The Wild Courage to Ask for What You Want

Jenny Wood

Jenny Wood is the author of the upcoming book, WILD COURAGE: Go After What You Want and Get It. She is also a former executive at Google who ran a large operations team that helped drive tens of billions of revenue per year. She is the founder of Own Your Career, one of the largest career development programs in Google’s history with tens of thousands of people benefitting worldwide.

Jenny’s writing has been featured in Harvard Business Review, Entrepreneur, Inc., and Forbes. She is an FAA-licensed private pilot, a tap dancer, and a zucchini bread connoisseur. She lives in Boulder, Colorado with her two young children and her husband, Jon. She met Jon by chasing him off the NYC Subway, and the New York Times featured their story.

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TRANSCRIPT

Jenny Wood – 00:00:04:

I call that the pitch pullback also. You know, this happened with a mom the other day. I was like, hey, do you think you could take Ari to this birthday party? I’ve got a lot going on on Saturday. But if you have any issue with that, like, just let me know. Not a problem at all. I’m sure I could work out something else. Don’t worry about it. Like, I gave her three reasons to say no. I should have just, like, that’s the pitch. Can you take him to the party? Pull back, saying, but don’t worry about it. I’ve got other options. No sweat. It’s the same thing, I think, applied in a different context. 

Jess Ekstrom – 00:00:29:

Welcome to Amplify with Jess Ekstrom. If you’re ready to Amplify your ideas, your influence, and your income, then you’re in the right place. Today’s guest is my friend, Jenny Wood, someone who knows exactly what it takes to step outside her comfort zone and go after what she wants. She spent 18 years at Google, where she built one of the largest career programs in the company’s history. She’s a Harvard Business Review writer, a licensed pilot, and the author of Wild Courage, which I’m already calling the book of the year. But beyond the impressive resume, Jenny is someone who has taken bold chances. Sometimes in unexpected ways. Like in 2011, when she was riding the New York City subway home from work and spotted a handsome stranger across the train car. Instead of letting fear talk her out of it, she did something that most of us would never dare to do.

Jenny Wood – 00:01:32:

I’m riding the New York City subway home from work. It’s the C line. It is a dirty, stinky, crowded train. And about 20 feet away from me is standing this really good looking guy, gorgeous blue eyes, perfectly clothed five o’clock shadow. And I’m thinking, gosh, I really want to talk to him, but something holds me back. And what held me back was fear, right? Is he a felon? Is he married? Are a hundred people going to stare at me while I try to talk to him? And so I made a deal with the universe. I said, okay, if he gets off at my stop, 72nd Street, then I’ll talk to him. And if not, then that’s, you know, it wasn’t meant to be. So he gets off at the next stop, 59th street, not my stop. And then all of a sudden this like wave of Wild Courage washes over me and practically pushes me out of my subway seat. And I run off the train and chase after him. I tap him on the shoulder. I say, excuse me, I’m sorry to bother you, but you’re, you’re wearing gloves. So I can’t tell if you’re wearing a wedding ring, but in the event.

Jess Ekstrom – 00:02:30:

Oh my gosh.

Jenny Wood – 00:02:31:

You were cute. Can I give you my business card? I didn’t intend to like say something so bold to sort of like open mouth exit, like blabble. So, um, that’s what happened. And, and, you know, having coached tens of thousands of people directly or indirectly, you know, leaders inside of Google leaders outside of Google on success, leadership influence. I realized that like the general theme that kept coming up was fear and it was the same fears I felt on that subway fear of failure. What if he’s a, what if he’s married? Fear of uncertainty. What if he’s a convicted felon? Fear of judgment of others. What if a hundred people stare at me while I make a fool of myself? And Wild Courage is the process of moving past that fear to success on the other side. It’s really the set of tools that help you go after what you want and get it. And by the way, one of the chapters is called Obsessed. And I am obsessed with the fact that this is not even. Do I need to straighten this? Because it’s driving me crazy.

Jess Ekstrom – 00:03:30:

It’s off to the side, so you can’t even really see it. But why don’t you go ahead and straighten it? Yeah, if it is distracting you.

Jenny Wood – 00:03:38:

I am so much happier right now. So much happier.

Jess Ekstrom – 00:03:43:

Because, I did a, reel the other day that said like my word of the year, words of the year is delusional optimism. And I feel like obsessed is similar where it’s like. Being delusional about something or being obsessed sounds like, you know, I don’t want to be that like crazy person that chases someone off a subway, but hey, it worked for Jenny. And so talk to me about like, what are some of the things that we perceive as negative? You know, I really like, I want to talk about manipulative too, because you had that in there. But maybe let’s start with obsessed and some of the other terms that you, that people perceive as negative that we should start reframing and owning them.

Jenny Wood – 00:04:27:

For sure. So there are nine traits in the book that basically create the bars of an invisible cage that keep you small. And I want, I want you to stop playing small and start playing smart because these traits used in a sane and savvy way can supercharge your success. So obsessed is a great one, whether it’s straightening the thing behind you, because you really want it to look right. Or it’s, you know, when I, before I do a keynote, practicing three times my opening and my outro and my key stories, because I haven’t done the keynote in a month. And, you know, or whatever it is. And it’s like critically important that I land those like that could be obsessed. It’s reclaiming this language. So obsessed, I say, is the courage to, you know, to, to seek excellence, the courage to push, perform, persist. Now, these can all be taken too far. It is not grinding yourself into a sad, tired pulp, right? It’s all about doing them in a smart and savvy way. And I love manipulative. You mentioned that one, already manipulative. Old, tired definition is like with the intention to harm or to control somebody, right? But I think of it as the courage to build lasting relationships through empathy and wield your influence in smart ways. Like that sounds good, right? I just think that the typical leadership traits are a little tired, right? Like influence, curiosity, work ethic, like these all fit into there, right? Influence, I call it manipulative. Curiosity, I call it nosy. Work ethic, I call it obsessed. And so I do think it gives some new energy around them. And like, you know, you said, like, I think somebody can relate to is that, you know, good looking guy or that good looking girl and, and going after it or wanting to go after it and not going after it because of fear. And even if you’re not a subway pacer, right? Like I want to think about like, what, what part of this was an extraordinary situation and what part of this was an ordinary situation, extraordinary that I chased a random person off the train, but very ordinary that, wherever you are sitting today, there is something, something between you and a thing that you want, a relationship, a goal, a speaking gig, a promotion, a salary raise, a really cool project, a great relationship with your boss. There’s something sitting between you and what you want. And oftentimes that thing is fear. And if we can push past that fear, we can achieve so much joy and wonder on the other side.

Jess Ekstrom – 00:06:47:

You know, some of the things that you’re saying, you know, around obsession, you know, manipulation and how these things are positive, being weird. I love it. But, you know, given the nature of this show and given, you know, Mic Drop Workshop, we help women become confident speakers and get paid to speak. Have you found in your career at Google that what might be perceived one way as a woman is perceived another way as a man? For example, being obsessive and following up. It’s like, oh, he’s a really hard worker versus, wow, she’s really annoying. And we’re doing the same thing. Have you found that?

Jenny Wood – 00:07:27:

Yeah. I’ll give you an example right now. I was negotiating a contract. It wasn’t for a speaking gig. It was for another partnership. And this organization I perceive as super cool, super impressive, super legit, right? Where it’s like little old me starting out my speaking world. And granted, I’ve done tons of speaking already. It’s just now I’m doing it full time in a very different elevated capacity, working with some really big name speaking agencies, et cetera. So for this particular contract, I got the contract. And you can apply this to anything in your life, right? A project contract, a keynote contract, a partnership contract. And I read it and I was like, ooh, this feels really intense and one-sided. And I spoke to my attorney and he’s like, yeah, this is really well written, but it feels unfair to you, quite frankly. But I was so scared. I had so much imposter syndrome. I was not shameless enough. That’s another one of the nine traits I talk about to ask for what I wanted. And I literally didn’t sleep for chunks of a couple nights as I was feeling so insecure about asking for some pretty basic adjustments to the contract. I think if I were a guy, I would maybe not have felt that way. And my male attorney was like, what’s the problem? He’s like, Jenny, you’ve written a book about asking for what you want. These are totally, totally fair things to ask for. But I was going to redline the thing. And there was a lot. And I was worried about losing the deal. I was worried that my value was not equal to their value. And they would be like, oh my gosh, this is not worth our time. This is not worth our attorney’s time. Goodbye. And it did take getting. I had to tap into my nosiness, my curiosity. What might they say if I ask for XYZ thing? I had to tap into my shamelessness, the courage to stand behind your effort, abilities, and who you are that deserves a fair contract. And probably a bunch of other traits too. But it was really, really hard for me. Oh, and spoiler alert, I did make all the requests. And within an hour, they were made within the doc, the electronic document. Accept, accept, accept, accept. They didn’t care. They were excited to do the deal too. And some attorney had drafted up their side. There was no emotion. There was no emotion in it for them, I perceive. There was a lot of emotion in it for me.

Jess Ekstrom – 00:09:43:

Yeah. You know, you talk a lot about like communication changes that we can make instead of saying like, sorry for being late, saying thank you for your patience. What are some of the changes that we can make when we’re making an ask, whether that’s for a speaking opportunity, whether that’s at work, like guide us through some of the magic behind your communication?

Jenny Wood – 00:10:08:

Yeah, well, let’s talk about making an ask. And then if we have time, maybe we’ll go to just communication in general and influence in general. So making an ask, let’s say you’re negotiating a salary or you’re negotiating a raise or you’re negotiating a speaking fee, because I know that’s your world and now my world too. Try the-

Jess Ekstrom – 00:10:23:

Welcome, yeah.

Jenny Wood – 00:10:24:

Yeah, I know. Not for the faint hearted. Try the ping pong negotiation strategy, not the ping, ping negotiation strategy. Okay. So what is that? Ping pong is they say a number, you say a number, they say a number, you say a number. Ping ping is negotiating against yourself. You say a number, they say, can you go lower? You say another lower number. They say, can you go lower? You say a third number. That’s like, you got it. The ping pong ball has to go back and forth, back and forth. And oftentimes I think women or anybody, like if you really want the deal, you negotiate against yourself, meaning you keep throwing out numbers. So for example, let’s say that you’re going to just for easy numbers, charge $10,000 for a speaking fee. And you say, hey, I’m $10,000. Then they say, that’s not in our budget. Can you go lower? Then you say, great. I could do $5,000. Not a problem. I’m so eager to make this work. Well, you’ve just potentially left a lot of money on the table because you went ping, ping, 10,000, 5,000, both on your side of the table, throwing out numbers. Ping pong is I’m $10,000. They say, we don’t have that in the budget. Can you go lower? You don’t take the bait and you say, cool. What is in your budget? What might be workable? They might say we could do $8,000. You say, cool, let’s meet at 9,000. So that gap between 5,000, where you would have landed before by ping pinging and offering two numbers on the same side of the table at the same time, that $4,000 gap between 5,000, where you would have landed and 9,000, where you did land is money you’re leaving on the table by feeling potentially insecure or unconfident and negotiating against yourself. So think ping pong negotiation strategy, not ping ping, don’t negotiate against yourself.

Jess Ekstrom – 00:12:03:

You know, that’s so interesting because we have one of the things we teach in Mic Drop Workshop. It’s just like being able to say my fee is blank without anything after it.

Jenny Wood – 00:12:11:

Oh, yes.

Jess Ekstrom – 00:12:12:

Because what we tend to do is say, well, my fee is $10,000, but let me know what you can do. I really want to make this work. So you’re already letting them know that this isn’t a fee. It’s a suggestion.

Jenny Wood – 00:12:24:

Yeah.

Jess Ekstrom – 00:12:24:

And yeah.

Jenny Wood – 00:12:26:

I call that the pitch pullback also. So it’s like, yeah, it’s like I’m pitching and then I’m going to pull back. Right. It could be, you know, this happened with a mom the other day. I was like, Hey, do you think you could take Ari to this birthday party? I’ve got a lot going on on Saturday. Um, but if you, but if you have any issue with that, like, just let me know, not a problem at all. I’m sure I could work out something else. Don’t worry about it. Like I gave her three reasons to say, no, I should have just like, that’s the pitch. Can you take him to the party? Pull back saying, but don’t worry about it. I’ve got other options. No sweat. It’s the same thing I think applied in a different context.

Jess Ekstrom – 00:12:58:

I know. It’s funny. I saw some meme one time that was like, I make an ask and say, if not, no worries, as I’m filled with worry as I’m sending it. And so many of these are in Wild Courage. We’re going to put the link in the chat for you all to pre-order. It comes out March 25th. But let’s talk about some of the nuggets that you say in these conversations whenever you’re negotiating or trying to get what you want, which has clearly worked for you, is really interesting for people to be able to take away. And remember, in just a few minutes, we’ll drop the eight scripts to say no from Jenny. But I want to talk about some of the things you say when you’re making the ask and when you’re in the negotiation, because you had a question that I pulled out that you asked, what does success look like for you? And so tell us when to use that question and why it’s important.

Jenny Wood – 00:13:47:

Yeah, so, well, there are a couple of things that are beautiful about this. First of all, this is like straight up nosiness. Nosiness, nosy is the curiosity to dig deeper, the courage to dig deeper, to get insatiably curious. The reason this is such a good question is because it’s expanding the pie. What does success look like for you? Maybe your goals are not aligned, right? And you can get aligned really quickly. Maybe success does not look like getting me the lowest speaker fee. Maybe success looks like getting 30% of the audience to say that they feel more confident after this keynote than before. Maybe success looks like the number of people who are attending. Maybe success looks like giving everybody free books, right? And I’m like a huge fan of bundling gifted books to the organization as part of my speaking fee. So when you say, what does success look like to you, you get out of just price or current thing that feels like the typical negotiation focus, right? And you expand the pie to other values or other goals or other, you know, success metrics. And also I love what, like the best nosy questions start with the words, what or how. What or how, what does success look like for you opens up so much possibility of answer that will allow you to learn more and then riff from there to build and have a great partnership together. Because we’re not talking about selling used cars here. We’re talking about partnerships with other humans. We’re talking about project work together with other teammates. If you work in a corporate job, we’re talking about a relationship with your boss or your VP at your company. We’re talking about humans. And I think that expanding the pie and getting on the same page through more, more, more sharing, is what helps everybody win at the end of the day and create a positive sum game, not a zero sum game, which is my nerdy economics.

Jess Ekstrom – 00:15:35:

Background. I love it. Let your nerd flag fly. I think my mentality around like numbers and negotiation changed. Like it would make my palms sweat. I would get so nervous. And when it changed from saying that it was a negotiation to saying that it’s a partnership, like how are we going to make this partnership work instead of like you pay me and I come do the thing. And it’s like this transaction it’s how is it a win-win and if it’s not a win or it doesn’t feel like a win for me or it doesn’t feel like a win for them. Then that’s that’s all it is. But what about like When you got to set the boundary, you know, when maybe you’re obviously you’re a mom, I’m a mom, there’s constant tug of war between where you’re going to be spending your time. You only have so much time in the day. What are some tips around being able to say no, and not just being able to say no, but like not having the overwhelming guilt that comes with it?

Jenny Wood – 00:16:32:

For sure. So related to being a mom, I learned this one from my nine-year-old son. Ari, we were playing Monopoly and he was crushing me. And I was collecting all these little teeny tiny properties like Baltic and other things like that, that, you know, you get like 20 bucks if someone lands on you. And he was collecting Park Place and boardwalks. And so as in the, and he was, he was like totally winning. And so in the moment I was like, oh my gosh, this is such a good allegory for saying yes to the big, the expensive, high investment properties that have really high return and saying no to the small, right? So the boardwalks are those big investments. And then the Baltics that I like, was scattering all my resources around. And now in life, your resources are your time, your energy, sure. Also your money. It’s not just your paper money and Monopoly, but think about your boardwalks versus Baltics. What are your boardwalks day to day, right? Maybe it’s the key speaking client that you know is going to give recurring revenue to you. Maybe it is if you work in an office or at a company, maybe it is that big marketing project that, you know, is going to have the CEO’s eyes on it. Or you want to increase customer satisfaction 20% year over year, right? The biggie that’s important for the company for H1. Your Baltics, there are so many Baltics that bat us down every day, going to every meeting where you never add value or derive value, but you’re like, well, I’m on the invite. I should probably show up and be one of the 13 people who are sitting there like a bobblehead, right? Or maybe a Baltic is replying all to every email that comes in your inbox, even though it doesn’t really add any value there either. Like, happy birthday, Larry. You don’t have to be the 18th person to reply all to that email. You can like give Larry a high five in the water cooler, right? Or, you know, in the speaking world, maybe a Baltic would be customizing your keynote within an inch of the client’s absolute desire, right? And there’s a lot of ways you can customize a keynote that I’m finding, like, I’ve got my base keynote. I send a Google form with five questions ahead of time that say, what are the key things you want your audience to feel? What are the main takeaways? Any buzzword do you want me to include? Any buzzword do you want me to avoid? And that is a decent level of customization I can do and just tweak around the edges. So it feels like it’s really relevant to that organization and will be without me literally starting from scratch and building a new keynote for every organization. That is a Baltic. If I did that for every single keynote I did, like, you’ve got to say no to those things, even if you’re tempted.

Jess Ekstrom – 00:19:00:

Jenny, I want to wrap with, I know how vulnerable and crazy it can be to put a book into the world. And I like to kind of get centered around anytime I’m putting something out into the universe that I’ve created and you’re like, this is my baby. But I want to think about what’s the person sitting in the coffee shop reading this book, what are they going to walk away and do differently after this? Because then it’s not like Jess’s story or Jenny’s story. It is about helping XYZ person in this coffee shop, like going outside and being like, yes. So what is that for Wild Courage? If there was a magic wand that you waved, through your words to a reader. What do you want them to do differently after Wild Courage?

Jenny Wood – 00:19:47:

I want them to recognize that. What typically gets in the way between what you want and what you get is fear. And that’s such good news because fear you can work with. Fear you can do something about, right? So Wild Courage is the process of moving past that fear to the success and the wonder on the other side. And when you do, like no matter whether you win or lose in any one given thing, nothing feels as joyful and as satisfying and as freaking awesome as moving past that fear. Because when you move past that fear, most things that you want, maybe not everything, but most things that you want are right there waiting for you. So I want people to move past that fear and reach for whatever it is that you want.

Jess Ekstrom – 00:20:48:

Thanks for listening to Amplify. If you’re a fan of the show, show us some podcast love by giving us a rating and review. This episode is brought to you by Mic Drop Workshop, where you can learn how to become a better speaker, how to land paid speaking gigs, and become a keynote speaker. This episode was edited and produced by Walk West. I’m Jess Ekstrom, reminding you that you deserve the biggest stage. So let’s find out how to get you there. I’ll see you again soon.