actually overanalyze everything in order to make any progress.” And I’m like, “Hmm, we work in different organizations.”

Aliya: And it’s actually interesting. So we’ve gone through, even though our team is small, and maybe because of it being small, and your second question was, how do we manage to get… I’m going to paraphrase it incorrectly, how do we manage to get anything done?

Allen: I think I said get the most out of a small product team. You can get anything done, you get lots of things done. It’s less about how do you get anything done. With a small team often it’s about there’s so many things that you could get done, how do you pick the things that you think will have the highest impact, or that will have the highest impact for that small team to do?

Aliya: Totally. I think there’s been a really interesting mindset shift on my team, driven fairly collectively, which is exciting. We historically have been fairly reactive. We hear of a thing going on, we change it, we move on to something, to whatever else the next reactive thing we have to do is. We launched a pretty significant product change in the beginning of June, so earlier this summer. And so much changed that it was almost impossible to measure exactly what changed. Which is a really scary thing, I think, for a lot of product and engineering people. But what it’s forced us to do is take on a much more proactive, to your point, “let’s do something so we can change it” approach. Where now we’re, I don’t know, weekly iterating on right now our signup flow. But it’s brought in this mentality of how do we learn and test and grow a thing rather than reacting to whatever’s coming in? And some of that reaction I attribute to just the nature of building, back to the original questions, building a physical business that has product requirements. It has many customers that you have to serve, kind of from the get-go. And so we are very reactive to the needs of our drivers and the needs of operations and the needs of our members and the needs of our marketing team, et cetera. And so I mean, the short answer is ruthless prioritization, but the really meaty thing is how do you actually prioritize anything? I don’t have the silver bullet. I think prioritization is really, really difficult, and depends so much on who you’re trying to serve and what your business goals are, and who your team and resources and what their skillset is. That even working with your team at Steamclock, it was like, “Well, we really want to do this mobile app. We believe it’s something that will make behavior change easier for our members and that our members will really love. We don’t have the resources to do it in-house. How do we make those resources elsewhere?” For me, it always goes back to who we’re trying to serve, probably first. And then second, what are their needs, what are their pain points? How does that line up to our business objectives, and what do we think the real world dollar impact, even, of this investment could be? And then what resources do we have? Can we actually get it done? And so for me, it’s a desirability, viability, feasibility, 1, 2, 3, that then usually has to cycle through a few times to find the right solutions or how we’re actually going to approach that problem.

Allen: I think every product leader and every team size will have different settings for this. But what’s your read on the value of having a big backlog? Some people are like, “Well, just keep the big backlog and we’ll get io it at some point.” And it helps us emotionally to just be like, “Okay, it’s in the backlog. We’ll maybe never see it again.” You mentioned spending hours in Jira. And some people are like, “Dammit, we’re going to keep five things in the backlog. And if you want to add a sixth thing, you got to remove.”

Aliya: Inbox zero versus inbox a million. Backlog a million. I have a very vivid memory of one of my early product mentors, his name’s Chris Butler, who used to have a garbage can labeled backlog, which just always sticks in my head. I think backlogs are like safety nets, I guess. I think they’re helpful, especially for things like stakeholder management, where it’s like, yes, we have captured this thing, it is visible. We have it, we’re not losing it and we can revisit it later, but it’s not in the sprint, or it’s not in the next sprint. And so somewhere between Asana, Jira and Excel, and we don’t have to get into the weeds on product management tools because dear God, please no. The value for me has come somewhere from having a living roadmap, having regular meetings, prioritization meetings with stakeholders where we’re listening to what’s important to them and what’s important to their customer. And then regular alignment, kind of roadmap alignment with the engineering team where there’s this give and take. And maybe this is just something that’s nice to do because we’re such a small team. Because I can go around and sit down with everyone and we don’t have to have a ton of process around it.

Allen: That’s part of why small teams are so powerful. Because it’s possible.

Aliya: Exactly. I can go sit down with everyone and not lose my mind. I think when things go stale is when things get dangerous, I guess, or when things get useless. And so focusing on keeping things living, keeping things updated, and being willing to change, which I think is the danger of backlogs is you get stuck on this order. And it’s like, “Well, this has been here forever. We should probably do it.” But that’s the wrong reason to do something. Is it important? Go talk to someone, find out if it’s important. So I don’t know if I have a solid answer there. I think, in short, backlogs can be valuable for communicating that someone has been heard but not necessarily valuable for the practice of prioritization.

Allen: Yeah, no, I mean, I think that’s a great summary. And I think that crystallizes why you tend to see larger and larger backlogs in larger and larger organizations. Not necessarily because there’s more potential things that need to be done. You could imagine the larger organization has a more mature product that actually needs fewer improvements made to it. But there’s more stakeholders and there’s more people who don’t want to see… Nobody wants to see the email from Jira saying, “Your thing is closed, this won’t fix it.”

Aliya: Exactly. So-and-so archived your ticket. Saying, “Oh.”

Allen: And if you don’t have a personal relationship with that person because the organization is so large, then it’s 10 times worse. Because then you’re like, “Oh, this team’s out to get me,” or, “They’ve gone rogue.” They don’t understand the importance of this minor thing that in fact the customers don’t care about or even realize.

Aliya: And even as a team of… We’re a product team of less than 10 in a company of almost 300, there’s disconnects that evolve there, where there’s this feeling of like, “Oh, well, the engineers never do anything to fix our stuff.” And so even at a team that small, we’re spending a lot of effort talking and learning and getting closer connections with people. Which is, again, a opportunity that we can do because we’re small. Otherwise, it would take 20 full-time people to be building those connections and be communicating back and forth.

Allen: Well, even at your size, you’ve surpassed that famous Dunbar’s number where you have more than 150 people in your org. So communication now has to be intentional, and everyone doesn’t know everyone. Your product developers don’t know all the van drivers.

Aliya: It’s so hard. I remember when I knew all our customers by name. That was a real fun moment where I was like, “Oh, we’re going to Mary’s house again.”

Allen: Let’s ask her how the service has been going and get feedback on the bag just by the nature of me just walking. And then you could generalize as, well, this is probably how things are going to work, because you were only in one city. And now you have like, well, how do things work in Seattle versus how do things work in Georgia?

Aliya: Exactly. Yeah. We just launched-

Allen: Oh, no, our bins are melting in heat.

Aliya: Please no.

Allen: To be clear, I don’t think that’s actually happened, but the kind of things that you could just assume, “Oh yeah, well, it should generalize.” Eventually it won’t.

Aliya: Exactly. And we’re learning that, the nuances of each of the markets we’re in. Both from a operations perspective and from a member perspective, they’re very, very different. And that’s been one of the biggest kind of exciting challenges for us is figuring out how we talk about the value of what we do, both agnostic to where we are, but also very relevant to where we are. Recycling and waste is a very local problem often, because the regulations change, the laws change, the pricing change. Everything is different and it can be different across the street. So as we’ve gone to Atlanta, as we’ve gone to the Bay Area, as we’re entering Los Angeles, these things have become harder and harder to individually hold in your head. And to your point about having to be very… What was the word you used? Intentional, which I like. Intentional about internal communications. It’s also true about external communications and brand and how we’re represented. That’s been one of the biggest growing challenges. I’m a first time founder. Not keeping that a secret or anything like that. So that transition past that 100, 150 point line where communication has to be intentional, and you have to be repeating the strategy in every meeting, repeating your values in every meeting. And I feel like a broken record, and I feel bad for the people who are in consecutive meetings with me. Because they’re like, “This is the fourth time I’ve heard this, Aliya.” But I want to get to the point where people are repeating that back to me. And having to figure out that intentionality around team building when I don’t get to interact face-to-face with every person, that’s been a challenge for sure.

Allen: Yeah. That has been a theme on the show that leaders, especially product leaders, but leaders in general, and the larger org they’ve led, the more likely they are to mention that you have to be repeating the strategy so many times that you’re sick of saying it and you think everyone must be sick of hearing it. And then still someone will say something that means that it’s somehow just either just gone over their heads or it went in one ear and it was in there for a while and then it started to… As much as you’re saying it repeatedly, you are only there some small percentage of the time of these people’s experience where they’re interacting. I had experience recently, I’m a smaller scale, 16% org. And so I am still hitting these things where I assume, of course everybody knows strategically what kind of work we do and don’t do and how we prioritize things and what we’re seeking to be doing and why. And then I went into a leadership meeting and realized it was only 80% overlap. Because it had been in my head, we’d never really fully written down some of these things. There’s the high level, but then the details when it actually got down to it. So yes, repetition.

Aliya: Yeah, and it’s interesting. It’s the repetition, piece because what I want people to do is have ownership and accountability. I think a startup’s unique advantage is that we can make decisions faster and we can move faster. The faster you make decisions, the faster you can move. And I think the death of us would be if we consolidate decision-making authority. And so by constantly repeating our strategy, my hope is that more and more people can make better, faster decisions without me being in that room, to your point of I’m only in the room so many percent of the time. That challenge has been right-sizing that strategy for the different types of people we have on our team. We have a really diverse team when it comes to the types of jobs that they have and the responsibilities. And so figuring out what’s relevant and important that people can make good decisions on has been another difficult challenge for us when we think about leading Ridwell and distributing decision-making power and ability.

Allen: Yeah. That’s actually perfect because it leads me to the question I had lined up for last as we run down our time, which is, I acknowledge, a hard one that I personally struggle with. So what the topic is, is delegation. And I know you’re somebody who likes to see details done well, likes to see things executed at a high level and make people feel great, as you mentioned before. And I have that same gene of I want things to be executed really well, and I delight in getting that delight through to the last detail. But you can’t do that for every single detail or every single surface of everything yourself. So how do you think about that delegation, and what level of detail you should be working at in your product work, and where the details it makes sense for, like you say, the strategy that you communicate to drive them?

Aliya: That’s a great question. That is a hard one. And I don’t have a solution yet, so as soon as you come up with a solution, let me know.

Allen: In between the two of us, if one of us solves this, then we’ll let the other know.

Aliya: That’s a big win. That’s a huge win. It kind of boils down to trust for me. So the question around how do I delegate is around how do I build trust. And some of that is in the early hiring process, finding people who understand the challenge that we’re facing as a business, understand the challenge we’re facing to our mission and who are engaged with that. And so in the end, if we have the same goals, I do believe that regardless of how the tactics get decided, we’ll be headed towards the same place. So that’s one part of trust building. Another part which is potentially sometimes painful for the people who work for me is a more slack, increasing amounts of slack as trust gets built, especially with new folks who join the team. So it’s like we work very, very closely together and we align on the same decisions over and over again. And then as that rapport and trust gets built, that the types of things that I would expect that person to come to me with get either higher level or just decrease over time because we’ve kind of aligned on decision-making frameworks.

Allen: I’ve heard that referred to as calibration.

Aliya: Yeah, I think that’s a good term for it. I should use that. As we calibrate our decision-making frameworks so that we have a shared set, we have a shared framework, we have a shared set of a rubric and principles, I suppose, of how we make decisions and where we’re headed. And some of that comes back to the repetition of strategy, where if we’re constantly communicating where we’re trying to go, hopefully most people can drive the car in that direction, given the right set of tools. And so honestly, some of it’s just been letting go. Taking a deep breath, closing my eyes and letting go, and it’s like, it will be okay,

Allen: Hire smart people.

Aliya: Yeah, it will be okay.

Allen: We’re pulling in the same direction.

Aliya: And also setting expectations with the people who I work with, where it’s like, “I want you to make the first decision. And I will be honest with you if I either disagree.” Or rarely if I would’ve made a different decision, because usually those are very tactical, like in a design example.

Allen: I tend to use font selection.

Aliya: Exactly. Font selection. Exactly.

Allen: It’s obviously subjective.

Aliya: Exactly. And it’s like, my brain went to button color. It doesn’t really matter. So what if we would’ve made a different decision as long as we’re moving towards the same guiding light and we’re measuring by the same metrics? But just a starting point, a foundation of directness, that if I feel like there’s a fundamental disagreement or misalignment with how you’re making decisions, I’m going to bring it up. And we’re going to talk about it so we can both move forward from a place of trust and alignment rather than someone feeling like I’m second guessing them or I’m overruling their decisions. Because I think telling someone that you give them decision-making or delegation authority, but then coming in on top all the time, is a really good way to make people feel really not great about their work, about their work environment.

Allen: You claim not to have an answer to this, but I feel like you gave a pretty good answer to this question. There’s a difference between not having an answer and it still being hard even though you have a guideline.

Aliya: Maybe that’s what it is, is I’m saying that it’s really hard.

Allen: It is really hard.

Aliya: That it’s a daily struggle. And to be honest, there are things that I still do myself, either because I don’t want to burden my team with it or because I can’t help myself. I’m trying to reduce the number of those things that there are, because usually they work outside of the process or something like that, and in the end kind of bum people out. But yeah, I still fall victim to my own desire for individual contributorship.

Allen: We all do. Well, thanks, Aliya. This has been awesome. Where can people go to learn more about you and your work?

Aliya: I think that the easiest place might be just LinkedIn. I have a website. I don’t remember the last time I updated it. Some people probably who you have, some other guests on this podcast are probably in a similar boat. But I would also encourage people to check out Ridwell at ridwell.com, because that’s really been my life focus for the past five years. But it’s been a pleasure. Thank you for having me.

Allen: Awesome. Well, thank you so much for being on the show. It Shipped That Way was brought to you by Steamclock Software. If you’re a growing business and your customers need a really nice mobile app, get in touch with Steamclock. That’s it for today. You can give us feedback or rate the show by going to itshipped.fm/contact. Until next time, keep shipping.

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