744: Where Being Selfish is Better, with Jenny Wood

Dave Stachowiak [00:00:00]:
Leadership is first and foremost about serving others and it’s also ensuring that we take care of ourselves along the way. Sometimes leaders over index on helping their organizations and teams to their own detriment in this episode where being a little more selfish might actually be better for everyone. This is Coaching for Leaders, episode 744. Production Credit: Produced by Innovate Learning, Maximizing Human potential.

Dave Stachowiak [00:00:35]:
Greetings to you from Orange County, California. This is Coaching for Leaders and I’m your host, Dave Stachowiak. Leaders aren’t born, they’re made. And this weekly show helps you discover leadership wisdom through insightful conversations. The word selfishness we think about it and most of us bristle a bit. We think about it as a word that isn’t really the kind of way we want to show up as a leader. And yet oftentimes we don’t think about the power of that word, the importance of it, and how we can redefine it to make it work better for us, but also for the people around us. And today I’m so pleased to have a guest with us that’s going to help us to redefine this word a bit, help it to make it work for us and for our organizations, and give us a little bit of a kick on maybe how we could do just a bit better in driving our own careers.

Dave Stachowiak [00:01:31]:
I’m so pleased to welcome Jenny Wood. She had an 18 year career at Google, from entry level to executive, most recently leading a large operations team that helped drive billions of revenue per year. In 2021, she started a passion project within Google called Own youn Career, which grew to one of the largest career development programs in Google’s history. Her work has since been featured in Harvard Business Review, Entrepreneur, and Forbes. And she’s now the author of Wild Courage: Go After What You Want and Get It. Jenny, perfect title. I’m so excited for this conversation. Welcome to the show.

Jenny Wood [00:02:08]:
Thanks so much for having me, Dave. It’s so much fun to be here.

Dave Stachowiak [00:02:11]:
This word selfish. We hear it, we think about it as leaders. I think we bristle about it. And you highlight the definition in the book “concerned excessively or exclusively with oneself. You invite us to redefine it though, as the courage to stand up for what you want.” And I was thinking about that and thinking that’s often really hard for a lot of well intentioned leaders who have been trained and taught to think about not just themselves but their teams and their organizations. And you run into that too, don’t you?

Jenny Wood [00:02:46]:
Yeah, definitely. I mean, I grew up through the ranks at Google. So when I became a leader and then a leader of leaders at Google, it was very hard for me to take a step back and think, well, what do I need right now and how can I be selfish? And you already mentioned the reclaiming of the word, the courage to stand up for what you want, to be your own champion. Because if you give everyone a leg up at your own expense, you’ll end up getting trampled. So start showing up for yourself.

Dave Stachowiak [00:03:13]:
There is a paragraph in the book that I love and I’m going to read it because I think it really captures the message about this in your work. You write, “being selfish doesn’t mean seizing everything you can, like a treasure hoarding dragon. It means championing your agenda at least as strongly as you champion the needs of others. Fighting for yourself just as enthusiastically as you fight for your friends and colleagues. In movies, the protagonist’s selflessness and modesty inspire a helpful mentor to raise them up. In real life, people help those who are busiest helping themselves. Allies flock to your side only once you’re going somewhere. Show them your success is inevitable. They’ll help you get there faster. We all want to join a winning team.”

Dave Stachowiak [00:04:00]:
I think about that paragraph and especially that last line. It’s kind of the thing that we all inherently know, but we don’t often say out loud, do we?

Jenny Wood [00:04:11]:
Well, so much of my work is common sense but rarely common practice. So I’m right there with you, that we know it intellectually, but we don’t always take action on it. And I’m so glad that you read that paragraph because I love that section of the book and I meant to go back and find where it was in the book. So now you’ll have to actually tell me the page number so I can explode it myself to people. But there’s something so powerful about the selfishness of advocating for yourself or talking about your wins or your talents. You know, just the other day, now you know the book’s been successful. It hit the New York Times bestseller list, which was a huge goal of mine. I wouldn’t recommend anybody attempting it because it’s a bunch of time, energy and money that it takes to promote your book enough to get it there.

Jenny Wood [00:04:49]:
But now that it did, I get a lot of people coming to me asking for advice. And it’s interesting, you know, I also want to join a winning team. So if someone is selfish and another one of the nine traits of wild courage is shameless to share, how big is your following on social media? Or what have you done to start a newsletter or what are your accolades at work? Right. If someone writes me an email and they have three bullets and they’re seeking my help, just, you know, free guidance on how to start writing a book. If someone says, I have a 2000 person Instagram following, I have a newsletter of 1500 people and these are three ideas I have for the book and this is what I want to do with the book in the future, that is, you know, it sounds like, oh, they’re bragging, but really it helps me understand, is this a team I want to join? Like, is it worth me giving you 20 minutes of free advice? But I want to join a winning team. And I have a lot of people who reach out to me, many per week, who just say, hey, I’m interested in writing a book. Could you mentor me for 30 minutes? But they aren’t selfish enough to tell me about their wins. They aren’t shameless enough to tout their talent, their experience, their numbers.

Jenny Wood [00:05:56]:
But that’s actually what I look for when I decide, do I want to help this person out? And that was the same thing at Google as well, where the more I could see evidence of someone’s success, the more I wanted to invest in them as a senior leader. And I think the disconnect here is that if the email from the person seeking my help to write a book or my help to help them get promoted at Google or whatever it is, if they’re putting the work on the other party to go out and see whether this person is worth spending time with, then you’re already doing yourself a disservice. If you are selfish and shameless and obsessed enough to get those numbers out in front of them, you’re much more likely to get a yes. So since you, you have to assume that the other party is going to do the research anyway, make it easy, make it simple, make it fast, do it for them.

Dave Stachowiak [00:06:42]:
Guilt, of course, comes up for a lot of us when we start thinking about advocating for ourselves more. And you say “guilt is natural, but caving to it every time is self defeating.” Tell me more about that.

Jenny Wood [00:06:57]:
Well, we’re all going to feel that guilt. We’re all going to feel like, why me? Or why me and not the other person? If I get promoted, then Anna can’t get promoted, right? Or if I raise my hand to lead this client project and to be the one who presents in the client meeting, which oftentimes gives you the lion’s share of the credit, then I’m taking it away from somebody else. But recognizing that guilt and pushing past it. And I think guilt goes hand in hand with fear. And so much of wild courage is pushing past the fear, recognizing the guilt, recognizing the fear and taking action anyway is where you’re going to find yourself being the most successful because we’re all going to experience it. I mean, recognizing it and pushing past it is where you’re going to end up being the most successful as a leader. Because we will all feel it.

Dave Stachowiak [00:07:40]:
Yeah, indeed. And you have some really wonderful and I think very simple invitations to start getting a little bit better at this. And one of them is saying yes to the big and no to the small. Tell me first about the distinction between how you think about what’s big and what’s small.

Jenny Wood [00:07:58]:
Yeah, well, big is the project that matters for your organization, the number one priority for your VP. So maybe it’s the H2 marketing plan or increasing customer satisfaction CSAT by 12% quarter over quarter. Or it is developing the AI strategy for your go to market team. I mean those are big things. Even if no matter what industry you work in, even just hearing me talk about those three examples, they probably sound pretty meaty and pretty material and the kind of thing that you could hang your hat on for that quarter’s annual performance review. Right. Or quarterly performance review. Now what’s small? Being the 18th person to reply all on the Happy birthday Jimmy email.

Jenny Wood [00:08:44]:
Going to every single meeting where you neither add value nor derive value. Always saying yes to being the person who plans the company off site. And some of this actually constitutes what? Some of the small constitutes what I call nap work. Not actually promotable work. And you don’t want to nap at the office, Right? But you know this stuff. On any given day, you wake up in the morning, you have your cup of coffee, you open your inbox, you are just pummeled with items that you could cross off your to do list. So when you write them down and you really articulate what’s big and what’s small, you’re able to focus on what’s going to move the business. Because what moves the business is what moves your career.

Jenny Wood [00:09:30]:
So I actually got an email this morning that hit this on the head. Someone wrote into me after they got my newsletter this morning and said one piece that really stuck with me. Is your point about how some people end up doing non promotable work. That’s what we’re talking about, right? This nap work, not actually promotable. I’m a director of the project management office at a global consulting firm, yet somehow I still Find myself organizing our in person meetings, planning team dinners, and even running logistics for our annual Workforce Software or our annual A Workforce Software user conference. Despite the fact that I’m not the director of that service line, a colleague of mine holds that role and truthfully, he should be handling that next year. This insight of avoiding the nap work alone gave me the clarity to reframe what I say yes to moving forward. And I loved that because it’s like, yeah, this stuff really does happen.

Jenny Wood [00:10:20]:
We are sitting there every day with decisions, the to do list, the inbox, the projects, and we are often not selfish enough to sit on our hands when the boss asks us, well, who wants to run the logistics for this user conference, right? Or we think, oh, I did it last year. The expectation is I should do it again. No, you did it last year. Sit on your hands and let somebody else raise their hand and do it. This year you had a blast. Now give somebody else the opportunity while you focus on more of the strategic, high leverage work that moves the business.

Dave Stachowiak [00:10:48]:
And to the point you make throughout your work that that may on its face seem selfish of like, okay, I’m not, this isn’t working for me. But in reality you’re doing a better service for the organization too. If you have your time and energy focused on the things that’s actually what your role is supposed to be doing and the promotable activities as you describe them as, as you were saying that I was thinking back in my own career, there was a time that I’ve always been a bit of a tech geek. And so people would, in every role I’ve had come to me for like, oh, hey, my computer’s doing this thing, that kind of thing. And I had sort of developed a reputation amongst an office and a role pass that, oh, I was going to be the go to helper for stuff. And no one ever said that out loud, but that’s just what had happened. And I found myself all of a sudden one day like I’d spend, I don’t know, two or three hours a week focusing on helping people with support. And not only was it starting to feel resentful for me, but I realized it.

Dave Stachowiak [00:11:46]:
One, I wasn’t getting paid for it. But secondly, it was taking time away from the things I actually was getting paid for and being measured for as far as my success. And it took me a while to realize because it sort of snuck up on me over time. Like it was, you know, 10 minutes here, 20 minutes there and then all of a sudden it was this hours A week. And I’m thinking about that and thinking about the person who emailed you and wondering like, how do we do a better job at recognizing it when we’re in that place where we’re doing a bunch of things that just are not the work that we should be doing?

Jenny Wood [00:12:20]:
Right. Well, part of it is the recognition. Right. And it does get back to the guilt. This happened to me when I was in a meeting at Google and someone said, jenny, are you going to continue to, to lead the well being pillar this year? And kind of I felt like all these eyes darting, darting at me in the room expecting to just be like, yeah, of course. Oh my gosh, it brings me so much joy. I’m so happy. But like being ultra responsive to email where nobody in the history of the Internet ever got promoted for responding to email.

Jenny Wood [00:12:45]:
Right? And you probably never got promoted by fixing someone’s spinning beach ball on their Mac if they couldn’t get their applications to load. You know, I knew I wasn’t going to get promoted for leading the well being pillar. So I sat on my hands and said I actually don’t think I have the bandwidth for it this year. Which is really hard to say publicly in front of a room of 12 people. But that’s what allows you to work on that higher leverage stuff. And by the way, ultimately it is respected. You say it respectfully, you say it without being a jerk. I’ve got actually a really nice freebie for people.

Jenny Wood [00:13:16]:
It’s a guide 8 tips, tricks and scripts to say no to meetings, projects and favors without looking like a jerk. People can download that for free@itsjennywood.com sayno and uh, but it’s hard, it is hard to do it without feeling like a jerk. And man was my heart racing when I sat there and said I actually don’t think I can continue to take this on when I knew the expectation was for me to do it.

Dave Stachowiak [00:13:37]:
Indeed. And, and that actually is a great lead into one of the other invitations you make, which is to play to win. And the WINN is WINN- what I need now. And there’s a story you tell in the book about working for a couple of years to get to co head a position in the Colorado office for Google. And, and that journey of going through that. Tell me a little bit about that story and just how that, how that comes up in the what I need now.

Jenny Wood [00:14:09]:
So I had been spending years gunning for this position of co-head of the Google office and it was a lot of prestige. It was A great way to be a community leader within the Google organization. It’s a fairly large office for Google in the United States. And I then was basically offered the position or I was very much being courted to do it when it became available. And all of a sudden, Dave, I didn’t want it anymore. I was doing my day job, which was a lot of work. I was running the own your career program which was being used by 56,000 Googlers in nearly 100 countries. I was a wife and a mom and there was all this external interest in my work and the book and all this was starting to brew.

Jenny Wood [00:14:49]:
But it was so uncomfortable for me to play to win and to say, okay, what I needed three years ago is not what I need now. And so how do I play to win? And I remember hiking with my dear friend who was a, you know, kind of on my board of advisors, someone more senior than me at Google and she’s like, Jenny, what is this going to give you? Wouldn’t you rather double down on writing a best selling book, putting all your effort into your newsletter, posting really good content every day on LinkedIn versus this thankless job that is no more money and no more. It’s just like a lot of headaches, right? You deal with things like Google, you know, allows dogs on campus and it’ dealing with things like this person has a dog allergy. Should we have certain floors? Should Floor 3 be a no dog Floor and Floor 2 be a dog floor? Right? It’s like stuff like that. But three years ago it sounded really fun to have that opportunity. But then as a selfish leader, I had to play A WINN and recognize what I need now is to say no to this position. And guilt made it hard, Dave. I will say guilt made it hard.

Jenny Wood [00:15:49]:
I remember going to the decision makers and I was like, but if I don’t this do, who’s going to do it? Kind of arrogant too, right? I felt very passionate. I felt like I was a good leader and I felt like I was the shoo in and people were expecting me to do it because I have a lot of enthusiasm and community spirit and I knew that I would do a good job. And they were like, this is not your problem to solve, Jenny. All you have to do is say do you want this role or not? And let us figure out a good backup plan if you’re not in. And I will never forget that moment. I know exactly where I was standing, where this wonderful leader said that to me. And she was like, this is not your problem to Solve. That’s our problem to solve and we will solve it.

Jenny Wood [00:16:26]:
And it ended up going to another awesome person who was so happy for the opportunity and my selfishness gave him a great opportunity. The site was still in a great spot and I was able to focus on other things that were more important to me at that time.

Dave Stachowiak [00:16:38]:
Yeah. And an important role and an important thing for the organization. And years before or after might have been perfect for you, but wasn’t right at the time. And I, I think that oftentimes when I’m in conversation with people about a situation like this where they put a lot of time and energy or even broadcasted, hey, I want to do this, this position, this role, whatever it is. And then the opportunity comes in for whatever reason, it’s kind of like all of a sudden it doesn’t. Or circumstances have changed or it doesn’t seem like it’s a good opportunity. More. And the phrase I hear often, either explicitly or in someone’s thinking is, but I owe it to them.

Dave Stachowiak [00:17:15]:
Oh, I owe it to them because I said that I wanted the job, I said that I wanted the position. I said that I would do this. And now that I’ve been offered, I owe it to everyone to say yes. And you invite us to sometimes say no to that.

Jenny Wood [00:17:30]:
Yeah. Well, are you chasing today’s dreams or yesterday’s? Are you chasing your dream or somebody else’s? And you even said a phrase, not intentionally, but it’s actually one of the most critical two word phrases in my work, which is circumstances change. It was hard for me to be, quote, unquote, selfish, or I would even offer reckless, which is another one of the nine traits of wild courage, which is about erring on the side of action and taking intelligent risks. It was hard for me to be selfish and leave Google. My executive coach, Julie Connolly, who was just a wonderful, wonderful mentor and guide of mine, had to put a mirror up to me. And every time I said, but I owe this to my team. I’m leading an experimental team at Google. What’s going to happen to them if I decide to resign and go work full time on this book and on keynote speaking and consulting and one on one coaching.

Jenny Wood [00:18:22]:
And I also, Julie always thought I’d be at Google for 15 more years and that I’d retire here. Golden handcuffs are real, Dave. Right?

Dave Stachowiak [00:18:29]:
Yeah.

Jenny Wood [00:18:29]:
And so it took her saying to me, circumstances change for me to play, to win myself. And that was very, very hard because, you know, there’s part of it. I owe this to somebody else. I don’t want to let someone down. I want to make good on a deal. And then there are also just the scripts and narratives we tell ourselves. And it’s like we don’t even want to go back on our own thinking. And that’s where I encourage people to separate what I call truths and tales.

Jenny Wood [00:18:58]:
And this would maybe fall a little bit more in the shameless trait, which is the courage to stand behind your. Your efforts, your abilities. It’s. It’s not falling prey to imposter syndrome today as much as you did yesterday, because we all have it. We’re not trying to obliterate it.

Dave Stachowiak [00:19:15]:
Yeah.

Jenny Wood [00:19:15]:
When you’re in a situation where you’re thinking about taking a risk or you’re evaluating what’s the right move for you or what’s the right thing for your team. Separate the truths from the tales. Truths are verifiable facts. I am talking into a black microphone. We are recording a podcast right now. Those are truths. They’re verifiable facts. Tales are the stories we tell ourselves to make sense of the facts.

Jenny Wood [00:19:36]:
And that’s fine. It’s what we need to do as humans to make sense of the world. But just notice the distinction between them. So in this case, I had so many tales when I was feeling guilty about letting my team down and leaving Google to go selfishly pursue my own endeavors as an author and a keynote speaker and a coach. And some of the tales I told myself were, I’m the breadwinner for my family. I’m going to let my family down. My parents are going to be disappointed in me because they think this could be an unnecessary financial risk. Another tail.

Jenny Wood [00:20:05]:
Or we’re going to have to move out of our nice house in Boulder, near all the hiking trails, which I use every day at 4:30, and move to the other side of the tracks. My kids are going to be mad at me because they can’t come to Google and ride the slides and, you know, get the free snacks.

Jenny Wood [00:20:19]:
Then when I started separating those or recognizing them as tales, just stories I was creating and I focused more on the truths, it made me feel much more comfortable with taking this intelligent risk. So what were some of the truths behind those tales? Rather than my parents are going to be disappointed in me. The truth was they’ve always supported everything I’ve done. Rather than my kids are going to be mad they can’t come and ride the slides. The truth was my kids are resilient. At the time, they were 6 and 8. Like, they’d be just fine.

Dave Stachowiak [00:20:45]:
They’re fine.

Jenny Wood [00:20:46]:
A tale was my. My team is going to be floundering if I leave. Nobody else will be able to lead them and have them be, you know, effective. The truth was similar to the head of the Colorado office truth. This gives somebody else an opportunity to step up. And this team is full of exceptionally high tal people. They will be just fine. So a really effective tool as a leader when you are trying to balance what you need and what your team needs is just identify the truth in the tales.

Jenny Wood [00:21:13]:
Literally, write them down. Write down in your situation that you’re facing your challenge within a project or within stakeholders or thinking about, you know, moving to something new. Write down of all those things that are going through your head. What are truths and what are tales? And then how can you rewrite some of those tales to be, if not more empowering, at least more neutral? Because we believe the things we tell ourselves.

Dave Stachowiak [00:21:36]:
You have a great line in this chapter that says, “believe me, when your boss’s personal situations change, they don’t hesitate to change course, even at your expense.” And I was reflecting on that and thinking about. When I’m in a conversation with someone in a situation like this, I often find myself using the language. If it is someone who’s working for an organization as an employee, which many folks in our audience are, is I’ll say, remember, you’re a hired gun. And that’s not the language I would normally use, but it’s intentionally a little bit edgy, because I want to make the point that to what you just wrote in the book of, like, if your organization made a different decision, they wouldn’t hesitate for a moment to eliminate your role, to not have the loyalty, all those things. And it’s not to say, like, while we’re doing, our roles and relationships don’t go on and continue to grow forever. But when it comes to our careers and our roles and the work that we’re doing today, we need to look at it selfishly and we need to be thinking about what that looks like for us, because the organization is not going to reciprocate that sort of I owe it to them mentality that sometimes we just get trapped in.

Jenny Wood [00:22:52]:
So literally just yesterday, a coaching client of mine said to me, the only thing my company owes me is pay for the last two weeks. Yeah, and what a brilliant line in an age of layoffs and restructures and reorganizations and the onset of AI where everyone’s a little bit nervous, right? I mean, that’s all they owe you. And so why do you owe them any more. Now I say this as an incredibly dedicated corporate person for nearly two decades and someone who loved Google and still loves Google. But you know, it also reminds me of one moment where I walked into my boss’s office, one of my favorite bosses I ever had, and I was like on the brink of burnout as a leader and I was just taking AAPAC meetings at 11pm and waking up at 6am, 5am for AMEA meetings and hadn’t taken vacation vacation in a long time. And he said to me, jenny, you’re capped out on vacation. You are going to burn out. When is your next vacation? And my retort to him was, I know, I just love this company so much.

Jenny Wood [00:23:53]:
I love Google so much and I’m so excited about what we’re doing. And he said, jenny, stop right there. It’s great that you love Google, but Google does not love you back. And I think that’s similar to what you just said. So again, how much do we feel guilt or do we feel this unnecessary sense of obligation to a company that would be very quick to lay you off or very quick to restructure you, or very quick to shift you from a manager to an individual contributor role if they’re trying to change the scope and flatten the org? Right?

Dave Stachowiak [00:24:21]:
Yeah.

Jenny Wood [00:24:22]:
And now again, I say this as someone who absolutely thrived in corporate and would go back to corporate in a heartbeat, but I think it’s really important, I think we can get and especially working for a company as phenomenal at Google, where the perks are amazing, the culture is fantastic, the collaboration, the camaraderie, the community is just next level. Even so it’s important to separate your identity from that company’s identity, your identity from your team’s identity, your needs from your team’s needs. And it doesn’t make you a bad person, it makes you smart. And you know what, people admire it and it’s so inspiring because who wants to be in an anxiety ridden frenzy all the time, you know, worried that they’re. I had a meeting this morning where someone said every four to six months, I’m worried that I’m just an inch away from getting laid off. And I’m talking about a really high performing leader at a, at a big organization. And so just imagine the frenzy, the anxiety, the tizzy that it puts you in when you’re so tightly wound, if your identity is too tightly, you know, wound around your company or you’re constantly worried about like treating it like a relationship. And yeah, I do see how this could sound really cynical.

Jenny Wood [00:25:33]:
It’s not at all my intention because I think there are phenomenal organizations out there who do right by their people. I mean, my goodness, I’ve only had the experience of companies largely doing right by their people. But at the end of the day, it is a business, not a family. And I think it’s okay to acknowledge that. And I think it makes everybody better off. And I’ve always admired the leaders who were really thoughtful about that and upfront about it. And I either observed them acting that way or they’re like, it’s just a job, Jenny. You know, like, you’ll be fine, I’ll be fine.

Jenny Wood [00:26:04]:
We’ll all be fine if things shift and we get laid off. But it’s very freeing. I’d always be like, oh my gosh, how do you, how do you think that way? Because I am coming from a place of being, someone who’s always struggled with lowercase A anxiety, as I call it.

Dave Stachowiak [00:26:17]:
Yeah. And speaking about being upfront on things, there’s a wonderful invitation in the chapter called Smart Start. And you say, appreciate the unvarnished truth when you get it, but don’t sign up for a burned out boss out of gratitude for their honesty. Tell me about that.

Jenny Wood [00:26:37]:
Yeah, well, this is a section where I encourage people to again, be selfish and interview the hiring manager without telling them. But if you’re looking for a role, a leadership role, your first line manager role, even an IC role, when they interview you in those 30 minutes, you also are interviewing them. And so as part of this Smart Start framework, which is a five part acronym, we don’t have to go into one of those five parts is their attitude that they bring to the table, their enthusiasm. And so I give the comparison of someone who says, let’s take the positive version of it, a manager, for example, who I’d want to work for someone if I were to say, what are the biggest challenges on the team? And they say, well, oh man, we are changing the face of AI for this company. It is incredibly exciting. We’re working hard. It’s complex, but it’s invigorating. We’re on the cutting edge of a shifting industry.

Jenny Wood [00:27:32]:
Even though we’re dedicated, we’re in it to win it. And it’s a lot of hard work. That is one way to approach that answer on a team that’s maybe very challenging. The other way, which is kind of the example I gave in the book for the kind of manager you don’t want to sign up for is someone who’s like our stakeholders are the worst. You know, work life balance on this team. I just want to prep you is not going to be good. People are up till 2 o’ clock in the morning regularly and we’ve got some really, really tough cookies that we have to appease on the board. Right.

Jenny Wood [00:28:04]:
Like, like they’re basically saying the same thing in both cases. It’s a big, it’s a big important project. There’s a lot of opportunity but it’s hard. But yes, the other person’s being honest. Okay, but I don’t want to sign up to work for that person who has that negative attitude, who has that negative outlook, who’s kind of and gloom whose glass half empty. And I always encourage any leader to warm the room with positive energy, be the leader that people want to work for because despite it being a big challenge or it being hard, you’re showing the bright side of it. Right. Cutting edge, you know, life changing work, fundamentally reshaping technology.

Jenny Wood [00:28:43]:
It can be the language and the attitude and the enthusiasm that you use even if you’re describing something hard. And that’s the leader I want to work for even if the other one is maybe being very honest. But they show up to me as burnt out.

Dave Stachowiak [00:28:55]:
Yeah. And speaking of having the courage to stand up for what you want, it starts before the role even begins. Sometimes I think oftentimes we think about like, okay, I’m glad to really like hear the truth from someone. I’m glad to know what’s really going on in this organization. And then we miss that we don’t really think about, okay, is this actually the kind of person that I do want to work for or may I look for a better opportunity elsewhere where I don’t spend, you know, several years trying to figure that out on my own or realizing that after I get into an opportunity.

Jenny Wood [00:29:27]:
Yeah. And I am working with someone right now in a coaching capacity where this guy just is his boss is just so grumpy and it just makes this person grumpy. Right. And so it really that the whole concept of warm the room with positive energy is so, so practical and real and it doesn’t have to be that you’re faking it or forcing a smile in every meeting. Even something as simple as for example, we. The book was called the Chase for over two years before we changed it to Wild courage at the 11th hour. I was really attached to the chase. And then marketing and PR was like, it’s never going to sell.

Jenny Wood [00:30:03]:
Nobody wants to be chased. People don’t want to chase Things. People are exhausted, people want to lean out. I disagree. I think a lot of people still want to lean in. But we then went through almost a 75 new titles and my editor warmed the room with positive energy and she. It made her such an incredible leader by doing that, my editor at Penguin Random House. So what did that look like? If she hadn’t been intentionally warming the room with positive energy, she might have just sent me an email that said something like, here are six new titles.

Jenny Wood [00:30:30]:
I know this is a slog, but, you know, hopefully we can pick one soon. But what she did instead was she would say, jenny, here are six more titles. I am so excited about this new direction. I particularly love titles 2, 3, and 5. We are nearly over the finish line on this and I’m super pumped that we’re going to land an even better title than before. I mean, look at the difference in how those two emails are written. One positive, excited, optimistic, enthusiastic, and the other just kind of plain. And if I read that first one, I would feel like, oh, this is such a slog picking this title.

Jenny Wood [00:31:07]:
But instead, I had so much fun picking the title because under her leadership, she made it fun and she made me excited about it, even though it was a really, really hard and stressful situation.

Dave Stachowiak [00:31:18]:
Indeed. And same situation, just different in how it’s. I love the invitation to like, be listening for how that leader, that stakeholder, whoever is framing that situation. And speaking of framing, your dad had a saying about being the lead dog, because that was the best view. And there’s a section of the book called Second Dog Advantage. What’s the advantage of being the second dog?

Jenny Wood [00:31:46]:
Well, other people paved the way for you. And, and I had this real aha moment around Father’s Day where growing up, for years and years, I was just, I. I thought my perception was that my dad had always ingrained in us. Unless you’re the lead dog, the view never changes. If you think of sled dogs, the one at the front gets to see all the trees and the fresh snow rushing by. Any dogs behind that? In the line, in the sled line, just see butts. Nothing but butts, right? And so I wrote about this in a LinkedIn post. I try to post every day on LinkedIn and, and I showed it to my dad as kind of a Father’s Day thank you.

Jenny Wood [00:32:22]:
And he’s like, eh, I don’t really believe you need to be the lead dog. And I was like, imagine cartoon, you know, brain explosion, mind blown. I was like, what do you mean? This totally shaped Me as a leader, this made me always really ambitious and tenacious and maybe really want to go after it. He’s like, well, as a real estate guy in Denver, I was always happy picking up other people’s crumbs. I didn’t need to be number one. And you know, I, I got to kind of draft in other people’s wake. I got to, you know, still make a good living despite the fact that I wasn’t being the trailblazer on everything. So I think for different peoples and different styles of leaders, there are times where you want to lean in and be the lead dog or be an 11 out of 10.

Jenny Wood [00:33:03]:
And there are times where the second mover advantage is really great again. Another email I got this morning was someone saying, you know Jenny, you have so much good content. What if you like built an AI model and people could do like a pay as you go model where you would give them specific scripts to write certain things like getting promoted or saying no to a meeting or negotiating a raise or something like that. And honestly my first reaction was like, I don’t want to be the lead dog in this. I don’t want to invest in all the tech, let somebody else do it and then I’ll do my version of it once I better understand like exactly how to run the tech on the back end of this. And so it was perfect moment of like, wow, that sounds exhausting to be the lead dog on the technology of this, on this kind of like emerging industry of AI and second dog advantage feels perfectly fine to me today on that.

Dave Stachowiak [00:33:46]:
I think it’s so what a wonderful example your dad is of like thinking that’s evolving right as we all age and we change our minds on things. And I know your thinking’s evolved too and I’m curious as you have put this book together, specifically thinking around selfishness and this word and reclaiming it a bit, what have you changed your mind on?

Jenny Wood [00:34:09]:
Well, this is a biggie, but I’ve dramatically changed my mind on how much money I want to make each year. I have always had a high value of money. I think being at Google for so many years probably instilled that where it’s a very lucrative job career to be in tech, especially a leader in tech. And so I always just assumed every year I would make more and that’s just a path I would need to continue up into the right. And then I was in Mexico with my husband and kids and parents and I really did a some soul searching and a deep dive and also had a number of conversations with my financial advisor around how much money do I really want to make each year, and I have dramatically lowered that number to about a fifth of what I thought I would want to make as an entrepreneur, keynote speaker, executive coach, because I haven’t read the book Die With Zero. But I feel like I get the idea where investing in memory dividends now when my kids are 8 and 10 and I only have 8 more years until my son Ari goes to college. Recognizing that by the time your kids go to college you will have spent 90% of the time you will ever spend with them. And so I am thinking about an inverse revenue model where I pull back a lot over the next 10 years and then think about maybe leaning in a little bit more when my kids are in college.

Jenny Wood [00:35:26]:
But that is dramatically different than the typical narrative, which is you’re in your highest earning years right now and strike while the iron is hot hot and you hit the New York Times. Go double down on that. And a well balanced life doesn’t mean a well balanced year. This is your year to really, really dial it up. But it’s just if I play to WINN, not what I need right now.

Dave Stachowiak [00:35:49]:
Jenny Wood is the author of Wild Go after what yout Want and Get It. Jenny, thank you so much for your work and your perspective.

Jenny Wood [00:35:58]:
Thanks for having me.

Dave Stachowiak [00:36:00]:
Foreign if this conversation with Jenny was helpful to you, three related episodes I’d recommend one of them is episode 431 align your calendar to what matters. Nir Eyal was my guest on that episode and we talked about the reality that is so true for many leaders that calendars get out of control. It’s often one of the first places we look when our Academy members come in and starting to think about how they’re utilizing their time well and also being able to say no. Episode 431 is the place to begin on how to actually put that framework together and how to think about your calendar and your time. Also recommended episode 596, the Ways Leadership Can Derail Us. Bill George, former CEO of Medtronic, joined me in that conversation and we looked at the most common places where leaders go wrong. It’s helpful to listen to that episode and consider are any of those paths emerging for you and if so, may be helpful to begin to set a different course. Also recommended episode 734, the Path to more joy in Work and Life.

Dave Stachowiak [00:37:07]:
A recent conversation I had with Judith Joseph. We talked a bit about high functioning depression, how that shows up especially for high achievers and one of the points she made in that conversation is that the majority of people who need help help think they’re doing all right and yet would benefit from looking a bit deeper at how they’re utilizing their time, their thinking, and how they’re approaching some of the boundaries in their life and their work. Episode 734 A good starting point to introduce to her work all of those episodes you can find on the coachingforleaders.com website. I’d invite you today to set up your free membership at coachingforleaders.com because one of the areas that’s inside of the episode library inside the free membership is personal leadership. I have been mentioning on Episodes for years the importance of, yes, us leading ourselves first. Not because it’s about us, but because leading ourselves first well means that we do a better job of showing up well for the people we support our organizations and doing it in a way that has good, healthy boundaries. That’s one of the key areas inside of the episode library. Many episodes we’ve had, in addition to the ones I’ve just mentioned over the years, Set up your free membership at coachingforleaders.com to get access to that, all of the other topic areas and the free audio courses.

Dave Stachowiak [00:38:25]:
One of the big challenges I find that leaders run into, especially if they’re running into situations with boundaries and being able to be a little bit more selfish with their time, is delegating. Oftentimes there’s ways to delegate much more effectively for most of us that we’re not thinking about. And not only does that help us, but it helps the people around us because we’re developing them and helping them to improve their skills so they can grow their careers as well. One of the free audio courses inside of the free membership isHhow to Delegate Better, 4 lessons from me on exactly where to start. It’s part of the free membership. Just go over to coachingforleaders.com to set up your access and you’ll have access to that in all of the audio courses there. Coaching for Leaders is edited by Andrew Kroeger. Production support is provided by Sierra Priest.

Dave Stachowiak [00:39:16]:
Next week I’m glad to welcome Mort Sherman to the podcast. We’re going to be talking about how music, yes, music can help us to lead more effectively. Join me for that conversation with Mort and have a great week.