The Learning Leader Show With Ryan Hawk - 627: Jenny Wood - How To Go After What You Want and Get It (Wild Courage)

Episode Date: March 23, 2025

Go to www.LearningLeader.com for full show notes     Notes: Serendipity isn't found. It's made. Make your own luck. The best leaders create serendipity for their teams. A success mindset precedes success. From Jenny - In 2011, I was single and living in New York City. I spotted an attractive guy across the train from me. I wanted to talk to him, but I was too nervous. Then he got off the train. She met her future husband by chasing after him off a train in NYC. "I was letting life pass me by." She used some wild courage to approach him.  What sits between you and the thing you want is fear. Who are your dynamic dozen? The 12 people you need to meet. Monday mini-festo. In 15 minutes, write the 2 things you did last week that you're proud of. Write 2 things you're excited about for this upcoming week. Focus on doing the work that helps the company be better. Solve problems. Read the VP email. Know your stuff. Get to know your boss's boss. Do it the right way by talking with your boss. Jenny's career at Google - First 11 years in sales, Go To Market, Operations. Own your Career project. She got 2,000 people to come to her first training. Used all resources within the company to do it. Use "for example." Don't speak in generalities.  Role, Objective, Impact - ROI At work, say no to the small. Don't reply all to the Happy Birthday emails. Don't do the NAP work. NAP stands for "Not Actually Promotable" Work. Sign up for the projects that help make your company better. Carlye Kosiak is one of their best hires at Google. She had the courage to stand out. She was specific. Her resume indicated interest in "recipe tasting in pursuit of the perfect oatmeal raisin cookie." Personality popped off the page. She was weird, reckless, nosy, obsessed, brutal. Must be yourself. Don't just be weird to play a role. Goal Setting framework - Rock, Chalk, Talk, Walk. Jenny's goal is to sell 15,000 books by the end of week 1 and hit the NY Times best seller list.  If you sell 12,000 copies in week 1, how will you feel? "You ask such great questions." Don't play it cool.  Play it hot. Don't decide to fit in. Stand out. Watermark your work. Put your name and picture on the deck. Let people know you made it. Lady Gaga – A group of students at NYU created a Facebook group called "Stefani Germanotta, you will never be famous." Have the courage to stand behind your work. Lady Gaga wanted to be a big star. Life and Career Advice - Performance reviews - Focus 75% of your time on your strengths. Say yes to 75% of the things asked of you. Start sentences with "YOU" instead of "I" - Focus on them. Build influence thru empathy.

As a leader, your goal should be to coach and support people to be better than they think they can be. And if your title is director, direct, don't shy away, don't him and ha around decisions. Have the confidence and have the shamelessness to make decisions to be a little bossy. And I think it can be a beautiful thing to steer others to success. This episode is brought to you by my friends at Insight Global. Insight Global is a staffing and professional services company dedicated to providing amazing people to their clients and taking great care of them. If you need to hire one person, hire a team of people, or transform your business through

talent or technical services, Insight Global can get you the people you need and help you develop them to reach their full potential. Developing your people can be tough, but having productive employees can be magic. Visit Insightglobal.com slash learning leader. That's Insightglobal.com slash learning leader to learn more. Welcome to the Learning Leader Show. I am your host, Ryan Hawk. Thank you so much for being here.

Text Hawk to 666866 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders from all over the world, will receive a carefully curated email for me each Monday morning to help you. you start your week off right. You'll also receive details about how our book, The Score That Matters, will help you become a more effective leader text talk to 66866.

Now on to tonight's featured leader, the great Jenny Wood. In her 18 years at Google, she grew from entry level to executive, and she most recently led a large operations team that helped drive tens of billions of revenue per year. In 2021, she started. a passion project within Google called Own Your Career, which grew to one of the largest

career development programs in Google's history. Jenny is the author of Wild Courage. Go after what you want and get it. During our conversation we discussed, the nine traits of courageous leaders who accomplish big things. Then how to create more serendipity in your life and why? This is the responsibility of leaders. Then how and why you should play it hot instead of playing it cool.

And then Jenny shares an ambitious goal she's set for right now and how we can help her get it. Ladies and gentlemen, please enjoy my conversation with Jenny Wood. Okay, it's 2011. You're single, you're living in New York City, and you spot a good looking dude across the train from you. You said you wanted to talk to him, but you're a little too nervous. Then all of a sudden he got off the train. What did you do next? Well, first, I did nothing as I sat there on the train while the train passed stop after stop after stop.

And frankly, Ryan, I let life pass me by. Because, you know, who goes up and talks to an attractive stranger on a subway, right? And also at all these fears like fear of failure. What if he's married? Fear of uncertainty. What if he's a convicted felon? fear of judgment of others. What if a hundred people stare at me while I make a fool of myself on this packed train? But then when he gets off the subway, this wave of wild courage washed over me. And I had this like,

oh, m.g, it's now or never a moment. And I chased him off the train. I caught up with him as he's exiting the station. 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 thought you were cute. Could I give you my business card? How did he respond? He, first of all, I think was stunned and said, I think most guys would like this, by the way, Jenny. I think those dudes would say, this is nice.

Okay. Anyway, go ahead. Yeah, it's like, you know, and that, like the fact that you said that, Ryan, is the epitome of wild courage. It's like we get in our own heads. We are our worst enemy. We stay stuck in fear of failure, uncertainty, judgment of others. And as a result, we don't take actions that could set our entire life up for success, right?

So he stares at me for a moment. But as you're describing, he was probably digging it. And so I think once he realized what was going on, he said, hi, I'm John. We went out a week later. We got married three years later. We've now been married happily for 11 years with two little hooligans, ages seven and nine. Wow. Wait, did I read this right that you also said, wait a second.

How do you spell your name, John? Is that right? I did, yeah. So I said, is it J-O-N or J-O-H-N? And he said it's J-O-N, the Jewish way. And as someone who'd spent a lot of time on the Jewish online dating website, J-Date, I was excited to hear about the lack of H. And his name, John, J-O-H-N is the Apostle, J-O-N is the Jewish way, short for Jonathan.

And then, like, in a cutesy response, I said, I'm Jenny, the Jewish way. There's no Jewish way to spell Dedy, but I was just, you know, being clever. But it was funny that he actually said that. He knew I was fishing and he took the bait. Hey, it worked. And I love the story. I read the whole New York Times story about it too. It was so cool.

What was it that day that was different from a previous day, perhaps, where you got some wild courage to say, I'm getting off the train. I'm going to lead first. I'm not going to wait for him to chase me. I'm going to chase him. What led to that? Yeah. So that day, it was tapping in to my right brain thinking, my going with my gut,

my feeling brain versus my thinking brain, which was what I used my entire time at Google, right? So ultimately, I was at Google for 18 years, grew from entry level to executive, always ran something that was in the analytical realm. So my most recent role at Google was a team that sat between sales and operations that helped drive billions and revenue, very left brain thinking, very spreadsheet driven, analytically driven, operationally driven. And even in my personal life, I was always thinking with my head and not my heart. I know Joe Ryan had a spreadsheet for my first dates. At one point, I went on five dates in 24 hours. Like, I was on a mission. I had a goal. I was trying to accomplish the goal. And it was all spreadsheet based. But in that moment,

what was different was that I didn't have time to consult a spreadsheet. And I went with my gut. So the New York Times, when they wrote this article that ultimately went viral, they called the article Serendipity 1 spreadsheet 0 because it was my gut, the serendipity that won that day. But I fundamentally believe that serendipity isn't found it's made. And I made my own serendipity that day. I love that quote in your book. Serendipity isn't found. It's made.

And we're going to go deeper and we'll pull the string on a few different parts of the book that I really enjoyed and found useful and entertaining. But could you go a little bit deeper on this idea of serendipity and how others who are are a little scared or they listen to that voice in their head that's lying to them. And they don't put themselves in positions to let serendipity happen. Yeah, it's like my dad always said growing up, you make your own luck or luck is 11 p.m. in the law library, right? You don't just luck into a law degree. You work hard to get it. You study. You make the right relationships to get that job at the law firm. You build relationships with your bosses, bosses and your boss's peers to get promoted to partner

and that you make your own luck. And part of it, I think, is that when you are seeking to create your own serendipity, and this is what leaders do well, right? Like the best leaders create their own serendipity for themselves and for their teams. Understanding that a success mindset precedes success itself is fundamental to this. Because when we do get in our own way, when those three fears block us from taking action, it is because we think, oh, somebody else deserves that. that would work for the person who's already the VP at the company, but I could never do that.

Like I could never push back on this idea of how we should run this go-to-market operational process. Or let's say you're at an ice cream factory and their CPG company and you think, oh, well, we should try a vegan ice cream flavor or whatever it is. Like, oh, but I'm just entry level. Like, why would I ever be able to bring that idea to the table? It's like if you realize that a success mindset precede success itself, act as if you're already the VP, act as if you're already in the room with that. higher ups and state your opinion, state your voice, diplomatically disagree with your manager.

If you have fresh eyes and you're new to the organization and you think of a better way to do it, that is what I mean by a success mindset, preceding success itself. So on the subway that day, well, heck, what would it look like if this were successful? Let's have the mindset of success. And that was the wild courage that pushed me off the train that day. Already speaking with you, Jenny, both off air and on air, it's evident that you're very bright, very thoughtful. You had a huge career at Google. You went from an entry level. to a big time job and not that long. So that could be seen or be felt as intimidating to somebody else.

It's like, well, of course, Jenny could do it because she's really smart. She's really bright. She knows her dad was good to help her push her. You know, like she's got all this stuff, but I don't think that's me. And I'm sure you get a lot of people who say that to you. What do you say to that person who says, Jenny, I'm just not, I'm not at your level. I'm not there yet. I don't know if I ever will be.

What do you say to them? I'm so glad you're asking this. question because you might not be a subway chaser, right? You might not be at a tech company. You might not even be in the working world. And no matter what it is, there is probably something right now that you want, a goal, a raise, a relationship. And I have realized by coaching tens of thousands of Googlers and non-googlors, scientists, researchers, you know, corporate, non-corporate people directly and indirectly, that what sits between you and achieving that thing, no matter how big or small that thing is fear. And Wildcourge is essentially the process of feeling

that fear and taking action anyway. It's the set of tools that helps you go after what you want and get it. But what you want right now might be seemingly small. Maybe you are looking for a new role and it's just a question of who you're going to reach out to. And so have you written down your dynamic dozen, the 12 people that you should meet in the next 12 weeks? That has nothing to do with chasing a stranger off the subway. That has nothing to do with leaving a large organization at Google, it's simply writing down 12 names. Or let's say you're seeking a promotion or raise at your company. Try a Monday minifesto. Like I get real practical, real fast, Ryan. So we can, like, I love the practical tools. It would break my heart if we had this conversation and we talked

only in theory. So I'm going to probably pretty often go to the tools. But the Monday minifesto is this mini festo, not manifesto, because it should only take 15 minutes to write. And it's four bullets. Two things you're proud of last week. Two things you're excited to work on this week. I cannot overestimate the power of communicating what you're doing in your role. Like it or not, it's not just what you do in your job. It's what your manager thinks you do in your job. And the standout performers to me were the ones who would send me this, it can be a Friday manifesto, but Monday is the alliteration. So the Monday manifesto, and you could even, if you're a leader, you could even send that to your team and then just

see see your boss and your boss's boss. Keep everybody in the loop about what you're you're doing. And yes, it takes a couple extra minutes. It is so worth it. And then when you're ready to write your accomplishment bullets, you are right there with everything, you know, all teed up to write those. Because who remembers in March what they did in January? I think it's good to create forcing functions in your life. If you know you're going to write those bullet points every Friday or every Monday, your mind is on the lookout for doing them, for are finding and searching out opportunities running towards the tougher things at work. That's how you get promoted.

We know this, right? The people who get promoted run towards the really challenging projects slash problems, tackle them to, like, form a team, do whatever they got to do to run towards the tough stuff, the things that everybody else runs away from, and then finding a way to get it done and then documenting the process. I think having your minifestos or bullet points on Fridays or Mondays to send to others is a great forcing function to keep you on the lookout for opportunities. Yes. And not just the challenging stuff.

Like, this is a yes and yes, 100% the challenging stuff. Also the stuff that matters for the organization. Like there are like 17 things anybody could do on any given week. Well, say yes to the big. Say no to the small. Yes to the big is the stuff that's challenging. the stuff your boss cares about. Do you read the VP's weekly email of their updates, or do you just archive that because it's not directly sent to you and it's sent to 5,000 people? Read that email.

Set up time with your boss's boss at least twice a year and say, these are my power assets, the three things I bring to the table in terms of strengths or expertise or passions or, you know, growth areas that I'm excited to work on. And what could you assign me to that might align with that? That is the stuff that's big. You know, increasing. customer satisfaction by 12% year over year or launching that vegan vanilla ice cream flavor or whatever it is, say no to the small. What's small being the 18th person to reply all on the happy birthday Jimmy email, right? Give Jimmy a high five in the kitchen.

The water cooler. What small is attending every meeting where you neither add value nor derive value. Those meetings add up. Or being the person who's always taking notes in the meeting or always organizing the dinner for the offsite. Sure, someone's got to do this stuff. But if you're always the person doing it, you're falling prey to what. what I call nap work, NAP. My mom coined this acronym. Love her for it. NAP, not actually promotable work. And that is when you say yes to everything, you're signaling responsibility,

but you're not signaling more authority. You're signaling responsiveness, but you're not signaling promotion. Let's get practical again for a second. When I was E.P. Love, I worked for a boss who was very insecure about me going above him. You know, I had a relationship with the CEO of the company. That's how I got in. And he was very insecure and weird about that. And so going above him, so you said email your boss's boss, going above him, it was dangerous. What do you say to somebody who has somebody like that, like an insecure ego, like the opposite of a learning leader? What do you say to people who have a boss like that if you want to do you just skip that for this person or how do you have those conversations? Okay. There are so many people out there that must feel this way. Right.

And first, I think the question is, what's the truth and what's the tale? Is the truth that they don't want you to go above their head or is that a tale you're telling yourself, right? Truth is a verifiable fact. Tale is the story you create to make sense of the facts. So first, ask them, right? You never want to go above without keeping them in the loop, right? You need your manager to be on your side.

If your manager is not on your side, that is like the biggest career limiter possible. So you definitely want to keep them in the loop. But how many people are scared to ask? How many people are scared to ask their boss because they're, you know, just assume they're telling themselves a tail. They assume that their boss will say, oh, don't do that. But if given the right context and the right understanding of what your intention is, then they might say yes. And then some of them might say, nah, I'm not comfortable with that. And then of course you respect that. You don't do it. Another option, like I call this managing hire, right? Managing up, that's the old news, like managing up to your boss.

Managing hire is meeting with your boss's boss. Managing diagonally is meeting with your boss's peers, who is up on the org chart above you. the right and left. That's managing diagonally, and those are your boss's peers. So let's say they say, I don't think it's necessary for you to be talking to my manager. You could then say, oh, would it make sense for me to meet with a couple of your peers for mentorship or to get a broader sense of the business? And you could bring three bullets to your one-on-one with your boss explaining why. You're looking for growth. You're looking to help them look good. You're looking to expand your relationships beyond your org. So you have a broader view of the business and the operations and the processes and the stakeholders. And if I'm the boss in that case, I'd be like, heck, yeah,

that's going to make me look great. So you do have options. You never want to go above their head without keeping them in the loop. And if they say no, you could suggest other people, perhaps their peers, which I call managing diagonally. Got you. Okay. So did you learn these tactics and ideas and frameworks along the way at Google? I'm curious, could you run through your career because you got promoted and promoted and promoted? What were you doing in order to go from an entry level to a really high up role where then you're also teaching others within Google thousands and thousands of them about how to manage their career. So there's obviously something that you figured out as you've gone. Well, I figured this out by making a whole ton of mistakes.

And also just I like observing really good people. But yeah, so I started in an analytical role. I was literally, I was 26. I mean, I was like a baby. And, and then I spent about 11 years in sales roles at Google. I spent years in our go-to-market, our strategy and operations team. And then ultimately ran, you know, this operations team that helped customers with bugs, kind of a technical sales, in between sales engineering. The own your career project that I ran was a complete passion project. I saw a need to help people outside of what HR was doing and learning and development was doing, I saw an opportunity to help people in a way that was like for the business by the business, meaning I've never worked a day in people operations or HR or learning and development

in my life, Ryan. But I think because of that, I was able to give a very real deal, honest, you know, view of this is how it really happens here. This is how you really get promoted. These are the relationships you need to make. This is what you should do when instead of feeling jealous of a coworker, you should build a relationship with them. kind of steal their homework, right? Steal their blueprint so that you can adopt those same skills that they have, whether it's a great go-to-market Gant chart or whether, you know, spreadsheet, or whether it's an incredible presenter,

rather than being jealous of that peer, I want to literally write on an index card how many times they say in a five-minute period when they're presenting and see if I can match them, like matching your pace to a faster jogger rather than getting jealous, use envy as your engine. And those are the kinds of things that I started adopting myself. And then as I saw really smart, talented, experienced people get stuck at Google and not get promoted and not get raises and not get on the most exciting projects, it was so heartbreaking to see these incredibly talented people not advancing that I just felt so compelled to do something about it by offering up these tips. I wrote down a couple of tips that had helped me succeed at Google. I put together a training thinking, no joke, that a dozen people would come. And 2,000 people came to the first training I led. In person?

No, it was virtual. It was during COVID. Oh, okay. That's still insane. How did the word spread so fast that you had the answers? So let's talk about this because we've got these nine sizzily traits in the book. And one of them is called shameless. Shameless is the courage to stand behind your efforts and your abilities.

It's about finding your swagger. Because audacity or shamelessness is a survival skill. So how will you learn whether you've got the goods if you don't act like at first? So I already mentioned like, act as if I acted as if I was already successful. I acted as if I was the head of this like massive career program at Google, even though I absolutely was not. And I used Google's internal aliases. Like we've got these miscellaneous aliases in New York and Mountain View where people are like,

hey, I've got Lakers tickets tonight, you know, or free car seat I don't need to use anymore. And people post all kinds of stuff on there. And there are thousands of people on these aliases. And I was like, well, I'm putting together this. training, let's just spread the word and see what happens, even though people wouldn't typically use those aliases for something like this. I was like, well, let's get shameless and do it. And people loved it. So I stood behind a really cool thing I put together, which was this training on how to, at that point, it was called Own Your Career at Google. And I just said, let's just

be confident in what I've put together and see what happens. And then people came and then word started to spread. And it grew to tens of thousands of people using it across nearly 100 countries. Wow. What do you think of the phrase, fake it until you make it? I love it. Really? Well, I love it to an extent. Okay. I love it because to me that's aligned with like, you know, the being shameless. Again, we're using all of these traits in a positive way, like selfish in a positive way, shameless in a positive way, reckless in a positive way. I like the fake it until you make it because that to me gets to the success mindset must succeed a success mindset must proceed success itself.

But I think there's also something about that it's not faking it so much as it is just continuing to learn and grow because I guess, I don't know, how are you defining fake it in that context? I know the classic phrase, but I'm what? Sure, sure. And I fully get it. I just have this, this feeling about the word fake that I'm not especially fake it. Like, hey, go fake it. I feel like there's a better way to phrase it than that.

I understand the concept. And I feel like some of it is in the realm of what you're talking about. But I don't see any part of you that's fake, Jenny. I'm reading your book and all that. So that's why I don't think it applies. I think like a sort of the concept does. Yeah. Okay.

Maybe. And this is a phrase I have in the book. Maybe I would invite people to think of it slightly. differently and think of it as action not thinking provides clarity. So action isn't faking it. Action is saying something in the meeting, coming off of mute, showing your face in the meeting versus being audio only, right? Or asking somebody to mentor you. Nobody at work should be audio only ever. I mean, especially everybody else's video, right? You got to go into the norms of the world. Like maybe you got to life happens. Yeah, sure. 99% of the time have your video on.

Yeah. For us. I mean, if your focus, if your career is, you're a lot of life. You're going to. I mean, if your Career is the North Star, be visible, be in the room. If you're not invited to the room, ask your manager or ask, you know, somebody if you can come to the marketing meeting if you're currently in sales and you want to get exposure to marketing, right? If you don't have a seat at the table, bring a folding chair. So that is action, asking to be in the meeting. It's action to speak up. It's action to ask for a mentor. It was action for me to chase this hot stranger off the subway. So maybe that's the invitation I'd give to people as action, not thinking, provides clarity because how much do we sit in our own heads? And Ryan, I got to tell you, I'm an entrepreneur

now after 18 years in Google. And it is hard as heck to put myself out there and to take that action. There are 300 books that I sent out to corporate contacts, heads of learning and development, you know, CEOs, chief sales officers for their sales kickoff or people who book keynotes for the year. And everybody got this like fancy book box and it was super cool. And now I have to send follow-up emails saying, hey, did you get the box? Did it arrive? Are you booking for 2025? I'd love to come in and add value by way of a fireside chat or a keynote or interactive workshop. And I sent 200 of the first 300 follow-up emails thinking, of course, 100% of people will book me within 24 hours of receiving this email. And guess what? The win

rate was not quite 100%. And it has been so hard for me to send the last 100 emails because I get down on myself. I feel like a failure. I feel like this book is never going to work. Nobody cares what I have to say. You know, those books been written a thousand other times, which is probably not true in this case, because I don't think anybody has a book with a chapter called manipulative. But, you know, I just have to keep tapping back into my own wild courage and my recklessness to err on the side of action and my shamelessness just to go out there and put myself out there and send those last damn 100 emails, even though I get in my own way too and live in fear as well. Yeah, I was going to say, I remember talking to James Clear about this with his personal habits. Do you feel like this responsibility

to live up to this thing that's almost impossible to do? I got to believe if anyone sees Jenny what, you're like, wait, didn't seem that courageous to me? What's going on? Like, how is that for you? It's real. I mean, it's especially making this transition as an entrepreneur. And this is what I've discovered is, sure, at Google, yeah, blast these email aliases with tens of thousands of people. but I'd already kind of made it at Google. I'd already reached a level of recognition or success that I felt like I had the right to do it. This book is all about taking action when you don't yet feel like you have the right to do it because that's what the most successful people do. And I'm sure you can relate whenever you're starting something new, maybe you launch a new podcast, maybe you write a new book,

maybe you start a new job, maybe you're starting a new project on your team, maybe you've moved to a new city and you're building friendships. It's that newness that gets you right back into those. those truths and tales, those insecurities, that imposter syndrome. And that's where I am right now. So I have no qualms about the days I get really stuck because it's just real. The hardest thing I've ever done is leaving Google and going out on my own. And in some ways, I was prepared for it knew exactly what I was getting into because of that, you know, thinking with my head and left brain tendency to get all the data and talk to all the James Clears of the world and figure out how you do it and how you build a business around it. By the way, you don't make money on a book.

You make money on the consulting and the speaking that comes as a result of the book being your calling card. So I kind of understood the nuts and the bolts and the go-to-market strategy of running a business. But being in it myself, it is incredibly daunting and hard and scary and anxiety-ridden. And I just don't pretend that it's not because I guess that would be faking it, right? And so people see right through it. And people, the stuff that resonates most with audiences, frankly, is me being real, like me talking about the story where I made a massive mistake as a working mom and didn't go to my daughter. when she had this terrible accident because I was in New York working and she, the accident, let me just give context there to not scare anybody. She was baking Eminem cookies with my mother-in-law

in New York about two hours away from where my meetings were. And there was an accident with her hair in the mixer and it tore out some hair. And instead of going to her right away, I made this terrible mistake to prioritize my meetings and my team in the town hall I was leading that day. And like I could shy away from that and say, I'm perfect. I always make the best decisions when it comes to, you know, saying no and like saying yes to my family and no to work. But no, I totally screwed it up that day. What made you want to leave Google? Okay. I was driving my son Ari home from choir one day and I realized we live in Boulder at the base of these, you know, at the base of the foothills and we live on kind of like windy roads. And I was on one of those roads at night

driving him home and I realized, did my eyes just flutter closed as I'm driving my son home from choir. And I think they had, but you kind of like, don't, can't really tell if you like they almost did or did. And I was at that point simply doing too much and the emotional, mental and physical toll that all of this was taking on my body, leading my executive operations role at Google, being the founder and leader of this own your career program that had taken off like wildfire with all of this external interest as well, starting to, you know, deal with writing a book and all of that comes with that. With my literary agent and publishers, being a wife and a mom, it was simply too much. I was frequently up with lowercase A anxiety from two to five o'clock in the

morning. And as a result, I was sleep deprived, deprived. I was unhealthy. I was tremendously stressed. And I was clearly falling asleep or almost falling asleep at the wheel. And I just said, something's got to give. You can do everything, but not at the same time. And I had to think about what I needed to give up in that moment, even though it was the absolute. hardest decision I have ever made because I just thought I'd be at Google another 15 years and retire there. Never in my plan to leave Google ever. And it's still shocking to me that I did. Do you still work with them? Like now, are they one of your clients? Number one client. I figured. Yeah. Yeah. Big sense. But I was so scared. What if they never

have me back? What if I can never get a job again? If the book fails, you know, like, and again, truths and tales, why would I think that they wouldn't bring me in? I was like a keynote speaker. I'm their, you know, keynote for International Women's Day this year. So it's all very exciting. Okay. In Wild Courage, your book, you write about the fact that there are these nine traits and you want to transform these nine labels. You've already hinted at a few of them. Yeah. Labels into powerful traits.

I'm going to read them and then we're going to drill down and do a few of them. Is that cool? Awesome. I can't wait to hear what you pick. Okay. Weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, bossy. Okay. We're going to start with weird, the number one, one.

And I want to actually, we're going to hit a couple of them because I want to talk about one of the favorite people that you've interviewed that you eventually hired. I enjoyed reading this story. Is it Carly Kosciak? Oh, yeah, Carly Kosciak. Is that how you say? Okay. You said this is one of our best hires at Google. Everybody in the world applies to work at Google. So you're getting the best of the best of the best. Amazing resumes. Probably even better when they interview. It's got to be tough to like to choose because you got so many good options. It's a great problem to have. But why did Carly stand out? What made her one of the best hires at Google? Well, she was weird on her resume. And weird doesn't mean pink hair. Weird means saying something like Carly did that isn't strictly necessary, but stands out because weird is the courage to stand out and to be authentic.

Because within your so-called weirdness, lie your greatest strength. So hone every ounce of weird you've got. And that could be as simple as saying something like what Carly said on her resume, which was at the very bottom. in constant pursuit of the perfect oatmeal raisin cookie recipe. Now, Carly could have played it safe and done what everybody else does, which is written foodie or enjoys baking. But Carly, in just one sentence, showed that she was weird, like I just described, right,

like had the sentence, that she was obsessed in constant pursuit, right? Obsessed is about push, perform, persist. It's the courage to set your own standard. it showed that she was nosy, right? That she had the courage to dig deeper and get insatiably curious, and she wasn't just going to stop it. One recipe she's going to keep looking until she found it. And so all of that in one single sentence is what I call brutal,

the power of concise communication and being clear and prioritizing concision. So that is why it certainly stood out to me as a weird thing to say on a resume. And then, of course, when she did interview, the colorful personality matched what was written on the resume. And she had the chops and the business experience and all the important stuff to go with it. And that's why she got the job. And she just kept, you know, being authentic and seeking growth opportunities within the role within Google and just kept moving up. One of the words that has come up recently, Jenny and my conversations on this podcast that I think Carly also embodies is specificity.

Being specific. Oh, my gosh. This is a core trait of people who sustain excellence. It sounds weird. But for example, you write a cold email and instead of saying, hey, Jenny, you're so impressive. Can I pick your brain? You get specific in your praise and specific in your ask. And there's much higher likelihood of you wanting to respond if the person writing you

is specific as opposed to being very vague or broad or general. That's what Carly did on her resume, right? She was specific, whereas everyone else says, I love to bake. I'm a foodie, right? She talked about oatmeal raisin cookies. And I think, even though I don't like those types of cookies, I like that she's specific in her description of herself and her pursuit. That says so much about a person.

I am all, my husband was interviewing for roles a bit back. And I was like, John, the best phrase you can use in an interview is, for example, because when you say, for example, it forces the specificity. Or again, let's talk about those accomplishment bullets or the Monday Minifesto. So here's what vague sounds like. Helped grow revenue a million dollars. Not everyone's going to have that kind of a huge accomplishment, but let's just say for easy example. Helped grow revenue a million dollars.

That I would give like a red stoplight on my report card here or like a red rating. Let's go to a yellow rating. Helped drive, you know, drove a million dollars in revenue, which was 12% year-over-year growth. when we've got context, right? Okay. But now what we're going to get to is this, what we're doing, by the way, is doubling our numbers, right? We're doubling our numbers by saying 12% year-over-year growth that tells us, was it a million on 100 million or was it a million on 500,000? Big difference, right? So 12% year-of-year-year growth by, and here's where we really get specific, by creating office hours that clients could come to every Tuesday afternoon for

two hours, which had never been done. So now we're both doubling the numbers, which I always say double your numbers, double your numbers, double your numbers, and we're also adding context around like what it was that you did, what specifically happened so someone can visualize the creativity of you thinking of this office hours idea or by, let's say, by bundling products that had never been bundled before, right? There are so many different things you can say. But think about, we think of classic ROI, return on investment. What's your ROI for a bullet like this in your career? It's your role, your objective and your impact. What was your role? you wanted to, your role was like the sales leader or whatever it is, right? You were the person who

created the office hours. What was the objective to upsell these clients? And what was the impact? It was the 12% year-over-year growth in a million bucks. So double your numbers and think ROI role, objective impact on any resume bullet, any accomplishment bullet, or any bullet in your Monday minifesto. You write about goal setting. And this is something that I personally struggle with. I have moments where I set these giant public goals for all to see and judge me on and hold me accountable to. And then I have other times where I'm like, I don't really want to set goals. I just want to stick to the process. I want to marry the process and divorce the results and what will be will be.

And so I go back and forth. I've had certain years where I do it. You have this formula that you call rock, chalk, talk, and walk. What does that mean when it comes to goal setting? Yeah. Yeah, so the rock is the big rock, the big goal you want to set. And Ryan, I'm going to touch into a little bit about the process too, even though this first explanation of rock, chalk, talk, walk is really about the goal setting process.

But I think what you're hitting on is really meaningful as well. So let me come back to that. But rock is what's the big goal you want to set? So I'm literally taking this sticky note off of my monitor right now. And all of you listening, I'm holding up to Ryan a piece of paper with tape on top because I just took it off. And it says rock, colon. So 15,000 U.S. hardcover copies, wild courage by March 25th, 20th, nice. Okay.

So that is a very, very clear goal. It's not make this book successful. It is sell 15,000 U.S. hardcover copies, hardcover because that's what counts for the New York Times bestseller list. And people don't realize that, but that's how the lists work. It's got a clear deadline, March 25th, or, you know, let's call it end of March. because it'll be that's the pub date that's why i put that but like that is the rock i did not say make the book successful like how do you measure that it goes goes back to doubling your numbers how do you know if you succeeded or failed on that goal so that's the rock chalk is you write it down right so first i

had to think what is the goal i wrote it down i put it on my monitor for me to see it every day talk is i say it out loud well i just practiced the talk right now i said it to you and all of you right here listening i say it to my husband i say it to my friends and i don't shy away from how this big, hairy, audacious goal. Not I want to be a musician, but a Grammy award-winning musician that's touring internationally by 2027, right? And you say it out loud so that people can give you ideas, they can introduce you to other people, and that you're not just living in your head with it. And finally, walk the walk. What is the one small thing I can do right now that will help me move toward that goal? It's sending out those last hundred emails that are plaguing me to get people

to bring me in for keynotes because bulk sales is a huge help to achieve these goals. So that's chalk, talk, talk, and walk. However, you mentioned sometimes you're like, I just want to live the process. Ryan, I think we can get stuck in the goals. And I think we can overwhelm ourselves. And I think that sometimes it can take the joy. And yesterday, I was writing a bunch of thank you notes, right, to people who've helped me on this book. And my goodness, that doesn't move me any closer to this 15,000 goal. But man, did it bring me joy and man, did it make this process fun? And I oftentimes, have gone down a rabbit hole on the wrong thing or gotten too focused on the North Star of making the book as successful as possible week one, right? And I've oftentimes lost sight in the

privilege of writing a book, the fact that as another big time author said to me, Jenny, you're already winning. I'll just say who it is because it's such a great quote. Seth Godin was like, Jenny, you're already winning. You are already winning. You have a big book deal. You've got this incredible gift you can give to people. You're already winning. And keeping that in mind and just leading with gratitude and enjoying the process, which is really difficult for me because I can be my own worst enemy on goal achievement and having too much ambition or obsession or recklessness or desire to achieve my goal. So it's tough and I have to remember to enjoy the process. If you sell 12,000 copies that first week, how will you feel? I, you're asking such good

questions. I'm going to feel great. I'm going to be momentarily bummed, but this is something called impact bias. It's a classic cognitive bias. It's a social psychological principle that states that when we anticipate a negative event getting laid off, we're not getting the raise we want, or not getting the project, or getting harsh feedback from our boss or a breakup, a relationship, we think that negative feeling is going to feel worse and last longer than it ends up feeling. And there's a ton of science around this. It's called impact bias again. And so I've already visualized that moment of getting the call from my agent that I did not hit the New York Times or only sold X number of copies. And what will still be true is that there will still be 12,000, not 15,000 people in the world who have

my book in their hand and who are going to be better because of it, who are going to be more confident, more able to ask for what they want. They'll be better able to kick their imposter syndrome to the curb. shared my stories about both my maternal grandmother and my paternal grandmother in the shameless chapter for my grandma and the nosy chapter for my bubby. And I will have shared those stories with the world. And this is the whole point of writing a book and putting the work out there is to help people. So what if I help 12,000 and not 15,000? The book, if it's good, will get recommended by other people. And eventually the book will find itself into the right hands. And I will feel thrilled about the individuals that I impacted and those notes I get back

from people because I'm already getting them about how this work is impacting their life and helping them get promoted and helping them get the raise and helping them be happier in their relationships because they're standing up for what they want confidently now. One of the things people say is you got to play a cool, let them come to you. I'm thinking of dumb and dumber. I'll be over by the bar, putting out the vibe. Sorry, that's just for me. But you play a cool, play cool, right? And you're like, No, we're going to play it hot. What does it mean to play it hot? Yeah.

So play it hot is a strategic decision to not fit in. We're going opposite of middle school, right? Where everyone's going to wear the same jeans and the same crop top. Oh my gosh. Side note, I see what these girls wear in middle school and I'm horrified. But that's a conversation for another time. But whatever it is, they all are shopping at the exact same place, getting the same style. That you don't want to stand out in middle school because that's like social suicide.

But at work, you want to stand out. It's the only way that you will get the cool projects. Like, leaders keep lists. They have a bench of who's going to do the maternity and the paternity backfills. By the time the job wreck for, you know, an official job is posted, sometimes it's too late by them. You need to be building those relationships. We talked about this at the top of the call, but it's building those relationships. It's writing down your dynamic dozen, the 12 people you want to meet in the next 12 weeks. It's saying something in a meeting. that might get your wrist slapped and get you a compliment in the same afternoon. If you're the intern, sure, where the expected, like here's playing it cool as an intern. We're the expected business

casual attire, nod in every meeting, keep your video off because you don't want to stand out. You want to play it cool. That is a perfect strategy. If all you need is that fancy company's name on your resume for the three-month stint. But if you want to be competing and getting the job against the 20 other interns there, you best be playing it hot. Asked to be put on a project, even if it's not what interns typically do. Ask to present the work, even if it's five full-time employees who also were part of the project. Be the one who sends the comms every week because the person who sends the comms oftentimes gets the lion's share of the credit. Be the person who diplomatically disagrees live in a meeting and get that wrist slap and that compliment,

but at least you're standing out and people know who you are. What does it mean to watermark your work? Watermarking your work. I almost pulled this from the book, and I'm so glad I didn't. Watermarking your work is putting your name, your title, and sometimes even your picture on any work document. And I almost pulled it from the book because it felt so obvious. But let's say you're giving a presentation to an internal team of 50 people. And your slide one says Q1 business review.

No names, no contributors, no picture, no way to get in touch with you. but sometimes that Q1 business review makes it way to 300 other people at the company. Let people know that you made this deck. And my editor at Penguin Random House, Lydia, is such a, she's just totally delightful. And she's like, I watermarked this presentation I did. And it went up to the top of Penguin Random House. And I'm so glad it had my name and my email address on that first slide because they knew how to find me and they knew what else I could do.

Like think about a remodel in your neighborhood. If someone puts a sign on the front, like oftentimes they'll put a sign on the front lawn saying what the name of the architect or the remodel company, the contractor is, right? So call that shameless. But shameless is about letting people know who you are and what you can do and what you stand for. And maybe somebody else in the neighborhood wants to remodel. And you're actually helping them by making it clear what you offer and the great work that you do. Is this true that there was an NYU Facebook group called, I'm going to butcher this name. Stephanie Germanada will never, you will never be famous. Is that true? That is true. Yeah. So,

so Stephanie Germanata is not famous. But Lady Gaga, her alter ego sure is. And so what did Stephanie do in college, right? She was shameless. She didn't set her bar against everybody else. She's like, these people are not relevant to me. My goal is not to please these peers at NYU. My goal is to be a massive pop star. So she just tuned out. the noise of the naysayers and the people who weren't relevant for her success. And that is part of what being shameless is. Huh. That was got to be tough. How do you help somebody? Like I personally, I think struggle with this. I remember talking to Adam Grant on this, which I know you guys are colleagues as well. And I said, dude, this whole like self-promotion thing is really hard. I want to sell

books too. I want to promote the podcast. Promoting myself gives me the ick about myself. He goes, You're not promoting yourself. You're promoting the work. And your work changes people's lives for the better. Keep doing it. And it really helped. But I still have those days. I still have those days.

What do you think about that? Yeah. So, you know, again, we're talking about the shameless chapter here. This is the courage to stand behind your efforts and your abilities. And because maybe I already said this, but it's worth repeating that audacity, shamelessness is a survival skill because you are there to create value in the world for other people. And the thing that made me want to call this trait shameless is because I was in a meeting and someone came off of mute.

She said, I have a shameless plug, but I created this document and like a spreadsheet, rather, and I really think it's going to save everybody at least 30 minutes on this call. And I cringed. I always winced when someone says, this is a shameless plug. Plug away. What is the shame, right? We get these things instilled in us as kids. Don't rock the boat.

Listen more than you talk. wait your turn, stand in line. But we are then doing a disservice to everybody else in that room or who might be interested in your work by not making it available to them. So as soon as she said that everybody had all these emojis flying on the call of, oh my gosh, this is so helpful. The chat was exploding. I can't believe I've been wasting so much time doing this process. And now I have this spreadsheet from you that saves me time. If we can even just start small, right like again you might not be a subway chaser that is a okay how do you start small maybe replace this is a shameless plug to i have something that i'm proud of that you might find valuable like

we're not selling we're helping people well the problem with this is everybody knows that person in the meetings that speaks up too much and doesn't add value that actually makes the meeting worse and yes some of us have the fear of like god i never want to be the meetings that's that guy. I don't want to be that guy. I want to be that guy. You know, and, and, and I'm picturing some of those guys right now. Yeah. And, and so, so I'm like, I would rather wait, or maybe I'm going to, you know what I mean? So like, how do you manage this balance? Because I want the things I say to be useful, to be valuable, to be helpful. I don't want to make this meeting worse. I don't want to make it longer than it needs to be. Right. How do you manage that balance?

Okay. So this is, well, there are, there's a concept I call trait traps, which is when you take these traits too far, right? Obsessed is about how you should push, perform, and persist. It's not about grinding yourself into a workaholic and grinding yourself into a pulp. But I would argue that I think the pushback, and I expect plenty of pushback on this book, it's terrifying to think about what the pushback might be. I already know of companies who say, ooh, this doesn't align with our values. We can't bring you in.

But what I offer is that, first of all, it's all obviously tongue-in-cheek, right? This is all using these traits in a savvy and sane way for good and expansion. of the pie for everybody, not redividing the pie. But if you are somebody who thinks, no, Jenny, selfishness is the big problem in the world. Being manipulative is where we're all getting it wrong, you know, being shameless and everybody just coming off of mute and saying too much is the problem. I would say that think about 20 people in a meeting, Ryan. Okay, I guess that's a big meeting. There's going to be the one guy who, or girl, who says too much and who's kind of annoying and who doesn't know when to shut up. But think about the 19 other people in that meeting

who I'm guessing you would feel struggle with too much imposter syndrome or don't get out of their own way or live in too much fear or have great, brilliant ideas and they're too scared to say them or too nervous or think, oh, what if it was already said before? What if anybody disagrees? That's whoever in this book for. If you've ever had a moment where you wanted to say something and you were too intimidated to say it, or you had a good idea and you held back, or you wanted to take action, but you thought, I'm not ready yet, or my website's not perfect yet, or I don't have the right label or, you know, position at this company to have this opinion. That's who this book is for. And I would argue there are far, far more of those people in the world than there are

of the people who say too much in a meeting. Yeah, I think it's just like the profession of selling. That was my background for 12 years before doing this full time. And you talk to a non-sales professional, someone who hasn't worked in the industry, and they'll say, oh my God, I hate that so much. I hate sales people because they had a bad experience with a bad buying a car or something. And so they just think they hate the entire profession because of that one or two or three bad experiences where if you actually interact with an awesome sales professional, it's you usually build a genuine relationship and that person only sells you something if they can genuinely help you. Like their solution solves a problem. It's the same way.

Like we're talking about like you get the one person sometimes ruins it for all of the rest. And I think that's what we're talking about here. That one person in the meeting can ruin it and makes you everyone else say, uh, let me just chill because we already had one loud mouth in here. I don't want to risk being the second, you know. Yeah. And you don't have to be a loud mouth.

It could simply be speaking your mind, sharing your good ideas, giving three options and sharing your opinion, right? Like even that's a very simple tactic of how you can show yourself as a leader. But if you, this is this, this is a lot of leaders listening right now. As a leader, your goal should be to coach and support people to be better than they think they can be. And as a leader, your job, like if your title is director, direct, right? Don't shy away.

Don't him and ha around decisions. Like I did earlier in my director career, have the confidence and have the shamelessness to make decisions to be a little bossy. And I think it can be a beautiful thing to steer others to success. I love it. Jenny, let's see you're meeting with somebody who's earlier in their career. Yeah. And they aren't 100% sure what they want to do, but they do want to leave a positive dent in the world. What are some general pieces of life slash career advice you'd give to that person?

Yeah. So everyone's going to have a performance review. And everyone is going to, because we have this negativity bias, right, which is another classic cognitive bias to focus on your strengths and your opportunity, sorry, focus on your opportunities, not your strengths. So when you walk out of your performance review with your boss and they say you were good at apples, bananas and pears, and I want you to work a little bit more on strawberries. What do you do?

You go home and you say to your partner or your friend or your parents, I'm no good at strawberries. When you are early in your career, I want you to focus on your strengths. I want you to put 75% of your effort into your strengths. Focus on your apples, bananas, and your pears, if those were the three fruits that I said, go to your boss and ask for more projects that align with apples, bananas, and pairs, right? And then also using that same 75% rule, this is tip number two of three, I will share here for early career professionals.

But number two is say yes to 75% of things. that come your way and say no to 25%. You never know where you might strike gold or, you know, find an incredible opportunity if you're protecting your time too much. Then when you're in your 40s, let's say flip that ratio and say no to 75% of things and yes to 25% of things because you have a better sense of what you actually want to be focusing on. And the final thing I will say for people who are earlier in their career is, and this is a totally different type of tool, but this is all about your written communication. And this is, is called woo with you. Woo with you is starting as many of your sentences in your emails

with the word you as opposed to the word I. I wrote an email, a thank you note to someone who had me in for a keynote recently. And every sentence started with I. I loved doing this keynote. I had so much fun partnering with your team. I love the gift basket that you sent me. I dove right in. And then I was like, oh my gosh, this is so focused on me. Focus on your audience. That is a great tactic. Call it manipulative, but in the healthiest way to build influence through empathy. So I rewrote the whole thing. You were incredible to partner with because of your speed, your creativity, and your energy. Your team was top notch and I loved their interactivity during the session.

You might benefit from this new leadership training I'm workshopping if I could add value to your team. You sent the most delicious gift box, right? The first version, all with I, the second version, all with you. That's really good, really tactical. And side note, if cauliflower could be pizza, you could be anything, right? It's sitting over your right shoulder. brilliant. What does that mean to you? It means that all the stuff can be learned, Ryan. You know, every single thing with these tiny little tools and tactics and tips and tricks, oh, we didn't get

to tame the octopus. I love the communication school called tame the octopus. That is something you can learn to be a more succinct speaker in an interview, in a one-on-one with your boss, in a meeting, and all the stuff can be learned. So to me, if cauliflower can be pizza, you can be anything. It means that if you have a growth mindset, if you think of maybe you're not X, Y, Z, but it just means you're not X, Y, Z yet, that you really can be anything. And who wants cauliflower pizza anyway? Not me. The book's called Wild Courage, go after what you want and get it. It is really good. A combination of story science, practical application, which is my favorite type of framework that the best of the best seemed like everyone tries it, but now everybody gets it right.

And I feel like, Jenny, you really have here. And I really enjoyed preparing. and enjoyed our conversation even more. So thank you so much for doing this. I highly encourage people to get wild courage. I like am really rooting for you to crush this 15,000 number. I give you credit for sharing that. I have never done that. And I don't think I have the courage to put a number on it.

Because then you could fail. Then you could fail publicly. And I give you huge credit for doing stuff that most people are not willing to do. And I think that's really cool. I think it's also inspiring to me and to others to be willing to put that out there even though there's a there's a good chance you could fail because that's a lot of books that's a lot of books to sell especially in the first week that is almost nobody does it so I think it's awesome I think it's really cool that you've put that out there thank you and if I don't

achieve it you know what people will think of me that I am a human who went to went went for something and it didn't happen and it's just part of life no no matter whether you win or fail in any one given thing, you will never feel as powerful, purposeful, and alive as when you're pushing past that fear to the joy and success on the other side. So put the number out there, make it big, and push past the fear because it's not the single thing that matters. It's the habit of wild courage. Yes. And by the way, people want to follow. People want to get behind a leader who is striving for something big, not a leader who's striving for something like, let me hedge a little. No, We want to get behind people that are going for it.

Like, going for something big. That's what we want to get behind. And I think you're a great example of that. So, Jenny, thank you so much for being here. I would love to continue our dialogue as we both for us. This has been so much fun. Likewise. Thank you so much for having me.

And thank you to everybody listening. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know what you learned from this great conversation with Jenny. A few takeaways from my notes. Serendipity isn't found. It's made. Make your own luck. The best leaders create serendipity for their teams. A success mindset precedes success. You have to believe it

and then go do it. At work, say no to the small. Do not be the seventh person to reply all to the happy birthday email. In fact, you should almost never reply all. Don't do the nap work. Knapp stands for not actually promotable work. Sign up for the projects that help make your company better. And then Carly Kosciak, one of the best hires she ever made at Google. Carly had the courage to stand out.

She was specific. Her resume indicated interest in learning and being in pursuit of finding the perfect oatmeal raisin cookie recipe, right? It was specific, actionable. It showed that she had a dynamic personality and that she wasn't afraid, right? Her personality popped off the page. She was weird, reckless, nosy, obsessed, and brutal, as Jenny would say. You got to be yourself, but don't just be weird to play a role, be authentically you and then be fearless in your pursuit of it. showing others. Once again, I want to say thank you so much for continuing to spread the message

and telling a friend or two. Hey, you should listen to this episode of The Learning Leaders Show with Jenny Wood. I think she'll help you become a more effective leader because you continue to do that and you also go to Spotify and Apple Podcasts and you click that subscribe button. You're right, a thoughtful review and you rate the show, hopefully five stars by doing all of that. You give me the opportunity to do what I love on a daily. basis and for that I will forever be grateful. Thank you so so much. Talk to soon. Can we?