How to negotiate effectively with Wendy Chow

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Planet Visionaries, hosted by environmental advocate and professional climber Alex Honnold, brings you real stories of discovery, determination, and research and initiatives relating to environmental change. In partnership with the Rolex Perpetual Planet Initiative, this is Planet Visionaries. Listen or watch wherever you get your podcasts. People just don't practice this. They don't think about it as something that they need to learn. They just think they're born with it or not, and some people are good at advocating for themselves or not. But the thing is, if you're quote unquote bad at it, it means that you're just not practiced at it, and you can get good at it. Hi, everyone. So this is the second episode in our series called How to Get What You Want at Work. Last week, we talked to Simone Stolzoff about how to know what you want at work, which is a surprisingly hard first step. This week, we're going to talk about what comes next: how to actually ask for it. And for that, I'm going to introduce you to a friend of mine, Wendy Chow. Wendy has spent the last eight years as the general counsel of Cityblock Health, a company that provides healthcare to people with complex medical and social needs. As a general counsel, Wendy's job is to negotiate and advocate on behalf of her company, but that's not actually why I asked her on the show. For the last decade, Wendy has made a hobby out of helping her friends and her friends' friends, and basically anyone that finds their way to Wendy, negotiate for what they want at work. Often, those negotiations center around what Wendy calls get your money: new job offers, promotions, performance reviews. But Wendy has a much broader perspective on asking for what you want, or what you need, as she would say. Because being good at your job and being good at advocating for yourself are two Completely different skills. I speak from experience. I have really struggled with this in my career, and I've watched a lot of my incredibly powerful, successful friends struggle with it too. You can be exceptional at what you do and still be terrible at asking for the money, flexibility, responsibility, support, or opportunities that would make your work and your life better. The good news is, asking is a skill, and Wendy believes you can learn it. I'm Molly Graham, and this is WorkLife, where we untangle the messy human side of work. Wendy Chou, welcome to WorkLife. Thank you. Thank you for having me. It brings me great joy to utter that sentence. Okay, Wendy, so you have made a hobby of helping people ask for what they want at work. Why did you start doing that? Yeah, so I'm a lawyer, and I think that you would think that, oh, all lawyers know how to negotiate naturally and are very good at asking for things at work. But that's not—I mean, everything has to be learned. So I didn't start my career negotiating, actually, and I was at a job. The company was fine, but I had a boss that was toxic, and I had a really long commute, and I just was ready to make a change. I got recruited to another job, and there was no commute, and it was just something new. I was so excited about it, and they were offering me the same amount of money. So in my mind, I was like, why would I negotiate? Like, I don't know. This is a much better situation, and I felt so wanted. I just was not going to jeopardize it in my mind, right? Which is what I think a lot of people think. And I had a roommate, still a dear friend of mine named Julie. And she was incensed that I wasn't going to negotiate. She got up in my face and was like, What do you mean? I was like, What do you mean, what I mean? I'm leaving something I don't like, and this is such an amazing opportunity. And she went away and came back and gave me several articles about how much less women negotiate than men, and it fired me up. And through not that much effort, like a couple of conversations, I got $20,000 more dollars in that job. And I remember standing outside the building of that job that I was not excited about and leaving, and I remember just feeling like so in awe that I had made $20,000 with a couple of conversations. And I was like, Oh, I will never go back. Like, it's on now, you know? So, and then, you know, Molly, because we're friends, I think you know this about me. I'm a hard no till I'm a hard yes, and then I'm an evangelist. Yeah. And when—tell us, like, when you realized you were actually good at helping other people do this. Yeah. So because I'm an evangelist, then I started telling everyone, like, Did you know you can do this with just words? You know? And so I started offering it to all my friends. You know, like when you're negotiating stuff, like, let me know. I'm happy to help you. And I just found it to be so fun and so rewarding and actually kind of like a game. And then actually I was—so I was just helping out friends and family, and then I got this women leadership fellowship out of the 92nd Street Y, shout out 92nd Street Y, called the Women Empower Fellowship. This is in New York, for those of you that are not New Yorkers. Yes, it's in New York, yeah. And that year— At the very first meeting, we were talking about what do we want the year to be like, and with the cohort, and I said, like, what if we do some skill sharing? I can help people negotiate their salary. I didn't think that people would need it because these are humans at the top of their game, and people were overwhelmingly interested. And that made me realize that, oh, this doesn't matter where you are in your career. It's this completely separate skill that is different than being good at your job, whatever it is. And so everyone needs this kind of help. I am bad at that. Like, I can think of many times in my career when I either didn't ask for, you know, more money, or I didn't negotiate a job offer, or I was struggling and I didn't ask for what I wanted because I was scared of, you know, all sorts of things. And it's so interesting because I think you can be, like, really good at negotiating and, you know, you can, you know, negotiate multi-million-dollar deals for your company, but then, you know, I've witnessed such amazing, powerful people become sort of paralyzed when they have to negotiate for themselves. Like, what do you think changes when the thing you're advocating for is you? What I would say I've observed is that people, you know, a lot of times when you're watching somebody else do something, you think they're just born with it, you know? And what I think a lot of us have learned is like, no, they're practiced, you know? And my best friend is a brilliant—Jess McCarly, brilliant psych professor, teaches classes on behavior change, and since we were 12 years old, she won't let me say I'm bad at anything. If I say I'm bad at something, she'll say— You mean you're not practiced at it? Like very gently, very kindly. And so I've learned, like, okay, everything just requires practice. So yes, there's a fear component, and I want to get into that. But even more upstream of that, people just don't practice this. They don't think about it as something that they need to learn. They just think they're born with it or not. And some people are good at advocating for themselves or not. But the thing is, if you're quote unquote bad at it, it means that you're just not practiced at it, and you can get good at it. You can get over the fear, just like when you're learning anything. Talk about the fear. So talk about what are the types of fear you see people struggling with? Yeah. So the first part of my framework is I want to normalize for people it's okay to ask, you know? And it sounds really simple because when people come to me for help, they think that they're over this part. But every time I've started with like, okay, we can get to the how, then I see them being paralyzed with fear. And I'm like, no, we have to go back to the first part, which is that it's okay to ask. So I think there's a few things going on. I think that a lot of people think they're doing something aberrant or that they're not supposed to. And the first thing is I just want to normalize: many people are having this conversation. And so it's not—it's banal. It's not even controversial or spicy in any way. You know, this is a very common practice that's happening all the time. You know, so that's the first thing, is just helping people understand it's very normal, you know? But the fear is also very normal. And if you break it all the way down, your job and the money that you make at your job is your access to food, water, and shelter for yourself and for your family. Or even if you don't—even if you're privileged enough to not have to work for money, it's your access to status. You know, which is another version of being accepted by your community, which is another version of safety and being worried about food, water, shelter, right? So actually, it makes a ton of sense why people are afraid. You know, they're afraid that if they do something proactive, that they will jeopardize their access to food, water, and shelter. That's what I think is really happening if you break it all the way down. And I help people in part three of the framework ask things in a way that in no way are they going to jeopardize their access to food, water, and shelter, and just help them see and have conversations that are just very run-of-the-mill, and you're just having a conversation. It doesn't need to be scary. Yeah. No, I think the fear is, like, so tangled up for a lot of people too. You know, just the fear of getting a no. Yeah, fear of rejection is in there too. And I think obviously that's also just like, what would I do if this happened? What do you think we lose by not asking, if we let those instincts win? Well, first of all, if you just talk about comp, right? Like, even if you don't get to the other things, if you just talk about comp, you're leaving so much comp on the table. Not just the $20,000 that year, or however much it is, but that aggregated year over year over year over the life of your career is profound. You know? So, like, that's the first thing, which is sort of stark, just numbers. You're just leaving money on the table. The second thing is there's so many things that can help you be your best at work that people don't ask for beyond money. You know, a lot of people think about money when they think about negotiation, but there's a panoply of things you can— of conditions and things you can ask for that'll help you be your best. And what I try to help people see is that by getting those conditions met, you're gonna be your best, which means you're gonna perform better at work or be able to stay in a job longer. You know, in very simple terms, you're leaving money and happiness on the table. Well said. Asking obviously doesn't carry the same risks for everyone. And I think I want to know your perspective on how you think gender and race and various identities change the experience of advocating for yourself at work. Yeah. I don't take for granted the fact that some people might not like that you're asking if you're in certain demographics. That's real, you know? Like, that's real. Or they might take it a certain way versus if you were in a different demographic asking for that same thing. That's true for even just existing in the workplace at all. Like, those biases occur every day, you know? And I can't design my life around other people's biases. I can recognize them and I can try to account for them in how I ask for things or how they might react. But I just think of it as a constraint in the game because I'm not gonna let somebody else's biases stop me from advocating for myself and getting what I need. And if you are in an environment where no matter how thoughtfully you design your ask, no matter how much you try to take the other person into consideration and blah, blah, blah, like you just keep hitting a ceiling or you just keep hitting roadblocks, then that tells me all the information that I need about that environment, right? And I might not be able to make a change right away because of my life circumstances or whatever, but I will be looking towards doing that, right? Yeah. No, you just said one of the things that I really both believe and have experienced, which is that when you ask, the response really shows you a lot about who people are. Absolutely. And I think, you know, I had this crazy experience like a couple of years ago where I was working with two friends who are both Black females on just, you know, same thing you do, negotiating for an offer or going through a process. And both of them asked for something in the process of negotiating the offer, and one of them had the offer rescinded, and the other one got an email back. And by the way, I think the things she asked for were like, Why is the title X versus Y? And like, Can you explain the rationale of the compensation to me? Like, they weren't even, they were barely asks, you know? And the email she got back was like, This is the most aggressive— All she got back was like, This is the most aggressive, like, negotiation we've ever experienced as a company. So, A, for people that don't think bias exists, welcome. B, like, you know, I, like, neither of those jobs ended up working out, but I think it really also made very clear that these were not the right places for those two people. A hundred percent. Yeah, I totally agree. I think there's a category. I've also seen some offers rescinded in different scenarios, like different than what you're talking about, where the way that the person asked was really unprofessional. The recruiter gave them the offer, they laughed and said, Try again, and that offer was rescinded, right? But yes, a hundred percent. I think there's some people that will, of course, will be biased and, you know, take it as more aggressive or whatever just because of the demographic or the person or the circumstances of the person that are asking. But I totally agree with you. That tells me everything I need to know about what's going on at that company, and that's not something that I want to be part of. And there's many, many people on Earth and many jobs where that's not the case. Doesn't mean that you don't—if you still want to go there, great. I'm not judging you, but, like, you need to know what you're walking into. Yeah, totally. Yeah. Just to stay on this for one more minute, like, does your advice change at all depending on who's doing the asking? My advice is really, like, 360 nuanced. It's about who's asking. It's about who you're asking to, what your relationship is, what you're asking for. The way that I teach people to ask, I don't change that based on demographics because I think whoever you are, you should make a thoughtful— And considered ask. And if you do that and the person reacts negatively just for the sake of you asking, it goes back to the thing that we said about then you have all the information you need to know about that person or that company. Yeah. Right. We did an episode last week on how to know what you want at work, which to me is like both like a necessary first step and something that can be very hard. And you have a framework I love for figuring out what you need at work that starts with paying attention to what makes you grumpy. Will you explain that framework? Yeah. So, you know, a lot of times when people come ask me for help, they say, it's usually about money, right? That's usually where it starts. And I say, okay, we can talk about money, but let's talk about everything else too. Think the furthest place out that you can think of. Like, I call it my North Star of like, what am I going for? It might be 10 jumps away. It might be one jump away. It might be my current job, but better. But what am I going for? And make that as specific as you can. And this is the part where the grumpiness comes in. That's like, don't think about your dream job on a good day. Think about what you, when you're having a bad day at work, immediately your internal dialogue is, I don't have the headcount that I need. Well, like, I just don't have the resources. Well, that other person has the same title as me, but they're making way more money. Like, then you start to really come up with the things that are blocking your happiness at work, right? It's like a more honest list. So once I have my grumpy wish list, which I love, how do you prioritize it? There's a few different ways. I want to say one more thing about making the list, though, that I see happen all the time. What happens is people start to make their list, and then in their heads they're like, But I'm never going to get that. Like, they'll never say yes. I don't know what company will let me do that. And then they cap their own dreams, you know? And so what I say is, we'll get to the how in a moment, but your how mechanism is overly conservative. So, like, when you're making your list, don't think about how. Just let yourself think about, you know, again, what is your dream wish list? And then, yeah, you're probably not going to get all those things at the same time, right? If you get real about what your north star is, then you can work backwards from that, and you can see, okay, say my goal is to be a CFO, and I'm a junior analyst today. You know, probably not going to be CEO in the very next jump. You know, that's fine. That's my goal. But if being a CFO is my dream at this kind of company with this kind of culture and da da da da, where am I relative to that today, and what do I need in order to get there? When I was on the chase to be GC, I was like, okay, I want—I need some management experience. I need to up my financial acumen. I want to get closer to the board work. I want to take on more executive tasks. I want my comp to be like X. I had a wish list of things that was going to help me be GC. So the years where I wasn't advocating for comp for myself, I was advocating for those other things, a lot of which were way easier to get. You know, a finance boot camp that I got one year to, like, up my acumen, or like, Oh, can I take over the internship program just as a first way to get management experience? These were things that were easy to get, you know? And then that led to, Oh, you're doing so amazing at work. Here's more comp. Okay, great. And then that led to, Oh yeah, let's give you more responsibility to help you get more, and then that helps you get more comp, you know? So it's like you kind of create this flywheel. That serves itself. Yeah, totally. Well, and I love, I think we so often almost narrow what we think we can ask for. And one of the things I love about your grumpy wish list is realizing that there's a lot of different conditions and things that you can ask to change. You know, there can be things you want that will ultimately help you get paid more, but they might just be a stepping stone. But also, you know, there are times when it's easier to ask for something that's not compensation for one reason or another. Absolutely. And it's also why, you know, something that you said made me think of, it's also why getting your North Star accurate is really important. Because if your North Star is as CFO, that's a really different wish list and path than if you decide you're not on the title hunt anymore. You want work to be important and good, but not your main focus in life. And you want to be able to pick up your kids at 4 p.m. and you want to work no more than 40 hours a week. I actually have a friend that this happened to. She was on the CFO track, and then she decided, I don't want to be on the CFO track anymore. And that was hard for her to admit to herself, you know? But then when she did, it organized her ask so differently. And so the advice that I've given her over the years is very different than the advice that I would give somebody else. And those things aren't necessarily hard to get. But if you only focused on money, you would miss all those other things that are actually contributing to your happiness at work. This episode is sponsored by MasterClass Executive. If you've ever wanted to learn business from the leaders shaping what's next, you need to hear about MasterClass Executive. MasterClass Executive is the first AI-native business education program, built with the University of Chicago Booth School of Business in collaboration with OpenAI. You'll learn directly from Fortune 500 CEOs, AI builders, and Nobel Prize-winning academics, with weekly live sessions, instructor office hours, and hands-on AI labs alongside practitioners. The coursework is self-paced, so it fits around a full-time job, and your own work becomes part of the learning. 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Starting from before a negotiation even happens, like, let's make this concrete. So let's say I've realized I'm significantly underpaid and I want a raise. Before I ever sit down with my boss, like, what should I do? Love this part. Okay, so I cannot tell you the number of people that call me and say, Wendy, I'm talking to my boss today in an hour. Do you have five minutes right now? And I'm like, it's not about my time, you know? It's about why are you not preparing? I think it goes back to the fear part because these people are brilliant and not lazy. The number one thing that I tell people is, we got to prepare, you know? You would never go up in front of the board or your manager and do a huge presentation and not prepare at all, right? So first thing is, let's prepare, you know? And the second thing is, what I tell people about the how is you need to make a merit-based ask. You need to give people a reason to say yes to you. There's this really old book that I still—the references are a little dated, but it still has a lot of wisdom in it—called Influence: The Psychology of Persuasion. But it cites all this really interesting social psychology research, and one of the things is humans need a reason to say yes. Even if it's not a great reason, that's better than no reason. And the example that I give people is, say you're in JFK, or we can use a California-based airport if that's better, SFO. You're just in an airport. Yeah, you're just in an airport, and you— are running late and you want to cut in front of people at the front of the line, you know, and you say, you get to the front of the line and you say, I'm so sorry, can I cut in front of you? People are going to look at you like you're crazy, you know? But if you say, I'm so sorry, can I cut in front of you? I need to get to my gate. Probably people will say yes, but everybody there has to get to their gate, so it's not really a good reason, right? But if you say, I'm so sorry, I'm running late. I have to get to my gate. I am going to miss my daughter's graduation if I don't make this flight. 100% of people are going to let you in and probably be nice about it. So it's like crazy the power of just even giving people some reasons to say yes. And I cannot tell you how often I see people just, even if they have the gumption to ask for something, they don't give people any reasons, you know? How do you actually make a merit-based ask? I'm glad you asked. So, yeah, so there's a lot of different things you can do, right, in making your case. You can do a little bit of research. I think people think you need a Radford set of data to make your ask, and that is not true. Which is, Radford is one of the big compensation databases that a lot of companies use to define their compensation. And your point is, you think you need all the data in the world. You need two data points, I'm telling you right now. And this is where my years of being a lawyer and negotiating all kinds of other things has come into play. One data point isn't—people can write off as an aberrance, you know, like, well, how come that person got to work remotely, you know, and I didn't? Okay, well, yeah, this is a special circumstance, blah, blah, blah. But if you cite two data points for the thing that you're trying to ask for, it becomes powerful. I have never seen somebody need more than two data points. And you can get that from Googling. You can get that from your friends at work. You can get that from all sorts of places. And the other thing I'll say about that is you don't have to have somebody in your exact same scenario. If you have two people in your network that are relatively the same kind of company or industry, those are your two data points, you know, or definitely at your own company for sure. The second thing is my same friend Julie, who was up in my face and started this whole thing about negotiation, she had this amazing thing she used to talk about at work where— Every day, you can't be doing a splashy dolphin trick, is what she calls it. You know? Like, you'll just burn out. Like, you can't do it every day. But to be successful at any job, you sort of need to do them at some regular cadence. You know? Like, you jump out of the water, you do a thing that, like, people see, you nail the landing, and then you go back under the water, and then people leave you alone until the next dolphin trick. So I've taught this to my team, right? And I'm like, I need you to be writing down your dolphin tricks. And so don't wait until the promotion to try to remember them, or something as big is about to happen, like they're going to do some big presentation. I'm like, guys, this is a dolphin trick moment. Let's nail the landing, and then we're going to put this on your promo case for the year. And as part of your dolphin tricks, or, you know, the other sub-point that I make is, how can you demonstrate that your dolphin tricks, or the things that you have achieved, are lining up with your manager's goals, or the company's goals, or your team's goals? That's a super persuasive fact, you know? Or what would be lost if you don't get this thing? That's another thing. You know, a lot of times when you're advocating for headcount or, you know, outside consulting budget or something like that, you know, it's like, well, let me show you what's not going to happen if—like, I get it if we don't have the resources, but then these—manage your expectation on X, Y, Z things, because those are not going to happen. And that's also another way you can manage your happiness and time. You know, it's not just that, like, you won't give me these resources and I just have to always eat it. It's, okay, let me just show you the business case, and then we're all going to kumbaya and agree that this is what we'll achieve instead. So as we're talking, I'm just going to name, I'm having PTSD from all the times I've done this really badly. But a lot of what I think was hard for me was— I kind of did it, like, on my timeline, on when it mattered to me. I almost used it as a test of, like, the person valuing me. You know what I mean? Where it's like, well, if you don't see me, I'm not going to explain it to you if you don't, like, see how valuable I am. Yeah. Like, you know. Ah, yeah, that's real. And I feel like it was almost like I was so much in my own head that I, like, made it really easy for them to say no, you know what I mean? But it is really interesting to hear you say that because I think it's important to realize, like, this other person has a whole other bunch of shit going on. Some of it you know about, some of it you don't, you know? And so it's, yes, maybe they value you, but, like, it's important to show up prepared, and it's important to show up with, like, clarity and make it as easy for them as possible. Oh, there are, like, a thousand things to unpack in what you said. I do think this is a common narrative, right? That why should I have to ask? Like, why should I have to ask? Why don't you just see my value? And I hear that, and that's real, you know? But like you said, this person has a thousand things going on, you know, and it might not at all be a reflection of how they feel about you or how the company feels about you. We all know how dangerous, like, assumptions and narratives in our own head can be sometimes. And you don't want them to guess what you want. Like, even if they are fully tuned in and you're their star player and they're going to do whatever they can for you proactively, you don't want them to guess. You want to tell them what you want because what matters to you in your dream wish list is not at all obvious to somebody outside of your brain. And the worst thing is when they, if they go through all this effort and guess and they get it wrong, and then you're not happy, and then they're not happy because they expended all this energy for you. You want to tell them what's important to you. Tell me, talk about leverage and, like— And also picking your moment. Leverage is not what people think it is. I think people think that leverage should be rational. It should be like, well, you would be screwed if I left. You know, these things would absolutely fall apart. And that may be true. But that's not always—people don't always act rationally, you know? And so leverage is actually what people think will happen, not what actually will happen. Because I think people overestimate their leverage sometimes by saying like, well, this person, I would absolutely be screwed, and they're underestimating how irrational the other person might be about it. And then the other thing is, I think people that do have leverage are afraid to put it on the table. They're afraid to use it. And unused leverage is not leverage. Leverage is only useful if you make it clear about what the consequences will be, you know? And I don't mean in a threatening way. Like, when you're making your grumpy wish list ask or whatever, one thing that's really helpful to get clear about is what's a deal breaker and what's a shoot-your-shot. Like, you know, this thing, if I don't get, I will leave the company or I will not take this offer, in your own head. I don't advocate people saying it that way. But versus like, I'm just gonna see what I can get, you know? Like, that's a very different ask. It's a very different way to ask, right? So if something is a deal breaker, say you're at your current company and you will leave, you know, if you don't get this thing. I tell people there's a way you can say it diplomatically that lets the other side know without painting yourself into a corner, which is like, thank you so much for having this conversation with me. I really appreciate it. I think you can tell how important this thing is to me. If it can't happen, I understand that, but I'll just have to think through my work, and I'll have to think through my options, you know, of like what to do with work. And if that person says, Are you saying you're going to leave? I would say, I'm not saying I'm going to leave, but it's going to give me a lot to think about, and I'm going to have to figure out what I want for my career, right? That way you haven't painted anyone to a corner. You haven't said you're going to leave. Maybe you'll stay and it's fine, you know, but you've let them know in a veiled way, yeah, probably you're going to leave, you know, or start looking for another job. Or if it's a new offer, you know, and you have a deal breaker number, tell them that, you know, say like, I'm so excited about this opportunity, but I just know where I'm at, and if, you know, we can't, if you guys can't meet X number, I totally understand, like that's your budget, and I respect that, but this is where I'm at. Yeah. Versus a shoot your shot moment, the conversation is different, right? It's, I'm so excited about this job. I just, like, cannot wait to work together. Would love if you, I don't know if you're open to considering this other number. This is what I think would help me be really aligned and excited, and if you're open to, I don't know where you are on budget, but if you're open to this number, would love for you to consider it. Those are two completely different—you're saying one's a, like, I'm not going to be able to take this, and one is like, I just want to see what I can see, what I can get, you know? Yeah. But it's important to let the other side know subtly which one you're at so that they can act accordingly. Just to go back to the leverage point for one second, like you said the words better or real leverage. Like, how do you—what is that? How do you know what that is for you? Yeah. I guess what I mean is when I think about leverage, it's just about who's more willing to walk away from whom. To me, that's all leverage is. You know, who's more willing to not do the deal? Who's more willing to not give you the promotion or to take the risk that you might not take this job or you might leave, you know? And whoever is more willing to walk away from the other has more leverage, whether that's rational or not. Yeah. I mean, you're talking about shoot your shot asks and all these things. Like, is there ever a danger of asking for too much? I mean, I don't think so. But, okay, sorry, I'll answer your question for real. So if you have made your dream list and you have prioritized it, and you are making a merit-based ask based on reasons, I guess it's like, what does it mean to ask too much? They might just say no, and that's okay. I'm not saying that you're going to do these things and you're going to get yeses across the board. I'm saying you need to figure out what you want, have diplomatic and thoughtful conversations to get there, and then see what you see. It's sort of similar to the thing we were talking about in the beginning. Is there a world in which you ask for things that have no basis? To me, that's asking for quote-unquote too much. But I don't think about it as a lot or not a lot. I think of it as, can I make an argument for why you should give me this thing? If you have reasons, your list is your list. Yeah. Hell yeah. And I think your point, and again, looking back on all my past mistakes, I think it's your point is any ask is valid if there's an argument for it, if there's a really clear set of reasons, and that you know where it sort of ranks on your priorities and happiness list. Because I think that should define sort of how you approach the whole thing. Oh, there was something that you said before that I just wanted to come back to, which is the timing of it all, right? Which is no matter where you are in the org, you need to learn about how your org functions. You know, are you at a company that's growing like crazy, has really loosey-goosey rules, and anybody can go ask for something at any time? Maybe you might not get it, but there's not a structured budget cycle, performance cycle, that kind of thing, you know, in which case any time is probably fine. But most people are working in companies where there is a performance cycle, where there is, like, budget season, et cetera. Absolutely learn how those things are done, and that information is not secret. And so you can ask anyone. You can ask your boss. Anybody who's a manager should know those things, or make a friend in HR and ask them. And then time your ask to those times. If you ask for a raise right after they close, Their performance management cycle, that's not going to work. You have to have way more leverage to get it done in there. And you're also asking your boss to spend way more political capital, you know, versus if you just understand the cycles and the rhythms of your company, getting something done in the way that the company does it is way easier than when somebody has to make an exception for you. No, and I think, you know, having managed a lot of people, there are people where it feels like every day is an ask, and there are people that are very thoughtful and strategic about like, hey, we're going into the, you know, the performance review cycle time. Yeah. Because I think the other mistake that I've both made and seen made is that you wait until you get the compensation letter, you know, or the thing on the output. It's too late. Yeah, exactly. So it's like, how do you prepare your manager when they're going through whatever process your company has set up for them, which, by the way, those processes are long and terrible as a manager, like, but it's their chance. It's their moment to advocate for you, and you actually need to, like, put yourself on their brain and say, to your point, like, not just, I want a raise, but like, hey, I need, I, you know, this is what's important to me. This is the amount of money I'm hoping for, because that lets them also then come back to you contextualized. Like, they might not have been able to get it for you, but at least they know what you were expecting. A hundred percent. A hundred percent. What I try to help people understand is like, you and your boss should be co-conspirators in this plan, ideally. It's not you asking them for something. It's you guys are working together on a plan, and you should know what they're going to need to do to do it, and they should be ideally communicating back with you about what's happening. This episode is brought to you by Wayfair. The holidays are almost here, and if you're hosting at home, you know there's a lot to pull together: clearing out the clutter, adding a little holiday cheer, and finding extra chairs for the surprise plus ones. Wayfair makes hosting simple with thousands of products across every style and budget. I got some spode holiday-themed dishes recently that I can use to liven up our family gatherings. I'm excited. They're such an easy way to add joy without any extra fuss. For all things hosting, Wayfair delivers high-quality, customer-trusted products for your home so you can host and celebrate without the stress. 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And you should know me in this podcast by now, there's a step even before that, which is a lot of people will do this during their regular one-on-one in the last five minutes. And I'm like, that is not a recipe for making your case well, you know? But again, it goes back to the fear, right? They just want to get it over with. They just, like, want to do it really fast, and they don't want to draw attention to it, right? But that's a recipe for not having enough time to make all of your thoughtful points. I think it's important to give your boss a heads up. Like, or I recommend that you give your boss a heads up, like, hey, I would love to have a discussion about comp and would love to get your thoughts on some things. I'm going to put on some extra time for us this week, or I want to carve out 30 minutes of our one-on-one tomorrow to talk about, or next, ideally not tomorrow, like ideally a little bit more in advance, because people are more generous when they're not surprised. And then, yeah, I mean, I start with a compliment. I'm giving away all my secrets here. I'm never going to get anything ever again after this podcast. But, you know, I like to start with the good. No matter what your situation is with your current manager, I like to start with the good, you know, of like, thank you so much for taking the time to hear me out. You know, I know you're super busy, and I really appreciate this discussion. Just having the discussion means a lot to me. So what are they going to do after that? Be like, nah, we don't have time for this talk, you know? So. Start with the good and thank them for their time. And then I lay out my ask and I lay out the argument. And then, you know, I think that's the part we already talked about. But it's also like, I think an important part of that talk is like hearing the other person's reaction and what do you feel like you need, boss, to get this done? And having a dialogue with them about what they think they're going to need to do, which then sets you up to say, okay, great. You know what? I know you're going to have to go make an argument. Can I just send you the bullet points so you don't have to write them yourself? Or like, I'll send you all my dolphin tricks, or I'll send you these stats. Like 10 out of 10 bosses are going to be like, Yeah, help me do this thing. Fantastic. Or give me all those talking points. Great. You and your boss probably want the same things, which is you both want you to do your best at your job. And so I do think saying that, other than just saying the thing explicitly, saying all your reasons, I think explaining that is really helpful. You know, instead of making it like you versus me, it's not a you versus me. It's us together helping me be my best so that I can make you look good, boss. Are there any phrases that you think people commonly use that weaken the ask? Like you actually use the word I'm sorry, which a lot of people say don't apologize, but, you know, sometimes. Well, anyway, what are the phrases you'd be like, Never say this. You can roll. It's not about never say this. It's about whatever you can deliver with confidence and authenticity. That's what I tell people. Because some people are like, Should I say a number or should I say a range? Or I shouldn't be the first one to say the number because all the negotiation books say don't be the first one to say the number. And I don't believe in any of that. I am like, even if you're practiced at this, you have to work at having these conversations. You probably will be someone— You probably will be somewhat a little bit nervous, and that's just natural. And whatever you can deliver with confidence and authenticity is what you should say, is what you should do. I say I'm sorry to be polite, you know, and I don't think there's anything wrong with that, you know. But that's for me, right? If you're going in shaking like a leaf, over-apologizing, saying I'm sorry a thousand times and, like, you know, like making it seem like you don't believe in your own existence, then yeah, you're probably going to undermine your argument for more things. Totally. So you talked about feeling nervous, and I do think, like, obviously, like this is a whole psychological game, and I know you have a ton of tiny rituals around negotiating. So first of all, what are they? And second of all, why do those rituals and those practices matter? Well, you know, everybody's ritual is different, but you should come up with one for you, you know. And the ones that I have come up for me are—well, the first one I actually think is universal and, like, do this thing, which is do not schedule something right before this meeting. Try very hard, if you can, to clear your calendar. If you can—you can't always, you know—but clear your calendar at least 15 minutes before so you can get your head in the game, you know. Professional athletes are not going from, what, you know, picking up their dry cleaning to then getting—playing the U.S. Open, you know. Like, they are getting their head in the game, right? And so, like, give yourself a minute to, like, breathe and recap your points and, like, calm your nervous system a little bit, right? So that's the first thing. I actually think that is universal. The second thing is I wear something that makes me feel powerful. Like, that's just me. Not everybody will care about that, but that's—I wear, you know, a piece of jewelry that makes me think of my friends or a trip that I took, you know, or something that makes me feel like my best, like a talisman. I do wall push-ups to just, like, help get the adrenaline out, you know, so. Um, yeah, those are my little rituals. Love it. So a lot of times I'm asking someone that's not my boss, like I'm asking someone that might hire me or someone that I want to work for or something like that. Do you ever do this over email or do you always do it as like an in-person conversation? Oh no, it absolutely can be done over email. You know, I mean, look, it's a kind of a circumstantial thing, you know, but a lot of times it's also a hybrid, right? You might, again, in the whole giving people a heads up so that they can think about it, I think an email, if you want to start with like, Hey, got the offer. Thanks so much. Like, would love for you to consider blah, blah, blah, you know, and then happy to chat about it live if that's helpful. That's for a new job, you know. If it's for a current job, I would have the conversation in person, you know, I think that's a little bit too awkward. So let's talk about when you get a response back. So like you ask for this thing and like sometimes you get a response in the meeting that's like, that's a lot or, you know, some off-the-cuff response. But, you know— Such a yes, that's common. People do say that, yeah. But like you also eventually get sort of a yes and maybe a not now or a no. How do you handle that? You know, what should I do? If it's yes, I don't need to tell you. Great, good, you got it. Victory lap. Yeah, yay. So let's talk about if it's a maybe or if it's a no, right? If it's a no, I'm always just really curious about why it's a no, you know? Some people just take the no and they go home and they're mad, you know? But I'm like, cool, help me understand why it's a no. Not to change their mind even, but just to be like, how can I turn it into a yes next time? Or how long is it going to take for me to turn it into a yes? Or is it possible for me to turn it into a yes, right? Is it a no because I did not take Wendy and Molly's advice on the timing and I just whiffed it on that and really like this could happen at a different time? Okay, all right, that's fine. We'll see you back here in nine months, you know, or whatever. That's one thing. Or if it's like literally no one has done this ever at the company, period, and they're not willing to do it for me, okay, that's different information. Or your boss just didn't try that hard. Or like, okay, they asked one person, but they didn't get it, and like that's it. All that is going to give you a ton of information, you know? And it gives you the information that you need to either help turn them into a yes, or it gives you the information that you need to consider your options. Yeah. Anything, Wendy, that we didn't cover or that you want to make sure people hear? I just want people to understand that you can learn this skill just like anything else, and that in the beginning it starts like maybe you're afraid, and that you think you only do this for big moments, like for new jobs or for promotion or something like that. And what I would challenge people or invite people to think about is, for me, this is like a low-key chess game that I'm always playing in the back of my head. I'm not always asking for something, but I'm always thinking about my North Star and the path to get there. And then when portals open up, I'm like, now's the time, you know? And the other thing I would encourage people to do is once they learn this for themselves, which I'm expecting every one of your listeners to do, do it for your team. You know, if you have a team, do it for your team. I do this for my team now. I use all these skills, and I make sure that we're going to land their promo, you know, that we are going to get the headcount or the resources that we need for the team, because you're nothing without your team. And so, like, spread the wealth. Once you learn how to do it for yourself, do it for other people. Love that. Yeah. So you have spent years practicing this. How has getting good at asking changed your relationship to work? Oh my gosh. I mean, it's immeasurable. You know, like even, let's just set aside the comp that I've been able to achieve because of these conversations, right? Let's set that aside. I am able to just have so much more energy and clarity at work. And I attribute my ability to be successful 100% to my ability to make these asks, right? It's not only about comp. I needed to make sure that we had tech budget, outside counsel budget, the right headcount. I needed to make sure that when I got asked to do another big thing at work, that I got the equity and money to do that, and then I did it joyfully. You know, it's all those things that help me do my best at work, you know, and so that I can have the legacy and the impact that I want. Love it. Yeah. Wendy, thank you so much for doing this. I think people now, everyone wants to know if they can call you when they need to make an ask. But I know you're putting together some resources for folks, and we'll make sure that they're linked to in the show notes. But I'm just so grateful that you took this time to help other people understand the Wendy magic, but also just how important and valuable it is to ask, and that that is so essential. So super grateful to you. Thank you. I was really honored to be asked to be on the show. Thank you. It was super fun. Okay, that was so fun. I'm so glad you got to meet Wendy. Hopefully you now understand what a special person she is. I just want to name while we were recording that episode, there's a story from my past that was just running around in my head. I had this job a couple of years ago where I worked for someone very successful, a white man, just to name it. And oddly, it was the job where I felt the most like I had to ask for things all the time. Like, I think I've been pretty lucky, and despite being really bad at everything Wendy just taught us, like I've gotten a lot of stuff in my career. I've had good bosses who've advocated for me. And this was a job where that wasn't, didn't feel as true. And at some point in the middle of one of my terrible asks where I did a bad job with everything that Wendy said, he turned to me and he said, You know, I've never had to ask for anything in my career. Like, he was like, I've never had to ask for a promotion. And I remember feeling ashamed in that moment. Like, I felt really like, I mean, the message was pretty clear. It was like, you know, you shouldn't have to ask for this. And like, I would give it to you when I was ready, kind of, you know? And I have thought about that a lot ever since. And the most important thing I just want to say after listening to Wendy and just all the experience I've had in my life is no. Like, Wendy's most important message is you should ask. Everyone should ask. And it can be scary and intimidating. And yes, sometimes people will pull the job offer and things like that. But better that you know before you take the job that they don't want all of you or they don't care about your happiness than to not ask. So, like, boo to that manager. Like, that, A, comes from a massive place of privilege, but B, just, like, is bullshit. You should ask. And I think the most important sort of reason why is, like, yes, $20,000 makes a huge difference in your life. But much more importantly, I think what Wendy said at the end, which is this is about your happiness and this is about being able to do your best work. And asks aren't just about money. They're about the circumstances and the resources that you need in order to be able to do your best work. And that is important. And it can change your entire relationship to work. So don't take that lightly and don't let anybody tell you that it's not your place, because it is. So we've covered— How to know what you want and how to ask for what you want. And next week, we're going to talk a little bit more about what to focus on when you're thinking about what matters to you. And there's so many different things that can feel, you know, distracting for sure sometimes in terms of, like, what you want at work. But honestly, there's some things that are important, particularly if you're like, I want to go crush, like I'm ambitious, I want to run the world. Like, what actually matters when you're trying to build your career and move forward? All right, I'll talk to you all next week. Thanks for listening to WorkLife. If you like the show and want more, hit that follow or subscribe button so you don't miss an episode. And share any episodes you love with a friend or leave a review wherever you're listening to this. WorkLife is a production of TED and Pushkin Industries. This episode was produced by Daphne Chen. Our video editor is Connor Titzworth. Ban Ban Cheng is our story editor. Mixing by Hansdale Shee. TED's executive producer is Daniela Ballarezo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Highlash, Valentina Bohanini, Lainey Lott, Tansika Sungmanivong, and Ashley Murphy. I'm your host, Molly Graham. This episode is brought to you by Apollo.io. Building a great team isn't just about having the right people. It's also about giving them the time and tools to do their best work. 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