9 'Bad' Traits That Get You Promoted | Jenny Wood

24 Mar 2025 · 58 min

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In short

Podcast Summary: The Art of Charm - Episode on '9 Bad Traits That Get You Promoted' with Jenny Wood

Episode Overview In this episode of *The Art of Charm*, career coach Jenny Wood, a former Google executive, discusses how seemingly negative traits can actually help individuals advance their careers. Jenny shares insights from her new book, *Wild Courage*, emphasizing the importance of embracing traits like shamelessness and being weird, which are often viewed negatively but can actually foster authentic relationships and career growth.

Key Themes and Discussions

Introduction

  • Guest Introduction: Jenny Wood shares her journey from an entry-level position to an executive role at Google, where she created one of the company's largest career development programs.
  • Core Message: Playing it safe stifles career growth, and reclaiming 'taboo' traits can unlock potential.

What Separates High Performers

  • High performers are not just technically skilled but also possess essential soft skills.
  • The importance of visibility and self-promotion in a corporate environment.
  • Managing relationships with superiors and peers effectively is crucial for advancement.

Visibility, Influence, and Strategic Self-Promotion (00:05:21)

  • Managing Higher and Diagonally: Importance of building relationships with higher-ups and peers, not just direct supervisors.
  • Bragging the Right Way: How to highlight accomplishments without coming across as arrogant.

Reclaiming “Taboo” Traits (00:17:31)

  • Nine Traits for Career Success: Jenny discusses nine traits often deemed negative but necessary to reclaim:
  • Weird: Embrace uniqueness to foster authentic connections.
  • Selfish: Standing behind one's efforts to gain recognition.
  • Shameless: Taking pride in one's accomplishments without feeling guilty.
  • Nosy: Cultivating curiosity to enhance learning.
  • Obsessed: Committing wholeheartedly to goals.
  • Manipulative: Building relationships through strategic influence.
  • Brutal: Providing honest, constructive feedback.
  • Reckless: Taking calculated risks.
  • Bossy: Leading with confidence and authority.

Frameworks for Career Advancement (00:34:27)

  • WIN Framework: Advocating for oneself in a professional context without guilt.
  • SAFE Framework for Feedback: Setting, action, feeling, and effect to provide constructive feedback.

Is It Time to Leave? (00:48:01)

  • FLIP Framework: Key indicators to evaluate job satisfaction:
  • Fun: Are you enjoying your work?
  • Learning: Are you growing professionally?
  • Impact: Are you making a meaningful contribution?
  • Personal: Consider personal life factors influencing job satisfaction.

Practical Insights

  • Visibility is Key: Staying unnoticed can hinder career progression. Managers need to manage relationships beyond immediate teams.
  • Embrace Your Traits: View traits traditionally seen as negative in a new light; they can provide advantages in career settings.
  • Take Initiative: Bold actions, even in smaller contexts, can lead to significant career benefits.

Conclusion

  • Jenny Wood emphasizes that reclaiming negative traits can lead to personal and professional growth. By embracing our unique qualities and advocating for ourselves, we can carve out our paths and achieve our goals.

Resources Mentioned

  • Jenny Wood's website and book, *Wild Courage: Go After What You Want and Get It*.
  • Tools for networking and self-improvement available through *The Art of Charm* platform.

Related Links

  • [Jenny Wood on LinkedIn](https://www.linkedin.com/in/jennywood)
  • [The Art of Charm on Instagram](https://www.instagram.com/theartofcharm/)

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This summary captures the essence of the podcast episode, highlighting key discussions, strategies, and insights shared by Jenny Wood on reclaiming traits that might typically be frowned upon, thus paving the way for career advancement.

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Transcript

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0:00When it comes to what your family eats and drinks, you know your choices matter. You're the expert because you know what fits your life. And getting it right starts with good information. That's why America's beverage companies are sharing more information about our ingredients at GoodToKnowFacts.org. No spin, no judgments, just the facts straight from the experts for more than 140 beverage ingredients. Visit GoodToKnowFacts.org. The biggest frustration I see in people is that they are really skilled. But what separates the truly successful people from the people who just kind of chug along in their career are the people who can shamelessly talk about their wins.

0:45If you are holding back and not sharing that explicitly with the world, whether it's an interviewer or your manager, you are really, truly limiting your full potential. And that's heartbreaking to me.

1:04All right, let's kick off today's show. Today, we're talking with Jenny Wood, former Google leader and top career coach, explaining why everything you've been taught to be successful is a lie. Jenny spent 18 years at Google climbing the ranks from entry level to executive. She also created one of Google's largest career development programs ever. And today, she joins us to discuss her new book, Wild Courage, Go After What You Want and Get It. She shares why being weird builds more authentic connections to being average, how to prepare agendas for meetings to control your career narrative, and the reason your manager's peers influence your promotion more than you think.

1:40Welcome to the show, Jenny. Great to have you. Hey, great to be here, Johnny, AJ. I had the pleasure of actually meeting you in person in Atlanta last year, and I got to see a lot of these qualities in action. So it's exciting now to dig into the book and hear your story behind the book, as well as share these qualities with our audience. Yeah, let's dig. So there's a quote that I'd love to start a discussion with, an insight you share in the book that I know rings true for Johnny and I, and we've seen firsthand in all the amazing guests we've had on the show. The quote is, successful people take action despite their fear.

2:09They muster the courage to do what's necessary to succeed before it's encouraged by others or even considered socially acceptable. Yeah. Why is that so important for us? It's important because I observed growing from entry level to executive at Google over 18 years that a key blocker to so many people's success, mind you, these are skilled, talented, capable, experienced people at Google. So a blockage is so much of their success was their relationship to fear, fear of uncertainty, fear of failure, fear of the judgment of others. And that last one is particularly interesting, and acute. And it shapes how we view ourselves.

2:55It shapes how we see ourselves. It shapes how others maybe see us. It creates a voice in our head that creates these labels, these labels we want to avoid, right? Like, oh, I might do that. I might go for that job or ask to participate in that team. But I'm worried that someone or I might disagree with my boss or my VP. But I don't do it because I'm worried someone might call me blank, right? Fill in the blank with any negative label that might come your way, right? That we want to avoid. And those are the nine labels that I like to reclaim because these labels create the bars of an invisible cage that keep us small, keep us quiet, keep us following versus leading.

3:34And for the skeptics in our audience, as we go through these traits, I think it's really important to highlight that not only did you learn about them in your own career path, but you also developed training at Google to help others break through. So I know in listening to some of these traits, they might sound off-putting at first or, hey, that works for you, Jenny, but that won't work for me. But really what your training that you put together and built at Google did was allowed others to grow in their career. So I'd love to really unpack what that program was like and how you developed it. And then we can get into the great traits.

4:03Yeah, definitely. Well, the book is very different from the training at Google, namely because once we get into the traits, you'll recognize how it never would have flown to have a program at Google that doubled down on these traits. But the program was called Own Your career. And it really just started as a lark. I ran an operations team that sat between sales and engineering that helps drive billions in revenue annually. And I was I've never been in HR. I've never been in people operations. I've always enjoyed coaching and mentoring. And just out of my own journey, trying to go from an executive role in the New York office to an executive role in the Boulder office, I found myself getting stuck and coming up against a wall and really spending six months trying hard to find this next leadership role for me at Google.

4:47So I wrote down these 12 tips or so to myself to help me be successful next time, just as notes, honestly, like a black and white document with 12 bullets, one page. And then when people would come to me for mentorship, I'd say, Hey, why don't you read this doc first? And then we can chat about your specific, you know, challenges, but this will get us ahead of the game. Well, that doc started getting shared, it started getting shared more, and then it became a 60 minute training, then it became a biweekly newsletter. And then I named it on your career. And before I knew it, these career tips, these tips to help with stakeholder management or networking or negotiations, the program grew to 10s of 1000s of people across nearly 100 countries.

5:29And it became one of Google's largest career programs in its 25 year history. Absolutely shocking to me. But what what it told me was like, I've struck a nerve. People want help with this. And especially like in the age of AI, the soft skills matter so much and people are always craving help with the soft skills. So that's a little bit about the program. I know for many of our audience members and even our clients, they lean so heavily on the technical skills to get ahead in their career. And then they hit that invisible wall where these people skills become invaluable. And they try to focus on the immediate relationships around them.

6:06So with their boss or their peers, but a lot of what's missing is showcasing these traits with people outside of just your small group to get that visibility, to move from invisible to visible in the organization. For you personally in your career, how did you unlock that visibility piece? First, we have to acknowledge that visibility is a good thing and it is critical. And if anybody tells you just keep your head down and get your work done. They are lying to you. They're lying to you. And I want to not lie to you anymore. I want you to recognize that visibility is critical. And okay, managing up old news, that's to your boss, we want to manage higher, we want to manage diagonally.

6:48So manage higher is have a twice a year meeting with your boss's boss, especially at a mid to large size organization. Get to know two or three of your manager's peers. If your manager has seven peers, get to know two or three of them in an organic, authentic way. Not, hey, I'm up for promotion. And I just wanted to introduce myself. My name's Jenny Wood, right? 24 hours before promotions are decided. Not like that in a way that is bringing a project to them that you're working on and you're excited about, and you might be able to offer to their team in the future or get feedback on because someone on their team has done something similar.

7:24Or asking one of them to mentor you because you're genuinely interested in their projects and their team and their work and you think that they might be able to give you guidance, career guidance, project guidance, relationship guidance. So managing higher is meeting your boss's boss and having a relationship with them. Managing diagonally is, if you think of your manager as up above you on the org chart and their peers are next to them, managing diagonally is building relationships with a couple key players of your your manager's peers and the reason i say key players is let's keep it real i'm not a bs-er not every single one of your manager's seven peers have equal influence equal weight and equally bend the big boss's ear so find the intersectionality between who has the influence who do people take seriously because some people just got that position because they got lucky right and who do you really genuinely connect with and who can offer you feedback and, and ideation and, you know, expanded ways that you can think about your work.

8:28That's, that's the Holy grail. But to me, that is like visibility at its core is going beyond your manager. And for those who are listening on the other side of this, I want y 'all to realize that of what time it is. And we had a little laugh earlier before the call of just talking about how even your colleagues are going to be using AI. So the skill gap that you think you might have the advantage of, that's closing fast. And so it is going to be your people skills that is going to do most of the heavy lifting, getting you to or towards your goals. And so if you do have those beliefs of, I'm just going to keep my head down and work hard, and I'm going to be seen for the work that I do, or I'm going to outwork everyone else around me.

9:14You are making this incredibly difficult on yourself. Yeah. And that's fun, by the way, because it's fun to build relationships and you derive excitement and energy and enthusiasm and ideas from these colleagues that you can extend yourself to getting to know better. It's funny that you bring up the mindset shift, Johnny. I was actually just coaching somebody last week and he was applying for a role. And I said, everyone's used to sending a thank you note within 24 hours after the interview. I was like, send a pre-note. Every touchpoint matters before an interview. Send a pre-note with three bullets, highlight your superpowers, add a couple links to projects you've done.

9:54And this was like blowing his mind. And I was like, and use numbers, double your numbers. Every bullet should have good ROI, not traditional ROI, but this is what is your role? What was your objective? And what was your impact, right? Use numbers. He was like in the top 1 % of production on his current team. And he was going to this product management role that was so perfectly aligned with what he'd been doing. And he was so nervous, so scared to share these bullets ahead of time. And I'm like, you want to bias? Bias is a loaded word, but let's use it in a positive way. When you walk into that interview, you want to bias before you even get there, that interviewer, that you're a rock star.

10:30So why not give them some data ahead of time? And your resume doesn't cut it. That is too long. There's too much going on there. It's way too overwhelming. Pick three bullets, send a pre-interview note 24 hours before you walk in the door. And here's where the mindset shift comes in, Johnny. He pushed back on me and he's like, Jenny, there's no way I can do that. Isn't that going to come across as obnoxious or a little bit arrogant or a little bit pushy? and I was like you've got to be bold because this is a competitive place and if you've got 50 other resumes that this hiring manager is looking at and they're going to have at least five or seven other interviews you want to be bold you want to stand out you want to share these incredible numbers and if there's ever a time to be bold and bullish it's in an interview like your resume is a brag document you're just tightening up that brag document document giving them like a little mini brag.

11:26And it was really interesting to see how much he struggled with this mindset shift and this leaning into boldness. And I talk about wild courage and the importance of that and how it helps you get ahead to go after what you want and get it. But it was really hard for him to have the wild courage to even just send that email.

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15:39And we're both going to get fired. I'm like, okay, well, you got the floor, sir. You got our attention. Let's hear it. What do you got? So it would definitely pique our curiosity and get us fired up. Now you better show up and deliver after that. But if you're touting that you're a rock star, then show up as the rock star. The biggest frustration I see in people is that they are really skilled. They are really talented. They are rock stars in their own way. Like, of course, you've got to have the goods, right? But what separates the truly successful people from the people who just kind of like go along to get along and like kind of chug along in their career are the people who can shamelessly talk about their wins, right?

16:28And I say shamelessly in a really positive way because I love to kick imposter syndrome to the curb and inspire people to have less shame in there and take so much pride in their accomplishments and their talents and their skills and their strengths. So assuming you've got the goods to back it up, which I think a lot of people do, whatever those skills and talents are, if you are holding back and not sharing that explicitly with the world, whether it's an interviewer or your manager, your manager's peers, your manager's boss, or your peers, you are really, truly limiting your full potential. And that's heartbreaking to me.

17:02It's frustrating to me. And that's why I like to help people do it. Yeah. And you're also shining attention in the spotlight to the areas that you want the interviewer to see. So now they can see where you're good and rather than just listening to you and trying to figure it out for themselves, help them out. Absolutely. You're signposting for them. You're even almost helping them figure out what to focus on in the interview. Heck, that saves people time. People are busy. People are distracted. People are overwhelmed. And by the way, all of this extends to your one-on-one weekly Tuesday meeting for 30 minutes with your boss, right?

17:43Come with a prepared agenda, come with four different categories, wins from last week, current challenges, number two, number three, where I need your support, number four, career. Those are four awesome categories to bring to every meeting with your boss, put bullets in there, share some wins with numbers, right? Focus your boss on what you want to talk about in that meeting. The people who reported to me, the managers who reported to me who were most successful, spent 30 minutes prepping their one on one doc before we had our weekly meeting. And I would love going in there and seeing the links they they had linked to with their projects and the specific questions.

18:22I love the ones that started with what and how those are always so much more powerful, their specific questions of what they needed from me, the ones who were advocating for their careers with that particular section in the one on one, not that you cover it every week, but you know, occasionally there would be some bullets in there. The ones who didn't do so well in their careers and who were always kind of just plugging along were the ones who just showed up to the meeting with me. They weren't focusing me. They weren't focusing themselves. They weren't focusing the conversation. And that is a gift to your leader.

18:52It is nothing but a gift. You have the power to set the agenda. You don't realize it. And this is what's interesting to us with our clients is like invisibility starts small. It's like that sense of relief when the boss cancels the one-on-one standup meeting because they're too busy. And then it snowballs. Okay, well, good. I got out of that meeting and now I didn't have to prepare. And then a couple weeks go by, you haven't talked to your boss at all. And then now you're showing up remote. And then in the group meeting, you haven't really had any results. So you don't raise your hand. You don't want to talk.

19:19And then months and months go by. And guess what happens around promotion? It's not just your boss vying for you to get promoted. It's his peers or her peers saying, I've never heard that name before. I don't know that I can put my power behind them getting promoted. And that invisibility then robs you of promotion, but it also robs you of relationships. And this is what I wanted to key in on because so many of these traits were taught and told make you less charismatic, less charming, less interesting. When in actuality, to build great relationships fast, you have to stand out. You cannot be average.

19:52You cannot be shy, timid, and hope that other people see this in you. You have to stand out to build relationships quickly. So I'd love to dig into, at least first, are any of these traits that you break down in the book something that you specifically had to harness or hard for you in the beginning? Or how did you unlock them as a part of this Wild Courage project? As we dig into these traits more, let me name them. So we have nine traits in the book. And as I mentioned, these traits create the bars of an invisible cage that keeps you small. And because I want people to stop playing small and start playing smart, I know that every single one of you listening has the capacity to do that.

20:33The nine traits are weird, selfish, shameless, nosy, obsessed, manipulative. That's a spicy one. Brutal, reckless, and bossy. And you're right, AJ, like these are eyebrow raising traits. These are sizzly. These are spicy, right? But I'm reclaiming these words. I'm inviting all of you rather to reclaim these words and to use them for good in a sane and savvy way that helps you get seen, get heard, and get ahead. So for example, manipulative, old definition intended to control. New, reclaimed definition, the courage to build relationships through empathy and create lasting partnerships. Or reckless, like acting without caution, reclaimed, the courage to take healthy risks and err on the side of action.

21:21Weird, win as you or lose as who selfish the courage to stand behind your efforts and abilities. So this is all powerful language. And when you think about the new definition that I'm offering to you today, it does seem like good stuff that that everybody should be taking advantage of. But people get scared of the labels, they get scared to be called. Oh, she's so bossy, right, especially as a female leader. Well, to me, Bossy is the courage to listen and lead. Or, you know, she's so manipulative, my goodness, like what a what a what a scary one to be called. But I mean, what do good leaders do, aside from getting other people to move a process or a program or an organization forward?

22:09Like, manipulation can be a positive thing. You take a lump of clay as an artist, and you manipulate it into something creative and innovative, a beautiful sculpture, a beautiful wall hanging. Well, good leaders manipulate teams to be creative, processes to be innovative, just like the artists. So these things, and manipulation is really straight up relationship building and recognizing that, why are we opening our mouths at any point ever if you're not trying to get someone to do something or say something? I mean, why do you have this podcast if not to say things, to have things come out of your mouth and my mouth that will hopefully help other people, right?

22:44We have a great example in the book of manipulative around meeting someone that had a great impact on you and recognizing that this might be your one chance to do so and acting accordingly. But of course, if you label it as manipulative, I could see a lot of people in the audience being like, well, I could never do that. But it ended up being such a huge win for you. So share that anecdote for our audience. I was riding the subway home from work in 2011 and about 20 feet away from me is this really attractive guy. Gorgeous blue eyes, perfectly clothed five o 'clock shadow. Can a five o 'clock shadow be clothed?

23:18Maybe, yeah. Yeah, he had great facial hair, right? And I was like, so taken by him, but I got stuck in fear, right? I wanted to walk up to him and be like, hey, I'm Jenny, right? But I was on a packed subway train. I had fear of judgment of others. What if a hundred people watch me while I make a fool of myself? fear of failure. What if he's married fear of uncertainty? What if he's a convicted felon? Right. And so I made a deal with with myself. I said, if he gets up at my stop, I will try to strike up a conversation with him. And if not, then say love it. That's the universe telling me it wasn't meant to be.

23:53He gets off at the next stop. That is not my stop. And I have this, this moment of wild courage, this wave of boldness and shamelessness that like pushes me out of my subway seat, basically. And I ran off that train as I thought, forget the universe, I'm making my own meant to be. So I chased to catch up with him as he's exiting the station. And I say, excuse me, 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. any chance I could give you my business card. And I wait for what feels like a slow forever for him to respond as I'm out of breath and my heart pounding.

24:39And finally, he takes the card. A week later, we go on a date. It was amazing. Three years later, we got married and we've now been married 11 years with two little rugrats. Again, if we were to label that as manipulative, we wouldn't have left the subway. Yeah. And let that opportunity pass you by. Or shameless, right? We can label that shameless. We can label that bossy, right? Like traditionally, think about societal norms or traditional roles. Like, no, the woman should wait there and wait for the man to ask her out. Like that is bossy and shameless and selfish for her to go after what she wants.

25:17How unusual and uncommon and atypical is that? But you know what? If you're usual and you're common and you're typical at work or in your life or in your friendships or in your relationships, you're going to get forgotten. You're not going to get ahead and you're not going to achieve the success that I know each one of you has in you to achieve just waiting there, waiting for it to come out. Yeah. I know in thinking about these traits, there's always the negative impact of being labeled it by others at some point in your past. So, you know, each one of those traits, there's probably one example in your past as you're listening to the show where you're like, I've been called that.

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25:56I hated it. I don't want to be judged by that. And now that label has persisted so much that you've dimmed that entirely. You've ran from it, avoided it, and it's cost you all these opportunities. So what can we do when that negative voice comes in and it's like, oh, Jenny, you're just going to be manipulative. You can't leave the subway car. I think the first thing you do is you start small. Like, let's say, depending on your background or your culture, whether you're listening in from a more bold culture or bold city like New York or LA or, you know, whatever you characterize or you were born in Japan or Beijing or Sao Paulo, right?

26:34All of these things can affect how we feel about this level of boldness. So no matter where you are coming from today, no matter what it is that you want to go after and get, there's always something small you can do, or whether you're introverted or extroverted. So you start small, you start maybe by sending a weekly Monday email to your manager saying, Hey, these are three things I accomplished last week. And these are three things I'm really looking forward to this week, right? It doesn't involve chasing anybody off the subway. It doesn't involve standing up in front of your company and presenting to 300 people.

27:05um maybe it's maybe it's as simple as when your vp finishes their presentation in the town hall you send them a quick ping a quick slap and you say hey that was really helpful and i appreciate your transparency walking us through this reorg right think about it your leader it has imposter syndrome too they're insecure when they're delivering this really trick tricky complicated reorg to the company they're worried about how it's going to land am i communicating this thoughtfully. Are we doing right by all of you? And so even just giving your leader the encouragement like, hey, that actually landed pretty well.

27:40I thought you did a good job delivering it. I know this is tough news. And it was really helpful how you unpacked it. That is such incredible relationship building and doesn't require some huge sweeping moves like chasing your future husband off the subway. And in the book, you start with weird as the first trade. Is there a reason that we lead with weird? Because I know so many of our audience members, and we laugh about this with Johnny too. And in the bootcamp, when they come to train with us, that's like the one that they avoid the most. I don't want to be seen as weird. If you go along to get along and you wear the, you know, if you're the intern and you like wear the requisite dress code and you sit there quietly in the meeting and you format your resume exactly to the specifications.

28:21Okay. That's cool. And you can put that company on your resume for the three months stint that summer. But if you want to land that highly competitive role long term, you got to stand out. Maybe as that intern, you're weird in that you disagree thoughtfully with something that's being said in the meeting. Heck, you might even get three reprimands and three compliments in the same day, right? Because when you're putting yourself out there and being weird and authentic, you take a risk and you might ruffle some feathers and smooth some other feathers. And that's just part of life, right? But weird is the foundation of the book because it's all about authenticity.

28:57And sometimes it's just simple authenticity. There was this one candidate, Carly, who was applying for a role on my team. And man, did she stand out because of one single line on her resume at the very bottom. Under interest, it said, in constant pursuit of the perfect oatmeal raisin cookie recipe. She didn't just say foodie. She didn't say, you know, a restaurant connoisseur or whatever, she gave this very weird, specific anecdote that showed so much personality that was a bit of a risk because it's an unusual thing to write on a resume that showed her curiosity. It showed her nosiness. It showed her shamelessness, right?

29:35That she would do something that was unusual and which was also weird. It showed her obsession, right? Obsessed is push, persist, perform that she was looking for the best, the best, not average, but the best oatmeal raisin cookie recipe. So all those traits, like she showed five traits in one sentence, starting with weird by doing something different. And it's one of the reasons I interviewed her. And then her colorful personality in the interview matched that resume. And we were off to the races. She was one of the best hires I ever made at Google. It's so fascinating how oftentimes just showcasing that weird side not only strikes authenticity, but really resonates with everyone because we all feel weird in different ways.

30:16We all have those passions that we know most people don't enjoy. Johnny has some musical obsessions that we've shared on the show over the years that I think a lot of our audience would label weird. I get way into cooking in very weird ways that I think aren't really going to resonate with most of our audience. We didn't start a podcast around those weird things, but they're part of all of us. And when you feel comfortable and confident enough to showcase that weirdness, you'd be surprised how much it resonates with others and creates the opportunity for a relationship. It creates the opportunity for a relationship.

30:44and it creates the opportunity for just partnership because people like to work with interesting people. People like to see you as a person and not just this worker bee. And it is, it's just such a powerful that like your, your weirdness slash authenticity combined with your enthusiasm. Enthusiasm can cover up so much lack of skill, talent, experience, because enthusiasm is just, it brings so much to the table. And I mean, I've hired people just based on their enthusiasm, like damn straight. Yeah. Being around people that bring great energy fuels the whole team. So why wouldn't you want to fill a team full of enthusiastic people?

31:29And that's critical for a manager, critical. Like if I had to pick between, you know, a leader who I was hiring, who was like killer at VLOOKUPs and knew all the shortcuts on their spreadsheet and could run circles around me on the API or whatever spreadsheet or dashboard it was that we were building. Okay, that's fine. That's good. But if I'm not looking forward to walking into a one-on-one with that person each Thursday morning, I don't want to hire that person. I would much rather take 80 % skillset on the spreadsheets, on the VLOOKUPs, on the shortcuts, on the API creation and have that person be someone who is thoughtful, engaging, fun, creative, um connected and uh and enthusiastic all day long all day long so you highlight that some of these traits can be overdone so let's talk about what are trait traps because each trait you highlight there are traps around them and let's start with weird because i think um for those in our audience are like great now i can be weird let me uh let my freak flag fly they might overdo it how how how much do you want me to get into specifics on this one on my own freak flag you you guide me here yeah we're explicitly rated here so you can get as freaky as you want okay not so it happened in seventh grade it's not so freaky it's just deeply deeply embarrassing so weird weird is showing your best self uh it is not saying something outlandish or obnoxious for the sake of attention.

33:01And on my first day of seventh grade, I was in a brand new school. And this middle school went sixth, seventh and eighth. So when I happened to elementary school, sixth grade in elementary school, so I was the new girl and everybody else knew each other. So my deep insecurity, my lowercase a anxiety, and my desire to be noticed to be liked to make my to make people aware of who I was as this new girl showed up in all the wrong ways. So it was we were in language arts class and the teacher, Mrs. Howard said she gave her spiel at the beginning that she said, Okay, does anybody have any questions?

33:35It was like an introduction about who she was. And I raised my hand, desperate for a laugh. And I said, I have a question. Are you a virgin? In front of my entire seventh grade class, brand new seventh grade class. And that is the wrong kind of weird. That was letting my freak flag fly in really, really devastating ways. I did not get the laugh I was seeking. I did not make any friends that day. And then I wrote weirdly, weirdly, I happened to see her in the greeting card aisle at the supermarket that afternoon, which is just a total coincidence. And I walked up to her took the longest, you know, 10 steps of my 11 year old life.

34:11And I said, Mrs. Howard, I'm sorry, I apologize. I don't know where that came from. I don't know why that did that. Why I did that. And she was very gracious. And she said, That's okay, I understand. And she's a lovely teacher. but like that's not the weird you want to be you want to be professional at work or in your relationships and your friendships on a date whatever it is you want to be mindful you want to let your best self show not just be weird for the sake of weird and say something you know for attention or um you know we've all seen the movie stars who do the the odd thing for attention i guess sometimes it works but if you're not a movie star um you know they're air on the side of the right.

34:51Dial your read up appropriately.

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37:37Don't put your love life on hold. Take back control of your confidence and intimacy. Get up to 95 % off treatment with Rex MD. Visit rexmd.com slash charm. That's rexmd.com slash charm. See full details and usage at rexmd.com. Prescription required. Results may vary. Mutine. Adjective. Used to describe an individual whose spirit is unyielding, unconstrained one who navigates life on their own terms effortlessly they do not always show up on time but when they arrive you notice an individual confident in their contradictions they know the rules but behave as if they do not exist mutine the new fragrance by mu mu defined by you well i know as a people pleaser myself and many of our audience members have shared with us that they've struggled in that category as well you know how often do we find ourselves elevating others at the cost of ourselves and that self championing and and being so self-assured whether it's sending that email with here are three great things about me or leaning into all of the self-promotion that a lot of these traits and allow in us can be very difficult especially when we're so clear on on others and and want to please those around us so to the people pleasers in the audience you know what advice do you have around highlighting these traits and showcasing these traits?

39:04This one's tough for me. You know, I think you alluded earlier to like, what do you still struggle with? This is one I definitely still struggle with. And, you know, people think like, oh, selfishness is the big problem in this world. I argue differently. I think selflessness in a professional setting can be an equally big problem because sure, there are a couple of bad opposites who spoil a bunch, right? And there are some people who truly are selfish. But when we're overly selfless, in our careers, you know, always giving that key project to somebody else, or, you know, there's, there's, there was this person at this, this company who was a pretty large company.

39:43And she was like a top performer, really good manager. But she got distracted by the side project. And she got this performance review that was mediocre. And she had this working with her with a peer on a project. And she knew that even though they were doing equal work on the project, the peer would get extra kind of credit, like the peer would be seen as getting the lion's share of the credit, if she was the one that presented the project in this 30 minute meeting to the leadership team. And so even though she wanted to encourage this peer, she's like, you know what, can I actually do the presentation, she got a little bit selfish, just like this tiny little anecdote of selfishness because she was starting to get concerned about her performance, right?

40:28She had gotten distracted by the side project, her manager said, Hey, get your eye back on the ball. And so she advocated for being the one to present because she knew the person who presented would get the lion's share of the credit. So it's just like this small moment of selfishness that doesn't hurt anybody else. Her peer could present on a future project. It felt critical for this person to ask for this, but we oftentimes feel bad. We feel like, oh, we're letting our team down or, well, why should I ask for what I want? Or why should I ask to present? Or, you know, it's like, if you give everybody else a leg up at your expense, you really truly will get trampled career wise, right?

41:04And those people will shine and go ahead and move ahead. You have a great framework in the book, Wynn, that I think is super impactful in these moments. I'll give one example, one story, and then one example of my own life. So the story is Claire Tori was a session singer that was invited to just do the little tiny moment on this Pink Floyd song. Okay. So as she's recording this for Dark Side of the Moon, not even knowing what it would become, she just does her vocals, they become these legendary vocals, like, right, these like legendary vocals on the song. And she's just making it up on the spot, she gets paid 30 pounds as a fee just to be like a backup singer or a session singer and then she walks out and she like goes along her day um so she doesn't even know that the song has made the album until she sees she sees it come out and then this goes on to be like multi like 14 times platinum massive huge hit dark side of the moon um and so she says okay well what i need now like selfless would be like oh my gosh i was happy to get my 30 pound fee but but she got a little bit she had some healthy selfishness and she said let's play to win what i need now what i need now is a songwriting credit and xyz lump of money right so she sues pink floyd and pink floyd was smart to settle outside of court for an undisclosed song and she was smart to be selfish in the right way and ask for what she needed because like it really wasn't an unfair situation given she had made that song what it was those legendary vocals are the key to that song so that was for what i need now what i need now for me i was really excited to do this volunteer role um to be head of the like quite large google boulder office and this had been a dream of mine for years i ran into i wanted to be co-head i ran into the person who was head at a street fair and uh where our kids were bouncing on this bouncy castle boulder's you know not a huge city and um and that despite having a large google office and i was like i aspire to be co-sightly with you.

43:07And it was like, on a Sunday, and our kids are bouncing, and everyone's got like snow cones dripping, like not at all the appropriate time to be asking. But I was asking for what I wanted. I was being a little bit shameless. Well, fast forward a couple of years, I'm actually offered the opportunity. And by that time, I had my full time operations role. I was writing the book, I was leading the owner career program, that was a massive undertaking. I was working every single night, every single Saturday and Sunday. And despite the fact that for years, I aspire to have that role to help lead the community.

43:37I said, all right, well, I got to play to win. What I need now is to say no, to not people please, to not look at Jenny's goals three years ago, but to look at Jenny's goals today. And they do not include this very, very heavy and time consuming role of being the volunteer co-head of the Google Boulder office. And as hard as it was for me to say, no, I did, because that was not what I needed now for this. And she was incredible about it. She's like, hey, it is not your responsibility to worry about who's going to do it. I did feel like I do a good job and I cared so much about the office and so much about the community.

44:15But she's like, that is my responsibility to find another next best option. It is not your responsibility. But I was like going to say yes to people, please. And be like, who else would do a good job? Right. That's just almost arrogant that there's nobody else who would do a good job. Of course there is. And she did say to me, Jenny, a man would not feel this way. So not to get too gendered, but she's like, a man would not be apologizing for saying no to this opportunity. So think about that too. That key piece of what I need now, I think it's lost on so many of us because especially in our career path, we're following what a lot of outside influence tells us will make us successful.

44:50So it's like, well, what my parents need to see and what I need to tell my peers and what I need to show on LinkedIn and how I need to be getting approval from those around me. It's really hard to zone in and be clear enough for you to turn down such a major opportunity. What I need right now is actually not this, even though that opportunity would have influenced all those people you could have put on your LinkedIn. Everyone would have looked up to you for that accomplishment. How do you really tap into that? Okay, this is what I need and that self-awareness. Very, very hard for me. um i remember hiking with my dear friend nina and and she was like jenny this gives you nothing like it's so much work and i think it's maybe a little bit of ego because you like being seen as like the head of something and jenny you love superlatives and she's like but just keeping it real with you you focusing your energy on making this book as good as it can be like if you had three hours next week and because sometimes this role is dealing with like some real uh unsexy kind of issues right like google has a dog called dogs are allowed in the office that like every once in a while someone's like i'm allergic to dogs like can we switch the dog allowed floors to floors two and floors floors four so you're like dealing with things like that um uh and then of course leading all the company town halls and things like that that are quite fun and energizing.

46:11But she's like, if you have three hours of your time, are you better off dealing with what floors allow dogs and what floors don't allow dogs in the Google Boulder office? Or are you better off perfecting chapter seven or improving chapter seven to be helpful to not just the, you know, thousands of people in this office, but to the millions of people you could potentially help motivate, you know, invigorate and inspire with this book. And I was like, okay, you have a good point, Nina. But it was still so hard for me to say no, so hard. I wrote an entire document of all the restrictions I'd have if I did take the role.

46:45And they were so thoughtful about working with me. But I was like, you know what, even though they're saying like, oh, you've got all these other resources and all these other admins you can lean on to help. I knew at the end of the day, it was going to be a ton of work. And I just had to be brutal. That's one of my nine traits. I had to be brutal, right? Yeah, we talk a lot about boundaries on the show and going along with that, like self-awareness of what you actually need, getting through the people-pleasing, boundaries can feel very brutal when you draw them for the first time. And when you're actually stepping into the no to say no to this major opportunity to actually say yes to what you need in the moment.

47:22And, you know, Dori Clark has this great saying in her book, The Long Game, like every yes leads to 10 other yeses, or maybe she says 20 other yeses. And it is so true. Like now when I do a keynote, like sometimes people will say, Okay, well, will you do this keynote at a discounted rate? Or, you know, can you just do this little, this little session with my cohort? And like, I want to say yes. I'm like, Oh, it'll just be 30 minutes of my time. They're like, Oh, you just show up literally don't have to prepare anything just this 30 minutes. That's it. Well, guess what? Then they send the questions in advance.

47:54And it's like, well, gosh, I want to put thought into this. I want this to be good. Then we have to get changed the date. So now I'm like in my calendar, right? So that's yes, number one, I'm like prepping questions in advance because I like to be helpful to people if I can. Number two, we're changing the days. I'm going back and forth in my calendar. Then I have a kid's dentist appointment that I have to reschedule. That's yes number three. One single yes can lead to 10, 20 additional yeses. Then someone follows up after the call and says, hey, can you take a quick look at my resume, whatever it is.

48:20I love that frame also that every yes can lead to many more yeses. Or if it's not a Hell yes, it's a hell no.

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49:01This episode is brought to you by Indeed. When your computer breaks, you don't wait for it to magically start working again. You fix the problem. So why wait to hire the people your company desperately needs? Use Indeed's sponsored jobs to hire top talent fast. And even better, you only pay for results. There's no need to wait. Speed up your hiring with a$75 sponsored job credit at Indeed.com slash podcast. Terms and conditions apply. And being brutal is also delivering feedback. And that can be challenging for young leaders. Being honest in a way that actually helps someone else grow can feel brutal in the delivery, can feel brutal in receiving, but ultimately can be that turning point in your career to really change your trajectory.

49:49AJ, brutal can be kind. and I will tell you about a moment where I was sitting getting a performance review. I think at this point, Google did them quarterly. It was like constantly we'd be doing them. We'd be done with one cycle and start the next one. And I remember sitting there and it was like seven minutes of windup and buildup until my manager finally told me my rating. And I was so nervous. I was sweating and I was scared. And I don't even remember what the rating was, but I do remember feeling like this feels terrible. So brutal is even if it's a bad rating or you're telling somebody that you're eliminating their role, which is such hard news to deliver, deliver that news within the first 90 seconds of that meeting, tear off the bandaid, ouch, move on.

50:35And you can do it with empathy. You can do it with thoughtfulness. And that's not just like sharing a feedback rating. It's also just day-to-day feedback. So AJ, if we got off this podcast and I were like, Like, well, you know, I didn't think this was great. You weren't a great communicator. You'd be scratching your head. Like, what does she mean? And how is she defining communicator? But if I'm brutal and I say, you talked 30 % of the time and I would expect a podcast host to talk 10 % of the time. Like, that's concrete. That's brutal, but that's concrete. And that's something you can work with.

51:09It is so true. And oftentimes we try to, you know, compliment sandwich it, speak in superlatives, and we don't add any concrete examples or ways that that person receiving the feedback can truly improve. And we're doing them a disservice because so many of these situations, everyone's looking for growth. I mean, if you're listening to this, if you're reading this book, which we encourage everyone to do, you're looking for growth and you need those moments, those gut check moments where you get the brutal feedback. And sometimes you got to be the one to deliver the brutal feedback to get the team back on track, to get back to that goal.

51:40I have a quick framework for this. It's called SAFE. How to stay safe as a manager when you're giving feedback. So SAFE is setting, action, feeling, and effect. So setting in this podcast, let's just stick with this ridiculous hypothetical example. In the podcast, let's say I'm sharing this with you two weeks down the line. In the podcast that we did together, AJ, so that's the setting, right? Like not, hey, you are a poor communicator. Setting is like, this is the specific situation where it happened. The client meeting, the phone call, the actual podcast, right? The action is, I felt that you spoke about 30 % of the time when I was expecting you to speak about 10 % of the time.

52:23That is the specific action that you took. Then I check in with you and I say, and this part is so key. And this is the differentiator of how to give like brutal but thoughtful feedback. F is feeling. So AJ, how are you feeling? What was going on for you during that podcast? And you might then say, oh, well, gosh, I felt like, you know, because of the fires in LA, I didn't have as much time to prepare as I would have normally. And so I wasn't quite buttoned up enough. And I kind of found myself like rambling, like whatever it was. That's an important one to check with the person, say, how are you feeling?

52:54And then you might give really good context. And then you close with E, and that's a fact. And if I were the manager and I were in charge of evaluating you on your podcast performance, then I might say something like, and this is kind of a big deal and it could impact your quarterly rating. Or I might say, oh, AJ, you are a rock star and you're always so on your game. And I know this was just a little blip. This is really kind of below the fold feedback, not above the fold feedback, meaning like on a newspaper, you know, top line headline versus like a tiny little footnote at the bottom. And so then you walk away knowing exactly when it was, what happened, you have an opportunity to share how you were feeling and you know if this is a big deal or a small deal with safe, S-A-F-E, setting, action, feeling and effect.

53:37I know in going through these traits, there are going to be some members of our audience who are feeling like they're in an environment where they can't express any of these traits. They've allowed these bars to not only close themselves in, but sometimes it's the environment that creates this. And we get this question a lot of when to leave. You know, you feel like you're doing everything you can, but you don't really feel great in this job market currently or how I'm leaving. So I know that you have a great framework for really diagnosing when it might be time for you to leave the flip framework that I think would be super helpful for our audience.

54:07As much as I hate to drop two acronyms back to back on all of you listening, I'm going to drop two acronyms back to back on all of you listening. All right. So how do you know when it's time to leave flip F-L-I-P fun, learning, impact and personal? Are you having fun in your job or are you rolling your eyes in every team meeting thinking, oh, tried that six quarters ago. that's never going to work. I is for impact. And that's your business impact. Because if your business impact isn't there, it's not going to bode well for you or your career. If you're moving the business, you're moving your career.

54:38So that's I did this out of order. That is I for impact. Let's sneak that L in there. That's for learning. And this is step function learning, not just incremental learning, because most people have some level of incremental learning every day, especially depending on your industry. But like with AI, everyone has incremental learning every day. But you want step function learning, you want a couple emails in your inbox that give you butterflies in your stomach, because you don't quite know the right answer yet. You want to feel like you're on a project, and you feel like you're out of your comfort zone.

55:11And then you finish that project, and you're like, Oh, my gosh, that kicked my butt. But now I'm such a better, you know, technical person or communicator or relationship builder, because like just been put to the test on skills that you didn't feel like you had previously. So that's F for fun, L for learning, I for impact. And then P, P is personal life, what's going on in your personal life, because that's valid, too. Let's say that you just found out you were pregnant, and you, you know, want to just kind of stay where you are for the moment, because you've got a lot of other stuff that are going to be a lot of other things that will be changing in your life.

55:46Or maybe you want to move across the country with your partner or to another country. And it makes sense to, you know, change roles because of that. So what's happening in your personal life is a valid reason to stay or go. And by the way, the other thing that underpins all of this is your manager, your manager can make or break your happiness at work. It's kind of like, you know, sex in the city, he's just not that into you. If your manager is just not that into you, peace out pronto, So, because it's not going to get better. They're not going to all of a sudden become a super fan. And if your manager isn't an advocate, your career is going to stall real fast.

56:23Going back to what we shared earlier, that invisibility starts subtly and all of a sudden it snowballs to a place where you're not getting any chance for visibility for promotion. Yeah, definitely. This was such a fun conversation, Jenny. Thank you so much for stopping by. Where can our audience find out more about the book? And I know you have some great tools and resources to share as well. So they can go to itsjennywood.com book to purchase it. Well, you can purchase it anywhere books are sold. And I have a newsletter that comes out weekly with like under a two minute career tip how to thrive professionally and go after what you want and covers everything from negotiations to relationship building to succinct email writing and all sorts of real practical stuff to build relationships with your boss with your peers with everybody.

57:09and that's itsjennywood.com slash newsletter. I'm also on all the socials and I post every day on LinkedIn so you can find me there too. Great, thank you so much for swinging by. Yeah, what a pleasure. Such a joy to be here and have this conversation. Thank you.

57:35And now comes the part of the show where we showcase one of our X Factor Accelerator members. Take it away, Ron. Hi, this is Ron Palermo, and I'm a corporate lawyer. Taking the X Factor Accelerator is one of the best decisions I have ever made. If you want to consistently show up as a high-value person, someone who makes a great first impression, effortlessly makes new friends and connections, and enjoys deep and authentic relationships, X Factor Accelerator will get you there. The AOC team is passionate about what they do and are totally committed to your success. And most importantly, they know how to get the results you want.

58:13My only regret is not taking the program sooner. If you are serious about showing up as the best version of yourself, I urge you to sign up for the X-Factor Accelerator. You will be so glad you did. Thank you, Ron. It was a pleasure working with you too. And good luck to you and all your future endeavors. if you've gotten value out of this or any of our podcasts head on over to your favorite podcast player and rate and review this show it would mean the world to me and aj and it helps others find the show all right before we head out a huge thank you to our producers michael harold and eric montgomery till next week go out there and make it amazing Yeah, I remember you You were the bad boy You threw your love away Like you were just a toy And you sold the world You're a song of a tragedy Cause you had your taste Of black on the yesterday Yeah, but I remember you Oh yeah, I know you In my best life Next up is a little song from CarMax about selling a car your way.

59:37You wanna sell those wheels You wanna get a CarMax instant offer So fast Wanna take a sec to think about it Or like a month? Wanna keep tabs on that instant offer With OfferWatch Wanna have CarMax pick it up from your driveway? You wanna get it, touch it. You wanna do it all. So, wanna drive? CarMax. Pickup not available everywhere. Restrictions and fee may apply.

From the publisher

In today’s episode, we’re joined by Jenny Wood—career coach, former Google executive, and author of Wild Courage. Over 18 years at Google, Jenny rose from entry-level to executive and created one of the company’s largest career development programs. Her work focuses on breaking the myths of professional success and teaching high performers how to reclaim “taboo” traits—like being shameless, weird, or even manipulative—to build authentic relationships, increase visibility, and take control of their careers.
Introduction
Join us for a bold and insightful conversation with Jenny Wood as she reveals why playing it safe is holding you back—and how to reclaim traits like weird, shameless, and even manipulative to fuel career growth. Jenny shares hard-earned lessons from her rise to executive at Google, the power of strategic visibility, and why soft skills are your ultimate edge in the AI era.
What to Listen For
Introduction – 00:00:00

What separates high performers who rise from those who stagnate in their careers?

What soft skills do tens of thousands of high performers crave—despite excelling technically?

Visibility, Influence, and Strategic Self-Promotion – 00:05:21

Why managing your boss isn't enough—and what it means to “manage higher” and “manage diagonally”

How to get noticed before a promotion cycle even begins.

What’s the right way to brag—and how do you do it without sounding arrogant?

Reclaiming “Taboo” Traits – 00:17:31

What are the nine negative traits Jenny says you must reclaim—and why are they the key to getting ahead?

How do bold, assertive actions (like chasing someone off a subway) illustrate professional courage?

Why being manipulative might actually make you a better leader

Frameworks That Help You Win – 00:34:27

How to use the “WIN” framework to advocate for your needs without guilt

Why saying “yes” to everything might be sabotaging your career

What is the “SAFE” framework for giving clear, kind, and honest feedback?

Is It Time to Leave? – 00:48:01

What’s the FLIP framework—and how can it help you decide whether to stay or go?

How to know when your manager is holding you back—and when it’s time to make your move

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Resources from this Episode
Jenny Wood’s website
Wild Courage: Go After What You Want and Get It
Jenny Wood on LinkedIn
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