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- [00:00]
Ayo Akemwaleere
This is Ayo Akemwaleere from the Athletic FC Podcast. Buying a car should be exciting, not exhausting. And if you're looking for a gleaming
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Podcast Advertiser
SUV to replace your old banger or
- [00:10]
Ayo Akemwaleere
you're taking the plunge and going electric,
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Podcast Advertiser
the good news is you can buy your car completely online on Autotrader.
- [00:16]
Ayo Akemwaleere
Really? Just go to autotrader.com and get picky. Search through dealer listings for the make, model, color and the features that matter to you. Then just drop in your info and you'll see all the cars that fit your budget. Really? Once you've found the car of your
- [00:32]
Podcast Advertiser
dreams, you can have it delivered to
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Ayo Akemwaleere
your driveway or you can pick it up at the dealership. Really? So buy your next car entirely online on autotrader. Head to autotrader.com or search the autotrader
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Podcast Advertiser
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- [00:48]
Molly Graham
this episode is brought to you by National Business Furniture. You can find them@nbf.com what your workspace looks like says a lot about the way you work and can make a big difference when it comes to productivity. The truth is, our surroundings can impact how we think, how we feel, and who we become while we're in them. Your workspace can affect engagement, productivity, and maybe even retention. That's why getting your workspace right matters. It's proof that you value your team. National Business Furniture believes that every business deserves furniture that lasts, service that cares, and a partner that gets it all on a budget that works. That's National Business Furniture's commitment to you. Find the right furniture for you and your team@nbf.com and use the promo code POD10 to save 10%. That's nbf.com and experience the better way to buy office furniture.
- [01:44]
Podcast Advertiser
This podcast is supported in part by Bill, the intelligent finance platform that helps businesses and accounting firms scale with proven results. We often talk about the habits and systems that help people do their best work. For many leaders, that might include building processes that reduce friction and create clarity. That is exactly why so many finance leaders turn to Bill with AI powered automation. Bill isn't just moving money, they're simplifying financial operations for nearly half a million customers. They're even trusted by over 90 of the top 100 US accounting firms to get it right. That trust is built on scale. Bill has securely processed over a trillion dollars in real transactions, supporting teams in handling payables, receivables and expenses. When financial tasks are organized and visible, it can free up time and energy to focus on what matters most. Whether that's your team, your mission, or your community. Visit bill.comproven and get a $250 gift card as a thank you after speaking with a bill expert. That's bill.com proven. Terms and conditions apply. See Offer page for details.
- [02:49]
Molly Graham
Most of us think about risk taking at work the wrong way. We imagine it as this big, dramatic thing. Quit your job, start a company. Say the thing that could get you fired. And yes, I will admit that I have probably helped cement that version of risk in my own TED Talk. Sorry, but that way of thinking about risk has a side effect. It becomes all or nothing. You're either a risk taker or you're not. If we think about risk taking that way, a lot gets left out. The question you didn't ask in the meeting because you were worried it would make you look stupid. The feedback you've been sitting on for two weeks. The boundary you've been meaning to set. We don't call those risks. We just call them things we didn't do. And here's what I've come to believe. The people who are actually good at taking risks didn't get there by making one giant leap or even by taking big risks. Over and over again, they built a practice. Small, uncomfortable swings over and over. Not until it stopped feeling scary, but until the fear stopped getting in the way. I know that's been true for me. So today I want to explore how do you actually get better at taking risks? And is it something that anyone can do? I'm Molly Graham and this is Work Life, a show where we untangle the messy human side of work. Today I'm talking to someone who has thought more carefully about the daily practice of risk than almost anyone I know. Julie Zhu was one of the earliest design and product leaders at Facebook, where she helped build and manage teams through some of the most explosive growth in tech history. She later wrote the Making of a Manager, which has become a field guide for first time leaders and is now the co founder of Sundial, a company using AI to help organizations make better decisions. Julie is a craftsman, and not just in design. When she wants to understand something, she dives in deep and builds a whole practice around it. For example, she did that with writing one blog post a week for a year and then landed a book deal. One of the things she has applied that craft to is risk because she decided it was something she wanted to get better at. So I want to talk to her about what she did, what she learned, and what she really thinks it takes to be brave. Julie, welcome to Work Life.
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Ayo Akemwaleere
Hi Molly, thank you for having me Here.
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Molly Graham
I'm so happy you're here.
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Ayo Akemwaleere
Oh, gosh, I'm so excited to be here.
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Molly Graham
You've written about this idea of everyday risk and pushing yourself to take small risks regularly. I'm curious, like, what gave you that idea? And why did you think it was important?
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Ayo Akemwaleere
I started to have this idea because I think one of the things that I'm worried about for myself, and in fact, I think I recognize about myself, is that I am just like a real scaredy cat when it comes to life. There's a lot of things that really scare me, and when they scare me, I sometimes have this inclination of, like, okay, well, maybe that's not for me. I can't do it. Somebody else is much better than that. And it gotten to the point where I started to see that as a pattern. But when I was little, I somehow got into my head that I was really not athletic. Like, in fact, I was just terrible at all things physical sports. I think maybe it was exacerbated by the fact that I had asthma. So my mom was always, like, very protective around me and, you know, going out and playing sports. And then my mom would have all these stories, and she's like, well, I'm not really very athletic myself. In fact, I hate running. I hate sports. I hate this. And so maybe you inherited those genes in addition to the asthma. So I just had this whole narrative that, like, these things were hard. And I think that, you know, I. I probably had this strong identity of, like, okay, if I'm not good at sports, maybe I'm good at things that use my brain. But in reality, what it was, I think, is that I was just kind of scared to try. I was scared to maybe validate the story that I'm bad at these things. And I think that that was a pattern that I had seen through many other things, right? And then at a certain point in life, when I look back, and I guess it was through the years I'd spent at Facebook and just being pushed to scale and try a lot of new things, I realized when I look back, the things that made me proudest were when I did something that I didn't think I was gonna do. That was scary for me. And I'm so proud. I'm so happy. Like, I gained a lot more confidence. And I think that's often the price that we pay, right? The price of confidence is that you have to do things that you are scared of. And once I saw that pattern more and more, I was like, oh, I kind of wanna, like, just do more of that. Like, I realize now what's on the other side. So I started to lean a little bit more into that feeling of being scared. And so the goal that I had for everyday risk is like, doesn't have to be the big things, you know, it doesn't have to be like, I took a new job or I jumped off of a plane, or I signed myself up for a marathon. Sometimes it can be these little everyday things and they're just all around us. And so for me, an example of, like, a smaller way to do something I'm scared of is just saying a thing. I'm kind of nervous to say, like, hey, I'm not feeling very good right now. Maybe when someone's like, how are you doing? That seems a little risky because people probably expect me to say, oh, things are great. I'm fine. How are you? Or sometimes maybe I wish that I could relax and maybe not go and sprint the extra mile in my workout. And it sort of scares me because I'm not sure I can do it. And whenever there's this feeling of, like, I'm not sure I can do it when I. Or I'm not sure how other people will feel about this, or I'm not sure, like, if I'm gonna be comfortable, that's the feeling I'm starting to lean into a little bit more. Which is like, oh, this is an opportunity for me to probably be proud or brave or whatever it is after the fact.
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Molly Graham
Yeah. First of all, I just wanna say, as someone that knows you, it's blowing my mind that you think of yourself as a scaredy cat. Cause I actually think of you as very brave.
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Ayo Akemwaleere
But.
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Molly Graham
But it sounds like you've turned that into a practice. It's something that you've taught yourself to be good at.
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Ayo Akemwaleere
Yeah. Another way that I sometimes play the story in my mind, and of course, we know that stories come and go. Right. Is I think I was forced to be brave in a lot of instances. Like, for example, coming to America and having to figure things out when I was at the age of six, or coming and meeting my parents after I hadn't seen them for a very long time. And a lot of those things, I look back and I'm like, yeah, I was really brave, but I don't feel like I had a choice in the matter. And maybe it took a lot out of me so that in other parts of my life, I wanted to stick to what was comfortable or what felt safe. And now the older that I get, the more I'm Able to, I think, push those boundaries a little bit more. And so I'm really happy to hear that you, you know, you think that I'm a brave person. I think that there have been cases where, like, I look back, I'm like, yeah, that happened, and I was able to do that. But there were also many times where I know that I was sticking to what felt more comfortable for me. And those are, like, the little boundaries that I now want to expand just because, like, I don't know, it gets easier to do so when you. When you practice over many years.
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Molly Graham
Yeah, totally. One of the things you said that really resonates with me is that confidence comes because of risk. I think sometimes people feel like you need to be confident, and then you can take a risk. But you said, like, looking back on your time at Facebook, you realized that some of the things that you were proudest of were moments when you took a risk. Can you actually remember some of those experiences and tell me some stories of what you were so proud of that felt uncomfortable and scary at the time?
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Ayo Akemwaleere
I think the first one was going and learning to be a designer, because when I started at Facebook, I was hired as an engineer. I was trained as an engineer, computer science degree. And so I felt that that was what I knew. But what I really loved to do when I was in middle and high school was actually design. I didn't know that that was what it was called at the time. I just like making websites. I liked going and opening Photoshop and creating images and then figuring out how to display those images on my website. But, like, I didn't know that was a profession. I didn't know that was, like, a thing you could do. I felt I picked the closest thing I could, which was, like, learning to code and learning engineering. But once I realized that this was actually a thing that people did for. For a job, I was like, wait, I kind of want to do that. But I had no formal training in design. And so when I first joined the design team, and everybody's, like, talking about typography and they had studied all this, and I remember even getting into a conversation about Macs versus PCs, and the entire design team was utterly convinced that Macs were so much better designed, and I've never even used a Mac, all I knew was PCs, and I was trying to be like, no, no, they're not so bad, blah, blah, blah. And people were just like, who are you and what are you doing here in this club? So I was proud that I was able to start to learn Some of those skills and like, you know, get the grounding and like, start to push myself in showing designs and getting critique and all of that. So actually even critique in of itself as a design practice, it is essentially where you come up with something and then you show it to a room of designers and the entire goal is the room is going to go around and kind of tear it apart and show you all the things that you weren't thinking about. And that was like, terrifying to me. And so practices like that, like showing up over and over to do that was really, I think I look back and I'm like, I'm really glad I did that. Even though I was so nervous and it was really hard at the time. I think also jumping into management was an example I was asked to manage and I was just like, sure, but had no idea what it really entailed or what that meant. And just the next couple of years were just me feeling like I didn't really know what I was doing. And all one on ones felt awkward and trying to figure out how to do things for the first time, whether was like, give an offer for the first time or negotiate for the first time or tell someone it's not working out for the first time. Like, all of these were hard and I felt scared.
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Molly Graham
Yeah. I am curious though. Like, sounds like you built that practice at Facebook and you started to learn how powerful it was to take risks and then you realized that you weren't naturally doing it. You had to push yourself to do it. And so I know. I think one year you built a daily practice around risk. Will you just. Can you just explain some of that?
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Ayo Akemwaleere
Yeah. I do challenges for myself every year. I love January. I love the chance to sit down and reflect and think about what we learned last year and what should we think about and dream about for the year ahead. So I have this magical set of rituals around January. And every year I try to do some things that I think will be kind of fun but be kind of challenging. And there was one year that I decided to blog and write publicly for the first time. And that was how I started started writing on the Internet, which eventually led to writing a book. And I couldn't have predicted that was where it went, but it kind of started from one of those Januarys. I think about two years ago was when I was like, this will be the year of everyday risks. And I try to come up with a little title and a theme for every year. So sometimes there were bigger things and sometimes there were smaller things, like speaking up in a room or trying to tell everyone else to be quiet because we actually need to listen to X person or I need to say something or bigger ones would be like, I went and tried surfing for the very first time, which was also something that terrified me. But it's a blend, right? It's not like all big things. A lot of it is very little things. Sometimes it felt risky to actually take a break and to spend instead of following my schedule. It felt riskier to be like, no, no, no, I'm actually just going to take this two hour block and I'm going to do something with my kid. So it's a feeling more than it is a particular action. Because sometimes following when you don't want to feels kind of risky. Sometimes following a plan when you actually kind of want to do something else is the thing that feels risky. So I was leaning a little bit more into how it felt more than what was the specific task.
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Molly Graham
It sounds like from naming it and reflecting on it, it made it easier to identify both what felt risky and when you should take a risk.
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Ayo Akemwaleere
That's right. Yeah. And I think one big learning I had was it doesn't always look like the same outcome or activity. It's not always, oh, I need to speak up more in this context. Sometimes it's like maybe I need to not say something even though I really, really want to, but maybe it'll actually be better. Or it's like me learning something to not say something in this case. So again, it's very much about trying to follow that feeling more than it is about being very specific. I think that's probably one of the things that I learned the most from that year. Like, if you look at my journal, it's like it's all a very different variety of activities, sometimes conflicting with each other week over week.
- [16:25]
Molly Graham
It's so interesting. I think of you as such a craftsman. It's actually the word that came up for me when I was thinking about you and thinking about talking to you today because obviously you're a designer and you're a craftsman because of that. And I feel like your book was actually all about taking management and turning it into a craft. And it actually turns out that what you did with risk is try to turn it into a craft, like believing that it was something you could actually get better at through a daily practice. I am curious though. What impact did it have on you? What did it unlock for you to actually name it and see it?
- [17:05]
Ayo Akemwaleere
I think about as training a muscle, which is also one of the things I'm doing now in my later years is actually getting more athletic and doing more sports and things like that. That. But, yeah, like, when I first started, like, I couldn't do a single push up. Like, it's been years since I've been able to do a single push up. And it's not easy to do the first, but after you do the first and, like, the second is easier and the third is slightly easier, so the distance between them gets easier the more you do. And I kind of love that feeling. I remember in Dante's Inferno, there's, like, a beautiful analogy that, like, you know, towards the second half, like, eventually, it's, like, so hard when you're, like, in the pit, but then when you walk yourself up, eventually, the higher you go, the, like, faster you go until you're finally flying. Right? And I just love that analogy because to me, that's how I think about it. At least in my mind. I'm like, okay, it is hard, but if I can do more and more of them, when I look back, it's like the number of risks that I might be taking now compared to three years or five years ago, it always still feels like the edge of it still feels kind of uncomfortable and a little sharp and jagged, but on the whole, it just feels easier to do because it feels like I've built up that capacity. Like, I've trained more of the muscle. But the good thing about life is it's always meeting you with, like, more and more things. So it kind of just. When you're like, oh, yeah, that kind of thing becomes easier. It's like, boom. It's like the next challenge, the next challenge, next challenge. And I think that's life totally.
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Molly Graham
That's the joy and the torture. The thing that I think is so cool about the way that you think about risk and what you've done is I. I do actually a. I. I think people think of themselves as either good or bad at this. Like, I am not a risk taker, or I am a risk taker. And you built a practice that said, I can get better at this, which is, like, such a powerful thing. And the other thing is, like, you're naming something I really believe, which is that it never goes away. Like, you might get better at one type of thing, or it might get easier maybe to, like, step into that discomfort. But it's not like you can ever live a life without the opportunity for risk. So actually, just what you get better at is, like, recognizing, oh, I'm feeling that way again. And it's like, I gotta get cool with the discomfort again. You know?
- [19:19]
Ayo Akemwaleere
I also think, Molly, there's such a big difference between the risk that you sign up for or the choices that you make. Like, the agency matters a lot. Like I mentioned earlier, like, I felt like I had to be brave because circumstances were such that it sort of asked that of me, right? Like, I didn't get to choose whether or not we were going to move from China to America. Like, I kind of had to, and then I had to deal with it. And even when I was at Facebook, I chose Facebook, but I didn't necessarily, you know, I felt like these opportunities were sort of both either asked of me or, like, you know, I was nudged in that direction. Or you could even argue it was, like, peer pressure because I was, like, around so many incredible people. And I just felt like I wanted to keep up in some way. But more and more, I find that it makes a big difference if, like, I'm like, no, I'm gonna try this. Like, I'm gonna try this for me, not because someone else is trying to push me into it or, you know, nudging me into it or saying that this is, like, the way it should be or that this is what's good for me. It's like I opt into it. And I think, regardless, either way, like, if you opt in, it's gonna be hard, but at least, you know, you chose it. If you don't opt in, life's still gonna give you a bunch of things as well. So, you know, like, all things being equal, I think there's something that comes from feeling like I am in the driver's seat of, like, getting to choose the kinds of things that are hard for myself. And I think there's a lot of joy in that.
- [20:50]
Molly Graham
This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire, they can change everything. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes and find the right fit. That's why LinkedIn Build Hiring Pro, your new hiring partner that screens candidates for you. So instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business. In fact, LinkedIn found that its users are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free@LinkedIn.com worklife terms and conditions apply. This episode is brought to you by Rula. I've been thinking about how we show up for the people around us, our teams, our families, and how easy it is to forget that we need support too. The truth is, getting help with your mental health can feel harder than it should. You try to find a therapist and suddenly you're navigating insurance long wait lists and wondering if you'll ever find the right fit. Rula helps take that friction out of the process. They work with over 100 insurance plans, so most people pay around $15 per session. And they connect you with licensed therapists who are aligned with what you actually need, not just whoever happens to be available. Thousands of people are already using Rula to get affordable, high quality therapy that's actually covered by Insurance. Visit rula.comworklife to get started. After you sign up, you'll be asked how you heard about them. Please support our show and let them know we sent you. That's r u l a.com worklife. You deserve mental health care that works with you, not against your budget. This episode is powered by AT T Business. If you're running your own business, you know that the Sunday scaries are real. You're thinking about the invoices, the client calls, the inventory, the list that never actually ends. And honestly, we usually don't think about our Internet or our phone service until it isn't working. Sometimes a simple glitch can feel like a total catastrophe. That feeling of powerlessness when your tech fails you is the worst. It's a reminder that our connectivity isn't just a bill we pay. It's the backbone of everything we do. AT&T business gets that. They know that for a small business owner, good enough isn't good enough. You need reliability that stays in the background so you can stay in the lead. If you're tired of the friction points and just want a provider that understands the stakes, check out ATT Business. ATT Business is a reliable provider for small business owners. For Small Business Month, we celebrate small businesses by helping them run better. That means reliable uptime, easy switching, smart communications powered by AT&T Business Built to Work get att business@business.att.com. One of the examples you gave earlier of the daily risks was saying something that was uncomfortable. Like pushing yourself to to like, say the unsaid thing or to like, you know the feedback that would be so easy to just not say, or the conversation that, you know, you can avoid having for months, and it just grows and grows. So, like, what have you learned from turning that into a practice, turning that into a craft? Like, what have you learned about what you need to do in those situations when you disagree with someone or when you need to give someone feedback? That's a little scary.
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Ayo Akemwaleere
Yeah, Great question. The first thing I've learned is, like, I need to be out of my emotionally heated zone. That's, like, the most important thing. So, you know, like, I've come to realize that whenever there's a feeling, it's like, there's something good in that feeling, right? Let's say, you know, you and I are talking. This will never happen with you, Molly. But, like, let's say you're talking, and I'm, like, real angry about it after the fact. There's a good reason usually, right? There is a good reason. There's something that's bothering me about that conversation, and there's something good and pure there. But if I'm angry right now, there's no way we can find the kernel of what was really important about why it bothered me in that moment. And the way I express it is always going to sound kind of egotistical because it's about my hurt, my anger, and why are you doing that thing to me? And there's no way I can communicate that and give it kind of the attention and the best chance of making it something productive. And so that's the most important thing is awareness of. Wait a second. Am I in a negative head space right now? Because if I'm in a negative head space, this is not the time. Maybe I can journal. Maybe I can, I don't know, try to process it a little bit. But let's come back to it. When I'm feeling more ground and what grounded feels like to me is like, I'm thinking about the bigger picture. Like, I'm thinking about something positive that I truly care about, right? Not my ego. Not that I'm hurt and angry. Why did Molly do this thing to me? But, like, I want us to create something great together. I want our team to be wildly successful. I want our team, I want our company to hit its goals. You know, I want our relationship to be better for the long term. If I am now starting to think in that zone, and that's my why, then I am ready to figure out what is the kernel of whatever it was and find a way to talk about it. So that's at least my personal litmus test. So it matters for that relationship. It matters that we can. For my values. That we can be the kind of people who. We don't bury issues. We don't pretend like everything's good because it's still there. I can still feel the energy, and I want to resolve that. I want to feel like you can trust me and I can trust you. And that's the why.
- [26:56]
Molly Graham
Yeah. It's so interesting because I think you use the word grounded, and what I hear is, like, you need to be grounded in a positive vision of sort of, like, the future and what you want. That has nothing to do with being right and has nothing to do with, like, it is about the outcome. Cause you're trying to create, like, a more positive relationship, but it's not about, like, the outcome you want necessarily, or, like. Yeah, to your point, like, your ego. It's about the fundamental thing underneath it that you're trying to accomplish.
- [27:24]
Ayo Akemwaleere
Yes, that's right. It's not about, like, making me feel better in that moment. Right. It's not about, like, removing a wound. It's not about validating that I'm right or I'm great or I'm. Whatever it is. We're building something collaborative and shared together because we both want a positive and creative vision of the future.
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Molly Graham
Yeah. Okay. You've gotten really good at pushing yourself to take risks. I'm curious. Like, how do you know when you shouldn't. Like, how do you know when it's, like, something you shouldn't do? Like, one thing you said was, like, when you're in emotions and anger, but, like, just more broadly too, like, when shouldn't you.
- [28:05]
Ayo Akemwaleere
I think, yeah, it's what you mentioned before. I think we have to ask ourselves, why are we doing this? Like, I know some people for whom, like, whenever, you know, something gets hard or something gets scary, they kind of want to, like, change everything about their lives. Do you mean, like, you know, they want to move to a different city and they want to, like, break up with someone or they want to and, like. And it's actually not related. It's like, there's something that's scary, and maybe the instinct is actually to flee or run. And it seems like taking risk, but in some ways it's actually a pattern. It's the opposite of risk. Like, it's doing the thing that they're used to doing because it feels safer somehow to do that. Right. I think that if it feels like it is, again, grounded in some kind of fleeing or some kind of like avoidance or some kind of trying to get away from a negative feeling or reaction and it's done when we're still feeling those things, then it might not be the kind of risk that serves our long term purpose. Yeah, it's very hard. I've learned this. It's very hard to judge from the action itself. Right. Sometimes what often looks to the outside of like, oh, that person is so brave. I've read somewhere that there's a real distinction between having courage and being fearless. And fearlessness is this idea that you're doing it because you're not afraid to do it because it just never. That thing was really ever scary. Maybe it's even intoxicating in some way. Right. Whereas like courage is a little bit more grounded. Courage is like you are aware of what all the consequences and ramifications might be and it is scary and there's no guarantee that they won't happen. But you believe this is important because you're doing it towards some greater end. So even though you will still feel scared, you're still taking that step anyway.
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Molly Graham
Dude, I love that. I love that definition. I've never heard the difference between fearlessness and courage, but it's, you know, it really resonates with some of the stuff you said around just like being grounded in what's making you afraid, but also in what you want. And if you have that, then you can take a risk knowing why.
- [30:24]
Ayo Akemwaleere
Right?
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Molly Graham
Yeah. Yeah. I genuinely think most people think I'm either good or bad at this and that's like a fake, fixed thing inside of me and my life and my personality. I'm either a risk taker or I'm not. And you've made it a practice of something that you are trying to get better at. And I think you can like unlock that for people, which is that this isn't a fixed thing. This is something that you can practice daily, you know, or weekly.
- [30:50]
Ayo Akemwaleere
Yeah, I do feel that way. I think that, like I used to be a very risk averse person and I don't feel that way anymore. So, you know, it's just like there's, there's definitely growth.
- [31:10]
Molly Graham
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- [33:13]
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- [33:44]
Molly Graham
One of the things I really wanted to talk to you about because you wrote a book on management. It makes you realize that those risks can feel really different depending on how much power someone has, particularly at work, but probably true in life as well. I'm curious how you think about the role of management and risk.
- [34:06]
Ayo Akemwaleere
So I think that what a manager needs to do is bet on certain things. And so when you bet on something, that means you do have to own it. You have to own the responsibility for how it goes. But the decisions are less about exactly what we should do in a lot of cases, but who should we trust? Who knows the best amongst our group what to do in this case or what great looks like here. And therefore they should be the ones made decision. But I also think it's super important that if it doesn't go well, you kind of have to own that outcome as well. Because at the end of the day, you made the bet. If I said, hey, I think that when it comes to this issue, George on the team has the most context. Let's follow his lead. He says, we're going to go with this decision. We follow the decision. I think mistake number one is if I believe I know better than George, and then I'm like, no, we have to do this. But it turns out George is better. There may be some cases in which maybe I do know better than everyone in my team and therefore I should make the decision. It's not that I think micromanaging is always wrong. It can be the right thing to do if you truly do know better than everyone else on your team. But at that point, you know, maybe you should be hiring a better team or, like, you know, maybe there's something else that's going on in terms of the structure. And it goes back to, like, I think good management is really about just being very aware and, like, continually testing your judgment against reality and being open enough to see when things are or aren't working. I think that at the same time, I think it's about trust as well. So, like, in this case, like, George has to feel that I am on his side. Like, I am doing whatever I can to help him succeed and do my best. And until, again, new information emerges that it was ultimately the wrong judgment call to make.
- [35:52]
Molly Graham
Yeah. I'm curious, like, what you think about the phrase, like, safe space or something like that. Because, like, I do think one definition of a great manager is someone who makes it safe for a team to take risks or an individual to, like, put themselves out there and try things that are scary or they might not be good at or to advocate for something. And a bad manager is someone that, likes, can make everything inside of that feel risky or like your whole reputation is on the line. Do you think safety is sort of like a part of what great managers create?
- [36:27]
Ayo Akemwaleere
Absolutely. I think it's really important for people to feel like it's okay sometimes that we try some things and they don't work out. Like, one of the things that I tell my team right now, we're all in this very, I think, intense AI period, where feels like every single week things are changing. Like, the way teams work are Changing the technologies that are coming out and what it enables are changing at such a rapid clip. And so in those cases, I think often people ask these questions of, like, well, what's the world going to be like in three months or six months? Like, what really matters? What are the big bets? And to be honest, I don't know that. I know. I don't know that a lot of people in this world really can say with any amount of great certainty what will happen in some number of weeks or months or years. And I think to pretend otherwise is not doing the team or anyone a service. So in those cases, what I told my team is, you know what? This is the time for us to try a lot of things and to take risks. The thing that I would ask of you is that we're here to learn. And so if you have a great idea and you have a hypothesis as to why this is going to be great for our product, our company, I want you to feel like you can take that. I also want you to know it's okay if you're wrong, but what I'm going to ask of you is if you are wrong. I'd like you to be the person most obsessed with figuring out as quickly as possible that you were wrong. I'd like you to be the first person to say, hey, I tried this thing, and I thought it was going to do this, this, this. And then I went and had a good go, and it turned out that this isn't the right path for us. Let's do something else that still allows people to take risks, but do so in a way where we all feel like we have the team's best interests in mind. Right. So it's really important. I think that when I think about the dynamic in a team, like, you know, we can't take risks. We feel like there's always going to be a evaluator or judge who is just looking at our every single move. It doesn't feel good. It's like someone is just like, Big Brother is watching you. And it's like, did you do this enough? Did you do this? And they're, like, looking at your activities or your behaviors and assessing whether or not you're here, you're going to make it. But I do think that what's important is this sense of trust. And what trust comes down to is, do we see things in the same way? Are our values aligned? Do we both understand what success looks like? I think that's such an important question, that what I believe is success for the team and what everybody on the team believes is success for the team, if that is unified, if that's like we're on the same page, we all know what we're trying to shoot for as well as we all know what values are there. Right. Like, what does it mean to work in a way that's respectful? What does it mean to kind of shoot for excellence? Like, how do we treat each other when things are hard? Like, these are all what I mean by like base values. I think if those two things are good, then you know what? People should have more and more freedom. Like, I really believe in that level of empowerment because that's what I hired people to do, is just to go and do their best work and use all that talent and skill and brain power and collaboration to make something that makes our team better.
- [39:44]
Molly Graham
Yeah. But I am curious because not everyone in the world has done the work to think through. What does it mean to be a manager? What does it mean to get the most out of the team? And I think a lot of people are trapped in work situations where a manager makes things feel unsafe or makes things, you know, a lot of those like day to day risks that you talk about feel scary, including like giving feedback or setting a boundary or saying, I'm not going to work, you know, at night. Like some of that can feel like your job or your reputation or your, you know, to your point about performance reviews, like that's on the line. How do you think about risk in a situation like that? Like, how do you actually influence or work with or like, how would you tell someone to think about risk in that situation?
- [40:35]
Ayo Akemwaleere
I think that for all of us, especially now in an era where things feel very uncertain in terms of like, what's the future going to hold, what's going to happen with technology? I think the most important thing for everyone, whether you're a manager, whether you're somebody who's on a team and you're worried about the environment of your team, to I think take a step back and to ask ourselves what really matters? It's sort of like the meta level, right. So we talked a little bit about sort of more maybe bounded areas. Like when you're a team, you're like, what does success look like for a team? But if we step back, we're like, what does success look like for my life? What really matters to me? Again, it goes back to like, what would I consider if I look back 20 years from now, 50 years from now that I would have been proud to do? What is it when I Look back and think about my values, like, how do I want to work? How do I want people to treat each other? What do I care about? And I think when we think like that, it's very generative. It feels like it comes from a very energizing and generative place, which is great. That's kind of the energy that we want to go into. Sometimes these harder decisions we want to kind of come from, what is our purpose? What do we care about? What do we want to be a part of? I think what can happen is, is that in the day to day, something can happen and we can often get very reactive about it. So, for example, to your point, this example of like, hey, I don't really want to work this weekend or tonight because something else is really happening in my life that really matters to me. Maybe it's family, it's whatever. And I think if you're able to zoom out and ask yourself, okay, no, 20 years from now, what's going to be important? It gives us a little bit more of a framework or a grounding to then go into those decisions and to be able to, I think, feel sturdier. Sturdiness is kind of, I think, this, like, sense of groundedness. It's like, you know what you stand for, you know where you come from. And therefore, when other things kind of react, right, Other things reacting, kind of feels like, you know, my mind, like weather. It's like there's wind that's blowing, there's a storm, there's this, there's that, right? And it impacts us. For sure it does. You know, it can make it very difficult for us, but if we can then take a moment to be like, okay, but what is the value that we have? Like, for me, it's like I want to go back and feel like as much as I love my job and working and like, being a startup founder, like, I don't want to look back in 20 years and feel like I, like, missed time with my family and my kids and the people who are close to me. Like, I let friendships, you know, wilt or whatnot, right? So sometimes just like having time to ask those questions and then be like, okay, so now this thing is happening. Like, yes, there is an urgent work task, what really matters. It becomes easier again. Our decisions are always going to be very personal. You know, what I decide will be very different than, like, what you or somebody else decides. But I think as long as we know ourselves more deeply, it will become easier for us to be able to then take that risk or do the thing that feels a little bit scary in that moment because we know why we're doing it. Like, what does it really ladder up to in the long stretch of time?
- [43:41]
Molly Graham
Julie said so many brilliant things that I want to remember. One is something I believe that is still kind of blowing my mind, which was the difference between fearlessness and courage. Because sometimes I think we think like, oh, the goal is to be fearless. But she defined that as acting without fear, which can actually be reckless, right? To not be afraid of things that are actually really scary. But she said that courage is being aware of your fear, being aware of the consequences of what could happen. That's bad. But still acting because it's important and because there's this positive shared purpose that you're trying to build towards and that makes you realize that the goal is courage, right? The goal is to have the courage to do the things that are important. And wouldn't we all be a little bit better off if we did that every day or every year? Work Life is a production of Ted and Pushkin Industries. This episode was produced by Isaac Carter and Leah Rose. Banban Chang is our story editor. Mixing by Hansdale Shih. Ted's executive producer is Daniela Balarazo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Hylash, Valentina Bohanini, Lainey Lott, Tansika Sungmanivong and Ashley Murphy. If you like the show and want more, come join the discussion on my substack lessons. I'm Molly Graham. Thanks for listening.
- [45:26]
Ayo Akemwaleere
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- [46:08]
Molly Graham
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- [46:13]
Ayo Akemwaleere
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