Angil Tate: Leveraging Failure to Shape Winning Teams

No matter your role or seniority, it’s critical to shift your mindset on “losses” and failure – from impactful cross-functional collaboration, to managing up, and cultivating a psychologically safe team.

Angil is a Design Leader shipping mobile/web apps at WillowTree. With a portfolio across travel/leisure, financial services, food/beverage, healthcare and entertainment she has a diversified well of experience to share. She highlights failures she’s encountered while shipping software in a client-facing, cross-collaborative environment and how those failures came to be leveraged to deliver great work.

Whether you lead or contribute your team, you’ll leave with actionable strategies and tactics to help you transform setbacks into springboards for success.

You’ll learn:

Failure is not a flaw – it’s a critical ingredient in building strong, innovative teams.
Psychological safety empowers people to take risks, speak up, and grow from mistakes.
Constructive feedback, when done with empathy, can repair trust and strengthen collaboration.
Shared understanding and clear roles are key to unlocking team synergy.
Mentorship and vulnerability create space for learning, resilience, and leadership at all levels.

Slides

BoSUSA24 | Angil Tate | Leveraging Failure to Shape Winning Teams from Business of Software Conference

Find out more about BoS

Get details about our next conference, subscribe to our newsletter, and watch more of the great BoS Talks you hear so much about.

Next BoS Conf – USA 2025

Get updates

Watch talks

Transcript

My name is Angel, I am a senior product designer at Willow Tree. I design applications and software that people love. You’ve probably interacted with something I’ve designed. I won’t tell you what, because I signed NDAs, unfortunately.

I love thinking through software and strategizing with clients. Willow Tree is a client facing consultancy, building, researching, strategizing and developing for clients. So that’s a little bit about me.

I’m from Atlanta, and that’s part of my personality. I’m not from Raleigh, but I do live in Durham, and I like it very much. So if you want any recommendations, if you’re staying longer than just today, please reach out to me and ask for some recommendations.

So we’re going to be talking about some Ls that I’ve taken, which I’m putting myself up here very vulnerably for your enjoyment and entertainment, so please remember that when you laugh at me. But most importantly, I want to talk about how you can leverage or how I’ve leveraged failure to shape winning teams, and how I believe that folks in your position, CEOs, founders, people, managers, can get a peek inside what it’s like for individual contributors to do that, and what I’ve observed from my teams and myself, how we’ve leveraged it and really created environments where failure is a training ground and not a punishment.

I’m really excited to be here. Y’all got some big brains, like I’ve talked to some of you guys. You’re like, I’m on my sixth business. I’m like, what? That’s insane. I have a dog, like this. That’s crazy, but I I feel very, very grateful to be here. At minimum, you’ll hear some good stories. At maximum, I hope that you can take something back to your companies and your teams and the people that you work with and that you manage, and hopefully you can relate to some of these L’s, because I’m sure you all have taken a few of them.

All right, so just one time I messed up so bad, I genuinely thought I was going to get fired, this was last year, so it wasn’t that long ago. But I missed a ton of meetings. Okay, I missed a ton of meetings. My clients were really pissed off, and I thought, surely I’m out the door with the next round of layoffs. But I really must have turned it around, because just four months later, I got promoted to senior. So all I’m saying is, you might want to listen to me. That’s all I’m saying.

Why Failure Matters

But I want to talk about what happened and how I leveraged that and obviously got promoted, but more importantly, recovered that relationship and really propelled my career forward, and also propelled my team forward. But before we get started, can I get a show of hands? Who likes to win? If all your hands aren’t raised, I’m going to teach you. Who likes to lose? Nobody. That’s fine.

I expected you to say that or to not have your hand up. But the interesting thing about loss that I realized when I was writing this story, there’s this phenomenon that happened. So some of you may play games like D&D. Might be kind of nerdy. You might play cards or poker or something like that, but have you ever played with someone who’s never played before and they win the whole game, like in a very dramatic way, like they just sweep the game? Right? Some of you, I’m sure you’ve played that way. I’ve been that person that’s won the whole game and has no idea what’s going on.

I think what makes that frustrating, right? Is that if you’re someone who’s really good at this game, you’ve likely lost, you’ve developed some strategies to win, and you understand what it takes to win and also what it takes to lose, but the person that won and has never played before, they don’t really understand what it takes to lose or win. They just played. They don’t have a strategy, they don’t have experience, they don’t have understanding. They haven’t had to take it on the chin and then learn from that and keep going forward. So their winning feels really bitter sometimes, and people aren’t nodding, but I know it’s true for you, so it’s fine.

But I think if we approach our work that same way, of having a deep understanding of failure and loss and having a good relationship with it and encouraging our teams to do so, I think that our products, our software, our sales processes and our teams will be way better because of it, and that’s why I believe that failure is a reliable advisor.

I don’t think that my career success is really about how much I get it right, even though I strive to always get it right, but many of my mountaintop moments in my career and on my team and even in my organization and the good strategies that come from that were really as a result of my failed moments and our failed moments as a team, and then investigating those further and asking how that happened and what we can do to grow from there, instead of hiding behind maybe shame, embarrassment, anger, resentment, all of those real feelings that we feel at work, but kind of tuck away and act like we’re not human beings, even though we absolutely are.

And so without failure, we really can’t reach innovation, which is something I had to learn over and over again. I’m sure all of you know that you’ve you have several businesses and several products that you’ve started, so you know this to be very true, but sometimes knowing it and actually applying it, there’s a roadblock there. And I know I’ve experienced that as someone who makes things that people use. So when you’re making things for people, you have to make them with people.

So there’s a two pronged failure that occurs. There’s failure that occurs within the team. So our failure to work together, our failure to communicate, our failure to thrive as a team, and then the failure of the product itself. And I would argue that that first failure is what contributes to that second failure.

I don’t know if you all are familiar with Bloom’s Taxonomy of Cognitive thinking. So it places remembering at the lowest level of the pyramid. So this is the ability to retain and recall information. But if you look here, I called out evaluation because you’ll notice that before you get to creativity and innovation, you have to evaluate and make judgments based on sound analysis. So in order for us to create and develop and design and innovate and generate, we have to assess, judge, defend, prioritize. So we have to get to this place where we evaluate, and it’s really easy to stay in this remember space. Like, oh, you you messed up, or I messed up. I remember it. I remember the cringe moment. I remember how it felt, and I just want to move past it. You have to work through this. And you have to get to this evaluation. You have to critique what happened. You have to evaluate it. And then only, then cognitively, can people really get to true creativity.

We talk about this a lot in design, naturally, because I’m sitting here thinking through, how do you engage with that interface? How do they make that next move? How do they do that action? And all of these steps kind of come into play before I can get to this place of invention or creativity.

And so when we shift our perspective on losing, we can appreciate winning more. So as you can see, what Bloom’s Taxonomy tells me is that it’s not enough for myself or you as leaders, or for your teammates, the people that build the things that you sell, to remember the loss, to recall that it happened. But for failure to serve as this reliable advisor, we have to intentionally evaluate it so that we can leverage it for that creativity and growth, which is what I just had just said. And so your teams have to know that they’re allowed to fail, and it’s up to the leadership, the people, managers and other people on their team, to create an environment where failure is leveraged and can be used as a training ground. It has to be a safe space for people to know that when I make a mistake, I can learn from it, I can evaluate it, I can assess it, but far too often, at least in my experience, and you can probably relate.

I make a mistake, and the first thing I want to do is hide. I want to cry, I feel ashamed. I want to get angry. I want to blame someone else, but when I’m on teams, we’re encouraged to really sit through and think through and own what we’ve done. We’re able to get to way better outcomes and deeper innovation and better products and better teams. So it’s important that your teams, your people, know that they have this space, the safe space to fail and try again and learn and grow.

So today I’m going to go through three of my most poignant L’s, as I like to call them, or lessons that I’ve learned. How those turned out. Then I’d like to talk about some strategies that I’ve both employed as a result of that, strategies that my team has employed from a larger level, like things that we do to both mitigate and learn from failure, and then some takeaways from that.

Want more of these insightful talks?

At BoS we run events and publish highly-valued content for anyone building, running, or scaling a SaaS or software business.

Unsubscribe any time. We will never sell your email address. It is yours.

Lesson 1: Fostering Collaboration

So here’s a switch I was on this really vague and chaotic engagement. Once again, I’m client facing, so companies like your own are ones that we typically interface with or larger, and we’re helping them maybe deploy a new feature or figure out what the next phase of their development would be. And this client was just like most clients, a little chaotic, a little vague, a little swirly, but we had a brilliant team of designers, strategists and content experts. They were all seniors, and so you would think that because we were all seniors, we were fast, we could get to the answer. We just knew what to do. That’s not what happened. We didn’t do anything. We couldn’t figure it out. And that’s kind of the downside of maybe placing an all senior team together, is because there’s a lot of assumptions and there’s a lot of brilliance in the room, but sometimes it can be hard when you’re kind of stuck behind your title and your experience, to remember to come out of that and to connect with other people.

So my strategist on the team was new. She was new to our organization, and what that means is that we didn’t have a shared language for how to work together. Our roles overlapped quite a bit. So at Willow Tree, designers are expected to strategize in a very visual way. Our strategy output is maybe not the same as someone with the strategist title, but we’re expected to do something very similar and have an output that is commensurate to our role.

So she thought designers just execute, but not strategize. She came from a really big firm where the strategist would create wireframes and then pass them to designers, and she didn’t know that, I don’t roll like that. You’re not giving me a wireframe. I’m gonna do my own work. As you can see, I almost got defensive when I said that, and that’s how I felt towards her. So we lacked this shared understanding of how to work together, and that seems like a very rudimentary issue, right? Like, okay, we’ll just figure it out. But I’d be willing to bet that everyone in this room can relate to being on a team, managing a team, observing a team that is just having a hard time getting it together, whether it’s craft, communication, synergy, you name it, it’s easy to say, and it’s very simplified. But developing a shared understanding is an intentional thing that you have to work at, both as a team and as an individual.

So me, oh, I took I viewed her as a teammate. I didn’t like that girl. I didn’t like anything she said. She showed up to the meeting. I’m not talking to her, I don’t like her. That’s awful. We have to work together like it’s five of us on this team. I was very focused on what was wrong, rather than moving forward. Can anyone relate to that experience? You’re just so fixated to two people. You’re all perfect, I know it’s fine, it’s fine. But because I was, I was in this spiral, I was like, Man, I just don’t like her. She doesn’t get it. She doesn’t know my job. Just so focused and fixated on that, rather than, well, how could I communicate with her what her job should be? She just got here. Maybe she doesn’t understand. And so things were really, really tense. We kept showing up to client meetings with nothing to show. And that is very cringy. These people are paying by the milestones, sometimes by the hour, and to show up to a meeting with nothing to show them is fatal in agency world, but that was a result of all the tension that we had. We just could not figure it out, could not get it together. I wasn’t the only one feeling what I felt, other teammates felt similar about other people. So it was just it was hard to really work together in that sense, and we didn’t have much clarity.

But after working through my emotions, I put on my big girl hat and I pulled our rubrics. And so if you don’t have rubrics for your teammates, I would suggest you develop them. There are plenty of HR consultancies out there, plenty of individual consultants that can help you write the language and really identify what roles are. But in this situation, having a shared database of what her role is and what my role is written down, and it’s across everyone, no matter who you are, what you look like, how old you are, was extremely helpful for us. So now I couldn’t really guess, like, what is she supposed to be doing, or what are they expecting of her?

So I pulled our rubrics to understand these expectations that we had and to locate the tension. Then I made a Venn diagram in something called Figjam. Designers use figma software to design our products if you dabble in design in any way, or you’re very close to your product, you probably are familiar with Figma and Fig jam. So I made this little Venn diagram. It was really pretty and cute. As you can tell, I like to get pretty and cute. And I wanted to show where our roles coincide and where they are unique. I thought that would be very helpful for us to understand.

And then lastly, I added some context and ethos about the design team so that she could understand who we are and how we function. But the most pivotal piece here is having the rubrics there for our access, so that we could really read what was expected of both of us. So then during our next one on one that I had to schedule, kind of had to eat a little bit of humble pie, because pie, because I didn’t like that girl, remember? So now I had to be the one and say, Hey girl, do you want to chat? Do you want to have a coffee? And that felt very weird, but you have to overcome those feelings.

And so during our next one, when we went through this document and we unlocked a major key. We discussed where we could amplify each other’s unique position, and then where we could team up in the overlap. So there’s a ton of overlap with storytelling. For example, owning the story, owning the client relationship. There was a ton of overlap with that. So we thought, how can we amplify that with one another? But then where it’s unique? Where can I give you the space to flourish in what you’re expected to do, unique of what I do?

And here’s the first lesson that I learned from that loss, that effective leaders, no matter what your title is, or how old you are, or if you have a real like leadership role on the team. Effective leaders know who is on the field and ensure that their players understand their positions. See, we made a ton of assumptions about our expectations about our abilities and our skills based on title. I thought, she’s a senior strategist. This is what she does, without ever looking at her rubric, without really talking to her. And I thought, well, she knows I’m a senior designer. She should know that this is what I’m responsible for. But she didn’t. She didn’t know that. And so while titles do provide us some hints, they don’t really tell the entire story or provide enough context. And this would have gone much differently if I didn’t have comfort with this conflict, or if I leaned in to how uncomfortable it would feel to talk to someone I felt like I didn’t like or had tension with.

But no matter what effective leaders do just that. They bridge that gap, and they foster collaboration by developing a shared understanding with their teammates, by ensuring that everyone on the field knows exactly why they’re there.

Lesson 2: The Feedback Loop

I actually spoke with Aubrey the other day and asked me, you know, how do you how do you give feedback to someone about their work and their quality of work? And I’m no expert, per se, but I’ve had to get really good at giving and receiving feedback, and I think that that’s difficult no matter what your title is or what your role is, because it calls us to be very vulnerable and very honest. And sometimes the people we don’t really know that well, so we may not know how they’ll respond. And so I hope that me sharing this helps, helps answer some of those questions, and I’d love to talk more about that afterwards.

But positive feedback serves a really good purpose. It’s encouraging, and it makes us feel good, makes us feel warm and fuzzy like you look so nice today. You did so great in the sprint. Your hair is pretty. Wow, you take great notes. Like it all serves a good purpose. But to drive our work, we need to be comfortable and confident delivering constructive feedback. This is especially challenging when providing feedback to leaders, people like yourself, individual contributors, and even folks who maybe aren’t ICs, but still a rung below CEO or founder, CTO or CFO, have a really hard time crossing that dynamic divide of providing feedback to someone who was in your position, because there’s a there’s a dynamic, there a power dynamic. And so it’s tricky to give that feedback to more senior teammates, and it’s the responsibility of leadership and also everyone else on the team to create an equitable space for constructive communication, because from that space is where we really get true innovation and better products.

So in this situation, I was working on a long term engagement for about 13 months with my associate design director, so he was about two levels ahead of me at the time. I was growing as a mid level product designer, and I really looked up to him, which was part of that dynamic piece I was referring to. So our relationship was tested when the client provided some constructive feedback that put us on the defense. I thought we had a great relationship. We work really well together, but our client was in a meeting and provided some feedback on something, and while I was leading this design review, my teammate interjected while that feedback was being given.

I’m sure you all can relate when maybe you’re watching someone who maybe doesn’t know something as much as you do, or you may feel like, Oh, they’re not telling the story I want to tell her. They’re not really hitting the proposition that I want them to hit. And you have the urge to kind of jump in and interject and kind of steer the conversation. Anyone can relate? No, no. Okay, cool, cool, cool. Yeah, that is terrifying as the other person that situation. So he did that, and I understood why, but I felt like he took the reins and didn’t allow me the space to receive and address my client’s feedback, so that I felt like a punishment, almost.

And that moment didn’t feel like he trusted me or really viewed me as a capable teammate, more of a almost like a liability, in a sense. And I thought, well, how can I even hear their feedback and understand what they need and what wasn’t right, if you’re just going to jump in and interject and almost attempt to save the day. So he shared his thoughts afterwards, and because I looked up to him, and I really do love what I do, I got to work right away to refine the work, to really think through what the client needed, and what they said. And I thought everything was okay, so I saw him later, and I was like, Hey, are you open to some feedback? No, he was not. His response was very defensive, and it poured a ton of salt into an open wound. That was really scary.

So rather than open up about how these tense interactions affected me, I gave him the coldest shoulder that I could muster up. I mean, it was ice cold. Don’t talk to me. Don’t look at me. I’m not acknowledging you at the stand up. I have nothing to say about you at the retro, we’re not friends. I resented him secretly. Probably knew that. It probably wasn’t a secret, but I refused to provide any explanation in my changed behavior, and I wasn’t willing to be honest and confronted because I felt justified. You don’t get to interrupt me in a meeting. You want to go tit for tat. I’ll go tit for tat. That’s kind of how I viewed it at the time, very childish.

But we were no longer receptive to one another on collaborating openly. And the thing about doing teamwork, especially on a team as big as we had, we had 25 people, when someone’s not open to collaborating and going back and forth with you and sparring creatively, the work really does suffer. So our productivity was impacted, our effectiveness was impacted, and our PM was just kind of frustrated, and we held up a lot of the work for a few sprints, which was a long time. What was once a good relationship now felt incredibly sour.

But I ended up meeting with my mentor, who was a project manager. And I love being mentored by people who aren’t designers, because they have so much perspective and so much insight outside of what I do every day, which is push pixels and make things look nice. But I met with her, and we worked through all of these emotions. And I could have gone to my manager, sure, but there’s this safety in mentorship where you’re not really afraid of punishment or being reprimanded like you would with a manager.

So she helped me work through these things, and I found my lead at a happy hour, which is great for me, because he was probably a little tipsy, so that really helped me out there. And I was like, Do you want to chat? But at this time, we knew the tension was there, like we could feel it. It was bad, it was awful, and he was open. So not only did I share my initial constructive feedback, like, hey, when we had that one meeting and the client gave feedback and you jumped in to help, it didn’t really feel like help to me. It felt like I wasn’t capable. You didn’t trust me. I shared that feedback, but I also opened up about the impact of his reaction as a leader. And so when I see someone that is a leader in my in my team, whether by title or by function, right? They just act as a leader, and they shut me down. They’re not open to giving feedback. That made me feel like my voice did not matter. So for a while, I just didn’t really say much. I felt like, if you don’t care what I have to say, I’m not going to talk to you. And that is extremely fatal on on teams. It’s very fatal. It’s fatal for me not to talk to you for sure.

It’s fatal for people to feel like they don’t have a voice, especially when you’re in a startup environment and you have a small team, everyone needs to feel like they have the voice to share their concerns and their thoughts and their feedback, and no one person is above receiving constrictive feedback for their actions. And I realized that when I was honest and I made space for this conversation, I saw my leader and my teammate open up, and we were able to see each other’s point of view. Like I said, that’s really hard to cross that bridge as someone who has a lower title, or as a woman giving this kind of feedback to a man who was a little bit older than me. There were a lot of dynamics at play that made it feel really uncomfortable.

But seeing him cross that bridge with me and open up was really helpful, and it took some time, but now we have one of the best work relationships I’ve ever had. We work together all the time. We just shipped another product in record time together, but because of something like this, because of this situation. Now, when we get together, we have a deep, almost intimate understanding of how the other person works, and we have a lot of trust. So now, when he says, yeah, that design is not really your best, I know that he’s not attacking me as a person. Or when I say, hey, you know, I don’t think that meeting went so great. I think you could work on this. He’s not as defensive anymore.

So the next lesson I learned is that honesty, vulnerability and trust work no matter what kind of relationship you’re in. And people know this, this is not rocket science. I know I’m not presenting anything new, but sometimes when you get into autopilot and you’re working and you’re trying to get things off the ground, and you’re trying to increase revenue, you’re trying to, you know, push your products, it’s easy to forget things like this, that good relationships really are the foundation of shipping. Really good work. And so my willingness to share my feedback and open up gave him the space to also. Be honest. So one of us had to be the first one to cross that bridge. It didn’t matter that it was me or that it was him, but one of us had to be willing, and also, like my director is human, and so when I when I remembered that and took him off of the pedestal, I could give him back his humanity, right? Like, I’m sure you all could feel the same way, like you wouldn’t want someone viewing you as this indestructible Superman or Superwoman or super person just because of your title, but you two are human. You can get defensive, you can get upset. You sometimes don’t do your best to work. And so it’s really helpful when people can see you in that light, versus viewing you as this other human kind of person.

But it’s important that, from the top down, psychological safety is cultivated, so that whether you’re the CEO and the founder or you’re a new grad, fresh out of school, everyone feels like they have a seat at the table.

Lesson 3: Recovering Trust

I opened this talk talking about when I thought I would get fired, and this is when I thought I would get fired. We’re going to talk about recovering trust and how that was done. We all know that trust is hard to build, it’s easy to ruin, and it’s incredibly difficult to recover.

So I was working with a new client to our consultancy. And the thing about new clients is they take much more nurturing in order for our relationship to really gel itself. We typically staff some of our bubbliest, nicest, friendliest, me kind of people to these engagements because we want new clients to have the best in class experience, not that we don’t want everyone else to, but there’s almost a mountain to climb with them because they don’t have any context. So that’s a huge point that we have to get past. Everything was going great, and then my outlook in my Gmail disconnected, which feels like such a corporate conundrum. I think I talked to someone else about outlook in Gmail, and it’s a mess. So they disconnected, and I missed not one, not two, not three, but four, back to back meetings in a row with this client.

My PM ping me, and he asked me if I knew that I’d missed these meetings. And obviously I did not, because I would have been there, but that was a chilling message to receive. Like, did you know that you missed all these meetings? Did you know that the client is upset? It felt very grave, and I knew that this client had no context. So immediately I thought, I’m definitely going to get fired. I felt extremely ashamed. I thought, if we have another round of layoffs, I’m probably top on that list. And I thought that this mistake was going to be a permanent spot on my record or my career, and it didn’t seem like there was a way to get back on track and recover from something like this.

I really dropped the ball on checking my email and my calendars, even though I had them connected, and you can never be too sure everyone in here or most people in here, build software or deploy software, and as much as we do a great job, there’s there’s always a bug, there’s always something to miss. And so while this wasn’t a direct loss on my part, the client didn’t care that the emails and the calendars didn’t connect. They care that they’re paying by the hour, and four times I didn’t show up.

So our design work fell behind due to all these missed meetings, which felt like just another dagger to the heart. Not only were the meetings missed, not only is the client upset, but the work is slightly behind, and we have a deadline, because this feature has to launch at a very specific time. The client felt like I didn’t care, and in their own words, they questioned if I was truly invested in them, was I really invested in their success as something else holding my attention? And as you can imagine, my VPS, my delivery partners, my directors, gave me such a huge side eye, and we were all pretty tense and frustrated, and it just didn’t feel good.

But my manager is incredibly kind. He’s truly a world class coach. And so after I had a one on one with my pm about this major L that I just took, I called my manager and I boo hoo on the side of the road in my car, as one does when they make a mistake, but he gave me the space to feel these emotions. And something that has stuck with me ever since is he told me not to walk in with my head down. And that seems so simple once again, but this is my manager, someone who has the ability to let me go, to dictate if I go on a career coaching plan, to dictate the next move in my career because of his his role in our org. So instead of punishing me or reprimanding me or reminding me like, Yeah, you really screwed up, he said you don’t have to feel ashamed and hold your head down. And in that moment, I felt more empowered to think of a path forward.

He advised me without judgment and punishment, which helped me like I said, confidently strategize more solutions rather than think about how badly I messed up. So I committed to micro tasks and I delivered on each one of them. Owning and delivering is a very strong way to recover trust, both internally and externally, whether you’re B2B, B2C, whether it’s recovering trust with your team, but saying I’m going to do X and then doing X really builds trust, whether you’ve broken it or not. Our onsite work went really well. I committed to flying up to the client and meeting with them despite maybe my own personal commitments, and that work went well. We ended up shipping some new features, but they signed two more contracts with us, and I returned both at their request, which felt like a huge hero story, because at one moment they were upset, they wondered if I was invested. And now we’ve increased the account. We’ve signed more contracts, and they’ve asked me to come back and lead design two more times, so I did not get fired. Thank God.

In fact, I got promoted, which feels like such a crazy story. But what I learned is that when you own it and you commit to a path forward, you can absolutely turn it around. Once again, not a revolutionary thing that I’m saying, but sometimes you really just screw it up. No matter what your role is, no matter what you do, there’s no avoiding this part of the human experience. And I realized that it was my hard work that got me to that place, but I also recognize that without a manager and a mentor to give me the space and encourage me to own my mistakes and then to own the solution, I would have stayed ashamed and likely deeply eroded that trust with that client even more. And so now I’m in this space where I don’t fear making a mistake, I know that I can move forward, and there’s a team of people behind me who aren’t reminding me constantly of what happened, but empowering me to be the owner and the hero of the story and find a solution.

Want more of these insightful talks?

At BoS we run events and publish highly-valued content for anyone building, running, or scaling a SaaS or software business.

Unsubscribe any time. We will never sell your email address. It is yours.

Strategies to Leverage Failure

So I want to talk about some strategies. Some that I’ve recovered or discovered as a result of my failures, but also some that our team has employed to ensure that failure, like I said, is more of a training ground and less of a punishment.

Encourage Ownership

It’s very tempting to step in and fix a problem, but when you encourage people to own what has happened and process through it, they’ll be more empowered to find the solution. Now you’re not doing the work of finding the solution and figuring out what’s next and then having to fix it, because you have other things to do. You have other teammates to tend to. You have other roles or responsibilities within your role. So when you encourage others to own what they’ve done and own the solution, it frees up your time as well, and it allows the team to move a little more fluidly.

And here’s what that can look like, actively listening, which once again, not revolutionary. But my manager could have just stopped me. He already knew what was happening. He could have stopped me during that moment, my mentor could have stopped me in that moment and been like, I already know what happened. It’s fine, whatever. But listening and actively listening and engaging, asking questions and getting curious. Why do you think that happened? What do you think should happen next? Where could we go from here? Asking questions rather than making assumptions or dictating, honing individual strengths and talents is really big.

My manager knows that one of my biggest strengths is communication. So rather than telling me what to do, he picks up one of my strengths and goes you should leverage this in order to find your solution. How can we hone in on what we know you do well to find a path forward. And to do that, you actually have to know their strengths and talents.

And then lastly, direct with optimism rather than punishment. I know some of us well, some of y’all, I don’t have kids yet, but I know some of you have kids, and it’s easy when they mess up to just lay the hammer down. You’re grounded. It’s over. I’m done. I don’t want to hear it rather, instead have optimism and direct with that sense of energy and encourage folks that they can move forward, they can find a solution, and obviously be transparent about what could happen if we don’t find a solution, but directing them instead with a level of encouragement and optimism rather than punishment and shame.

Prioritize Connection

So teams aren’t great or synergetic because they just wake up that way. You think you can throw a bunch of adults into a room and they’ll just figure it out, they’ll work together, they’ll play nice, but that’s just not the reality. We’re all kind of just slightly bigger kids with like, more mature skin and wrinkles. You know what I mean? We’re not that much evolved from where we started out.

So productive and satisfied teams are cultivated through meaningful connection, not through just coming to work, getting on Slack, checking their emails, doing the stand up and going home. So what does that look like? That looks like Team critique. We do something on my design team where we get together once or twice a week and we take volunteers, throw your work up on the screen, and let’s all critique it. That gets us all confident and comfortable taking critique and also giving it. No one in the room is exempted. It doesn’t matter your title, put your work up there, and we’re all going to talk about it and discuss it and find ways to make it better.

So now we’re more connected. We’ve prioritized connection and cultivated safety in that way. We all know this, outings and bonding, that’s a freebie. Getting together outside of work, or maybe during work, and doing something that’s not work related. At Willow Tree, we call it wolf time because wolf is the opposite of flow. Flow means we’re working wolf means we’re not. So we’re in wolf time. We’re playing a game, we’re having lunch, we’re cracking jokes, we’re doing the thing.

Something I really love, is lunch and learn programming, very similar to critique, but instead, we’re inviting people to show us something. Teach us about that engagement that you just had, show us how you did that code. I don’t code things, but show us how you did that. Give us a demo, show us how that worked, talk us through how you connected those APIs for the back end services, talk us through how you nailed that pitch to land that client, right? So we’re all sitting around, and we want someone to teach us and show us what they’ve done that also gets them comfortable and confident with sharing their work outwardly and fostering an environment of trust.

Once again, next is pair working. I love peer working. I think I suggested this to Aubrey yesterday. Sometimes you have someone or some people that aren’t really doing well, and it can be hard to figure out, how do I get them to do better? Like, just do it better. Do your job, right? That’s what you want to say. But that doesn’t really work. And so we do a lot of pair working together, where, especially if you have a senior title or higher, you identify someone that maybe isn’t doing so great, and you pair with them. So you may spend three weeks or four weeks or two weeks or a sprint, and you work side by side together to identify where the weak spots are and maybe show how they can be better together, versus just leaving people out on their own. And now we’ve prioritized a connection that way.

And lastly, I think you should jazz up the retro. If you don’t do retros, you should do them. But if you do do retros, maybe break out of the norm, right? Get people to connect during retro. Something really fun that we do is we write the retro like it was a Google review. And so maybe we pretend that this last sprint was a restaurant or it was a store, and we write narratives about what happened. We get really objective about it, and we share our honest emotions and honest opinions, rather than saying, Oh, the sprint went fine. Lisa could have, you know, pulled her PR sooner, but that’s okay.

But now, when we’re honest and we’re open and we’re having fun, we feel more connected to one another. We also have a more psychologically safe environment full of honesty and vulnerability, where people feel like they can be heard. Another way you could jazz up your retro is having people pair off during retro and maybe share their thoughts one on one, and then when you get together, they switch off and share what the other person told them, just some things that we’ve seen that I think really help us prioritize our connection and become a stronger team.

Develop a Shared Language

Next, you have to develop a language. So we know that shared language creates for shared understanding, and so when people have a shared language, a cultural foundation is built that can help reduce confusion and barriers. So if I think back to that first lesson. We did not have a shared understanding, or really a shared language, but we just expected that the other person knew what we were thinking what we were doing. I heard a quote that the worst mistake in communication is assuming it’s already happened. We always think that the other person knows what to do and what’s next in what’s expected, but that’s far from the truth.

And so some ways that you can develop a shared language is having an accessible knowledge base, once again, very simple, but if you don’t have a space where people can learn more about everyone else’s role, then you should develop that, whether that’s a Google Drive or a confluence, or a notion, or a JIRA, whatever tech stack you use. Find a way for people to access the same amount of knowledge and that can be spread to each other so that there is no lack of understanding or unclear expectation. Team ceremonies is a good, good one. Stand ups, retros, post mortems, things like that. But having these ceremonies help us develop a shared language with one another.

Having regular norming. Show of hands who doesn’t know what norming means? Great. Thank you. So now I will assume that you know. Look at that. So norming is when we get together and we. Ask really fun questions, like, how do you like to work? How do you best receive feedback? Do you like it in Slack, do you prefer Zoom? Do you want me to call you if it’s constructive? Are you okay if I just throw it all right? So in norming, we ask, how do you best receive feedback? How do you like to work? What are your core hours? Do you work eight to four or nine to five? Do you even like zoom? Do you want your camera off? Do we want to have stand up? If we do have stand up? Do we want to have that every day or only every Monday? Those are very basic questions, but I guarantee you, if you’re not asking those things, you have maximized the amount of frustration on your team. Well, you can have these normings at the start of engagement. If it’s a long or a start of a team, rather start of a sprint, if you’re going to be working together long term, having a regular norming is helpful. So maybe every quarter you revisit and you say, Hey, we said that we like working nine to five, and we like having cameras on and we have stand up every Friday. Does that still work for everyone just checking? And if not, let’s change that. Let’s do something else, and let’s continue refining our shared language together.

And lastly, having shared steps for escalation. We should always know who we can go to when something doesn’t go right. We should all know what happens next if a client or a customer is unhappy. We should all have access that information, and it leads into the accessible knowledge base, but just sharing that information out and say, hey, if things aren’t going well, this is what we all know to do, and this is how we all know how to escalate it.

Grow Your Mentors

Glow and grow, which is my favorite. So I developed this feedback framework after lesson two. I don’t wait to provide feedback weeks or months later, because that builds resentment. You also start to construct a narrative, the longer it sits. The further you get from what happens like time wise, the more your brain will form a confirmation bias to what you believe to be true. If I believe Sally is a liar and I wait a long time to give her feedback, that time in between what actually happened and when I give her feedback allows for me to build resentment, for my brain to form itself around a bias. She may not be a liar, I may just have had the wrong information, but the longer I sit on this information, the longer I sit on my feedback, the more this confirmation buys.

So I create space on our team for everyone to share their thoughts on a regular basis. This framework has become quite popular in our organization. It started with our design team, now our engineering team and our PM teams use it, but basically what it is is this framework where we share a glow. So a moment that you shined, you did something great, your strengths really came through. Or a moment where you could be stretched or calibrated, maybe something is your strength, but you could use a little bit of calibration. Or maybe this is a growth area for you, and I’m just providing you with some micro dosed feedback, if you will, on how to strengthen that growth area. This is expected and agreed upon when we come up with the cadence.

So on our team, we agree to meet every week, if we’re designers. If I have a PM now it’s maybe every two weeks, and we sit down and we say, give me a glow moment from this past week, or these past two weeks, and I’ll give you one. You really owned that client call. Like you shared a great story and the client was really engaged, great job, or a grow moment. I noticed that you’ve been late for meetings in a row, should we push the time back? Are you okay? But now I don’t have to go these long distances and allow for one the details to become really hairy, but allow for resentment to build up. But I’m only having to remember since the last time we talked. And what this does is this helps people to have an expected, normal, regular cadence of when I’m going to hear from you about what I did, when I’m going to hear from you about how that meeting went, what I’m going to hear from you about my work, right?

And also foster psychological safety. So now that I know you’re going to tell me what happened and how you feel about it, I don’t have to guess. I don’t have to feel like I’m under this maybe microscope or I’m just on stage playing for you, and I don’t know what you’re going to say about my performance, but now I understand and know how we’re going to communicate and what you’re going to say on a regular basis. This may not work for really large teams, in which case we’ve decided to prioritize proximity. So the closer you work with someone, the more often you meet them, the least close you work with someone, the least often you meet with them. But either way, everyone’s getting constructive and positive feedback at the same time from their teammates. Everyone is sharing and everyone is heard.

Lastly, grow your mentors. Yes, we have a thriving mentorship practice at willow tree, and my mentors are a source of wisdom to help me navigate my career and to navigate my engagements and my clients. I’ve also become a mentor to help others learn and grow. You’re able to mobilize mentors way more than you can mobilize that single one manager or director or CFO or what have you, and they can leverage their own failures and their own losses to influence their mentees.

It was my mentor who had empowered me to have that conversation with my associate director and gave me some strategies on how to approach him. She had insight. She’d worked with him before. She’d been through this similar situation, right? And so she wasn’t afraid to be honest with me, because we didn’t have a manager and, like, direct report relationship, and I wasn’t afraid to open up with her and be honest because she wasn’t my manager, and I wasn’t afraid that she would reprimand me for being honest.

So some ways you can grow mentors, new hire and long term mentors. We always pair someone with a new hire mentor. They’re going to show you the ropes. They’re going to show you that shared language that we have. They’re going to talk with you about what the word swirl means and why we say it all the time. They’re going to they’re going to talk with you about team lunch and how we usually conduct retros, team outings, quarterly swag, all of these, like shared things that we have as an org.

And then you get assigned to your long term mentor. You can choose your long term mentor. This person is going to be there with you over a quarter, maybe six months, maybe a year. Maybe they help you focus on one specific aspect of your craft, or maybe they’re helping you generalize in your entire career. And so you can switch them out. You can pair cross collaboratively if you want to. But I would encourage both organic mentorship and assigned mentorship. So when people feel like this is an environment where we can learn from each other, they’re going to organically ask to be mentored, or ask if someone would be their mentee.

Also, assigning is perfectly fine. This leaves people to be accountable and to be owners and to all have a shared stake in their team’s success. You also have to provide resources. So training people on what a good mentor looks like training folks on the fact that being a mentor is not about your title or your seniority. I currently mentor a staff level web developer. I don’t know why, we don’t work in the same field, and he’s a couple levels above me, but there’s something to be learned there. So I mentor him on design and code relationship, which is really fun and interesting. But it doesn’t matter that we don’t work in the exact same field, or that we are, you know, levels apart from each other. So that’s cross role mentorship.

And then lastly, executive mentorship. This is where your C suite folks will commit to mentoring a person or a group of people for a defined period of time, breaking down those barriers from the top leadership down to the individual contributors. I said lastly, but I lied.

Hold Space For Risk

So risk is a scary word, but the most successful people on Earth are people who aren’t afraid to take risks. And we know that. I know that you know that, because a lot of you are on your like seventh business venture, which is very risky and very, very inspiring. You have to provide clear boundaries. In order to hold space for risk, you have to allow juniors to lead. When I say allowing juniors to lead, I mean in a low stakes environment, maybe they lead a code review. Maybe they lead the sprint. Maybe they take the lead on a sales call or a client call, of course, with some coaching. But allowing them the space to work that out and have some some real experience.

Exploring new ideas and new ways of thinking. It’s easy to get caught up in what we know to be true, the tried and true way that we’ve always done things. But when you explore new ways and ideas of thinking, explore other teammates ideas, we can hold that space for risk.

The good old mess around and find out, I don’t want to curse so. But you know what mess around means. We just try it. We see what works. Maybe it’ll work, maybe it won’t. Once again, you don’t want to do this in a high stake environment, but when mistakes are relatively low, good old fuck around and find out. You know what I mean, see what happens. Let’s see what we get when we just try out something, and maybe it won’t work, but what will we learn from that?

And lastly, incorporate play. Have fun with it. We role play a lot when someone maybe wants to grow in a skill, the other of us will pretend to be maybe the client. The other of us will maybe pretend to be another teammate and help them grow in that way. We try to make a game out of things. We have fun naming sprints fun and silly names. Um, you know, we utilize our Slack channels for more than just work stuff. So I think when you want to hold space for risk, you also have to incorporate some play in there, so people feel a little comfortable being risky.

What I find can be most interesting about risk in human beings is that if you were to put a bunch of kids on a field, right? An open field, they’ll all probably just stand there. But once you put up like a fence, like a structure, maybe you add a slide or a swing, now they understand where they can go, what they can do, what’s available to them, where the limits are. And it’s the same way with grown adults, when you have some clear boundaries. Now people feel comfortable taking a risk and having fun and trying something new and asking, what did I learn from that? So the first part about holding space for risk is to define what those boundaries are for your team.

The Real Impact of Psychological Safety

So when failure is not used as a purposeful training ground, tying this all together. Mentorship is not effective as it could be. People are not very open to sharing how they failed and how they can help you work through something. We miss the innovation that risk can bring. Perfectionism stifles open communication, and ultimately, people do not grow when we don’t allow for failure to be a purposeful, intentional, psychologically safe training ground. But really, all of this just points us to what we call psychological safety. And I’ve said that plenty of times. It’s the cycle of discomfort, of admitting mistakes, being able to learn from your failure, everyone sharing their ideas and knowing there’s a space for them better innovation and decision making, and it just goes over and over and over again until we die.

But this is important. It seems so simple and so silly. You’re like, why is she talking about me about safety? Because I kid you not. If you were to survey your team, someone would probably say, I don’t really feel like there’s a place for me here. I don’t feel like I have a voice. I kind of just do my work and go home. They may not be as invested as you are in the product or in the team. One, because they probably didn’t find it. They’re not the founders, but also because they may not feel like they have ownership or connection to what’s being done, and so that has to be intentionally cultivated.

The Only Ls You Take Are Lessons

I want to wrap up with this. I hope that my candor and my stories of me failing helped other people embrace their own mistakes, or at best, just laugh. And gain some insight on what can drive drive teams forward. What I’ve learned is that the strongest people on the team are people that aren’t afraid to take a risk, to speak up, to share their ideas, to challenge the norm, to receive that hard feedback, to give that hard feedback, to have crucial conversations and to find a path forward, even when it feels hard and impossible. But we have to be intentional about creating cultures where people can feel like all of those things are possible for them, and just remember, the only Ls you take are lessons. Thank you.

Angil Tate

Senior Product Designer, WillowTree Apps

Angil is an Atlanta native who moved to Durham NC where she’s a Product Designer at WillowTree. Before WillowTree, Angil was a solo designer working with entrepreneurs and small businesses developing their brands, but a love for tech and complexity pulled her into Product.

She studied music in school only to discover that it was an uncertain career so decided to use her design skills to pay bills while she awaited her big break. Side projects for friends became big budget projects for small businesses and entrepreneurs when she realized she was in love with product and UX. The most consistent aspect of her work and story is perseverance.

She loves FinTech, brunch, and Atlanta.

More from Angil.