Kris Safarova  00:45

Welcome to the Strategy Skills podcast. I’m your host, Kris Safarova, and our podcast sponsor today is StrategyTraining.com. If you want to strengthen your strategy skills, you can get the Overall Approach Used in Well-Managed Strategy Studies. It’s a free download we prepared for you, and you can get it at firmsconsulting.com/overallapproach. And you can also get another gift, McKinsey and BCG-winning resume, which is a resume that got offers from both of those firms. And you can get it at firmsconsulting.com/resumepdf. And firmsconsulting is F-I-R-M-S consulting. And today we have with us a very special guest, Jenny Wood. In her 18 years at Google, she grew from entry level to executive, and she most recently led a large operations team that helped drive billions of dollars of revenue per year. Jenny’s writing has been featured in Harvard Business Review, Entrepreneur, Inc. She’s a licensed private pilot, very rare, a daily hiker, an improv student, tap dancer and zucchini bread enthusiast, and she lives in Boulder, Colorado with her two young children and her husband Jon. Welcome Jenny.

Jenny Wood  02:00

Thanks so much for having me. Kris, it’s a pleasure to be here.

Kris Safarova  02:03

So let’s start with your career at Google. What were the critical skills or mindsets that helped you rise from an entry level role to an executive position over 18 years at Google?

Jenny Wood  02:14

Yeah, the critical skill. Here’s an unexpected one. I think the critical skill that helped me grow from entry level to executive was getting out of my own damn way, overcoming my limited beliefs, my limiting mindsets, my imposter syndrome, my fear of failure, fear of the unknown, fear of imperfection and fear of judgment of others.

Kris Safarova  02:48

And we all experiencing it, it is a tough thing. And I know you just recently wrote the book that is coming out soon that covers it in detail, and I’m looking forward to discuss it more. Let’s talk a little more, though about your time at Google. So what do you think were some of the key aha moments early in your Google career that influenced your leadership style and the way you approached your career and the way you were able to progress all the way to executive level?

Jenny Wood  03:15

Yeah, so one is something that felt a little bit I’d say brutal, and that was really early on, like this was just a couple months into my tenure at Google. I was 26 brand new entry level position, and everybody was walking to this meeting and that we were having in the little, tiny Google Denver office of about 30 people at the time, and everybody was walking to this, like, town hall meeting, and my boss, who I looked up to so much, said, I’m not. He wasn’t. He wasn’t getting up from his desk. And I was like, Hey, are you not coming to the meeting? He’s like, No, I’m not gonna go. And I was like, What do you mean you’re not gonna go? Aren’t we all supposed to go? He’s like, Well, yeah, technically, but I don’t think I’m going to add any value. And I don’t think I’m going to derive any value from this, like, large group meeting that’s just kind of reviewing the previous quarter. And he said, I’m going to stay here and get actual work done. And I was like, mind blown. Like, he was so brutal about his calendar. He was brutal about his ability to separate the important from the unimportant on any given hour, any given day, any given month. And he was particularly good at this. And to me, that is strategy. That is being strategic about where you spend your time and what is good use of your time and what is not good use of your time. And so I remember that moment so distinctly because I was so surprised. And I was like, What do you mean? What do you mean? You’re not going to go like we were told to go, don’t we just all go? And so being able to have the courage to say, Nope, I’m not going to do that, because I need to be a strategic thinker. I need to sit here and get actual work done. That’s the kind of stuff that when he taught me that, it made me realize that I. Don’t let other people dictate my schedule. I decide what is the best use of my time that is going to have the hardest, highest ROI for the company, for me, for my career, for my team, for my peers, etc. So being brutal about what you do is so critical to moving up in your career, and that helped me get from entry level to executive.

Kris Safarova  05:19

Do you remember the specific adjustments you made after this moment?

Jenny Wood  05:23

Yeah, one, one thing that I just started being more discerning around was saying yes to the big and no to the small. So what’s big? Big is the quarterly marketing project that matters a ton for the company and for your career and what small attending every meeting like this guy didn’t, that my boss didn’t, or replying all to every single email that comes into your inbox, or taking notes in the off site because someone asked you to. And you feel bad, right? You feel bad saying no, even though you really don’t think it’s a good use of your time, right? You’d rather be using that time in the meeting to meeting to think, Okay, how do I apply these concepts that I’m learning to my next project? How do I kind of whiteboard out some ideas, and saying yes to the big, saying no to the small, has helped me be really strategic and have the highest impact for me and for the company. And 111, thing I like to call this is being mindful of the nap work. It’s a it’s a term my mom coined nap. We were chatting about this at the kitchen table one day at her house, and I was like, this is the concept I’m thinking about. I think this was so helpful, and helping me, like, not waste my time on any given day, because time is our most precious resource. And I said it’s work that’s not actually promotable. And she’s like, well, there’s your acronym right there. It’s nap work. Like, don’t nap at the office, right? And that’s the small stuff I’m describing, the, you know, just the performative work, right? Or the meetings, the emails, when really the window gazing, the high level strategic thinking, the opening up a blank document and writing down a couple of key things, like, what are my goals for the quarter, and what are the who are the three people I want to meet to advance my career? And what are the who are the the stakeholders that I don’t yet have influence over but want to have influence over, like that is the high level strategic thinking that we so often don’t make time for because we’re in this hustle bustle of trying to get all these little, tiny things done right, all this nap work, this not actually promotable work, and it just eats away at our day, and it doesn’t leave any time for the strategic thinking.

Kris Safarova  07:33

Jenny, and what would be your advice for someone who is struggling to say no, concerned about how do I say no to my boss? Yes, this is not actually promotable work, but if I say no, they need to find someone else to do it, it can negatively impact our relationship.

Jenny Wood  07:49

Yeah, so I love offering people scripts of how to say no, because it is so darn hard to do it. So a couple ideas. There’s the the agenda of venture, right? So let’s say that somebody asks you to hop on a call. Your boss says, you know, hey, I’d like to meet about this. You can always write back and say, Great. Can you send me the agenda for what you want to talk about? And if it’s your boss, then maybe it’s a little bit harder to say no, but you can still say no to your boss. But think of all the other people that ask you for time. Just this morning, somebody asked me for time, and she’s like, Hey, I’d love to talk about this email. And I was like, Oh, I’d love to not talk about this email. Can’t we just keep it as an email, like, I don’t really have time to talk about a call today. And so I wrote back to her, and I said, Hey, what’s the agenda? You know? What would what are? What are the topics you want to talk about on the call that you think are better handled for a call than over email? And she wrote back one, two and three, and it turned out that I could just send her a couple of documents that she needed and that we really didn’t have to hop on a call. So the agenda Avenger, when you ask somebody for an agenda, you oftentimes can decide whether you should use your time for that that meeting, or it could be handled a different way. Slack, chat, text, you know, email another. Another tactic is just recognizing that when you this is a great one for your boss, actually, when you rather than just saying, No, I can’t, you tell them what’s happening instead that oftentimes is so that’s all you need. That’s really all you need. Because if someone says, Hey, Jenny, can you, can you work on this thing for this client that’s due Friday? And I say, I’d be happy to do that, but, but I’m currently planning to work on this project for X client that is three times as much in revenue, right? Like your boss will probably know, who are your more important stakeholders or clients? And as soon as you say, I’m actually already planning to work on this thing, and then you say, Do you want me to deprioritize that so I can work on this other thing? Once they realize, no, you’re already working on the bigger client, they’ll oftentimes find somebody else to do it, right? So if you give something back to them that seems more important, then that’s almost all you need. But then finally, like no. O is just something that is okay to say. I asked somebody for something, a favor. And he wrote back over, over chat, and he said, sorry. Heads down now on this project, unfortunately, I can’t help you right now. And I was like, he gave no excuse. He gave he did not ask me for an agenda. He did not ask me. You did not tell me you know this client name or revenue amount of why it’s so important that he doesn’t work on my thing and works on this other thing, he just simply said, I can’t I’m heads down right now. And honestly, I loved that. I respected that so much, because it’s so hard for people to say no. It’s like, Ooh, look at this guy owning it.

Kris Safarova  10:34

And when you started saying no, do you remember the transition you had to go through to get the point where you felt comfortable?

Jenny Wood  10:44

You knew what to say, Kris. You’re assuming, I’m still you’re assuming, I’m comfortable with it now. It’s still really hard. It is really, really hard, and I still struggle with it every day, because I struggle with people pleasing, and my work around having wild courage is is to help people feel like they don’t have to please other people, to be selfish in the decisions they want to make, because that’s just owning your calendar and owning your time, right? It’s to be shameless in what you do, which is kicking the imposter syndrome to the curve. But so many of the things that hold us back, including me, I’ve realized are my own desires to fit in or to go with the flow, or to be a people pleaser, or to say yes to everything, but ultimately, that all leads to not a whole lot of good. And it doesn’t help you stand out in your career. It doesn’t help you stand out in life. It doesn’t help you stand out in your business. So you’re asking, what is the moment like? You know what that transition looks like? I’m just very honestly acknowledging that it’s still quite hard for me in a lot of ways. And of course, I have lots of tools that I teach others and try to implement myself.

Kris Safarova  11:54

Jenny, beyond saying no where there’s other things you implemented that allowed you to be more successful than average?

Jenny Wood  12:03

Yeah, part of being more successful than average is recognizing when do you want to be a maximizer and when do you want to be a satisficer. So there’s research on this by Professor Barry Schwartz from Swarthmore University, and he has studied that when you try to optimize everything, let’s say be a 10 out of 10 on everything or or have every paragraph you write for the book be the absolute best paragraph for every bullet you create for your cue, for accomplishments, for your boss, is the best written bullet you’ve ever written. If you’re trying to maximize everything. You might get slightly better results, but you will be much less happier and satisfied with the outcome. Satisficers, just as it sounds. On the other hand, might get slightly worse results, but they’re much happier with the outcome. So another key to my success is recognizing when do I want to satisfy and when do I want to maximize? And that means that sometimes I’m going to have to be a three out of 10 on some projects and be okay with that. It gets back to the people pleasing. It’s really hard, but identifying where do you maximize and where do you satisfy on any given project, on any given meeting, on any given presentation, and just really forgiving yourself for not being perfect at everything is just a huge key to success and, quite frankly, happiness. And then if you want, we can talk about being obsessed, which is when you do want to be really out of the park on those key projects that are not the nap work, that are the big things that matter for your career, that are worth maximizing. Well, then how do you do that so you can really stand out? I think that’s the flip side, which is mostly what my work is about. I think you’re just catching me at a moment today where I’m being really introspective about, wow, how am I still people pleasing? And what am I still saying yes to that I should be saying no to because we all still struggle with that every single day.

Kris Safarova  14:05

That is very true. Let’s definitely talk about being obsessed. Yeah, all the best know what it feels like, and it’s a powerful, powerful way to approach work. Yeah. And at the same time, what you said about forgiving yourself when you don’t achieve what you wanted to achieve, and understanding just step you haven’t failed, as long as you did not give up you haven’t.

Jenny Wood  14:26

Yeah, yeah, yeah. We could certainly talk about failure and what I call recklessness, but I’d love to chat a little bit here about obsessed, because that has been something that I have seen help people really succeed. And I define obsessed as push, persist, perform with all these traits. And I’ll maybe just share the overview of the traits I try to instill in people, because it feels like we’re now expanding to some of these other traits, these nine traits that I just love, that. Help lead to success. The nine traits are weird, selfish, Shameless, nosy, obsessed, we’ll talk about that now, manipulative, reckless, brutal and bossy, so obsessed, push, perform, persist. The old definition, the original definition of obsessed is preoccupied or haunted by some idea or interest, right? I was obsessed with that person, or I have this weird obsession with Star Wars, right? That’s the that is the definition that I want us to shed so that we can adopt a new definition, which is simply the courage to set your own standards, the courage to set your own standards. So, great example here, Tina Fey, right? Amazing household name. Tons of people have been through Saturday Night Live over its 51 years, I think, now in existence. But how many have risen to the level of fame as Tina Fey? Tina Fey was obsessed. The typical working schedule for cast members on Saturday Night Live was you start writing your sketches and start kind of crafting the show on Tuesday. So that gives you Tuesday, Wednesday, Thursday, Friday, and then part of Saturday. Tina Fey started on Monday. And that might seem insignificant, but it’s really significant, because if you assume Tuesday, Wednesday, Thursday, Friday, only four full work days, she was adding another 25% of work time, and this is why she became a standout. She wanted to put in the extra time, she wanted to put in the extra work. She wanted to come in early and stay late and mold her craft. And that level of obsession set her apart from all the other Saturday Night Live folks who, for sure, some of them reached that level of fame, but few reach the level of Tina Fey fame because she was obsessed. So what might that look like at work? How does my obsession show up? And what does that mean for you? More importantly, so let’s say that your boss could do a scary project and you just don’t even know where to start. Let’s say that they come to you and say, okay, Kris, I want you to put together a product around fly, a marketing plan around flying sneakers. And you’re just like, what? Where is this coming from? What are you talking about? And you might even be in fight or flight. And I’ve sat in that meeting. I’ve sat across from my boss like a deer in headlights, thinking, Should I know more about this? Should I’ve been paying more attention in our quarterly town hall? Should I have gone to that meeting that my boss, early back in the day said, don’t even worry about it. And you know, like, what did I miss? Where am I behind? Why do I not understand this, no matter what that big, scary project is, and of course, it’s not gonna be flying shoes, but it’s gonna be something else that to be something else that is scary in your world, or overwhelming, or big hairy and audacious. You go back to your desk and you get a little bit obsessed, and that simply looks like opening up a blank document and starting a pencil sharpener. A pencil sharpener is just kind of getting things out there so that white, black and white document might have a couple key sections, goals, self imposed deadline, stakeholders, to meet questions. I still have deliverable you’re looking for and you sketch out as a pencil sharpener. Just kind of like getting it sharp, getting the wheels turning, doesn’t have to be perfect. A couple bullets under goals, right? We’re trying to we’re trying to beat the wearables market. A couple people to meet under stakeholders, Mary Jane and Niraj. A couple questions that you have. Hey, is the deliverable a PowerPoint deck? Is it a presentation? And just sketching out a half a page and delivering it back to your boss by end of day, or worst case scenario, the next day, but within 24 hours, you look obsessed in the best way, proactive, buttoned up like a leader, like you’re moving the ball forward. And so as a Google exec, the employees who impressed me the most and who I would see quickly rising to the top were those who did that type of activity within 24 hours, you get something on paper, five key categories you do a pencil sharpener. The ones that were always less impressive to me and had less potential and did not move up into leadership positions were the ones who waited seven days until our next weekly one on one and came back to me and said, you know, Jenny, I’m still not totally sure what the goal is of this project. Could you help me think through it? I’m a little bit nervous, I’m a little bit overwhelmed, and in some sometimes it’s totally fine to be transparent and and bring your whole self to work to your manager, but your manager has a lot going on. They’ve got their own business problems to solve, and if they could solve the flying shoe challenge, they wouldn’t need you. They hired you to come up with ideas to be proactive. And oftentimes what that takes is just taking a stab at something, getting something down on paper that moves the project forward. And then they’ll give you feedback ideas, you’ll riff on it together. And the expectations are so low, because if you see. Send them something within 24 hours, then it’s not like anybody who expected to have beautiful slides or a well thought out plan. You’re just sending them a couple bullets to riff off of, and it looks so impressive when you do so. That’s one example of obsessed push, persist perform. It’s the courage to set your own standard, the wild courage to set your own standard, like Tina Fey did, and like you can do any given day on a project that makes you nervous.

Kris Safarova  20:26

This is very, very valuable advice for people listening to us right now. Can you give us another example? If you don’t mind?

Jenny Wood  20:33

Yeah, I would love to. I mean, sometimes obsessed bleeds into weird a little bit, which is being authentically you, you know, winning as you or losing as who I should say. So here’s an example of when I was a little obsessed and also got a little bit weird. My team was up for a project and an award, and to be entered into this corporate award, this really big award, with a really significant prize, you had to fill out this form of like, what was the client impact, and what was your approach, and what was different and what was strategic? And I was like, where I said to my team, number of people at the time, we’re not going to fill out this form. We are going to make a music video. And my, oh, my Kris, did we get obsessed making this music video, and we spent a tremendous number of hours doing this like so much so that it was maybe a little over the top, but that’s obsessed, right? We were eye on the prize. We wanted to win. We wanted it to be fun. We wanted to stand out, because the easiest way to be forgettable in your career is to blend in, to slink back in your chair, to do things like everybody else. So we wanted to do things differently. We put together this music this music video. We thought it was awesome. Well, guess who didn’t think it was so awesome? The people deciding the award because we did not get first place, we did not get second place, we did not get any place, we just did not get any recognition. And man, was I embarrassed. Even thinking about it now makes me kind of want to cringe, though the outcome was nice long term, a couple years down the line, but I would walk by these, these decision makers, these senior, you know, senior leaders, the top, top, top dogs in the hall. And I would kind of like cringe thinking that they were thinking, there goes Jenny Wood again, Google leader who’s wasting precious company time and resources on some ridiculous music video. And I could just picture people rolling their eyes as they watched it, and talking about me in this meeting, and Frank, to take side note, I think we oftentimes worry about what other people are saying about us at work, and that can be really difficult, and we can talk about that too. But fast forward a couple years down the line, I was meeting with one of those senior execs, execs in his office, and he said he was mentoring me, and he said, Jenny, remember that music video you made a couple years ago? And I was like, oh, gosh, yes, please don’t bring it up in my mind. And he said, keep doing that. That will serve you well, because you stand out and you do things differently and you take risks that people wouldn’t dare to take, and that’s going to set you apart? And I do think that that helped me continue to be someone who grew and who helped coach others to be better than they could think that to be better than they thought they could be. Because it is really about how do you make your mark? And let’s also keep it real, highly unlikely Kris that you are going to go advise people, or that you yourself are gonna go make a music video right to like, win some award. Everyone’s flavor of obsessed, everyone’s flavor of weird, should be natural and authentic to them. I was teaching a negotiations class to about 1200 people earlier this week, and someone said, you know, how do I do this if I come from a culture that isn’t as, you know, bold, as maybe I perceive the American culture to be? And I said, you start small. Maybe you’re not going to make the music video. Maybe you’re not going to chase a VP out of a town hall and say, Hey, could you mentor me? But maybe your flavor of weird and standing out is that you send them a quick little ping afterwards and say, Hey, this is what really stood out to me from the meeting. Thank you so much for sharing the context behind the reorg. Or maybe your boss gives you the flying sneakers project, and you thoughtfully disagree with them and say, I don’t know that flying sneakers is the right direction to go. Maybe it’s flying boots. Or maybe you ask to present the project, because you know that if the four people working on the project, the person who’s going to get the lion’s share of the credit, even if you did the lion’s share of the work, is. A person who stands up there in front of the client or in front of the team or in front of the stakeholders and does that 20 minute presentation. So maybe it’s not a music video, and maybe it’s not something as big and bold and wildly courageous as some of the examples I’m sharing, but every single person has the ability to do a little bit more that is out of the box or out of the ordinary or out of their comfort zone, whether it’s a polite disagreement or a pushback on a project, or saying no, like we talked about earlier in the conversation, or sharing with somebody who’s very senior that you admire them and you like their work and that maybe one day you could have a 15 minute coffee chat together. So whatever your flavor of bold feels reasonable right now. Dial it up by just 3% push yourself just a little bit, not by 93% but by 3% and think about what weird action can you take that’s authentically you, that allows you to stand out? What can you do that’s slightly more obsessed tomorrow than it was today, which is working just a little bit extra on the right stuff, not on the time wasters, but on the right stuff that matters for you, your business or your career.

Kris Safarova  26:06

Jenny and do you have any advice for listeners who really like this idea? And they want to be more obsessed and showcase it and take bold moves, but they feel right now, you know what? Jenny has such great ideas, and she knows just what to say. And I kind of get unsure about what to do, what I could do to be more obsessed?

Jenny Wood  26:30

So I think oftentimes we underestimate how helpful it can be to have an open conversation with your manager. When was the last time you had a career development conversation. And by that, I don’t mean it’s bullet seven out of seven bullets on your weekly one on one that says, you know, let’s talk about a raise for next year. Right? When was the last time you went to your boss and said, hey, could we talk for 45 minutes about my career development? And put a dedicated 45 minute conversation on the calendar with the title career development, as opposed to weekly one on one and and you prepped a couple of key questions ahead of time, right, which can very much lower the intensity or the feeling or the nervousness of bringing these things up, kind of off the cuff in a live meeting. Some of these questions might look like here’s what I’m really proud of in or the questions might be, what are you proud of? You know, in the last six months, and you write down, here are three things I’m proud of. Maybe you prep. Here’s a skill that I most want to develop. You write that down, maybe you prep. Here are two of your peers, Mr. Or Mrs. Boss, that I think I should get to know, because I know that they matter for promotions and they matter for end of your salary, or, you know, q1 bonus conversations, and maybe I write down here are some areas where I’d love your help and support by doing that prep work, right? So we wildly underestimate the value of prep work, right? I’m assuming when you go into a podcast, you’re not just showing up with no plan of what you’re going to ask the guest, right? And maybe you are. Some people are really good at winging it, but when we feel imposter syndrome, prep work, 30 minutes of prep work is just an incredible, incredible antidote to anxiety, to imposter syndrome, to fear, to shame, right? I talk about this in this shameless work, and how we can kick imposter syndrome to the curb. And so when you prep, you’re almost giving yourself this huge advantage that you wouldn’t have otherwise. If you’re just showing up, you’re going to try to improv, and that helps you be obsessed, like the prep work, in and of itself, is obsessed because it doesn’t take much to make your boss feel that you’re obsessed. And that’s a good thing. You want your boss to think that. And again, we’re talking about an obsessed as the courage to set your own standard, the courage to push, perform and persist. This is a good thing. We’re reclaiming these, these, these traits here, and I think the prep work can just do a lot of that. And by the way, this is common sense. It is rarely common practice. It’s common sense. It’s rarely common practice, because we get busy and we have back to back meetings and and we de prioritize things if it’s not right there in front of us, and prep work is rarely right there in front of us. But when we carve out the time to do that pencil sharpener like I talked about earlier, or to prep for that career development conversation, or to do three minutes worth of research on somebody before you go interview with them for a job you’re excited about, it makes an enormous, enormous difference, and it lowers the bar of what wild courage might look like, because you’re mustering that courage as you get those ideas down on paper. And then you just rock up to that meeting confident, finding your swagger, knowing exactly what you want to talk about. And that’s when you look buttoned up, strategic. And like a future leader,

Kris Safarova  30:01

Jenny and what would be your advice to a listener right now who is not working for a large corporation, but they already left and started their own business?

Jenny Wood  30:11

Well, someone once said to me, if you can do anything but be an entrepreneur, go do that other thing, right? So for all of you, it’s tough. I’m an entrepreneur. Now. I have been an entrepreneur for a handful of months, left corporate after 18 years, never thought that I would leave, and what I’m embracing right now is my own recklessness. And again, reckless is not a bad thing. Reckless is a good thing. Reckless is simply erring on the side of action. Old definition we’re going to throw out is marked by lack of proper caution. We’re going to retire that one so we can embrace reckless, the courage to take calculated risks, and so as an entrepreneur or as someone or as a teacher or a therapist or a librarian or an engineer or a mechanic, reckless is taking risks, right? That could be taking risks in how much you pitch to a client, right? What is the price you’re gonna throw out there? Maybe you’ve been charging $5,000 for the last 10 years, and you’re getting steady business. Might it be time to get a little bit reckless and raise your price to $5,700 because inflation and the market value has changed. Might it be reckless to if you’re thinking about leaving your corporate job and being an entrepreneur, not having a perfect plan and not having a perfect website and not having perfect business cards or a perfect logo. Maybe those are some things that don’t have to be a 10 out of 10, like we’ve talked about earlier. Maybe some of those are things that can be a six out of 10. But what’s a 10 out of 10 is just going and asking for your first client, or asking somebody to come hire you twice, twice a month, instead of once a month, or asking for somebody to partner on a new creative project that you feel like you don’t fully have the skills to execute without that particular talent or skill set that that they have. So when we get reckless, we’re going to fail. But when we double our failures, we sometimes quadruple our success, because it’s in those moments of failure that we learn the most, that we grow the most, and that we push the boundaries, and that also is what having wild courage is all about.

Kris Safarova  32:37

Jenny and during those years at Google and now as an entrepreneur, are there specific personal habits, daily practices you rely on to stay focused, to make sure you’re not burning out and resilient?

Jenny Wood  32:50

Yeah, I live by limits and leeway. Kris and limits and leeway are, how much time am I going to spend on this thing? What is my limit and leeway is? How much time am I going to pad on this thing. Okay, so let’s take this morning as an example. I am. I’m reworking my keynote to be not just about leadership, but also to be more about resilience. And that takes some significant work, but I could easily go into a rabbit hole and say I’m gonna, like, or not even have any kind of plan around how much time I’m gonna spend on it, and I know that at some point the ROI will not be as high. I will reach asymptotic benefits of X number of hours put in. So it’s gonna it’s gonna be diminishing returns, essentially. So this morning, I said I am gonna spend a 90 minutes reworking this keynote. And that is the limit I’m going to put on myself. I’m going to put it on calendar. I’m going to set my timer for 90 minutes. I also know my what’s called ultradian rhythms, which is basically, if you think of circadian rhythms, as the amount of time we need to be awake and then asleep. And it’s pretty typical each day. I know my ultradian rhythm is the amount of time that I can be on focus and working versus the amount of time that I need to pull back and and take some some breaks. So I know that I can’t really go more than 80 or 90 minutes. So I set my timer for 90 minutes, I closed my tabs, I closed my email, and I worked heads down on this project for 90 minutes. That was my limit. Now let’s talk about leeway. How do you not be so hard on yourself? And this actually ties a little bit more to that entrepreneurial question where, let’s say I’m doing client work for a company, let’s say I’m going in and I’m helping train all their managers on how to be better managers, something I absolutely love to do, or helping all of their employees be more engaged or more proactive or feel like they’re thriving and motivated in their careers. Another thing I’d love to do. And let’s say somebody comes to me with a project, and they say, we’ve got X, you know, X amount of money. And I say to them, okay, I think that. And this, they give me the scope of the project. Then I say to them, I I, let’s say I think it’s going to take five weeks. Six leeway, the live by limits and leeway. The leeway part of that is padding it by about 20% so if I think it’s going to take five weeks, I’m going to tell them six weeks. And it’s taken me time to learn how to pad because I always want to be the fastest. I always want to be the most responsive partner. I always want to be the most helpful and the most eager to get it done quickly, partner, business partner, they have. But when I realized that I had to live by limits and leeway. Limits, how much time am I going to spend on this project, like the keynote this morning, 90 minutes. That is my limit, and then leeway. How much leeway am I going to give this client, or myself, rather, to finish this project, even though maybe it could be done in five weeks, I’m gonna say six weeks. I’m gonna pad by 20% Same thing goes with like, if you’re building a house, right? You’re doing a house remodel, you think it’s gonna cost $100,000 live by limits in leeway. Give it, you know, more time it’s probably gonna take longer than you think. And give it another 20% it’s gonna cost you $120,000 not $100,000 so limits in so limits and leeway are great tools for all other areas of life as well.

Kris Safarova  36:06

And it will easily cost you more than 20%.

Jenny Wood  36:09

Yes, it sure will. So live by limits and leeway, but whatever the leeway is, is up to you. That is for you to decide.

Kris Safarova  36:15

Jenny, in your book, you say that within your weird lie your greatest strengths. How can someone find their weird?

Jenny Wood  36:27

Yeah, there are a number of different ways to tap into your weird. It’s truly about what makes you happy each day, what makes you thrive, what makes you feel like it’s you being you. So for example, my three power assets are stakeholder management, building things from startup to scale, and people leadership and those together make up my power portfolio. And I know that that is what makes me weirdly me, right? I am not amazing at organization. I am not amazing at, you know, the like, technical prowess. That is not my flavor of weird. My flavor of weird is leadership, building scale, creativity. And how do you get there? Well, you probably have some inclination of what you enjoy doing. So what I recommend is you write down three columns and just start free, free writing, just all ideas. Column one is what you love to do as a kid. So for me, for example, I love selling magazines as a kid. There was this, like, not that I did every day, but there was this there was this magazine sale that we did in middle school, and I was so excited. I was so driven to get people excited about buying magazines so I could win the prize. Okay, so that tells me that one of my flavors of weird is that I’m driven, and that, to me, falls into, you know, building things from startup to scale, which becomes my superpower as an adult. Okay, so that’s column one is, what did you love to do as a kid? Column two is, what did you love early in your career? Okay, so you can even think like college days, when you’re starting to figure out what you want to do with your life, and then early in your career, what were your go tos? Did you sit down and you loved working on an Excel spreadsheet, or did you open up the PowerPoint deck and you started to build things out visually, right? Were you a numbers person? Were you a visual thinker? And then column three is this week. What is it this week that is most giving you joy when you open up your laptop? Do you want to hop on calls with people and relate to people and exchange ideas and have conversation? Or do you want to quietly sit back and, you know, write something that you know might be shared with a lot of people, or something like that. So as you look across these three columns, childhood, early career, and this week, you’re going to start to see themes, you’re going to start to see themes, and then you take those themes and this will start to build what is, what are your power assets that make up your power portfolio? And then you validate it with others, and you talk to some people you trust, you talk to your manager, you talk to mentors, you talk to sponsors, and you say, hey, what do you think my strengths are? Because sometimes something that you think is a strength is not necessarily what somebody else thinks. For example, I love analytics. I love data. I studied economics, and I always thought that I go more toward, you know, a numbers driven type of role. And then I had this boss that I said, Hey, what do you think my strengths are? And he’s like, I think you’re a generalist. And I was so I was like, a generalist, doesn’t that kind of mean I’m good at nothing? And he’s like, No, it means that you can be a Jill of all trades or a jack of all trades. And he’s like, the best leaders that I admire are generalists, because they really relate to people. They can get they can get people excited about their ideas, and they can have their hands in a couple of different areas without going deep in any one thing. He’s like, I think if you go deep in any one thing, like, if you go deeply technical or deeply into the data, I think that you are missing out on an opportunity to just be a good. General people leader, and so hearing what his perspective was versus what my perspective was helped me find this happy medium of, where can I go deep on some things, but also maintain this new career direction of, oh, I think I actually do just want to lead a large organization at a large company and have a lot of impact to a lot of people, even if it means that I’m not going to be like a financial analyst or an economist or, you know, a coder, right, which I realized over time, but it was very hard for me to let go of that like, No, that is actually not my flavor of weird, even though I initially thought maybe it was. So it’s a combination of these three columns you write down and then the feedback you get from others that all taken into consideration and triangulated allows you to land on what kind of weird Do you want to be and what kind of weird? More importantly, are you all ready? Because win as you or lose as who?

Kris Safarova  40:53

What do you think are the skills leaders need to focus on developing, given what is happening right now in the world? Hmm?

Jenny Wood  41:01

World, hmm, well, the leaders that I admire the most lead with enthusiasm. So yes, we want our leaders to be empathetic. Yes, we want our leaders to be smart. I want my leader to be positive. So if I have a choice of walking in to a room with a leader who says, Oh, this reorg is killing me, and it is just, you know, it’s, I just don’t know how we’re gonna we’re going to get the team on board with this, right? We’ve got 1000 people that we’ve got to get on board with this new direction. You know, that is not the leader I want to work for. I want someone who warms the room with their positive energy. So you take that same scenario, you’re leading 1000 people through a tough reorg, and I walk into a room with the leader who’s designing this, and I need to help implement the reorg, right, and get these 1000 people and get these 1000 people on board. And that leader says, We have a tremendous opportunity. The industry is shifting at a rapid pace, and we are privileged to be able to meet that moment and to be on the cutting edge of this technology, of this industry, of AI of this transformation, and there’s no team that I better believe in doing it and being part of that transformation than this one. And he’s saying it with a smile and he’s saying it with warmth, and he’s saying it with energy, and he’s saying it with positivity and Kris even now as I’m saying that, I’m like, Oh man, let’s be part of this reorg, like we’re changing the world, as opposed to that first conversation. I’m exhausted. It’s going to be tough, man. Jenny, I’m really losing sleep over how we’re going to get these 1000 people on board, and these cuts are going to be terrible, and there are going to be layoffs, as opposed to the other person, we’re going to have layoffs, and that is not going to be easy. But I also feel so confident that the talent on this team that unfortunately is not going to be part of this team going forward, is going to land on their feet. It’s going to be a forcing function for them to find their next awesome opportunity. They’re going to learn new things and gain new skills. And I am right now Kris taking the most absolute, extreme example of probably the hardest thing a leader could have to lead through a layoff, a reorg, letting people go. And I use that as an example by design, because even positivity and warmth and a and an uplifting outlook in a situation like that is possible.

Kris Safarova  43:43

Jenny, in your book, there’s a quote that I really liked. I posted it on LinkedIn today. Thank you. You said, remember that the unwritten rules we obediently follow to fit in aren’t rules at all. They are trapped filters to beat out people without the guts to transcend them study the careers of notable figures in business, science, politics or the arts. Breaking with convention is the only rule they consistently follow. Yeah, what do you want to say about that?

Jenny Wood  44:12

Sure, there’s something called the Red Sneaker effect, which, which is data and research that shows that you know when you stand out. And this gets back to weird, when you stand out, like, if you have the audacity to wear red sneakers to, you know, some black tie event that you are shown to, you’re like, perceived to have more power and more influence and more authority, and that you’re breaking the unwritten rules, right? Like, black shoes are probably the go to for your the tuxedo. But when you’re wearing the red sneakers, it really makes a statement. And so, you know, here’s here’s here’s a of course, again, you’re probably not going to wear, I’m not going to wear red sneakers to a black tie event. That’s not my flavor of weird. But here is my flavor of weird, and how I see unwritten rules as as, as you know, traps and nothing more. When I was applying for my role. With Google. I was 26 totally new, you know, just come back from living abroad after doing research at Harvard Business School. Had no idea what I wanted to do with my life, but got really, really excited at the idea of working for Google. It was in the news with their lava lamps and their Bing bag chairs and their delicious gourmet, you know, miso dusted cod and and i i applied online to this random job I knew nothing about, and I heard nothing. And I heard nothing for another day and another day and another day, and then a week and then longer. And I was like, Well, let me just go see if everything was okay with my application. And I realized, to my horror, to my horror, that the formatting looked like it had been uploaded in kind of a funky way on my resume when I had to upload the document, and I don’t know, maybe, like, I don’t so many years ago, almost 20 years ago, but, but I, I was like, Okay, I know there is nowhere in the Google application manual that Google how to apply to Google manual that says you hop in your car, and you drive up to the Google office, and you sit in the office until someone comes out and takes your printed out resume that is now nicely formatted. And I said, that’s an unspoken rule, and I’m going to break that unspoken rule. And so I got in my mom’s 10 year old Honda stick shift, and I was living with my parents at the time, and I drove to the Google office, and I sat there until someone came out and spoke to me, despite the fact that they, the receptionist in this shared office space kept trying to turn me away, and I just was professionally persistent, and with a smile, said it’s important that I speak to somebody at Google because there was a problem With my application. And as the smile muscles quivered and my knees started to shake, I just held firm and stood there like an unwavering tree rooted to the ground until someone came out, and then eventually someone named Elizabeth came out, and I handed her my resume and casually mentioned the work I had been doing at Harvard Business School and studying abroad, which felt like a very Googly thing to talk about international experience, and and then, and then, after that, the recruiter called, and I shortly had a whole bunch of interviews and then a job offer. So I think it’s, it’s, it’s the unspoken rules, the unwritten rules that really can get us caught up on what we should or shouldn’t do, because we think, Well, if I break that unspoken rule, that is going to lead to the judgment of others, like we talked about earlier. But that is the stuff that’s actually going to set you apart, and that is where I want people to have wild courage in their life. That is what I want to inspire them to do is to break with convention, to be weirdly, shamelessly recklessly who you are, to go after what you want and get it.

Kris Safarova  47:53

Jenny, I could speak to you forever. I loved your book. Thank you. When can our listeners learn more about you? Get your book? Anything you want to share?

Jenny Wood  48:02

Yeah, sure. So you can bring me into your company for training or speaking, and you can find all of that on my website itsjennywood.com and you can also join my newsletter there as well. I send a quick tip out every Tuesday. It’s always under a two minute. Read lots of practical tactical strategies. But the thing I’m most excited about is to share my book with you, because it really does take all of these nine traits and break them down into very easy, bite sized ways you can apply them and to help you find your own wild courage that you can be more weird, shameless, selfish, nosy, obsessed, manipulative, which we didn’t even talk about today. And you’ll have to read the book to hear about that sizzly one, reckless, brutal and bossy, and you can find that at itsjennywood.com/book or anywhere books are sold.

Kris Safarova  48:59

Thank you, Jenny. Thank you for writing this book. Thank you for doing the work that you’re doing, and thank you for being so open. You’re not holding back. You’re really sharing examples that can help people tremendously well.

Jenny Wood  49:11

Thank you very much. I’d be a fraud if I didn’t, I wouldn’t be having wild courage if I, if I didn’t share some of my own struggles.

Kris Safarova  49:18

So our guest today, again has been Jenny Wood. Check out Jenny’s book. It’s called Wild Courage. And our podcast sponsor today is StrategyTraining.com. If you want to strengthen your strategy skills, we prepared a gift for you. It’s called the Overall Approach Used in Well-Managed Strategy Studies. It’s a free download you can get for yourself at firmsconsulting.com/overallapproach. And then there’s another gift for you, McKinsey and BCG-winning resume, which is a resume that got offers from both of those firms, and you can get it at firmsconsulting.com/resumePDF. Thank you so much for tuning in, and I’m looking forward to connect with you all next time.