526: AI-Powered Leadership with Waggle AI

Hosts Will Larry and Victoria Guido interview Sarah Touzani, the founder of Waggle AI, an AI leadership skills coach. Sarah shares insights from her entrepreneurial journey, discussing how her past pottery hobby has influenced her focus and patience, which are crucial skills in her role as a founder. She explains how her transition from a traditional business school path to a senior role in a fast-growing startup, and eventually to founding Waggle AI, was driven by a desire to foster better managerial skills and workplace culture. Sarah talks about the early challenges and pivots in developing Waggle AI, such as incorporating AI for automatic note-taking to reduce user friction. She describes how Waggle AI assists in meeting preparations, records notes, and provides feedback on leadership skills, helping managers improve their delegation and empathy skills. She also highlights the importance of blending productivity tools with leadership development to enhance team performance and individual well-being. The discussion also touches on the ethical considerations and core values driving Waggle AI, to emphasize user privacy and minimizing additional workload for managers. Sarah concludes by outlining her vision for the product, focusing on deepening the AI's understanding of managers and adapting recommendations to individual team members' needs. Waggle AI Follow Waggle AI on LinkedIn, Instagram, TikTok, or X. Follow Sarah Touzani on LinkedIn. Follow thoughtbot on X or LinkedIn. Transcript: WILL: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Will Larry. VICTORIA: And I'm your other host, Victoria Guido. And with us today is Sarah Touzani, Founder of Waggle AI, your AI leadership skills coach. Sarah, thank you for joining us. SARAH: Of course. Thanks for having me. VICTORIA: To open us up here, what is a past or current hobby that you enjoy? SARAH: I need to be honest. I haven't done much outside of working since I started the company. But prior to that, I used to spend a lot of time in a pottery studio making pots, and bowls, and mugs, and gifting them to anyone I meet. WILL: That's really impressive because I tried it for, like, I think a college class. And if you make one mistake, the whole thing gets ruined. I think I made, like, a little, very small bowl, and that was all I could get [laughs]. SARAH: Yeah. I'm not surprised. It takes a lot of practice and a lot of extreme focus in a way because, like you said, like, the single moment your hand moves slightly off, the whole thing is over. WILL: What's the item that was the most complicated or you're the most proud of? SARAH: I would say a big bowl that I made, which has a bit of an odd shape because, actually, it was going bad. And I kind of caught it back and made that mistake into something done on purpose in the design, and it worked quite well. But it's also not your average pot or average bowl you see everywhere. VICTORIA: That's really cool. And I echo Will's sentiments of being impressed by people who can do pottery because I did take a class right before the pandemic. And then, the pandemic hit, and we weren't able to fire any of our pieces [laughs]. But I found that it took just a lot of patience, even to be able to figure out the first step. Like, putting the clay onto the spinning wheel and doing that correctly just takes a lot of practice. And so, I'm curious if you find any of those skills or values from doing pottery translate into being a founder. SARAH: Yeah, actually, this is funny because I wrote a blog article about this a few years ago when I first started. I think there are a lot of learnings to take away from that and bring into work, weirdly. It's that sense of focus. When you're starting a company very early, there's a million things that you want to be doing and, actually, you can't. You need to do one thing and do it well. And the ability to zoom in and focus on one single thing is a massive game changer. Also, my last job was as busy and insane as the current one, which is being a founder, because it was, like, a senior role in a super-fast-growing startup. And I was always on my phone, or always thinking about work, or always having something coming at me and trying to answer questions and do stuff on Slack. And with your hands dirty, you're actually forced not to do any work and go back to that focus and that mental clarity. And that was also, like, extremely valuable back then. So, saying this out loud makes me think that I probably should go back and do it. VICTORIA: I recommend it. I did a hand pottery class with my little sister. I have a big sister, little sister mentorship relationship. And we made little ceramics, and it was super fun. Just, like, an hour a week. SARAH: Super nice. WILL: So, Sarah, you mentioned a little bit about your background. Tell us more about that. Where did you get started? How did you become a founder of your company? How did the idea come up? Just anything in those areas. SARAH: Yeah. Sounds good. So, I have a bit of, like, a traditional business school type of profile. I was a good student. I didn't really know what I wanted to do. So, I went into a business school, graduated, went into banking and consulting, which are, I guess, those, like, sexy jobs that you want to get when you are still at school. And I had done them and felt a bit out of place because I wanted to get things to move way faster than they were moving in these, like, very corporate set-in-their-ways type of companies. So, left that industry and moved to a very early-stage startup. I used to live in Paris back then, and I moved to London. At the same time, joined a very early-stage startup in FinTech. We were four when I joined. And we didn't have a product, didn't have any revenue. And I had to grow that company to about 200,000 customers, 50 million series A, and 80 people in the team, of which I managed about 50. All of this happened in 4 years. And I was hired into that role because of my background and because of my experience in risk management, compliance, like, all of the very technical aspects of my career. But at the end of the day, I spent most of my time trying to build a culture that motivated people to do their best work that enabled people to perform. And that's not something you really get to learn either at school or, in most cases, at work either. You just need to figure it out. So, I was trying to find a way where we could enable managers to learn these skills once they're in the job. Because when they mess up and when I messed up as a manager, it had a cost not only on the company but also on the wellbeing and mental health of the people that I was managing. And I couldn't really find a solution existing. So, I started working on one and spoke to one of my best friends about it, who is a multiple-time founder, and we just got to work. And fast forward a year and a half, here we are. VICTORIA: I'm wondering if there was anything in the early phases that surprised you in the customer discovery process, maybe caused you to shift direction. SARAH: Yeah, definitely. So, early days, we started with this problem, which is that most interactions between a team member and their manager happen in meetings. And that, overall, everyone is kind of frustrated with meetings, especially post-COVID, where we started doing a bunch of them online. It seemed to not work. And it seems that meeting management skills were a bit absent, and they should be part of the toolbox for a manager. So, started by trying to help managers run better meetings. And we relied on them taking notes from those meetings, like, in writing preparing for those meetings and taking notes for them in writing. And quickly realized that a very small portion of people were actually doing that note-taking. It seems obvious saying it out loud now, but back then, we didn't really know that. And so, we kind of had to switch gears and use way more AI than we intended, at least at that stage, to enable that automatic note-taking and gathering of data for us to be able to support the managers. Because if we don't know what they're working on and what's happening in their world, it's super hard for us to give them any feedback. But if they don't take notes and share them with us, then we can't really do anything. So, I had to shift gears and build an embedded note taker within the product to remove, like, a big portion of that friction that we saw with early users. WILL: I love that and just your whole product. I'm a productivity nerd, so I just love it. And I was a manager for a couple of years, and it's not the easiest. So, I love what your product is doing. Can you give us an overview of exactly what your product does so the audience can know what we're talking about? SARAH: Yeah, of course. So, the product is an AI coach or an AI co-pilot for managers. And the way it works is it connects to your calendar. It creates a space to collaborate with your team on each of the meetings you have. Prior to the meeting happening, we also give you access to one-click templates and ways to run those meetings. And then, when the meeting is happening, the Waggle Bot joins the call, takes notes for you, picks up on both action items that you mentioned during the conversation, who they were assigned to, who mentioned them, but also decisions that were made or about to be made that you need to either come back to and confirm or make sure that everyone is aware of. And finally, and the most exciting part, to me, is that it gives you feedback on your leadership skills, a bit like if your coach was listening to your conversations with your team members. And it will say things like, "You mentioned a few tasks during this call, and you didn't delegate any of them to the team while you had the opportunity to. So, next time you have a call, think about what tasks you could actually delegate," or it will say, "Well done showing empathy when Will, in your team, mentioned that their daughter was sick and that they had to leave work early today." So, it really works as a feedback loop to reinforce good behavior, but also give you tips and show you those unknowns that you didn't really think about and what impact they can have on your team and on your team's productivity. And finally, from that, we build a full picture of where you're good at, and where we can support you, and how those skills evolve over time through the feedback we give you. VICTORIA: Yeah, as a manager myself, I'm thinking about all the things I do to try to make my meetings as efficient as possible by, you know, having automatic Slack updates that say, "As a reminder, go look at your tickets, update them before the call," like, rotating who's taking notes and facilitating the meeting, and thinking about how that could reduce the burden from the team and just help everyone save time and share that information more widely. Because sometimes I do have maybe a dozen meetings in a day, like, 12, 30-minute meetings [laughs]. And that's a lot of notes to take. So, I usually estimate every meeting takes another 30 minutes to an hour to wrap up and follow up afterwards. SARAH: Yeah, I think that's a good assessment. And if you actually stick to spending those 30 minutes extra for each one of the meetings, I can tell you you're one of the best performers. Because what we've been seeing is that a lot of people, especially in startups or, like, fast-moving environments cannot afford to spend that time. So, we're trying to see how we can remove that friction and make those 30 minutes that you need to spend more like five minutes pre-meeting and potentially another five minutes after the meeting. And that's it. You're done. VICTORIA: How many people did you talk to in the first 30 and 90 days of your startup? SARAH: So, that's all we did in the first few months because we wanted to validate that this was not, like, an us problem. So, I spoke to about 75 managers over the first 2 to 3 months. So, that's in itself a lot of meetings, and a lot of calls, and a lot of recorded calls. And we still speak to an average of 5 to 10 managers per week to make sure that we keep a pulse on what our users are really experiencing and the pain points they are going through. WILL: Yeah, I could tell that you did talk to a lot of managers because I wish I would have had this whenever I had direct reports. Because I remember, early on, someone told me "No one cares what you know until they know that you care." But on the flip side of that, a lot of times, like you were saying, you're just so busy. Most companies they give you multiple direct reports, more than three or four. And it's almost impossible to really show how much you care in a small amount of time. But this seems like it makes it way more helpful to say, "Hey, I not only care about you as a worker but as a person, too." So, like you said, show empathy because they mentioned X, Y, Z, or take notes around, you know, whatever happened in this so that you know next time that, hey, ask him about that. So, I really like this idea that you created. The question I have around it is leadership is not easy. So, how did you come up with the direction to go with the leadership? If that makes sense. Because I've seen different leaderships, I've seen some leaderships it's like, yeah, show empathy. Show that you care about the person. And some it's like, no, it's all about work. All about work. And it seems like you lean more towards, I want to show that we care about the worker. So, where did you decide to take which route and things like that? SARAH: I love this because you're right. There's an art and a science to leadership. And I think, actually, there's way more science than we think. It's this common belief that leadership is something you are born with, and you don't need to learn that it's, I think, hurting both managers and the people they manage a lot. Because then people think, "Oh, but it must come naturally," or "This is a natural born leader." And as a result, the person who isn't or that people think isn't we think they're never going to change, and I don't think that's true. There's a set of behaviors that have been researched by organizational psychologists, behavioral scientists that have been shown to have impacts on people's motivation, productivity, outputs. So, we make sure to follow those best practices and those scientific data points. One of our advisors is a behavioral scientist. A couple of our advisors are leadership coaches. And one of them has even published a book around how to scale high-performing teams and high-performing companies. So, we try as much as we can to really embed what we're doing in science and in things that are known, albeit not super widely. And as you said, you need both. You need to care about the person doing the tasks, and you need to care about the tasks being done. But they can't really be separate. And you need to balance the act between the two things. So, that's why we have blended the productivity app with a part that is more centered around skills and skills development because those two things need to communicate. You can't just throw a tool at people and expect them to know how to use it. And at the same time, if you don't make sure that the upskilling and, like, feedback you give is rooted in that person's context and what they're going through, it's not going to be leveraged or used. So, our approach was really to blend these two things and make sure that, yes, this is going to make the manager's team happier, but it's also going to make them more productive. So, it's not just about happiness. It's about linking both productivity and well-being at work. VICTORIA: That's really interesting. I'm curious, how do you measure the impact you're having on wellbeing at work? What are the success indicators, and how do you know you're successful in a year or five years from now? SARAH: We only have been onboarding customers six months ago. So, I think we're starting to see some of the results we want to see, but it's still a bit early days because, as you said, behavioral change and habits take a long time to form and become sticky and start showing an impact on wellbeing. But overall, the feedback, the qualitative feedback we got was that managers feel way less imposter syndrome using the app. They feel that they are on top of what they need to achieve. They know what they're doing. They know what's expected of them. And their team also appreciates the fact that they are spending time and effort trying to get better because they know that they are using this tool to improve. So, they also get a signal that, okay, they are really trying. But at the same time, we do measure these. So, that feedback we give is actually based on measurement or assessment of each one of the skills that we measure for our users. And we have seen those scores evolve and go up over time just over the last few months. Personally, I'm quite bad at delegation. Potentially, that's why I brought it up earlier. And I have seen my score improve over the last few months using Waggle because it's more front of mind. I'm aware that I'm being assessed that almost someone is looking at what I'm doing, even if it's an AI. So, it feels a bit more safe than if it was a real person looking at what I was doing. But I know that I need to be on my A-game every day, and so I put in intentional efforts to try and delegate when I'm in a team meeting. And, potentially, I wouldn't have had that same level of awareness if I didn't get that feedback. I would just not delegate but not to be aware that I wasn't. WILL: I like what you said is AI is not like your manager sitting in the meeting with you and saying, "Hey, you have to get these scores up," but it feels safer that AI is telling you, "Hey, you have to improve your empathy and get better at that." So, I really like that idea. SARAH: Nice. Let's get you on the app then. MID-ROLL AD: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at tbot.io/entrepreneurs. WILL: So, I'm looking at your website now and, you know, I'm looking at the side, and it's like, "Hey, you know, Emily presented well, you know, send them a note of encouragement, or share a summary of the email." I made so many mistakes when I was a leader, so many. I wish I would have known the benefit of...because I almost...when I first went into it, I was like, they're adults. They can take their own notes. And now that I look at it, it's like, I could have easily helped out just saying, "Hey, here's a summary of the meeting that we had, and this is how we get better," and just helping each other out. So, I really like what you're doing here and what you have already in the app. What's on the horizon for the app? What does success look like in the next six months or five years for you? SARAH: So, the way we see it is we want to know more about the managers we're helping, know more about their context, what's going on in their daily life. Because the more we know, the more we can help them and support them. So, the way we see it is now we basically get data through the calendar connection, and through the meeting notes, and transcripts that we get. But we would also like to know how they communicate with their team on Slack. How do they get their tasks done, and how does their team get their tasks done? How do they follow up on those tasks? But also, how fast do they reply to emails? What's the context of their emails? All of these things are data points that we can use to know their context and know them better and really tweak the AI so that it knows them better and it adapts to their setup. So that, as we go, what the AI tells you is completely different from what it tells me, for example, because it's got to know you, and it's got to know what interventions work well for you and which ones don't and get smarter at that. And also, it gets to know how your team reacts to those behaviors that you show and attitudes. Which types of management work for Amy in your team versus Jim, right? Because they are different people as well. And so, whatever works with one person doesn't necessarily work with another and help you adapt and flex your management style with them. VICTORIA: Do you have any other core values that drive your everyday decisions? SARAH: We want to make sure that this never turns into a spying tool, and this is super key in the way we thought about the product, and we built it from very early days. We're conscious that we're having access, and our users trust us with a lot of data. And we're never going to share that data, even with your own manager. Because this is a tool for you as a manager to work on your skills and have that growth mindset, not for someone to spy on you or know how you're behaving. So, that's a commitment that we'll never share any specific data from users to their leadership team, to their HR team, no one else in the team, really. What we also have as a guiding principle is we want to minimize the amount of work that is required from you to leverage these skills. So, we are trying to save managers' time whenever we can and wherever we can and never just, like, load a lot of content and feedback on them that they're not going to have time to process an action. So to strike a balance between, okay, well, you probably need to spend a bit more time on this specific skill or following up on this specific meeting. But we also saved you two hours today throughout the day so that you can focus on that extra half an hour work that is going to help your skills improve. WILL: What are some of your biggest hurdles? SARAH: Well, basically, this didn't exist until now. And so, just finding how we talk about it and, like, I mean, no one is looking for the solution because they don't know it's there, right? So, the first part is, how do we find people that we can support and help who aren't necessarily looking for this but are looking for alternative solutions that exist right now? And how do we talk about it in a way that makes them click and makes them envision this new way of doing things as a potential better way? A lot of startups go through this journey. But basically, no one was looking for Ubers before Uber existed. People would hail a cab. And so, at the beginning, Uber pretended to be a cab service before they said, "Okay, we're actually not a cab. We're something else." And so, that something else is what we're trying to define right now. VICTORIA: I used to live in a neighborhood in DC where the cab drivers would not go to [laughs]. So, I really loved Uber when it first started because I could actually get a ride. So, that's where some of the innovation comes in sometimes. It's like, solving a problem and seeing the demand and then building a product around it. I'm curious about how you're building an AI product and how are you thinking about controlling the cost and the kind of infrastructure demands of an app like Waggle? SARAH: To be completely honest, we're not focused on that so much right now. I think it's a very fair question, and it's something that we're going to start to have to look into as we start to scale. But, for now, we're really focused on figuring out are we delivering the value we want to deliver to our users? Can we fix the problems they are hiring us to fix? But yeah, for sure, at scale, this is super costly, and we'll need to figure out the unit economics of the product and how to make it work, but we're not there yet. VICTORIA: And how are you finding the resources to be able to experiment and have the time to build this product? What networks, or communities, or venues have you found to create space to build your app? SARAH: So, we've been through Techstars last year. And I think the network around Techstars was super useful in gathering a lot of feedback in a very short amount of time over the three months that the program lasted. And we try to put a lot of content out there to try help people who are looking for solutions to communicate with an employee who's not performing at the level they expected them to or for a manager that doesn't know how to do a one-on-one. This type of content we're putting it out for free because it's solving our end user's problem, partially at least, and puts us on their radar. So, they might think, "Okay, I started looking into this first problem because that's what's front of mind right now. But as I see this product, it potentially could help me through a lot more issues that I'm currently having," and get visibility across those users that are exactly our perfect type of user. But yeah, overall, trying to put content out there creates a community around us. Lots of connections that happen through LinkedIn, through existing networks, through our users talking to other users about us, and even a number of coaches and L&D experts who really, really love what we're doing and talk about us to their users, to their customers and spread the word that way. WILL: You're talking about, like, explaining the product to your customers and everyone. I think, for me, it resonates fairly easy because I made so many mistakes as a leader. And I'm like, oh, this could have helped me so many times to be a better leader. And so, I'll make an assumption. It seems like your product was made out of you making mistakes and learning from them, and you built a product because you want to be a better leader. So, my question for you is: What advice would you go back and give yourself when you first started? What's some advice that you can go back in time and give yourself? SARAH: One of the first ones, and one of the biggest mistakes, and I've also heard this from so many other managers, is that as human beings, we tend to treat people the way we would like to be treated. And very quickly, we understand that that's not how things work. So, I used to like having space not to be managed very closely. So, I would just naturally give a lot of space to the people I started managing when I first started. It might work for some of them, but not for all of them. And that's what created the most issues and lack of performance, I would say, coming from them. And it's easy to think, oh, it's their fault. They're not performing. But no, it's my fault as a manager because I didn't adapt to their needs, and I didn't give them what they needed to perform. And that's, again, very different from one person to another. VICTORIA: Yeah. And I'm curious to go back to something you mentioned earlier about empathy. And just maybe how do you build an AI with a sense of empathy that helps managers be more empathetic? SARAH: So, again, interestingly, AI can pick up on human behaviors way more than we think. Like, the feedback we get from the app sometimes is super interesting and, like, sometimes even a bit scary because these are patterns, right? AI is good at recognizing patterns. If you tell it what to look for, it will find it. So, it works. It just works. VICTORIA: Well, I'm very curious to try it out. And I have some people I'm thinking about who work in building empathy with developers and engineers, and they probably would also really love to try it out. SARAH: Nice. Send them our way. VICTORIA: Of course. Do you have any questions for me or Will? SARAH: Yeah. What's the hardest thing you're currently doing at work that you would love support on? WILL: I think as a developer, there's a lot of things that I don't know that I wish I know what direction to take. Because I feel like as a developer, you come in and you're like, I want to learn X, Y, Z, but there's so much to uncover. For example, mobile, there's so many directions to learn with mobile. In the technical part, probably sometimes what direction to go in my learning and things like that. Because, like, I'm a senior developer, and I've reached a certain part. But I feel like now it's like you learn on the go. Like, oh, I have this problem. Let me solve it. So, sometimes I wish I can get ahead of that and be like, hey, go learn how to do this because you're going to use it later. So, that's probably my biggest thing with technical. And probably relational, you touched on it a little bit, but naturally, we're bent towards treating other people the way we want to be treated. And so, what that says is everyone around me has my exact background, my exact trauma, my exact upbringing. So, if you treat them that way, this should make sense, and that's just not the way it is. And so, I think, for me, it's making sure that I remind myself of that and to listen, to understand that background, trauma, whatever, of the people that I'm working with so that I can get to know them better and understand them better, and then I can know how to treat them. So, I would say that's probably my two biggest things that I have to continually work on and fight to make sure that I'm doing it the right way. SARAH: I love that. VICTORIA: Yeah. I really appreciate that perspective, Will. And from a slightly different angle, I think I'm someone who really enjoys complex tasks. So, I think those are actually more fun and easier to do [laughs] but that more mundane tasks are kind of difficult. And making sure I'm on top of those, like, tiny, little to-dos that make you effective just consistently with certain managing tasks. But I think in terms of complexity and one of the hardest things to do, kind of along the lines of what Will was saying, you have to establish a common language between your team. And you have to have a system for managing your work so that everyone feels heard and everyone understands each other, and so you can move quickly and make decisions. So, I think that's a really complicated task. And the more people you have, the more complicated it is. There's just so many different ways of solving that problem, and everyone comes back from different cultures, different corporate cultures, different tools that they've used, and their preferences. And people's preferences on tools can almost be religious, and that's interesting to me how strongly people can hold on to how they've been doing things. And making that shift in direction step by step and having the patience for it, I think, is difficult. SARAH: It's so funny that most problems, at the end of the day, are people problems, even if they don't start by being that. WILL: I totally agree with that because I chose what company to work for based off of the people and the culture more than the other problems. Because I've worked in some companies that had a great culture, but the people were treated right. And I enjoyed working with the people that I was working with. And then, I had some that I'm like, uh, I got to go in today and deal with such and such, and ugh. I think you're spot on. That caused me more stress than trying to solve the actual tasks that I was working on. So, yeah, I actually choose companies that I like working with the people. So, with thoughtbot, I love my co-workers. I love getting to know them the diversity in it. So, that's one of the reasons why I love thoughtbot so much. SARAH: What a great way to end this. VICTORIA: Yes. Thank you so much for being here with us today, Sarah. I really enjoyed listening to your story. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, you can email us at [email protected]. And you can find me on thoughtbot.social@vguido. WILL: And you can find me on Twitter @will23larry. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at: tbot.io/referral. Or you can email us at: [email protected] with any questions.Sponsored By:thoughtbot: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at: tbot.io/entrepreneursSupport Giant Robots Smashing Into Other Giant Robots