"Do People Not Like Working With Me? Help!"

Summary

Help Wanted Podcast Summary

Episode: "Do People Not Like Working With Me? Help!"
Release Date: April 1, 2025
Host: Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine
Guest: Jenny Wood, Former Google Executive and Author of Wild Courage: Go After What You Want and Get It

---

Introduction

In this insightful episode of Help Wanted, hosted by Jason Pfeiffer of Money News Network, the focus is on addressing workplace interpersonal challenges—specifically, concerns about whether colleagues enjoy working with you. Jenny Wood, a seasoned executive from Google and the author of the transformative book Wild Courage, joins Jason to share her personal experiences and provide actionable advice on fostering positive work relationships.

The Challenge: Perceived Difficulties in Working Relationships

The episode kicks off with a pressing question from a listener: "Do people not like working with me?" Jenny Wood steps in to narrate her own encounter that led her to introspect about her professional demeanor and its impact on her collaborations.

[03:36] Jenny Wood:
"I have a newsletter that I write every week, and it became the bane of my existence... I was barely keeping my head above water."

The Story: A Misunderstanding with a Service Provider

Jenny recounts a pivotal moment when she sought the expertise of Lauren Kinney, a reputed email newsletter ghostwriter. Despite Lauren's esteemed reputation, Jenny's initial interactions were fraught with missteps—being late to meetings and appearing disorganized—culminating in Lauren deciding not to work with her.

[07:14] Jenny Wood:
"Lauren, did I push you too hard on the price?... she just don't think you would value me."
[08:20] Lauren Kinney:
"I cannot do this deal with you because I don't think you would value me."

This candid feedback was both shocking and enlightening for Jenny, prompting her to delve deeper into understanding how her behavior may have been inadvertently off-putting.

The Impact of Feedback and Self-Reflection

Jason and Jenny delve into the significance of receiving honest feedback and the emotional turmoil it can cause. Jenny describes her initial mortification and subsequent determination to rectify her approach.

[10:51] Jenny Wood:
"Lauren is considerably younger than I am... to have the confidence to share it, I was shocked."

Strategies for Effective Communication and Relationship Building

Through her experiences, Jenny emphasizes the importance of:

1. Asking for Feedback:
   Jenny shares another instance where she solicited feedback immediately after offering a job, revealing that her intimidating demeanor was a barrier.

   [14:17] Jenny Wood:
   "I offered her the role... I'm curious, do you have any feedback on me as an interviewer?"
   [14:27] Jenny Wood:
   "I almost didn't want to take the job because you were really intimidating."

2. Being Open to Constructive Criticism:
   Embracing feedback as a tool for personal and professional growth is crucial. Jenny highlights Google's culture of continuous feedback, which shaped her openness.

3. Taking Calculated Risks:
   Jenny advocates for boldness in addressing issues head-on, likening it to building a muscle that strengthens over time.

   [25:40] Jenny Wood:
   "Be bold, take the risk, say the thing that's on your mind. Rationalization is a weapon so powerful it should require a background check."

4. Building Psychological Safety:
   Creating an environment where team members feel safe to express honest opinions fosters stronger, more collaborative relationships.

Overcoming Fear and Building Confidence

Jenny discusses how pushing past the fear of confrontation can lead to deeper, more meaningful professional relationships. By addressing issues directly, individuals can prevent long-term resentment and misunderstanding.

[30:36] Jenny Wood:
"Push past that fear, you find joy and success on the other side. It's all about pushing past fear."

Real-World Application: Jenny's Success Post-Feedback

Despite the rocky start, Jenny managed to mend and strengthen her professional relationship with Lauren Kinney over the course of a year, demonstrating the long-term benefits of confronting and resolving interpersonal issues.

[24:30] Jenny Wood:
"Lauren and I have been working together now for almost a year, and she's unbelievable. We have the best possible working relationship."

Additional Anecdote: Providing Feedback to Senior Leadership

Jenny shares another instance where she boldly provided feedback to a senior leader at Google, which initially seemed risky but ultimately led to enhanced mentorship and significant career advancements.

[32:17] Jenny Wood:
"He responded well... by being bold, by being confident, by taking a calculated risk... it created so much success for my career."

Key Takeaways

1. Solicit and Embrace Feedback: Actively seeking feedback can uncover blind spots and pave the way for personal growth.
2. Communicate Transparently: Honest and direct communication builds trust and respect in professional relationships.
3. Take Calculated Risks: Stepping out of your comfort zone can lead to valuable opportunities and stronger collaborations.
4. Foster a Culture of Psychological Safety: Encourage an environment where team members feel safe to express their thoughts and feedback.

Conclusion

Jenny Wood's experiences underscore the transformative power of honest communication and the courage to seek and accept feedback. By addressing her perceived shortcomings head-on, she not only improved her professional relationships but also advanced her career, reinforcing the episode's central theme: the importance of effective interpersonal skills in the workplace.

---

Notable Quotes:

• Jenny Wood [07:14]: "Lauren, did I push you too hard on the price?... she just don't think you would value me."
• Jenny Wood [14:17]: "I almost didn't want to take the job because you were really intimidating."
• Jenny Wood [25:40]: "Be bold, take the risk, say the thing that's on your mind. Rationalization is a weapon so powerful it should require a background check."
• Jenny Wood [30:36]: "Push past that fear, you find joy and success on the other side."

---

Resources Mentioned:

• Book: Wild Courage: Go After What You Want and Get It by Jenny Wood
• Company: Google
• Service Provider: Lauren Kinney, Email Newsletter Ghostwriter

For more insights and solutions to your work-related challenges, reach out to Help Wanted at [e-mail].

Transcript

[Nicole Lapin]

So I just went to the grocery store and I actually flinched at the cost of eggs and I don't even really eat eggs. That's how bad it is. Everything feels more expensive and the last thing I want for any of you is to go into credit card debt. Enter Chime Credit Builder Card. This is a secured credit card with no annual fees. You can build credit with money you set aside and avoid interest or expensive debt. Start building credit with your everyday purchases and regular on time payments with no annual fees, interest or Credit. [e-mail] helpwanted do and when you go to chime.com helpwanted you'll start thinking about all the doors that will open once you start building your credit. Like lower rates on loans. Who doesn't want that? Turn your everyday purchases into steps toward your financial goals with Chime Secure Credit Card. Get started [e-mail] helpwanted that is chime.com helpwanted Chime feels like progress. The Chime Credit Builder Visa credit card is issued by the Bank Corp. NA or Stride Bank NA Spot ME eligibility requirements and overdraft limits apply. Chime Checking account required to apply out of network ATM withdrawal and OTC advance fees may apply. Timing depends on submission of your payment file. Late payment may negatively impact your credit score. Results may vary. Go to chime.com disclosures for details.

[Jason Pfeiffer]

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of.

[Nicole Lapin]

Entrepreneur Magazine, and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

[Jason Pfeiffer]

And on Thursdays, I give you one way to improve your work and build a career or company you love.

[Nicole Lapin]

And it starts now.

[Jason Pfeiffer]

Jenni, do you think you are easy to work with?

[Jenny Wood]

Ooh, yes.

[Jason Pfeiffer]

Why did you have to think about it?

[Jenny Wood]

Because I think when people first meet me. Correction. I have evidence that when people first meet me, they don't assume that. But then once they get to know me, they love working with me.

[Jason Pfeiffer]

Okay, let's zoom in on the evidence. The evidence that sometimes they do not feel like you are going to be a good person to work with. Because I bet, I bet people worry about this for themselves. What are they putting out into the world that they might not be aware of that might be turning people off that might say, hey, this person is not exactly who you want to be doing business with? That's a really scary thing to be doing unintentionally, right?

[Jenny Wood]

Oh yeah, for sure.

[Jason Pfeiffer]

And it has happened to you, correct?

[Jenny Wood]

It has. More than once.

[Jason Pfeiffer]

Okay, awesome. We're going to dig into all that first. Why don't we zoom out for a second? Jenny, you are not Nicole. You are not Nicole Lapin. Nicole Lapin is my usual co host on the show. She is on maternity leave. If you are Jenny Wood, you are my friend. You are a former executive from Google. You have a book that is fantastic, that is new, that is called Wild Courage. Go after what you want and get it. And you have been co hosting some of these episodes with me. Welcome back.

[Jenny Wood]

Thanks. So fun to be here.

[Jason Pfeiffer]

Always great to have you. Okay, so we're doing this episode because you told me this story a little while ago about exploring a working relationship with someone who decided that you were not someone that they wanted to work with. Yeah. And you agreed to tell this story on the. On the podcast.

[Jenny Wood]

Yeah.

[Jason Pfeiffer]

Which I'm very grateful for. So tell me that story.

[Jenny Wood]

Sure. So I have a newsletter that I write every week, and it became the bane of my existence. Like, it was just, you know, I'm like, working on this book. I've got my Google executive role. I've since left, but I was there for 18 years. Like, not a job, you can just kind of phone it in. So I needed help and I had gotten this name, Lauren Kinney. I have Lauren's permission to share her name because this does get to be, like, a pretty detailed story.

[Jason Pfeiffer]

And thank you, Lauren, for being willing to have your name involved in this 100%.

[Jenny Wood]

I don't know. How cool is that? And so someone said Lauren Kinney is the best email newsletter ghostwriter that exists in the world. And I was like, I like superlatives. Like, how do I find this Lauren Kinney? Funnily enough, her website, I think it's like the laurenkinney.com. so that's so perfect. It's like, where is the Lauren Kinney? Right? So I. I reach out to Lauren Kinney. We set up time, and I have to share what an incredibly tumultuous time this was for me in life. I'm working at Google. I've got this really intense job. I'm reorgang my team. I'm like, working on this book. Right. I've got so much going on. I can. I'm like, managing two calendars. I have so much going on internally at Google, externally, outside, like, lots of excitement. And I was barely, barely, barely keeping my head above water.

[Jason Pfeiffer]

Yeah.

[Jenny Wood]

So I was very excited for help, but I was just like a mad scientist. I was Kind of all over the place. So I have a chief of staff and my chief of staff texts me, hey, Jenny, are you joining this meeting with Lauren? Okay, never a good sign. That means that I'm like, I think it was like nine minutes into the 30 minute meeting and so I'm like, oh shit, I totally forgot about it. I'm literally still in my pajamas. I get onto, I hop on the call, I'm like adjusting my computer, I'm like, you know, straight. I'm literally like brushing my hair. I think I was actually brushing my hair in the meeting or like trying to straighten it out or something. And then, you know, and then I like have that anxiety the entire rest of the meeting of like I am so late and I was just really frazzled. This was also outside of my chief of staff who, you know, my like kind of person who was really just helping me with any, with everything. This was a. So basically we have the meeting, I get the information, Lauren shares her prices with me and I was like, whoa, that is higher than I expected. And now to be fair, I think.

[Jason Pfeiffer]

She is, she is the greatest email ghostwriter of all time.

[Jenny Wood]

How can you be the greatest email ghostwriter of all time and not command.

[Jason Pfeiffer]

The best and be at a discount?

[Jenny Wood]

Yeah, no, exactly. It all makes sense on paper, right? But my reptilian brain was like, how I never had put this as a line item in my budget. It hadn't occurred to me that I would ever have this as part of my overhead. So I was freaked out. And, and so, you know, we had that call, I'm thinking about it, we trade a couple of text or emails back and forth and I'm like really negotiating hard. I'm pushing her on the price. I'm saying, could we do either, you know, more newsletters or a lower price or could we include some other like social media stuff? And I, you know, I talk about, with my work trait traps, like, you know, I talk about these nine traits that are, that are good. Selfish, shameless, you know, manipulative. And we reclaim these traits. But then you can also get caught in a trait trap. And I think I was getting caught in a trait trap where I was pushing a little bit too hard. We end up getting on a call to talk about the pricing stuff and something nutty happens where I have to talk to my Google administrative business partner that day. And so we're about to hop on the call, I text her, I'm like, oh, can we push this call by a half hour? I have to talk to my Admin. Right. And it was a really critical reason that I had to talk to her.

[Jason Pfeiffer]

Right, but now you were late to the first call, and now you've pushed the second.

[Jenny Wood]

Push the second call by half hour. And because I am not yet an entrepreneur, I'm still working at Google. I'm like, you know, it's like, I don't even know how to act as an entrepreneur or as, like, a business person. To me, this is all just kind of like a hobby. I'm like, not really even treating it like a business. This was going to be like my first real big business expense. And so it didn't really occur to me that that was problematic. I was like, sure, it's like her hobby, too. Like, no, not her hobby, her profession. She has a schedule. Anyway, so we get on the call and then we discuss it. We discuss it more. And whatever happens with the price, we. She then calls me up. I'm going to sleep on it. She calls me up the next day. She's like, jenny, I know you're thinking about whether we want to do the deal, but I want you to know that I cannot do this deal with you. And I'm like, whoa, whoa, whoa, whoa, whoa, whoa, whoa, whoa. And. And I'm like, oh, my gosh, Lauren, did I push you too hard on the price? And she's like, no, I just don't think that you would value me. I'm like, so you think I'm not valuing you at the right price? And she's like, it's. It's really not that. And she kept saying, I just don't think you would value me.

[Jason Pfeiffer]

Yeah. What she mean by that?

[Jenny Wood]

Okay, can you help me understand what that means? And she took a deep breath and she basically said, like, I'm going to share something that I wouldn't normally share, but I feel like you may be. Actually are interested in hearing. And she's like, jenny, you were nine minutes late to our first meeting. You were totally disheveled, brushing your hair. You were. Then you then pushed our second meeting. It has nothing to do with price. My fees are what they are. Right? It's not hard for me to get this fee. I've got a lot of great clients, but I just don't think that we're the right fit for each other because I know I'm good at what I do. And just the way you've shown up so far, I just don't think you would value me. And that's where I was first of all, mortified. Jason, I Was like, I felt like I had the wind knocked out of me, but in the best way, because I was actually sitting in the same spot. And I remember staring at the wall right over here to my left, about 15ft away from me or maybe 10ft away from me. And. And I remember thinking, oh, my gosh. Oh, my gosh. How do I recover? And that's so not who I am. When you're working with me, Like, I am incredibly appreciative. I'm incredibly responsive. I am occasionally late to a meeting, but so you. I. I can't. I can't. I. I can't. I can't claim that one. But, man, I value my team. Like, you cannot imagine. That was one of my bonafide superpowers at Google. And so to hear her say that, I really went into solution mode, and I was like, how do I convince her that that's actually not who I am and that I really messed up, but that I understand where she was coming from and how grateful I was for that feedback? Because I swear to you, of any feedback I've heard in my professional life over the last 25 years, that has been the absolute most impactful. Lauren and I have been working together now for almost a year, and she's unbelievable. We have the best possible working relationship.

[Jason Pfeiffer]

Before you go on, I need to. I need to have a step back and acknowledge that although this was difficult for you to hear, it had to be so hard for her to say, I don't know that I have ever said something like that to somebody. Like, even when they were incredibly annoying, I generally just got the hell out of there. Like, I think if I was her, I probably would have just been like, hey, actually too busy now. And like, I. Like, that was a lot for her to tell you.

[Jenny Wood]

New phone. Who this?

[Jason Pfeiffer]

Yeah. Right? Yeah. I cannot believe that she. She did that. Like, that she told you that that could not have been easy.

[Jenny Wood]

And I hate that I'm adding this because I feel like we should all be age agnostic. But I have to add that something else that impressed me so much is Lauren is considerably younger than I am. Lauren has considerably less professional experience than I have. She's just fairly young in her career. So to have the presence of mind, a. To do that, to have the confidence to share it, to have the eloquence with which she shared it, I. It, like, it blew my mind. And. Yeah, it just blew my mind.

[Jason Pfeiffer]

Okay, we're gonna get to eventually how the two of you have. Have actually been working together now. Like, this. This is a. There's a happy ending to this. But what did you do in that moment? And I mean, did you even want to recover? There's part of me. There's part of me that in the same way in which I. If I was Lauren, I would want to have just gotten out of that situation. That if I was you, I would have wanted to get out of that situation too. Because, you know, it's almost like when you're on a date and the date is going really bad and you're just like, okay, we just need to pull the ripcord here. Like, I just need to get out of this situation as fast as possible. There's no reason to recover this. There's no reason to put this back together. Like, you. You're. You're shaking your head as I'm saying that, like, you wanted to make this work for some reason.

[Jenny Wood]

Why it was so. Okay, so you mentioned my book at the top of the hour. The book for two years was called the Chase. Right. I met my husband by. By chasing a stranger off the New York City subway. Everything. Like, I wanted the best part in the musical in high school. Like, I wanted the guy who was the, you know, kind of like, sleazy guy who would never pay attention to me. Like, the harder he was to get, the more I wanted to chase him. So the second she told me no, I was like, I'm in.

[Jason Pfeiffer]

I'm in.

[Jenny Wood]

Like. Like, you can. You're so good that you can tell me no. Like, you have the best clients that you don't have to work with this a hole, Jenny. Like, I am in. I was chasing. I was like, how do I recover? How do I win? How do I win her back?

[Jason Pfeiffer]

I wonder if that is a normal or not normal response. I don't know. You.

[Jenny Wood]

I think it's not normal.

[Jason Pfeiffer]

Yeah, I think you do a lot of things that are not normal. So I'm going to go with probably not normal. But this is interesting. Let's. I. We're going to get back into the story with Lauren. But first, let's. Let's take a pause here and just reflect upon the theme that we were talking about, which is like, what if it turns out that you are giving signals that you are bad to work with? Like, this is a moment that you're not that used to. Although you said this is not the only example. Like this.

[Jenny Wood]

I have another great example.

[Jason Pfeiffer]

Yeah, so. So like, what are. What is someone to make of? Or what do you suggest, like, when. When a moment arises where you realize you are putting out bad work vibes. This is what's happening here. Bad work vibes. What do you do with that?

[Jenny Wood]

Ask for feedback. It's like this other example I'll share. It's a much shorter example, but I interviewed someone for my team, a manager for my team at Google, and I thought she was fantastic. I offered her the role, she got the role. She's ended up being like, we're still super close touch. And she was such a rock star, performer and leader. But I, after the interview, I said, I gave her the job. And then I said, I'm curious, do you have any feedback on me as an interviewer? And she's like, I do. I almost didn't want to take the job because you were really intimidating.

[Jason Pfeiffer]

Wow. Yeah. Wait, remind me, remind me, remind us when you asked for feedback. Like, when specifically did that happen?

[Jenny Wood]

It's funny because I also remember the conference room I was sitting in when that happened. So very soon after I offered her the job. I don't know. Like that same conversation, like, so, like.

[Jason Pfeiffer]

As soon as the question is answered, right? Like, as soon as she knows she's got the job, then you're. Then you're immediately, Jenny, I have to say, this sounds crazy. This sounds like the weirdest, like, gauntlet to put somebody through. If I was just offered a job and then you were like, hi, I'm, I'm now your new boss. Give me some feedback. I'd be like, no fucking way am I giving you any feedback. The feedback is, you're fantastic and I'm excited to work with you. Like, that's. It's crazy.

[Jenny Wood]

Yeah, it was weird. Had you ever done that before?

[Jason Pfeiffer]

Is it just like that? That was just a spur of the moment thing?

[Jenny Wood]

I don't know, I. Maybe I picked up on some vibe in the interview or like, we have pretty different personalities. She's much more kind of like even keel. And I'm. I am pretty intense and full on. And so maybe I was. I'm always looking to improve. I'm always looking to improve as a leader. I think an interview is a time. And like, the Lauren thing was basically an interview for both of us. Right? I think an interview is a time that is. It's one of those moments that matters. It's one of those critical moments, both for the interviewer and the interviewer and the interviewee, where you're straight up evaluating each other. And, you know, it's. It's like you say, oh, it's a tight job market or whatever, but like as a leader, as an executive at Google, man, I wanted to steal the top talent. I didn't want to offer someone a role and have them not take it because they got an intense vibe for me in the interview. So I want to know how I can show up better so that in those moments that matter, people want to work with me and I can get the best possible talent on my team. It was not something I did all the time. I remember doing it in that particular moment. And maybe it was a couple of weeks after she had accepted the role. We also already knew each other a little bit. It was an internal person. So, you know, maybe there was some level of trust or psychological safety there that was, you know, a baseline.

[Jason Pfeiffer]

Yeah. When would you suggest other people do something like this? Like, if you're going to ask for feedback. When do you ask for people for feedback? You know, like, I guess I could see if, that, if, if you are going to work with someone and then like, it doesn't work out for some reason, you feel like there's some lesson to be learned there. I guess you could ask for feedback. At this point, they have no obligation to give it to you. But you're not working together. Maybe they will, maybe they won't. If you are working together, I guess, like, do you wait a certain amount of time? Do you wait until somebody leaves? Like that. That would be the most comfortable if, if I was leaving a job, if I was leaving a job and on the way out the door, my old boss, who now has absolutely no sway over me, asked for feedback. Nobody in that, Nobody has ever done this in my life. I'm not sure anyone has ever done this in the history of working. But I, I would have feedback. I would, I would have feedback, but I can't imagine. I've, I've never been asked.

[Jenny Wood]

I mean, at Google, we had a, like you evaluate your manager, you take an entire survey about, it's anonymous, about your manager's performance and how they show up. Are they a micromanager? Are they, you know, do they, they, do they trust you? Do they respect you as a person? Do they, do you feel like your ideas are valued by them? Like, I don't. These aren't the exact questions, but like there maybe was just also a system and an acceptance and an encouragement of feedback that I was so used to for, you know, almost two decades there that it felt like a totally normal thing to do. So maybe it was even that ingrained system that made me think to ask Lauren that day. Because, because Google is Such a trusting culture of high psych safety and feedback.

[Jason Pfeiffer]

Right? Okay, so, yeah, let's see how, let's see how you saved this one with Lauren.

[Jenny Wood]

Okay.

[Jason Pfeiffer]

As you've teed this back. Okay, so, so she tells you, Jenny, on, on our first call, you're a disheveled mess and you show up late. Our second call, you bump the time back. You're negotiating like crazy here. But that's not even the point. The point is that you just don't seem to value my time. And, and, and now because you, Jenny, are, are a. Or a crazy person, you now want to work with her even more because she says this. You're, you're remembering something as I'm saying this. What are you remembering?

[Jenny Wood]

I remembered she also said, I don't think I have the flexibility that you need. Again, I thought it was price flexibility, but it was like, apparently time flexibility. Or I also just wasn't buttoned up. Like, my goodness, kudos to her. Unbelievable how much she stuck to her guns. Because I was like, could you do. Because like, again, this, I, I had, you know, I was like, oh, I hadn't budgeted for this. Totally normal prices, by the way. She has totally normal pricing. But in my mind I was like, could. I was like, kind of like wheeling and dealing a little bit. Like, could we add social? Could we do this? Could we throw in a, throw in the kitchen?

[Jason Pfeiffer]

What else can I get in here?

[Jenny Wood]

Yeah, so maybe that's what she was thinking of as like, flexibility. And maybe that's what she. Or that's what I thought. And she kept saying like. And she was like, jenny, it is one newsletter per week. It is 10 LinkedIn posts. Like, that is what it is, what it is.

[Jason Pfeiffer]

And she.

[Jenny Wood]

And another half brutal, like, in the best possible way.

[Jason Pfeiffer]

Another compliment for Lauren here, which is if you're in the kind of business where you're getting clients, like, you have to. You're in client work. The absolute worst thing that you can have is like a black hole of a client. Like, as a client who just sucks all of your time and all of your energy.

[Jenny Wood]

Yeah.

[Jason Pfeiffer]

And I'm sure that, like, if you have one of those, then you become very alert forevermore to try to avoid them. I mean, I have a friend right now who just asked me for advice because she has a client who is consistently late on paying and, like, does not get back to her on what she needs.

[Jenny Wood]

Oh my gosh.

[Jason Pfeiffer]

And it's so. It's like, it's causing, it's causing all sorts of problems. And, like, the client will, you know, will send something like, super last minute on a Friday afternoon. And now my friend has to find some employee who can, like, work on it over the weekend. And they know that they're probably not even gonna get fully paid for it. And she's trying to figure out just, like, how to get out of this as fast as possible. And that's what she was asking. But part of this is definitely also, like, once she gets out of this terrible client situation, which she needs to. She needs to know how to recognize that kind of client in the future and never work with them. And so maybe that's also what happened with Lauren.

[Jenny Wood]

Oh, my gosh. I am. This is. You're reminding me of something else that happened here.

[Jason Pfeiffer]

Stick around. Help Wanted will be right back. Welcome back to Help Wanted. Let's get to it.

[Jenny Wood]

So basically what happened was a false proxy. Right. Seth Godin talks about false proxies all the time. And, like, sometimes something that you think might be a leading indicator of how. What something. How someone might perform. Like a resume. Right. You. A resume he calls a false proxy. You don't really know how someone's going to perform if they've got great pedigree and credentials. So he says, always do, like, a trial project with them. So. Okay, here's what I'm remembering now. Happened in that moment. So, you know, I, like, live and die by these nine traits. Weird, selfish, shameless, nosy, obsessed, manipulative, brutal, reckless, and bossy. So I got shameless in that moment because I. What went through my head was like, oh, my gosh, Lauren, that's not me. That is not me. I have all this feedback from the large teams I've led at Google that I'm, like, their favorite boss or I am. Or I got those really high scores on those manager feedback surveys that I was just talking about.

[Jason Pfeiffer]

Yeah.

[Jenny Wood]

And people have written things to me like, you're the best manager I've had in 20 years. Like, I knew in my core that that wasn't me. And so I had this wave of, like, shamelessness or confidence that I was like, oh, my gosh, could you please give me a second chance? I begged her. I was like, could you give me a second chance? Those were my words. Could you give me the opportunity to prove that I would value you? Because I really do. I really will. And I'm just. In this. I don't do well with indecision. And I was actually at that point talking to, like, a bunch of agencies, and I was. My head was Spinning in the process of leaving Google, becoming an entrepreneur. Had no idea what the costs would look like, had no idea what kind of a team I'd have to build. Marketing, pr, chief of staff, newsletter, ghostwriter. Like, I just. I was in such analysis paralysis that I think I was hiding my. My anxiety in, like, just continuing to ask her questions. Or I was, like, delaying the decision because I couldn't pull the trigger because I was so damn scared that I was leaving my Google exec role to start this business, and I couldn't. I couldn't do it. And so now it's like, I talked to someone, they gave me their price. We don't even get on the. Or, like, whatever. I just, like, hire them. It's like, no problem. Here's my credit car. But I wasn't there yet. And here's the funny thing about the black hole. And this is why I just got so excited. Because, man, do I pay her immediately when she sends the invoice. Like, I have overcorrected. Like, I. I mean, she didn't intend to put me in this state. And, like, yes, things have gotten so incredibly busy with the book launch now. And, like, it's all exciting and blah, blah, blah, blah. We've got 440 people working on the team. But believe you me, if I have. If I have, you know, between Penguin, Random House and macmillan and, like, you know, pr, like, not all people who report to me or who I pay, but I got to say, If I have 37 emails in my inbox from people who need something and Lauren's is in there, I go to her first. She might not say that these days because I still feel like I'm delayed on everything. And sometimes, you know, we do. But, like, I, to this day overcompensate or feel insecure that she wouldn't think I'm doing right by her as a.

[Jason Pfeiffer]

Partner, which is a real endorsement for what Lauren did. I mean, she put you on notice, and it's like, you're still on notice. Like, that's kind of what's happening. Right?

[Jenny Wood]

Wait, I, like, want to pull up a text from her because she'll say things now. Like, but, like, I. I told someone that you're my absolute most beloved client, and I don't think she's blowing smoke. Like, I think we genuinely have an incredible, incredibly, incredibly close relationship.

[Jason Pfeiffer]

That's great.

[Jenny Wood]

She feels that way about me.

[Jason Pfeiffer]

Yeah. Oh, she shouldn't be telling you that because then you're going to get lazy. Like, she's got. She's got to, she's got to keep you on your toes. She's got to make sure that that email is still the first to respond. All right, well, let's, let's, let's just, let's just flip it for one second before we end this conversation, which is, you know, Jenny, you give people advice to do the kind of thing that Lauren did, right? Like to stand up for yourself and go get what you want. So, like, you experienced this from the receiving end, but now go be Lauren in that moment where you've got a new client or a potential new client and they seem like, they seem like a train wreck. Let's just be honest. They're like, they're not, not someone who you're interested in working with. What, I mean, what were, what, what are they supposed to do? What? I, I mean, you know, like, it's interesting because we, we've told the story, we've seen what Lauren did, but like, I don't know, even absent of this story about Lauren, like, would you have suggested that people do what Lauren did? And, and how would you suggest that they get there?

[Jenny Wood]

I mean, this is having a little bit of healthy recklessness, right? Like, this is one of my nine traits that I'm so passionate about. Like, you err on the side of action, you take calculated risks. She took a calculated risk that day. And I guess maybe you win some, you lose some. In this case, she won, I won. We've got this amazing partnership together. But, you know, it's like people, people won't have the three minute awkward conversation with their boss and then they'll suffer for three more years of resentment or disappointment or unspoken heart, you know, stress and anxiety about what their boss might think about them or what they think about their boss. I'm not saying that in every situation, go have the conversation and you're always going to win. It's. You're kind of rolling the dice, right?

[Jason Pfeiffer]

Yeah.

[Jenny Wood]

And maybe, maybe, maybe read the room, right? Like, maybe she felt like I was the kind of person who could handle it. And so maybe like decide Kate, is this person, someone who can handle it. But, and I was really, I guess, as the leader, quote, unquote. Right. I guess I'm thinking more of like a Google context. I would be more of like the actual leader in this case. It feels like a partnership with Lauren, but maybe as a leader, send off a vibe that you're open to the feedback. Like, that's the best thing a leader can do, is be open to feedback so that they can learn and grow. So I know I've twisted this a little bit more to be about what the leader can do, the recipient of the feedback, and not the person who, like, has to just, like, put on their big girl pants and say it. I guess it's just, be bold, take the risk, say the thing that's on your mind. Because, you know, there's so many ways we can rationalize not saying it right or like, rationalize not doing the thing. But rationalization is a weapon so powerful it should require a background check. Like, it needs. It's just, you got to overcome that, and you've got to overcome the rationalization. You've just got to go for it and say the thing on your mind.

[Jason Pfeiffer]

Yeah, well, when you said calculated risk, to me, the answer here snapped into place, which is to say Lauren was making a calculated risk. But the, the thing about a calculated risk is that there's a calculation, and the calculation in that moment is nothing to lose here. Lauren has already decided she's not going to work with you, and, and so she's not going to lose a client by saying this. She doesn't want this client, frankly, at this point, and definitely not. And so, and so the, the like, it was actually not much of a risk at all when you think about it. Right. I mean, that's the interesting thing about your answer is, is we think about risk as this kind of general thing. If, you know, if you're taking a risk, then something is at risk. But if you step back for a second, you're just like, what is the calculation of this risk? Then sometimes the answer is that there's actually nothing left to lose. And if there's nothing left to lose, whether you might as well just gotta do whatever, you might as well try something. In this case, when you make the calculation of whether or not there is something to lose and you realize that there is nothing more to lose, then actually, interestingly, the only other option is a gain. Because in this case, whether Lauren said to you, I'm just too busy now and I can't work with you, or she said what she told you, which was like some very frank feedback. Either way, worst case scenario is the thing that actually at this point, she already wants, which is just like, you guys aren't going to work together. But very interestingly, whether or not she thought about it like this, that there was something to gain from this, I guess if I were her, and I would say, and I was able to do the calculation in my head fast enough, the thing to gain at that Point, frankly was probably just. It'll be interesting to see what happens when I say this to a client, like, or to a person I'm not going to work with. Like, it's just, I'm going to say this and I'm going to see what happens and that will informed the next time that I'm in a situation like that. And I do that sometimes I will just take an action solely for the purpose of seeing what on earth happens, because I will know then what happens next time when maybe there feels like there's more on the line.

[Jenny Wood]

And so, or even just like you're building a muscle. You're building a muscle of taking a risk. You're building a muscle of being confident. You're building a muscle of speaking your mind. You're building a muscle of standing up for yourself. And even just that muscle building in and of itself is a gain. It's a personal gain.

[Jason Pfeiffer]

Yes, yes it is. And I mean, I've certainly learned that just about being frank with people. I've discovered that in my own professional life, the more frank I am, the more, the more bold my question is to somebody or the more if I'm getting to know somebody on a more personal level, it's just like the more personal the question is, the deeper you go, the more the relationship flourishes. And people are just afraid to do that. And I have over time just gotten really good asking personal questions because I just started doing it and so yeah, it is. It's a muscle.

[Jenny Wood]

Yeah. And it's all about pushing past fear. Right. Like you just said that. Like it's. I think what you're insinuating is it feels scary initially to ask those questions, those more personal questions. And it feels safer to ask the like gimmes or the softballs.

[Jason Pfeiffer]

Totally.

[Jenny Wood]

But like the thing that feels the scariest to you actually helps provide the more flourishing conversation or the deeper relationship. And so when you push past that fear, you find joy and success on the other side. And that is true. Not just in an interview, it is true. Not just in the negotiation, it's true in all areas of life. Push past that fear.

[Jason Pfeiffer]

Okay, so before we end this, I just, I gotta hear, so what was the story where you were at Google and you had to take a risk and there was like a lot more to lose?

[Jenny Wood]

Yeah, it was kind of a similar situation where in this case I was working with someone really high up at Google and I was new to his team and we'd met in person for the first time and we're in A women's. Like a DEI women's roundtable. And it's this guy and a table of 12 women, and it's a 60 minute conversation. And for some reason, and like, the guy did not do a good job. And for some reason, I found the chutzpah, okay? The gall, the nerve.

[Jason Pfeiffer]

They give him a.

[Jenny Wood]

As a total newbie on this team to. As we're walking out of the room, Jason, to be like, hey, can I give you some feedback on that? Wow, this is the first time we've ever met in person, and this guy's real senior at Google. Okay. And he's like, sure. And I was like, is he like.

[Jason Pfeiffer]

Sure, or is he like, sure?

[Jenny Wood]

I don't remember. I. I don't remember.

[Jason Pfeiffer]

I'm gonna go with the latter. I think it's option number two.

[Jenny Wood]

Okay. So I said, listen, this was billed as a women's roundtable. You talked like 47 minutes out of this 55 minute meeting. That is not a roundtable. And it was a DEI conversation. It was a women's roundtable for us to. For you to meet with the women on the team, the women leaders on the team, and for us to have time with you, for us to hear, for. For you to hear from us. And I walked away from that conversation like, okay, I really effed it up. Like, that did not. That was not necessary. I should not.

[Jason Pfeiffer]

How did he respond to it?

[Jenny Wood]

He actually responded well, but I didn't know how he really felt. And he was like, hey, wow, I can't believe that you were able to share that with me. You know, this is our first time meeting in person, but I actually do really do respect that you gave me that feedback. Jason, I kid you not. He would finish a town hall with the entire org, right? Lots and lots and lots of people. He would ping me and say, jenny, I know you'll be honest with me. How did that go? There was a time where I was talking to him about my career goals. He said, you know what? Just hop on the plane to California. Let's do a half day deep dive mentorship session, just you and me. That is not a thing. That is. That is normal, Jason. Like, that was not a thing that was offered on the regular. By being bold that day, by being confident, by taking a calculated risk where there was a ton to lose, this guy could have written me off right away. And it could have been a total CLM career limiting move for me for like the next 10 years. It was just the opposite. And so even when I had a lot to lose when I had the confidence, when I pushed past that fear and realized the success on the other side, it created so much success for my career because this guy really did help shape my career.

[Jason Pfeiffer]

That is a great story. All right, well, Jenny, we have come to the end, not just of this episode, but of your time co hosting Help wanted with me as you step in for Nicole, who's on maternity leave. It's been such a pleasure having you.

[Jenny Wood]

It's been really fun. Like, really fun with a capital R. Oh, thanks.

[Jason Pfeiffer]

Okay. Your book is called Wild Courage. Go after what you want and get it. And if somebody wanted to go after what they want and it's this book and get it, then how do they.

[Jenny Wood]

Do that anywhere books are sold? Although I never know what I'm supposed to say to that question, because it's. It's available everywhere. What do I say to that?

[Jason Pfeiffer]

Because people ask this at the end of podcast interviews when you're promoting a book, and it's like, what are you supposed to say? So because I went through a book launch a couple years ago, I will tell you first, have a line. Have a funny line. My line was, you can get it in any format except for Stone Tablet. So that's hardcover, audiobook, or, like, ebook. And the reason why I said that was because I had lunch with my editor a little after the book came out, and he said, here's a hot tip. If you don't tell people that it's available in audiobook, they won't assume that it's available in audiobook, which is so weird because every book is an audiobook now. But it was true because I was getting emails from people. I have also emails from people. You're getting it, too, who are like, is your book available to audiobook? Which is so weird because it took so much work to track down my email address and then email me, whereas it would have taken less time to just go to Audible or Spotify and see if the book was there. I don't know why they do that, but they did it to me many times. They did to you, too. And. And I. I found that once I started. So first I was just like, it's also available in audiobook. And then that felt weird. And that's how I came up with this line. It's available in any format except for Stone Tablet. And then I listed it off. Once I started doing that, audiobook sales went up. Like, it was so weird.

[Jenny Wood]

Way.

[Jason Pfeiffer]

Yes. So, like, I. I did it on Gary. I. Like, I knew to do that by the time I did Gary V's podcast and, like, that sold a bunch of audiobooks. So anyway, so the answer is that when somebody asks you where to get the book, just, like, be like, you know, you could be like, wherever books are sold, or you could find something kind of like a little cheeky and memorable to say. And make sure you say audiobook book.

[Jenny Wood]

I like it. By the way, it's really funny you say that, because yesterday I was with a friend who read an advanced copy, and I was like, so honest answer. Scale of 1 to 10, how likely are you to recommend it to a friend? And she's like, nine. And I was like, well, what would get it to a 10? And she's like. And she goes, now. And mind you, the the advanced copy is only available as a paper copy. And so I was like, what would get it to 10? She's like, if it were available on audiobook.

[Jason Pfeiffer]

Amazing.

[Jenny Wood]

And I was like, dude, I haven't recorded it yet. And by the way, I meant, like, did you like the content of the book?

[Jason Pfeiffer]

Amazing. All right, everybody. All you need to know. Jenny Wood. It's available in audiobook. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[Nicole Lapin]

Pfeiffer, and me, Nicole Lapin. Our executive producer is Morgan Lavoy. Do you want some help? Email our helpline@help wantedoneynewsnetwork.com for the chance to have some of your questions answered on the show. And follow us on Instagram at Money News and Tik Tokoney News Network for exclusive content and to see our beautiful faces. Maybe a little dance?

[Jason Pfeiffer]

Oh, I didn't sign up for that.

[Nicole Lapin]

All right, well, talk to you soon.

[Jenny Wood]

It.