
Stop playing it safe—embrace the bold, unexpected traits that actually get you ahead.
Loading summary
A
If you used Babbel, you would. Babbel's conversation based techniques teaches you useful words and phrases to get you speaking quickly about the things you actually talk about in the real world. With lessons handcrafted by over 200 language experts and voiced by real native speakers, Babbel is like having a private tutor in your pocket. Start speaking with Babbel today. Get up to 55% off your Babbel subscription right now at babbel.com Spotify spelled B-A-B-B B E L.com Spotify rules and restrictions may apply. This episode is brought to you by Progressive Insurance. Fiscally responsible financial geniuses, monetary magicians. These are things people say about drivers who switch their car insurance to Progressive and save hundreds. Visit progressive.com to see if you could save Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states or situations.
B
Foreign welcome to the Radical Caner Podcast. I'm Kim Scott.
C
I'm Amy Sandler. Today we are so excited to welcome Jenny Wood to the podcast. Jenny's going to talk about her new book, Wild Go after what yout Want and Get it, coming out March 25, 2025. Jenny spent 18 years at Google, rising from an entry level position to an executive role. And most recently, Jennie ran a large operations team that helped drive billions. That's with a B of advertising revenue per year. Jennie also created one of Google's largest career development plans which was really, really popular. And she is now a speaker, an author who is aiming to challenge conventional thinking about professional advancement. We are so excited to hear more about that. So welcome Jenny.
A
It's so great to be here. Amy and Kim. Howdy.
C
We are thrilled, absolutely thrilled. And one of the things Jenny, that you do is that, that we find really interesting because I think Kim prides herself on being a rebel, is that you make an argument that the traits you need to get ahead are the exact opposite of what you've been told. So what are these? Tell us everything.
A
All right, so these nine traits will raise eyebrows. Kim, I know they raised yours when we first talked about.
B
Yes, in fact I gave you some feedback and, and, and you pushed back on the feedback. And so one of my questions is first of all, thank you for pushing back on the feedback because when you get it, it's not always right. And did I make it hard or easy to push back and what could I have done to make it easier?
A
Okay, well this is just fascinating right here because I think I've my perception of that feedback is that I Took it in and that it totally made the book better. So. So what an interesting example of different perceptions of giving and receiving feedback. Right?
B
Yes. Wow. It all worked. It all worked then. All right, so talk about the nine traits.
A
So, yeah, and then let's. Let's. Let's dig into the feedback you gave and my interpretation of me taking it in and your interpretation of me pushing back. So the nine traits that raise eyebrows are weird, selfish, shameless, obsessed, nosy, manipulative. That's a spicy one. Brutal, reckless, and bossy. And these words can create the bars of an invisible cage that keep you small, that keep you quiet, that keep you following instead of leading. But I find that more people need to dial these traits up just a little bit as opposed to pull back on them. And so the feedback that I recall you giving me is, Jenny, you've got to be careful to not take these too far. So perhaps you need to position this as, you know, the right side of shameless.
B
Yes.
A
A little bit manipulative. So I thought I took that. You did. No, but in terms of the way, unless you're talking about the intro feedback from the book, this feedback I'm talking about is two years ago. But there was also feedback you gave me on the intro to the book, which I very much appreciated. I'm so curious to hear what you have to say.
B
No, I think I. I suggested different words and you convinced me you had the exact right words. You were right and I was wrong.
A
Were you suggesting softening them? Because that's the biggest risk of this book. I mean, talk about reckless.
B
You know, I don't. Now, I don't remember what I said, but I think manipulative, I was suggesting a different word for that and you convinced me that was the right word.
A
That's the hardest one for sure.
B
Yes.
A
But to be manipulative is the courage to build lasting relationships, to build influence through empathy. Because whether you're selling a product or an idea or frankly, yourself, the ability to win friends and allies and supporters is all about mutual benefit. And essentially you have to figure out people want and get it for them. And that's the flavor of manipulative that I want to encourage people to tap into more. Not manipulative with the intention to harm or, you know, or trick or lie or anything like that.
B
Yeah. Yeah. I think that I was viewing manipulative in a zero sum world and you were viewing manipulative in a. If we. If we do this, we'll make the pie bigger for both of us, kind of.
A
Yeah. And just be being. Being comfortable, using your influence and using your power. If you don't, then it's just left to the people to use it who actually are manipulative in the bad way.
B
Yes, yes, exactly. Exactly. All right, so let's talk about one of my favorite things that you say. You've got to take calculated risks and are on the side of action. And you have a great story about this. So why don't you tell the subway story? Yeah.
A
It's 2011, and I'm riding the subway home from work, and about 20ft away from me stands this really good looking guy, like, gorgeous blue eyes, thick, wavy hair. And even though I want to approach him, something holds me back. What if he's a convicted felon, right? What if he's married? What if a hundred people stare at me while I make fun of myself on this, you know, packed train? So I sit there and I do nothing while the train passes stop after stop after stop. And frankly, as I let life pass me by, but still, something makes me just. I'm still really taken. Taken by him. So I make a deal with the universe and I say, if he gets off at my stop, then maybe I'll try to strike up a conversation with him. And if not, then that's the universe telling me it wasn't meant to be. So my stop was 72nd street in New York. He gets off at 59th Street. And I was like, the doors were about to close, and then all of a sudden this wave of, I swear, like this wave of wild courage washes over me and it practically pushes me out of my subway seat and pushes me off the train as I like.
B
So you got off at his stop?
A
I got off at his stop.
B
You told the universe what you wanted. You didn't let it tell. I love that.
A
Exactly. So I catch up with him as he's exiting the station at Columbus Circle. I tap him on the shoulder. I say, excuse me. I'm sorry to bother you. You're wearing gloves, so I can't tell if you're wearing a wedding ring, but in the event that you're not married, you were on my subway and I think you're cute. Any chance I could give you my business card?
B
That is wild. That is some wild courage right there.
C
I am so curious. Had you ever done anything like this before as part of wild courage that it's like the first time, or have you sort of build the muscle of wild courage?
A
I built small muscle. I did like, you know, two pound reps, but this felt like a 30, right? Yeah, 300, Kim, exactly. Because I lived in such a left brain world, I studied economics in college. I ran an operations team at Google that like interfaced with engineering. I kept spreadsheets for everything. I, no joke, kept a spreadsheet for all of my upcoming first dates.
C
Okay.
A
Name, height, what we talked about in our first conversation. You know, is he funny? Scale of one through five. Like, I know, no pressure, gentlemen. Right. So did I do stuff like that?
B
A little bit. Bit.
A
In that I was always confident as a kid. I was always, you know, excited to win the magazine sales competition and go door to door and ask people for magazine sales. But like I was also very analytical, very pro con list. So in terms of the, like going with your gut, that was the, that was the recklessness, the moment of wild courage, the airing on the side of action, you know, thinking fast and fearless. If you're, if you're on the fence, do it like. That was something that I always really struggled with. But in that moment, wild courage became a habit for me because it taught me like, no, when you think with your gut and when you tap into your right brain capabilities, then incredible things can happen. Serendipity isn't found. It's made. It's made. And I made my own serendipity that day.
B
And you went on to marry this man.
A
Oh, yeah, sorry, spoiler alert. Important detail. He called the next day, we went on a date a week later, three years later.
C
Did you have a spreadsheet?
A
I know. And at that point, I dropped the.
C
Spreadsheet through the spreadsheet.
B
Yeah.
A
And here's the thing about the spreadsheet right about, like when you get reckless, a world of possibilities opens up for you. Because he's five. John is five years younger than I am. Nobody in my spreadsheet was five years younger. One year younger, same age, 10 years older. Like societal norms. But just by going with my gut that day, it's like, huh, this whole world opened up that I never thought would be possible because I'm living in this box of these defined characteristics and this spreadsheet that I keep meticulous track of.
B
And it's so interesting.
A
I mean, one of the things I.
B
Love about this story and one of the things I love about your title is go after what you want and get it and you knew you wanted. That's actually figuring out what you want may be harder than going out and get it. Like, what was it about him that attract he just see, like, it's interesting to think what, what it is. That makes, you know.
A
Yeah.
B
And.
A
And also recognizing that you don't know, but if you take enough swings.
B
But you wanted it.
A
Yes, I definitely wanted it. Well, first of all, I really wanted to get married. Like, I had just turned 30, which made John 25 at the time. He had just moved to New York, had no interest in, like, getting, you know.
B
Getting married.
A
Getting married, yeah, basically. But I mean, so a. He's attractive and that was, you know, like, that was what started it. So I'm. I hate to sound very superficial, but.
B
Like, there's nothing wrong with that. Like, sometimes you really like somebody's looks and sometimes you really don't, and it's okay to pay attention to that.
A
Yeah. And. And that's the thing about, like, online dating versus this person I happened to see across the subway is like, I knew exactly what it looked like. But you also have a vibe. He gave off a vibe. He gave off a vibe of thoughtfulness and confidence. You can give off the vibe of confidence. For sure. He did. He gave off a vibe of kindness and seemed like someone who would be interesting. I remembered his pants were too short, so I judged him a little bit for that. But, you know, we can get over that.
C
Jenny, I'm curious. When you were on the subway and you were getting to your stop and you made the agreement with the universe, you also actually said about the wedding ring, had you already thought of the line, like, what was actually happening to you? I don't know how many stops we had or how much time before 59th because you thought you had till 72nd. So what was actually going through your mind? Can you remember of how much planning or did you just leave it all up to whatever you wanted to say in the moment? So you know that feeling when you're doom scrolling and suddenly it is an hour later and you feel even worse? I have been there, but lately I've been swapping that time for something way more energizing. Masterclass. These are not your average online classes. This is Robin Roberts teaching effective and authentic authentic communication. Chris Voss teaching you how to win any negotiation. And our very own Kim Scott teaching you how to use radical candor to have those tough conversations you've been putting off. Whether I am in between meetings or just swinging a string toy for my cat, I pop into the app. I soak up real insights that I can apply immediately. And I'm not alone. 83% of members have used what they learned to improve their lives. With plans starting at just 10amonth, billed annually and over 200 class classes to choose from. Masterclass is a no brainer. So get an additional 15% off any annual membership today@masterclass.com radical. That's masterclass.com radical. For an additional 15% off, go learn something that'll change your day and maybe your life.
A
That's the part where like I had. It was totally unplanned, Amy. The whole thing was unplanned. Again, not. Which is not like me. I am very operational, I'm very methodical and that's what made it very different that day. And unlike anything I'd ever done. But no, when I said you're wearing gloves so I can't tell if you're wearing a wedding ring, that was not.
B
That just popped out of your mouth.
C
That just because they're like, who said that?
A
That would never. Like, what a terrible opening line.
B
Like, it's awesome. I love that opening line. Like you're basically. You're saying, I am not an asshole.
A
That's exactly right, Kim. I was trying to say like I don't mean to be disrespectful if you unavailable. And I guess because I had just recently turned 30, I did look for wedding rings because I wasn't 22. So like half the population that I was interested in was married at that point. So it was pure. This is my left brain thinking it was very logical, very practical. And it was also practical like you are wearing gloves so you are covering the data that I need to make an informed decision about whether this is a respectful thing to ask. But it just all kind of came out in a way that is like absurd because it's so intense. I love obviously already an intense move to start with.
B
It all and it all. And you know what, like if someone, if he couldn't handle that level of intensity, he was not the right guy for you.
A
Well, I, I contrast him with this other guy, Brian that I dated when I was working at Harvard Business School. I was doing research there. He was a student and like my flavor, this is the, the weird trait is, you know, weird is the courage to stand out and be authentic because within your so called weirdness lie your greatest strength. So I say hone every oun weirdness you've got. But Brian did not appreciate my favor of weird. I'm like I mentioned, Amy, I am bold, I am outspoken. I dance down the sidewalk like fake tap dancing to acapella show tunes on my headphones. And Brian wanted someone who's demure and quiet and a wallflower and literally said to Me once I want to be with someone who's gorgeous, but she doesn't think she is, and that's just never gonna be me. So at minimum, when I chased John off the subway, I was like, well, we're starting this relationship on like you, like, like wysiwyg know what you're getting. As opposed to Brian, who like, I would never be able to fit my square peg into a round hole with him, even though I tried for nearly six years.
B
Yeah. And do you think that working at Google gave you some of that wild courage?
A
Yes, it was.
B
So I want to move on to other stuff, but like, because I, I met my husband thanks to some advice I got at Google. Actually, I don't know if I've ever told you that story.
A
Yeah, tell me, what was the advice?
B
So Hal Varian, who was the chief statistician, I mean, he knew data better than just about anyone on the planet, explained to me that when women date, they, and when heterosexual women date, I should say, they disadvantage themselves 10 to 1 because they don't ask men out, they wait to see what offers they get. And so a man will look at a thousand women and choose 10 of them. And a woman will get 10 offers and choose from among those 10. Amy, you can maybe. How does this work in.
C
It's complicated and it's been a while, so I think my data is out of date.
B
Okay. Anyway, this is how it works. But maybe we'll have a follow up conversation if the audience would like one. Okay. Yeah, yeah, absolutely. So, you know, that's a big difference, like looking at 10 people versus looking at a thousand. You're going to make a better decision if you look at a thousand. And so I went and looked at every single match.com profile of every man who lived in a 5 mile radius of my house. And luckily my husband, now husband, lied about where he lived.
A
Love it.
B
Wait, I don't think I ever knew that. So why did he lie? Well, he was temporary living somewhere, he was going to come back to Palo Alto and he was living in kind of an oddball place. So he cleverly lied, but he was reading a great book. I chose his profile because he loved this book, Atonement, which is one of the great books. Or maybe it was Enduring Love, it was something by Ian McEwan, I should know. But anyway, that was why I chose him. And also because he seemed, I realized as I was doing this, looking at a thousand people, I realized that I had my criteria wrong. I used to say, I want a man who is smart, funny and decent. And I realized it needed to be decent, funny and smart. And so anyway, that was my story. Yeah. So what was it about Google that gave us. And I reached out to him.
A
Sure.
B
And he wouldn't have reached out to me because I. That I was 38 at the time. So I said I wasn't sure I wanted kids because I wasn't sure that was in the cards for me.
A
Yeah, it's a great thought exercise. I think Google helped me realize my value. Google helped me. It's a tough place, especially when we started, Kim. Right. I mean, I started in 2006. You started 2004. 2004. Okay. So it was in all the news segments. Right. It was, it was, you know, promoted as the top place to work and the mo. The hardest company to get into. So like, if we made it, we probably. It probably gave us a little bit of a confidence boost that, like, we've got the goods, we're bright, you know, we're capable. And understanding your value and recognizing your value gives you the confidence to ask for what you want, gives you the confidence to ask somebody out, gives you the confidence to ask for a project or to ask your boss for a promotion or whatever it is.
B
And it also prompted, I think the thing for me that was good about Google is it it allowed that weirdness. Like, you were really allowed. You were encouraged to be weird and quirky as you were. You really were at Google and totally, you could really do all kinds of. I remember thinking, this is the first place I worked where I feel like I can really be myself.
A
Yeah.
B
You know.
C
You know, it's so interesting because Kim, you just recently shared something like that around how Google was like the first place you felt like you really belonged. And I was. We didn't have a chance to kind of double click on that. So I was really curious what that looked like for you. And also, Jenny, as you're talking about sort of weird being one of the traits. Like, I'm aware that the organizations I was in did not. I did not feel safe kind of being weird and what that does to your own confidence, not just in the company, but sort of societally. Absolutely. So I'm just curious, like, because, you know, at the same time Kim was having that, I was kind of getting smaller in some ways. And so I'm just really curious, like, what advice do you have for folks who may not be at a Google or just sort of feeling like they can express their weird. Whatever that might be.
A
I mean, to me, a success Mindset must precede success itself. And when you feel like you can, it's like the success and the ability to be yourself are tied. Right? Because I actually feel like I can be much less weird now being an entrepreneur. This is the hardest year of my life being feeling like I haven't, you know, not only did I get into Google like we were talking about and that gave me confidence, but then rising to executive there gave me confidence. I felt like I had the permission to ask for big things or ask for, you know, a million dollars for XYZ project or ask for Headcount. And so, you know, my weirdness. I felt more confident in my ability to be weird or to, for example, because I did this once when we were, when my team was putting our project forward for this big award, we made a music video as our entry as opposed to just filling out the data in the spreadsheet. And I only felt like I could be weird and do that because I was already at this senior level, so. And I now see that contrast, Amy. So I feel like I now am in the boat of the people who are at the companies that aren't embracing the music video making or the go create any idea that comes to you or like, you know, bring purple hair to work or whatever your flavor of purple hair is. Because I now feel as I'm newly starting out again, it's very hard for me to ask for something or ask XYZ very impressive author or influencer for their help or do something on LinkedIn where I post every day that feels different or unexpected. And so I think maybe it's a. That's why I say like a success mindset must proceed success itself. I felt successful at Google already and it enabled me to tap into my weird. More I don't yet feel successful or at the quote unquote executive level of entrepreneurship or authorship that I now feel like I'm back to playing it safe again. And it's, I'm doing such a disservice to my future business. But it is interesting that I fall right back into that. Like I sent out, you know, 350 galleys of the book advanced reader copies and I need to follow up with every single one of them to say, would you like to buy Wild Courage in bulk? Would you like to bring me in as a keynote speaker or a workshop facilitator? Both things I love to do. And you know, I sent out the first 250 thinking, well of course 250 will respond immediately with a check half written And a date they're ready to secure.
B
And that's not what happened.
A
And that's not what happened. And it has been so hard for me to send those last hundred having the rejection of the first 200. Not rejection, but like the ghosting or the non answers or the not nows of like some of them of the first 250.
B
You know, when I was. When Radical Candor, when I was two weeks out from Radical Candor's pub date, which was PI Day.
A
Oh, that's fun. Great. Pub date.
B
Yeah. 343-1417 or something. Isn't that pie? Anyway, I remember deciding that this was my. The time in my life when I was gonna beg. That was my calculated totally. And I just like, I. I literally said that to myself, this is a time to beg.
A
Yeah.
B
And I begged. I begged a lot of people.
A
Yeah. And I'm doing it. But it's hard. Like.
B
Yeah, it's really hard. And not everybody, certainly. There are plenty of people who did not invite me to speak or buy hundreds of copies of the book.
A
Right.
B
For sure it is. Writing a book is a labor of love. And this book that you have written, Wild Courage, is going to help so many people be successful in their careers. But I want to go back to Amy's question quickly because I think what you said was really good. And I have an addition to it, which is that, like, when I was in a job where I was literally shrinking, in fact, I physically shrank. My. My doctor said, you've lost half an inch. What is happening? And the best advice I got in that situation was don't forget to quit. I mean, get out if you possibly can. Oh, which is what you did, Amy?
C
Yeah, I mean, I definitely. I went to another place and. But it really wasn't until I. I did go on my own and. And Jenny, So I. I really can understand that. That shift. And you know, frankly, it hasn't really been till working at Radical Candor, where I felt like I can really sort of bring all the weird.
B
Bring.
C
Bring your weird self to work. And you know, I will just say like. And maybe part of it's just a function of age, but I am convinced that the more authentic and weird that I can be, actually, the more success there is. But it's like it's been so wired to not have that mindset that it's to kind of that process you're going through. Jenny, I. I can really. I can really relate to. You know, one of the things I think in your book you talk about how to self promote with, with tactics that don't necessarily feel like, so awkward. So how do you bring together that kind of self promotion and weirdness in a way that folks can learn from?
A
Yeah, well, I think the first step is knowing your power assets. Like if I, I, I think of my power assets which make up my power portfolio. Right. Kind of like a financial investment portfolio. Mine are people leadership, influencing stakeholders and building things from startup to scale. I both want to put you on the spot, Amy, and I also don't want to put you on the spot. Do you want to take the challenge of like, if you had to say what your three power assets were, would there be any that you could come up with? I'm trying to slowly to give you time.
C
No, this is, this is great. I mean, I'm actually going through the process right now because I recently recorded a TEDx talk. It hasn't yet come out. And so part of it is sort of what are those distinguishing features? I was actually gonna ask you. Cause how did you actually discern those were your power assets? But I will say one of the things that I think is a power asset is what we do on the podcast, which I love, which is I'm super curious and so I love listening and asking questions. So I think curiosity, I would also say humor and just an ability to kind of see the lighter side of things. And then I think on the weird side, I mean, I've definitely been on the consciousness, like, whatever, woo woo path. So just very aware that we're more connected than maybe we think and see. So less on spreadsheets and more on jumping after the subway car.
B
Can I add a superpower that I think you have, Amy?
C
Oh, thank you.
B
I also think you're like one of the most empathetic people, kind people I've ever met. And that is really just a wonderful thing. Especially in this. You're flooding the zone with love. And that is what we need to do right now.
A
That is awesome.
C
Thank you.
A
So like, that's a great start. Is understanding your power assets that make up your power portfolio. Now this is a different context, right? Because this is, you know, radical candor. Has a mission of helping people be successful. Like, those are all the right things. If we were in a business context, I might push you to think a little bit more about the hard skills. Right? Like, what are you doing to transform? Like, what are the metrics where you transform a user? Right. Like a listener or, you know, like someone came to me and said, so I always say like one to Two hard skills and, and then one to two soft skills with a combination of three together. So if someone came to me and they said, you know, I am a great collaborator when it comes to product launches, I might say, well, okay, position. That sounds like collaborator. Sounds like really software. Why don't you think about positioning that as a go to market strategist, right? Like, that's still about collaboration, that's still about, you know, helping something get launched. But like go to market sounds like a very hard skill in terms of a product launch or something like that. Now that is not the context here, but this all gets back to tasteful self promotion. Well, actually I would call it shameless self promotion because I want to, I want to remove shame from the equation. Equation. Nothing makes me cringe more than being in a meeting and somebody says, I have a shameless plug. But I just created this spreadsheet. It's probably going to save you 20 minutes of time per project. This happened once and like everybody in the room was like, oh my gosh, finally someone created this spreadsheet that I can just like click a button and all the data is there for me. So like, where is the shame? Why does it need to be a shameless plug? Why can't it be? I'm proud of this spreadsheet I created and I am excited for you to use it and save 20 minutes per project. So that's like, you know, whether it's knowing your power assets that make up your power portfolio and starting there and talking about those with your boss, or every six months setting up time with your boss's boss, which I highly recommend everybody. It's like, you know, old, old news to manage up. To me, the more counterintuitive thing is to meet your boss's boss twice a year. Like manage higher, right? Maybe manage diagonally. Think about an org chart. You've got your boss above you, you've got their peers to the right and left of them. Managing diagonally is building relationships with two or three of your boss's seven peers. Not everybody, because it's, you know, gonna waste your time and theirs. But find a few who actually have influence. You know who they are, right? It might not be by their title, but you observe it every day. Find the ones that you like the best that you connect with because it's not worth wasting your life connecting with people who are a holes, right? We all know this from radical candor. And then go meet them, right? So once you know your power assets, you're then in a position to share Those with your boss managing up, but that's old news. Manage higher, share them with your boss's boss, manage diagonally, share them with your boss's pe. And that's the start.
B
And I think when you do that, it's really helpful to think about this in terms of you're asking these people to invest in you because you're a good investment. So they will get a good. What's in it for them when you succeed, they will get a good return, whether it's emotional or practical.
A
Right.
B
And you're not trying to be political. You know, you're asking people to invest in you. That's not political.
A
Yeah. And can I. Since, since. Since Kim, you pushed back on me on the book. Like, I think that, I mean, there is a section in the book called Play Politics, and I mean it in a good way. I mean it in a good way. And I unders. I totally understand where you're coming from, where you're saying, like, we're not trying to get political. But I find that there's nothing wrong with connecting with the people who have influence. And to me, that is kind of the base of politics. Like, it is, I guess, politics, especially these days. Oh, my goodness. We're not going to go down this rabbit hole. But. So politics is a very loaded word. But if you think about it at its core, and you think about it as building relationships with people who can give you good feedback, who can advance your agenda, who can give you 15 minutes in their leadership meeting, who have the budget and the ability to greenlight your project, who have the power to say yes to something. You know, if you, if you give, if you go to them for feedback ahead of the big meeting of nine people. And like, I think that sometimes it's okay to understand how people tick and who holds the power and what you need to do ahead of the meeting to get their buy in. Right. And you call that politics or not. But I think it's just being smart and thoughtful about how relationships work and how influence works.
B
Yeah. And, and, and I would say, and I, I think you'll agree with this. Like, it's not because you're trying to get an unfair adv, because you're trying to do better work.
A
Yes. And collaborate better and exchange ideas. And maybe you go to someone and you say, hey, I'm working on this ice cream project. And know your team did an ice cream project recently. What can I learn from you? What can I add to your team that might save them time, that might give them feedback that Might give them ideas. Do we have seven people working on this when we only need four? Should we collaborate together and make this more efficient? It's for all of those reasons. It's, it's knowing what the right hand is doing, you know, knowing what the right and the left hand are doing. And here I'm talking about a context of like, like big complex organizations that are multi, that you know, have multi. Multiple touch points and, and just, it's really kind of guarding against how siloed we can be.
B
Yeah.
A
And if we live in fear, like I don't want to be a brown nose or so I don't want to meet my boss's boss or I don't want to look political. Right. So I don't want to go build a relationship with that person. I think that holds so many people back when those relationships could increase the buy, increase the pie, increase the collaboration, increase the amount of excitement and energy and motivation and, and improve the bottom line for the company.
B
Yeah, yeah, I think it's. Or, or for yourself, like.
A
Yeah, sure.
B
Like it's okay to be, it's okay to say my goal here is to improve my skills and to do better work because I want to build these skills. Like there's. The company gets something out of it, but you also get something out of, of improving your skills.
A
For sure.
B
There's a world of difference between that and saying I'm gonna brown those so I get a promotion.
A
Oh, definitely.
B
That's not what you're talking about. And I think you make that very clear in the book.
A
Yeah. And also people see through that. Like you're not, we're not kissing anybody's butt here.
B
Oh, I don't know that people see through that.
A
Oh, really?
B
It works. That's the problem with politics. So, so that's why I think it's important. It's important to be aware of what's going on. Like some people, some people who do not deserve it get a promotion because they play politics.
A
Absolutely, absolutely.
B
But that's not what you're encouraging people to do. You're encouraging people to make sure that it's a little bit in radical respect. There's another Googler, Mecca. Do you know him?
A
I don't think so.
B
Anyway, he's amazing. He has this notion of a difficulty anchor and he says if you're underrepresented along any dimension and you're on a project, there's a greater risk that people will dismiss the importance of your project because you're you. Oh, if Kim did it, it Must be easy because she's a woman.
A
Sure.
B
And you know, or in Mecca's case, if Mecca did it, it must be easy because he's black. And, and it's not that people say that explicitly, but that's kind of what happens, so.
A
Interesting.
B
Yes. And so he's. He recommends finding someone in the organization who's way more senior than you are, who's, who's got a reputation as kind of a hard ass. And tell them what you're trying to accomplish, get their feedback so that you're more likely to succeed. And then when somebody says it was easy, this hard ass is going to say, oh, no, that was not easy. Yeah, I love it. That's the kind of thing you're talking about.
A
Yeah, exactly.
C
I really appreciate you bringing that example up, Kim, because I was really curious on the idea of getting rid of the shameless self promotion, but was coming up for me, certainly this group, all women, and then bringing in your example, Kim, of underrepresented folks, people of color, I can just say for myself, I think part of the shame around self promotion is partly a societal norm of what that might look like and how that might be received. So not only is it maybe wanting to advance other people, but it's also because of previous experiences where that has not been strategic benefit.
B
So you've gotten punished more for self promotion.
C
We can obviously see that in. Sorry to go back to politics, but where sort of a woman with ambition is not necessarily rewarded in the same way.
A
Yeah, well, I'm not saying this stuff is easy, folks.
C
That's why it takes wild courage.
A
Exactly, exactly. I mean, you're. Amy, you're talking about the double bind, right? You're talking about, at least for women. Like women are, you know, it's like we're in this double bind of if we want to be ambitious, we also have to like balance that with being kind and thoughtful and soft spoken and all these things that women are expected to be. And then you, you know, you look at the intersectionality of that. Right. And you lay on other kind of historically underrepresented groups in tech or in any industry, and it just gets super, super complicated. So, yeah, I have defin. And again, I feel it more in the entrepreneurial author world, which totally feels like a boys club. I'm just gonna, I'm just gonna put it out there way more than I felt it at Google. Like, I think Google, I did not, I did not realize or appreciate how incredible Google was at DEI and at women leadership until I left and was like, oh, wait a second. I mean, you know, you look at the top 20 bestselling books on any given week and ain't a lot of women in that group. Like, you're often there, Kim. But you know, it's not, it's really an anomaly. And I do there, I do feel like there are boys club circles that I have just not been invited into.
B
Yeah, yeah, 100%. So I think that part of it is, you know, often it's these biases that help hold us back. So for example, women are not allowed to be funny. And so some women have said, should I try not to be funny? Because people will think I'm not serious. And I'm like, be fucking funny. Yeah, I'm just gonna drop. Enough. Yeah, like, don't allow the punishments that you get for these biases because you're going to get punished every either, either way, like Audra Lord said, your silence will not protect you. So you may as well be funny and get punished than not be funny and get punished. Yeah, you may as well self promote and get punished for that. Then be a wallflower and get punished for that.
A
Right? Because I think the punishment of being a wallflower is a guarantee. And I think, you know, at least when you're speaking up in a meeting, when you, let's say you're the intern, right? And let's say you are, you've read Wild Courage and you're like, I'm gonna go into this three month internship at this fancy company for the summer and rather than just wearing the expected business casual attire and nodding along like a bobblehead in every meeting, I'm gonna raise my hand and I'm gonna come off of mute and I'm gonna play it hot and say something that might, you know, respectfully disagree with the leader. You might that same afternoon get three high fives and three reprimands from three different people. But at least you're memorable to me. That is weird. Like, that is both getting nosy, getting nosy about what the reaction might be. Right. Getting insatiably curious. And Amy, I love that you said that curiosity was one of your power assets. It's being reckless. It's erring on the side of action. Right. And thinking fast and fearless. And if you're on the fence as that intern, like, yes, I'm going to press unmute, I'm going to raise my hand, I'm going to say the thing. And it is also being weird, it's being authentic and it's standing out like, like playing it hot. Is a strategic commitment to not fit in in any given two minute conversation or one hour meeting. It's a strategic commitment to not fit in. Strategic because at least at the end of that summer, that intern is remembered and therefore he or she is much more likely, they are much more likely to get asked back for the full time role. If you're forgettable, then you will have that company's resume on your. On your, Sorry, that company's logo, on your resume for the three month stint. But you're much less likely to make enough of a splash that you actually do anything big in the world or at that company or get the big offers or get on the big projects. Because if you want to get promoted, get assigned to the projects that matter most for the company, you're not going to get on them. Leaders keep lists, keep lists of maternity paternity backfills, keep lists of attrition, you know, succession planning, keep lists of who to put on the big projects. If you're not frequently like top of mind to people, which only comes from playing it hot, being weird, being shameless, being reckless, getting nosy, then you're gonna be forgotten. You're gonna get overlooked 100%.
C
Can we talk about something hard?
A
Yes, absolutely.
C
You talk about embracing the power of no without feeling like a jerk. And so part of it's like, there's the action, but then there's also like our own kind of emotional mindset about that.
A
Yeah, yeah, there is. I am so excited we're talking about this, Amy. This is like, it is one of the most important.
C
I mean, and you could have said no.
B
I could have said no, but I.
A
Absolutely would not have said no because first of all, I have. It's extremely hard. I don't think we have to talk about why it's hard. A lot of us are people pleasers at our core, but people pleasing pleases no one. And it keeps you small. And so no, you know, this is, this is what I call brutal. It is, it is the courage to protect your time and energy. And frankly, being brutal, saying no is, it's cleaner, it's more effective, and it's far kinder than like equivocating or the mealy mouth, you know, wind up to like eventually saying a maybe it's cutting through the bull and sparing everyone's time and energy and attention. It's essentially radical candor. It's like, can you do this? No, I can't. And here's why. But what? Now that we agree that there's a baseline of it being helpful and productive because it allows you to really put your effort and energy into what matters most in the world. And it helps you not fragment your day into 70,000 little mini bites. Right. And allows you to do something meaningful and meaty. Let's talk about how you do it. So I call this let's drink to Async. Okay, so this is if someone asks you to attend a meeting and you just don't want to do it. So let's drink to Async. Hey, I'd love to help. Can we start by collaborating on email? Right? Like, let's see how far that takes us and see if we need to hop on a call after that. That is saying no to the meeting, which is so, so helpful. Right. We've also got the Power Postpone. This is tactic number two. And this sounds something like this. Hey, I'm heads down on a project. Can we revisit this next week? Well, sometimes when we say that when we use the power postpone, it gets solved by somebody else, it goes away. Right? And then we've got the Agenda Avenger. This is is tool number three. And this is can you send me an agenda first? Because then it forces that person to think through, well, what is it that they want from you? Why do they want your time A again, it might be solved over email, but they might not have enough that they can come up with that warrants an hour of your time. So we all agree that no is critical. That is not a surprise. But I think the counterintuitive part is how do you do it in a way that you don't sound like a jerk? Will you do it with let's drink to Async, the Power Postpone, and the Agenda Avenger. And. And can I add one that just happened before this call, before we started recording?
C
Yeah.
A
Okay. So I hired this illustrator. He's awesome. His name is Ash Lam. Shout out to Ash Lam if anybody needs an illustrator. And he's illustrating some images from my book or some concepts from the book. And so I was looking at an illustration and it was two sections of the illustration. A top section and a bottom section contrasting an idea and me being obsessed. That is the courage to set your own standard. And that's like really wanting to achieve excellence and sometimes perfection and everything I said, hey, could we take this sentence? So here's the top sentence. Wild. Courage is temporary discomfort. And it's a guy pushing a boulder up the hill, actually looking, like, excited that, like, he's moving it forward and playing it safe. Is permanent regret. And it's a boulder, you know, chasing him down the hill because he doesn't have the courage to push up the hill. Help. And I said, hey, could we split the line into two lines instead of having it in one line? I thought it would look better stylistically. And he basically just wrote back. He said, let me see if I can find it. I tried that, but in all honesty, I think it will work better with the way I have it. It is also going to take me a lot more time to do that. It was a more complicated change than what I'm describing. I think it'll take me more time to do that, and I don't think it's worth it, given my bandwidth. This episode is brought to you by Lifelock. When you visit the Doctor, you probably hand over your insurance, your ID and contact details. It's just one of the many places that has your personal info, and if any of them accidentally expose it, you could be at risk for identity theft. LifeLock monitors millions of data points a second. If you become a victim, they'll fix it, guaranteed, or your money back. Save up to 40% your first year@lifelock.com podcast terms apply.
B
That's a no.
A
That's a no.
B
And not only that, that's a never.
A
That's a never. That's. That's. That is not a power postpone. That is not. Jenny, give me the agenda of why you think this matters. Right? That's just like a no. I'm not doing it. And guess what? I respect him more for it. And it tells me that his time is valuable and it benefits him in additional ways beyond this little adjustment for this illustration. Because now I'll be more thoughtful next time I ask for a minor tweak, knowing that, like, oh, he doesn't have endless time. He values his time.
B
Yeah.
C
Can I give you a name for that? You can say no. It's called the Sisyphus. No.
A
There you go. I love it.
B
The Sisyphus.
A
No. You heard it here first, folks.
C
That's right. You know, that's my gift to you.
B
And it's a good one. It is. You know, this may be my favorite part of your book, because when I lived in Russia, in Moscow in 1990, my nickname. I was right out of college, and My nickname was Gas Baja Da, which means Ms. Yes.
A
I remember this.
B
I said no. I mean, I said yes to everything, everything, everything. And I realized how burnt out I was a couple of years later. There was a New Yorker cartoon, and there was this guy on the phone and he was saying, no, Thursday's out. How about never? Is never good for you? Yes. Oh, my gosh, that was my favorite part.
A
I mean, how common is it that you start, that you start reading a saying, a caption of a New Yorker cartoon and somebody like, I just did.
B
Finish the caption for you.
A
That is the best New Yorker caption that has ever been written in the entire history of the New Yorker magazine.
B
I agree.
A
I agree.
C
I love that one. Can I give you another one? Kim, you might like this for the radical Candor story. There's a dog saying to either the therapist or another dog. It's always good dog. It's never great dog.
A
I love that. I love that.
B
Yes.
C
How about never? No, I, I love that. I love that story. And actually, Jenny, just to kind of bring it back to your, you know, wanting to, you know, promote and getting the meeting with your boss's boss to me, like, how would you feel if it was the boss's boss saying to you, come, bring me an agenda? Because then that would give you the opportunity to get clear. Like, just if the shoe was on the other foot, how would that land for you?
A
Oh, it would land great because it would tell me they're invested. It would tell me that they care about this meeting. It would tell me that they're valuing, that they, like, deeply want to help me. And I would read that as a signal that they can help me more if they're focused. It would tell me, wow, they might do some prep ahead of this call. Wow. I was only expecting 20 minutes of their time. I think I'm going to get 25. If I send them questions ahead of time, they're going to spend five minutes thinking about it. It would honor me, Amy. It would honor me. And by the way, there's a flip side here that would fit into the bossy trait, which is steering others to success. It's the courage to listen and lead. And that is when you, you know, you make it, you make it, you lower the barrier to people coming to you. So, like, in that case, you're kind of creating a barrier and you're saying, like, no, I, I, I want to say no to this. So I'm going to make you give me an agenda first. But, but there's a flip side here. When you're the leader, because when you're the leader, you want to lower the barrier to people coming to you, because you want to be a boss with, like, an open door policy, and you want to be there and available for them. So I would office hours as a leader at Google every Tuesday 10 to 11am, three 20 minute slots and in the calendar invite that was on my entire orgs calendar as a reminder, I would actually do the agenda for them. So it was the opposite. I said don't worry about some fancy 30 slide deck you could come bring me. You know, here's what you could talk about in this meeting with me. It might be a project you're excited about, something keeping you up at night, a skill you want to develop, a strength you're proud of, heck, even just what you did on the weekend. So in that case it's the actual, it's the opposite effect. As a leader I want to encourage them that it is not something that you have to do a lot of work around to, you know, set up time with me. So Amy, if that boss said to me, what's your agenda? I'd be excited to do it. But you're right, I might feel a little bit intimidated. So as the boss, I tried to help people overcome that intimidation right from the get go and that imposter syndrome right from the get go and actually lower the barrier to entry of setting up time with me.
B
But Jenny, knowing you, you would when you sent the email, tell them exactly what you wanted to talk about because you're very, you're. One of the many things that I love about you is how respectful you are of other people's side. Like when you first reached out to me, I was like, oh, here's a woman who gets shit done. And it was like a breath of fresh air. I felt relaxed in your presence.
A
How interesting.
B
We're on it and I think that you teach people in your book book how to do that.
A
Yeah. Well, that's a tool. It's in the obsessed trait and I call that pull it and bullet. If your emails to important stakeholders, you're. You're laughing at me.
C
I'm laughing.
B
I love it. These are such good. Very Bullet.
A
I, I did a keynote. I did a keynote in front of like 250 people in D.C. on Friday. And, and I, I walked the room afterward like you know, worked the room because I think there could be more deals that come from it. And I was like, hey, if I change this keynote from 45 minutes to 30 minutes, what would you recommend? I absolutely don't cut. It's a creative way to say what you like best, right? Yeah, but I love data and the number one thing people said was do not cut the section with the four tools at the end So I think you're laughing at me here because you ask a question and I give a tool as an answer. But I think people want stuff that's practical and that's not just like ivory tower therapy. Okay, so the tool here is pull it and bullet. If your emails to important stakeholders or to your boss or to your boss's boss are just full of long, prose.
B
Filled paragraphs, they're not going to read it.
A
They're not going to read it. And so what I attempt to do, like when I reached out to you, which very much intimidated me, Kim, when I reached out to you, I literally had written on a document on a flight home from Chicago, when I was thinking about goals, it was, I want to meet Kim Scott one day, like, I wrote that down, I could take a screenshot and show it to you. Like, that was a bona goal of that year. And here we are. You've been like the most incredible mentor to me. Your name is on the COVID of the book. Like, Kim Scott, your name is on the COVID of my book with a quote that says, your candid career coach for unstoppable growth. Kim Scott, New York Times bestselling author of Radical Candor. Like, I did not expect that. Okay, wow, talk about a tangent. So no, it's.
C
It's actually perfect because right next to the book, you have if cauliflower can be pizza, you can be anything. So just going back to that success mindset set, like, you made, like making that happen, right?
B
Yes, exactly.
A
So you were impressed with my first email. It's because I used the bullet and bullet method rather than writing in long, clunky paragraphs. I probably, knowing me, sent you three bullets.
B
Oh, yes.
A
I love it. 50% pull. It is pull out 50% of the text and bullet is right in bullets instead of paragraphs. I probably had three bullets. Three things I wanted to learn from you. I probably bolded the first few words of each bullet. I probably did not have any bullet exceed one line of text, which looks very intentional and very thoughtful and very buttoned up. And that's what I did. Pull it and bullet pull 50% writing bullets, not prose.
B
I knew that you were a woman who was not gonna waste a minute of my time, and I love that that makes me. Nothing makes me feel more relaxed than.
C
Well, speaking of relaxed and time, I feel like we should respect your time, Jenny. I know it's a busy time for you. I certainly wanna respect Kim's time. So before we wrap, is there anything that you want our listeners to know we haven't asked and I know they wanna know how. How can they get the book?
A
Yeah, well, the book is available anywhere. Books are sold in hardcover, audiobook, ebook. And ladies and gentlemen, I'm about to get shameless. If you are indifferent to how you consume a book audiobook versus, you know, paper copy, buy the hardcover. It helps authors so much during week one. It's actually all that counts for bestseller lists. So I'm getting shameless. I'm asking you to buy the hardcover.
B
If you're indifferent, buy 10 copies of the hard copy.
C
Is there a URL that you want them to go to?
A
Oh, just Amazon Book. Honestly, like wherever they buy their books, Amazon, you know, books, a million. They can go to wildcurriagebook.com, but that'll just give you other options to buy it. And then I love coming to companies and helping out with keynotes or consulting or workshop facilitation. And you can just email me jenny'sjennywood.com j e n-n y t s j e n n y.com I also have a newsletter that comes out every Tuesday. It's so short, it's like under a two minute read. It's on all these practical tools that I've been sharing.
B
She pulled it and bulleted it.
A
She pulled it, bulleted it. That's it'sjennywood.com Newsletter Awesome.
B
Thank you so much, Jenny. Loved the conversation.
A
So fun. You two are just top notch and I'm so honored to be here.
C
Well, we love to have you. And if you want to check out the show notes folks, go to radicalcander.com podcast as we like to say, praise in public, criticize in private. So if you like what you hear, please do rate and review us us on Apple Podcasts. And if you've got criticism, you know we always love to hear that. Email it podcastradicalcandor.com Go order Jenny's book Wild Courage wherever you want to find your books. Remember, pull it and bullet it. Did I get it right, Jenny?
A
You did. Pull it and bullet.
C
All right. Pull it and bullet. Bye for now.
B
Take care everybody.
C
The Radical Candor podcast is based on the book Radical Be a kick ass boss without losing your humanity by Kim Scott. Episodes are written and produced by Brandy Neal with script editing by me, Amy Sandler. The show features Radical Candor co founders Kim Scott and Jason Rosoff and is hosted by me still Amy Sandler. Nick Kharisimi is our audio engineer. The Radical Candor podcast theme music was composed by Cliff Goldmacher. Follow us on LinkedIn, Radical Candor the company and visit us@radicalcandor.com.
Radical Candor: Communication at Work
Episode: The Wild Courage to Get What You Want, With Jenny Wood
Date: March 26, 2025
Hosts: Kim Scott, Jason Rosoff & Amy Sandler
Guest: Jenny Wood
In this episode, Amy Sandler and Kim Scott have a lively conversation with Jenny Wood, former Google executive and author of the forthcoming book “Wild: Go After What You Want and Get It.” The discussion explores Jenny's provocative thesis: the very traits we’re conditioned to suppress—like being weird, shameless, or even a bit manipulative—are the traits most critical for advancing our careers and leading fearlessly. The trio digs into practical stories, memorable tactics, and tangible advice to help professionals unlock their own “wild courage,” overcome self-doubt, and achieve audacious goals without compromising authenticity.
[03:07]
Memorable Moment:
On “manipulative,” Jenny emphasizes reframing:
"To be manipulative is the courage to build lasting relationships, to build influence through empathy... It's all about mutual benefit. And essentially you have to figure out what people want and get it for them."
— Jenny Wood [04:34]
[05:42]
"Serendipity isn't found. It's made. It's made. And I made my own serendipity that day."
— Jenny Wood [08:41]
[09:05]
[09:10–10:00]
[13:14]
"Within your so called weirdness lie your greatest strength. So I say hone every ounce of weirdness you've got."
— Jenny Wood [14:05]
[15:15–19:12]
"A success mindset must precede success itself... the ability to be yourself [and] to ask for what you want are tied." — Jenny Wood [20:02]
[21:59]
"It's so hard for me to send those last hundred [emails] having the rejection of the first 200...But it's a labor of love."
— Jenny Wood [22:14]
[24:44]
Tactic:
“Whether it's knowing your power assets that make up your power portfolio and starting there and talking about those with your boss, or every six months setting up time with your boss's boss... manage higher, right? Maybe manage diagonally... That’s the start.”
— Jenny Wood [28:02]
[29:34–32:46]
[33:00–36:57]
"I'm not saying this stuff is easy, folks. That's why it takes wild courage."
— Jenny Wood [35:01]
[39:03–43:56]
“People pleasing pleases no one. And it keeps you small. And so no, you know, this is what I call brutal. It is the courage to protect your time and energy.”
— Jenny Wood [39:29]
[47:38–50:36]
"Pull it and bullet. Pull 50% [of the text] and write in bullets, not prose."
— Jenny Wood [50:13]
For more, get Jenny Wood’s Wild: Go After What You Want and Get It (preferably the hardcover, as Jenny shamelessly and strategically recommends in week one), subscribe to her newsletter at itsjennywood.com, and visit radicalcandor.com/podcast for show notes and more resources.
Remember: Pull it and bullet! And go make your own serendipity.