Work can be one of the biggest drivers of positivity in your life, but no one ever really explains how to be successful without sacrificing everything outside of the office. When you enjoy your work, you’re more successful and any joy you feel on the job spills over into the rest of your life as well. Kind of like practicing empathy at work and bringing that skill home with you!
My guest today is Jason Silver, author of Your Grass is Greener: Use What You Have, Get What You Want. At Work and in Life. We discuss why leaning into values matters, what he learned about people-centric leadership at AirBnB, and how he carried that into his other successful endeavors. He shares 9 of the most common workplace challenges, why the term “best practice” is dangerous, and the difference between intention and purpose. He shares powerful habits to find more enjoyment at work – which he says is not the fluff but the fuel – and he tells you exactly how to ask your boss to allow you to do your work in ways you enjoy more! Finally, we discuss why it’s easy for leaders to attribute cost but less easy to attribute exponential benefits when you focus on enjoyment and people first.
To access the episode transcript, please scroll down below.
Key Takeaways:
- Take care of your people first and they will take care of any problem your business runs into.
- The earlier you start, the more you can bake the values of the organization into the company and team members, which makes it easier to make every decision based on those values.
- It is not a waste of time to reflect and learn from our weeks. If we don’t know where we were unintentionally pulled sideways or intentionally set other things aside, we won’t know what we need to focus on going forward.
- You are not going to find every aspect of your job fun or enjoyable, but it doesn’t have to be constant fun for you to find overall enjoyment in your career.
“Enjoyment isn’t the fluff. Enjoyment is the fuel. The more you’re enjoying your work, the more likely it is that you accomplish bigger and bigger things.” — Jason Silver
From Our Partner:
SparkEffect partners with organizations to unlock the full potential of their greatest asset: their people. Through their tailored assessments and expert coaching at every level, SparkEffect helps organizations manage change, sustain growth, and chart a path to a brighter future.
Go to sparkeffect.com/edge now and download your complimentary Professional and Organizational Alignment Review today.
About Jason Silver, Founder and author of Your Grass is Greener
Jason Silver is a multi-time founder of kids and a multi-time founder of companies. He gets his biggest thrill helping modern employees and their teams unlock a better way to work—surfing is a close second. He was an early employee at Airbnb and helped build an AI company from the ground up back before AI was the cool thing to do. Today, he as a self-professed “Startup Personal Trainer”, advises a startup portfolio valued in the billions on how to build great, lasting companies that people actually enjoy working for. He’s a sought-after public speaker, instructor, and advisor on how to transform work into one of the biggest drivers of positivity in your life. When he’s not busy helping people solve their hardest workplace challenges, Jason’s kids are busy reminding him just how much of a work in progress he still is too.
Connect with Jason Silver:
Website: thejasonsilver.com
Book: Your Grass is Greener: Use What You Have. Get What You Want. At Work and In Life
LinkedIn: linkedin.com/in/silverjay
Connect with Maria:
Get Maria’s books on empathy: Red-Slice.com/books
Learn more about Maria’s work: Red-Slice.com
Hire Maria to speak: Red-Slice.com/Speaker-Maria-Ross
Take the LinkedIn Learning Course! Leading with Empathy
LinkedIn: Maria Ross
Instagram: @redslicemaria
Facebook: Red Slice
Threads: @redslicemaria
FULL TRANSCRIPT:
Welcome to the empathy edge podcast, the show that proves why cash flow, creativity and compassion are not mutually exclusive. I’m your host, Maria Ross, I’m a speaker, author, mom, facilitator and empathy advocate. And here you’ll meet trailblazing leaders and executives, authors and experts who embrace empathy to achieve radical success. We discuss all facets of empathy, from trends and research to the future of work to how to heal societal divisions and collaborate more effectively. Our goal is to redefine success and prove that empathy isn’t just good for society, it’s great for business. Work can be one of the biggest drivers of positivity in your life, but no one ever really explains how to be successful without sacrificing everything outside of the office. When you enjoy your work, you’re more successful, and any joy you feel on the job spills over into the rest of your life as well, kind of like practicing empathy at work and bringing that skill home with you. Jason silver, author of your grass is greener, use what you have, get what you want at work and in life, is a multi time founder of kids and a multi time founder of companies. He gets his biggest thrill helping modern employees and their teams unlock a better way to work. Surfing is a close second for him. He was an early employee at Airbnb and helped build an AI company from the ground up, back before AI was the cool thing to do today, he’s a self professed startup personal trainer. Advises a startup portfolio valued in the billions on how to build great, lasting companies that people actually enjoy working for. Today, Jason and I discuss why leaning into values matters, what he learned about people centric leadership at Airbnb and how he carried that into his other successful endeavors. He shares nine of the most common workplace challenges, why the term best practice is dangerous and the difference between intention and purpose. He also shares powerful habits to find more enjoyment at work, which he says is not the fluff, but the fuel. And he tells you exactly how to ask your boss to allow you to do your work in ways you enjoy more. Finally, we discuss why it’s easy for leaders to attribute cost, but less easy to attribute exponential benefits when you focus on enjoyment and people first. This was a great one. Take a listen. Welcome Jason silver to the empathy edge podcast. We’re here to talk about all things empathy, all things values and all things about loving the job that you have. Welcome to the show.
Jason Silver 02:46
Thank you, Todd for having me, Maria, excited to chat. So before we
Maria Ross 02:49
get started, I want to ask you. What I ask all my guests is, what is your story, what got you to this place and the work that you’re doing, and especially to writing this book, your grass is always greener. Great title, by the way.
Jason Silver 03:00
Thank you. It’s a bit of a circuitous journey that, like, makes sense when you look back and was is still always frightening while I’m my way through it. But, you know, long story short, I never intended to write a book. You know, people will be like, oh, there’s, you know, the author of the book. And I’m like, looking behind me, like, who are they talking about? But I was an engineer by training. Thought I would be technical work on a bunch of technology got really interested in everything that goes around the technology. How do you build a team? A great company joined my first startup in business, which was kind of the first entrepreneurial thing I did. I wanted to work in business. Didn’t want to get an MBA. Said, Hey, let me come and work here for free, for a little bit nothing on paper says I can do business, but like, let’s just see what happens. I got very lucky. It went great. CEO kind of took me under his wing and was like, You don’t talk, but you sit here and you take notes and you can sit in a bunch of different chairs. Great, great. So I learned about, you know, fundraising and partnership deals and commercialization and yada yada yada yada. The company got acquired. I had a software project on the side which was taking like 30 hours a week. It was a lot on the side. So I jumped. Started my first company hit like a double or a single. Wanted to go bigger. Founded another company, raised venture capital, built a team. Crash that company, which was always an interesting story, happy to talk about
Maria Ross 04:20
it. Oh yeah. I mean, I lived through, through both tech bus, both the night, the one in 99 and then the one in 2008 so, yeah,
Jason Silver 04:27
yeah, it was, that was an experience for sure. You know, I thought my career was done. Like, that’s it, you know, I was 20 something, and I was like, Well, I will never get hired again. Nobody will ever put money in a company again. Like, I peaked. We’re done here. That was a nice run. Let me go be a barista. Yeah, that’s right, yeah, that’s not what happened. One of my investors, whose money I almost entirely lost, thought enough of the way I handled building the company. What happened? He called me up one day and he said, Jay, there’s this team. I think you could be a great fit while you have a chat with them. And that was the folks at Airbnb back before. Airbnb. Was Airbnb, right, met them, got to, you know, experience what the the unicorn in the valley was before it was the big, cool thing to do. So, you know, I was there and we were a couple 100 people got to feel the like scale up to a couple 1000, which was, you know, crazy, lots of learnings there. Wanted to do a startup. Again, had my first kid coming, wanted to be based in the city that, you know, my family’s in. So I did the only thing that feel logical, like, jump started another company. I joined a company that had been started, but there were, like, two people and a half a pitch deck and, like, right, you know, times, and that was in artificial intelligence before artificial intelligence was the coolest thing that everybody was working on. So it was, you know, fun to be kind of early in there, you know, hit a moment in my life where I wanted to do something different and pay forward all the things I’ve been very fortunate to learn. And now I basically advise other people how to build their companies so that, you know, they love their jobs, and the people who work for the companies love their jobs and have a great experience as well, and yada yada that led to the book in a way I never would have expected. Okay,
Maria Ross 06:05
so, so many things in there. First of all, you need to play the lottery just how you fell into these tech companies that did well. Also, I love that you call yourself a startup personal trainer to really guide a startup to success and help them achieve their goals. But you made a shift in your career from numbers to people, and you say it started with your time at Airbnb. Can you talk about that? Yeah,
Jason Silver 06:28
sure. You know, I think because of my engineering upbringing, you know, everything for me was like a technical problem. I I value the education I got in engineering, like the problem solving skills and what have you, but it led me astray in a lot of leadership ways. And what I learned from airb, what I thought I knew about leadership, was, okay, we’ve got a job. We need to get done an outcome we’re trying to deliver. People are one of many inputs, but they’re interchangeable, right? What we need are humans that can do certain things, and if you get humans that can do certain things and will accomplish certain things as a result. For me, I learned that for me, that is wrong. Might work for other people, it doesn’t, you know, work for me and I don’t. It’s not what I’ve seen create the best teams, and what I learned at Airbnb, and the way I think about business now is, you know, you show me a problem. My first question is not going to be, let’s say we’re trying to double sales. Most people will start with, oh, like, what market are you in? What does the product look like? I’m like, tell me about the people who are working on this problem. What are they doing? What are they interested in? What are they motivated by? What’s going on in their in their lives? You know, really like people first. And it’s that old adage, you know, you know, you take care of your people, and they’ll take care of the problems. And so I really genuinely believe that, and Airbnb is the first place that I saw in action, to the point where, after I joined, I was, like, a month or two in, and I was just like, What the heck is this place like this? Can’t, if not for the if not for the scaling I was seeing us doing. I would not have believed somebody describing to me that these business practices would lead to these kind of outcomes. I’d be like, Oh, yeah. What you’re describing is like, you know, not the way that a type A should strive and drive and whatever right. Super long about that. Can
Maria Ross 08:18
you give a few examples of some of those,
Jason Silver 08:20
like, things that Airbnb did, or things that I kind of took that were
Maria Ross 08:24
surprising to you, of like, how can you lead your company to success operating that way?
Jason Silver 08:29
Yeah, I maybe two would kind of pop out. Airbnb, in my personal experience, is like the lead worldwide leader in off sites. You know, this was way before remote work was, like, the hottest topic and all that kind of stuff, but the amount of time that I spent flying to, like other offices to meet with their teams with very loose agendas, and I would go to these things, or people would come to, you know, where I was based, like, a lot of high horsepower individuals who are being paid a lot of money to sit In a room and talk about what’s going on inside of the business. I was just like, hey, can we stop doing this? I have work to get done. Like, we gotta go do stuff. Yeah, what I didn’t realize is there’s so much that comes out of that. If you can’t, there’s no straight line ROI for a thing like that. And it was just baked into the culture. You know, every so often we need to get together in a room. And when things are growing so quickly, you just put people in a room, and there’s some kind of cross pollination that happens, and you can’t predict the outcome. You just do the job very you know well, and the job being, put people in the room, create the right atmosphere, get the right people around the table, give them the right prompting question. And you know, more often than not, something great is going to come out of the other end. You just don’t know where or when it’s going to happen. And I think that I looked at it as a detractor, you know, this is a thing that slows us down. I think it was the opposite, in retrospect. It was something that sped us up. It was a thing that allowed us to go much more quickly. Because. As, you know, as I was kind of progressing at Airbnb, I started to work on more global stuff. And, you know, I would know the team from Japan, like personally, I know what’s going on for them. I know how they’re thinking about things. It doesn’t come up in regular meetings, you know, just doesn’t happen, yeah, but because I know them, it’s like, I could call them up. We can move a thing faster. I can put myself in their shoes better than I otherwise would have been able to. And huge, huge, huge benefit.
Maria Ross 10:25
I love that realization, because that is the crux of my work. Is that, you know, when people say it takes too long to be an empathetic leader, they make the same argument about strategy. It takes too long to sit down and do the strategy when we’ve got to get the tactics going right. That’s a very quarter to quarter mindset, very short term thinking. You’re going to pay the price for that at some point. So you might as well put the money and time in up front and accelerate faster to your point that when you take the time to build those relationships, when you take the time to get to know the people on your team, when you take the time to work, not in the business, but on the business. Like, let’s pick our heads up and look six months out, one year out. And I love what you said about putting the right people in the room, prompting them with the right questions, and then, sort of like, you know, getting your popcorn out and seeing what happens. Because people, if you’re hiring the right people, they will rise to the occasion in many circumstances, not all, but in many circumstances that the command and control model doesn’t work anymore. In today’s world, it’s moving too fast. It’s changing too much, and our problems are too complex, and it requires us to spend the time on these interpersonal relationships to actually be able to, in the end, move forward faster. And I love that you came to that realization having come from an engineering background.
Jason Silver 11:51
You know, I think there’s a good expression, like, if you want to go fast, go alone. If you want to go far, go together. And I think that kind of always stuck with me. And, you know, pulling the thinking out of Airbnb, that the challenge that I’ve seen that similar to what you described, is, I think there’s a big attribution mismatch. The challenge is that it’s really easy to attribute the cost to something like being an empathetic leader or to doing an off site or what have you, and it’s very difficult, bordering on impossible, to attribute the benefit, right? Because I can tell you, Okay, I spend this much time traveling to the place, and I spend this much time at the off site that I could spend working on other things, and it costs us this much money to run the off site. And then you’re like, Okay, great. The cost is X amount of hours, X amount of dollars. Well, what did that get us right. You know, you’re not going to know the benefit that it is providing over the years as things are evolving and changing, because there’s no through line. And I think that would kind of take me to the second point, which we touched on a little bit before we hopped on here about values. This is one of these things that I think you have to invest in, because you believe that, you know, taken on the whole an investment in this nature will be better for the business than it will than that. And you just have to say, okay, you know what? We can’t win this attribution game, right? We’re never going to know exactly what it does. It’s baked into our core values that people matter. And here we’re going to make business decisions behind that, believing that it’s the right thing to do. Airbnb was the first place that I really saw lean into values in like an appreciable it’s not a poster on the wall. There were a lot of things we could improve, for sure, but there was such a heavy lean into values, yeah, that it stuck with me. It’s so much of what I learned there became the foundation for the next company that I was a part of building, and I’m so grateful for it, because we got to put it in from ground zero versus Exactly.
Maria Ross 13:44
Yeah. I mean, that’s why I love when I do my brand strategy engagements, which are fewer now, but it’s really great to work with companies at an earlier stage, because you can start to bake that into the DNA, and you can take the energy and the excitement and the values that they actually do bring to the table when they’re a smaller team, and figure out a way to operationalize that so as they scale, they don’t lose who they are. Yeah, versus it’s way easier. Yeah, exactly, exactly. And I love what you’re saying about assessing the cost, because this is often when people say, Well, how do I measure empathy? And I used to try to do, years ago, I used to try to do a song and dance around that of like, well, you know, it depends on what your definition of empathy is, and how do you measure that, and is it about, you know, increased collaboration. Now I’ve moved completely away from that, because you shouldn’t be measuring empathy. You should be measuring your objectives and your goals, and empathy should be fueling the ability to achieve them, right? So we’re not measuring that. That’s like saying we need to measure respect in our organization, or we need to measure hierarchy, or, you know, it just, it’s not the end goal. The end goal is not to say, you know, check a bunch of boxes that, yep, we’re an empathetic organization. I mean, we tanked our quarters, but you know what? An empathetic organization, so that doesn’t really matter. So it’s lever you can pull to get to those objectives faster, more cleanly and without leaving anyone behind. And you get people excited about working there. You get people excited about coming to work every day, because they all know that they’re to achieve that mission and that objective, and that the objective is not necessarily, you know, let’s be empathetic to each other. The objective is something else, and we’re going to get there by practicing empathy with each other. I think that’s a paradigm shift for people. I
Jason Silver 15:32
think about it the same way, you know, the objective is where we’re going, and empathy, for me, is a value which describes how we get there. Yeah, exactly. You know, assuming our company had a value of empathy, we would say, Great, we can list all the ways we’re not going to accomplish this particular objective. Like, I’m not going to accomplish it by the command and control style that you mentioned, and I’m not going to accomplish it by I could list all sorts of, you know, less than stellar leadership traits. If we want to go down that particular we’ll do that in another episode. Yeah. The point is, it’s all about, you know, you’re making a bet, and you’re saying, of the of all of the possible versions of our company accomplishing these objectives, this is the one that we’re betting on. It acts in this way. It behaves in this way. And for me, that’s all about the values and whether or not they’re truly a part of the company.
Maria Ross 16:17
Well, I think, you know, my new book, clarity is one of the five pillars of effective and empathetic leadership, and part of the clarity discussion in the book is that you have to actually explain and articulate your values. Again, not just a bullet point, but when we say empathy is a value, what does that actually look like in practice? Give people tangible examples of behaviors or practices that exhibit empathy. So they have some bearing. They have some way to know how they’re getting there. And for different companies that could look different, maybe they’re not even calling it empathy. Maybe, like Airbnb, they’re calling it service, or they’re calling it something else, and it the name of it doesn’t matter as much as the if you’re going to say this is your value, you need to explain to each and every person what that actually means and what it looks like in practice. And so I’m curious, because you did have this wonderful experience with Airbnb, and then you move on, and you’re working with other companies that are, you know, a little less enlightened about looking at values and looking at people centered leadership that way. So what was there, sort of a culture shock moment for you, of like, oh, not everybody does it this way.
Jason Silver 17:28
No, you know, I think everyone, every company, is different, right? And I think it would be arrogant of me to say, Okay, this is the right way or the wrong right. Of course, it’s not right or wrong. And I think a thing I struggled with, you know, because I went from Airbnb, built the company, obviously, I didn’t define the way that company operated, but I was a part of it. And, you know, fingerprints were all over. And then I started talking to other companies, and I found that in my role, people would often, yeah, I’d be working with a CEO, and we would work on a thing, and they’re like, hey, is this right or wrong? What do you think? Right? And I struggle with that question, yeah? Because, you know, the number of times that I’ve seen a business or a product, I’m like, that is just going to absolutely crush it. This is going to be the greatest thing ever, and it Hey, or the opposite, I’m like, what this is not, yeah, ever, yeah, work. And it goes through the roof, you know? And I think I struggle with it, because I’m not really an Oracle. And so the thing that I try to do, like my work with a lot of companies, is so intentionally focused on intentionality. What I try to help them understand is, like, what is your intent? And then what I can do for you that’s hard when you’re in the weeds, is I can tell you, are you aligned or not with the intent as stated? And for me, that was the thing where I, when I see that I really try to help a company, is like, you’ve told me you want to be empathetic, you’ve told me you want to have your values in or you’ve told me that you’re, you know, trying to create upward mobility for your people. Here’s what I’m seeing, the actions feel misaligned from the intent. I’m not going to tell you whether that’s right or wrong, because maybe we need to change the intention. The market has changed. The business has changed, we change our intention and we march forward, right? But right? It’s that simple, but not easy. Yeah, if you have an intent, you’re either aligned with it or you’re not. And if you’re not, you either get aligned with it or you change a decision to be changed. That’s why. But we should always be trying to be intentional. Do
Maria Ross 19:18
you equate intent with purpose? Ah,
Jason Silver 19:23
I think in the way I interpret your question, no, you know, for me, like the conventional definition of purpose, you know, like, why are we here? Yeah, yeah, it’s like a big overarching philosophical thing. So they’re related. Maybe I would think about them as, like, first cousins or something. But like, the intent can get highly tactical. You know, you can go right down to the intent of, like, we’re trying to accomplish this objective. What’s the intention behind it? Right? Like, the intent can be, we value empathy, like, what is the intention behind that? You know, that’s the key piece. And I don’t think I’m doing the world’s perfect job of articulating the difference, but they feel. Little different in my head,
Maria Ross 20:00
I get you, I think what you’re if I can reflect back, it sounds like you’re saying purpose is, again, more of the like, it’s the mission we’re on, why we’re here, but the intent is maybe related to specific initiatives and maybe even programmatic elements or actions that you’re taking in pursuit of that purpose.
Jason Silver 20:18
Yeah, I think like purpose sits on top of the intents, like every intent should fit inside of the purpose, for sure. Yeah. But I think, you know, every objective, why do we have that objective? What’s the intention behind it? If this is a value, why is it there? What’s the intention behind it? Are we acting in accordance with our intentions? Yes or no. And that can go from, you know, everybody, from the CEO, down to like, you know, you’re working in your job, and you a common problem I talked to lots of folks about is, I get to the end of the week, I feel like I’m really busy. I’m very burned out. I did so much stuff, but I did, didn’t accomplish what I needed to accomplish. And so you don’t feel great like, Well, why did that happen? You know, was it an intentional week? Did you get pulled off of your top priorities on purpose? In which case, great, that’s probably, you know, you made an on purpose decision to move off of what you thought was the most important stuff. Or did it drift unintentionally? Right? And is that an opportunity for you to say, Great, I can have much more intent around what I’m being pulled off of how I’m being pulled off.
Maria Ross 21:16
Yeah, I think we could all do in our companies with as fast as they’re going to have that kind of reflection modeled and rewarded more that it’s not a waste of time to sit and think about, how did the week go? What went wrong? Why did it go wrong? We’re always on to the next thing, and then with that, we lose the learnings from even if something failed, we should be able to learn from that, and we can’t learn from it if we don’t take time to stop for a second and say, let’s look at this. Was this actually the way I wanted this project to go? Was this actually the way I wanted this week to go? Was this the way I wanted this meeting to go, or this interaction or this performance review? We don’t take enough reflection time and again with my book, The first pillar is self awareness, and self awareness requires that pause that let me take a look and from you know, float above myself and try to be objective about why this is going right or why this is going wrong, and how am I showing up in the interaction. So I love that idea of intentionality, and you being that sort of coach and Sherpa to get them to drift back on course, so to speak.
Jason Silver 22:25
Yeah, it’s the difference between being responsive and being reactive. Exactly. Reactive is you just, you’re flying around, doing the thing, and responsive is, my intention was x, you know, I’m moving towards y, quick check. Is that what I want to do? Yeah, it is. Okay, great. Now my intention is why, and let’s go. It doesn’t take a lot.
Maria Ross 22:43
What’s really interesting is, I worked for many startups. I did a whole startup, merry go round for a while in the early 2000s and a few of them, it was just so running, running, running, and feeling like we didn’t know where we were running towards. And it was and it was so frustrating. Yeah, yeah. It was so frustrating, because it felt like the whims of whoever the CEO talked to last would become part of what we were supposed to work on that week. Yeah. And it just leaves you, you know, from a, you know, kind of segueing into your book. It leaves you really demoralized by the work. It leaves you very like, either I’m just like, I don’t even want to start something, because I know it’s going to change in three change in three days. I don’t want to put all this work into it, or just feeling unmoored, like I don’t know why I’m here. I don’t know where we’re trying to go, and if I do finally get a grasp of where we’re trying to go. And, you know, I was younger then I was like, manager level, you know, very early director level, and I didn’t even know I was supposed to know that. I didn’t even know that that was actually that I was being shown. A bad example, I guess I should say I didn’t realize. I thought that’s just the way it was. And so frustrating, because I look back on those roles and I’m like, gosh, we could have done so much more. We could, you know, and I could have done so much more if I’d known what it was supposed to look like and the questions that we should have been asking. It doesn’t mean I would have been able to impact it any differently, but I kind of internalized it as like, well, I don’t know what I’m doing, because I constantly felt like I didn’t know what I was doing in those jobs, because the strategy changed every day, depending on the last analyst the CEO talked to, or the last person they talked to, or the last peer. It was like, Nope, this week, it’s this. And then I was like, Okay, well, let’s crumple up that plan. And so I’m curious to know, you know, what is kind of your overall thought about enjoying your job? We hear that right? Like that’s something people want. They want to enjoy their job. So I want to just get strip that down and in your definition from the book, what does it mean to enjoy your job?
Jason Silver 24:51
Good question. So, you know, I think we often confuse the words enjoyment and fun in a way that’s unhelpful. So fun is always. Is enjoyable. Enjoyment is not always fun. You know? I think the best example of that is, you know, you go for a run, you’re running a marathon, you’re in the last mile, you’re probably not having fun. You may not necessarily be enjoying that particular moment, but when you finish the race, you enjoy the entirety of the race. Assuming you’re somebody who enjoys running, if you hate running, if you hate running, you’re probably not going to like that process at all. None of it will be good. Yeah, right. When I think back on some of the most enjoyable times in my career, it’s not the moment when, like, there was no stress, there was no adversity, there was nothing challenging. You know, it’s the moments where a bunch of us are in a room there’s a major problem. We don’t know if we’re going to solve it. The impact is going to be huge. We’re all jamming away on this problem. We don’t know if we’re going to get it. Figured out it figured out. You know, you play the tape board and whatever happens, happens. I’m like, that was such a professionally enjoyable moment. I was not having fun at that time in that moment, but it’s about enjoying the job overall. And I think what I struggled with earlier in my career is this idea that, like the most common pushback I get is, man, I don’t have time to enjoy stuff. I’ve got things to get done. Yeah, right? I’m busy. I’ll enjoy it later. You know, my usual, my model years ago, was, it’ll be great. I’ll enjoy it when I insert accomplishment here, sell this company, that company goes public, like, get this promotion, find some new job. What I’ve learned is like, that’s not the way our brains work. It’s not what you wind up enjoying. You know, you got to think about, in my experience, you got to think about the day to day. And there’s a lot that we have control over. A lot of times it just feels like I have no real control over this, because I have to get these things done, and because I have to get these things done, and they’re not the most fun, I can’t enjoy my job right now. There’s nothing I nothing I can, right, right? And so I wrote this book to show people that actually, you know, enjoyment isn’t the fluff. Enjoyment is the fuel of your accomplishment. The more you’re enjoying your work, the more likely it is that you accomplish bigger and bigger things. The more you accomplish, the more you enjoy, it. The more you enjoy it, the more you accomplish. And it’s a big, gigantic flywheel of greatness that just goes up and up. The problem is, you know, Google it and you know, how do I enjoy my job? You’ll get a bunch of useless platitudes. Find a job you enjoy. You’ll never work a day in your life. Yeah, great. Show me that person. Yeah, right. You know, work smarter, not harder. Like, I’m waking up every day trying to work dumb, like, what do you I don’t know if I knew it to be differently, I would do it right. And so the book is effectively nine of the most common workplace challenges with very I’ve been told, unconventional tactics that are completely within people’s control, like they can read the book, put it down, try it at work tomorrow. Doesn’t matter. You know who your boss is, or what your job is, or what your to dos are. You can try them and you know they’ll make a difference. And if they don’t, it’s a great indication, if you try all nine and nothing changes for you, then it’s a good indication that there might be something external that you need to do. Maybe it’s something maybe it’s something about your environment. Of course, there are toxic work environments. I’m not saying you can, you know, change all of those, but Right, most of the time we think it’s out of my control, or I have to change my environment. And I’ve seen the
Maria Ross 28:15
so this is so funny, because everything you’re saying keeps coming back to the book, and not to be like plugging my book either, but it’s this idea. My fifth pillar is joy, of what makes an effective, effective and empathetic leader. And I don’t mean I say it right there. It doesn’t mean you’re the funniest workplace in the world. It’s can you find moments of levity when the work is hard? Can you find things that are enjoyable when the work is hard? You know, I looked at emergency room departments. I looked at like police stations. I talked to people from different environments that even if you can create, it was one example, if you can create a sense of camaraderie and have a friend at work, that’s an indicator that you are actually going to be more engaged. You are going to perform better. In some cases, it’s going to be less absenteeism, all of these things come about when you encourage work friendships in your team or in your environment. That’s just one example, and that’s why I didn’t call that pillar fun, because it’s not really fun because, again, sometimes you do have to do budget spreadsheets. That’s not fun, unless the reason why it’s called you love accounting, right? Yeah, exactly. And I see a lot of advice going out there to people, you know, and it started with the whole follow your bliss, or, you know, live your bliss thing, that whole movement. But, you know, advice to young people of like, well, you need to have a conversation with your manager if you find that doing reports is really draining your energy. And I think this is the like, you know? I mean, it’s not always fun, 24/7 right? Yeah,
Jason Silver 29:47
well, yes. And I think there’s always going to be stuff that exists on the fringe that you accept, right? But I think on the most part, it is possible to enjoy the majority of your work, and I think you’re hitting on. A point, and I’ll give you like an example and an exercise people can try and if they have a thing to do with their teams. So you’re the point you’re hitting on that I talked about in my book, that I think is really critical is I really think that the term best practice is misused and very dangerous, and the reason why is because the best practice for me is unlikely to be the best practice for you, and it’s unlikely to be the best practice for somebody else. So the analogy, you know, I would use, is like, you open up your phone and you go to Google Maps, and you’re going to a restaurant, right? And you plug it in, it’s not just going from A to B, it’s like Google gives you options. Do you want to take public transit? Do you want to walk? Are you going to walk? Are you going to be on a bike? Do you if you’re going to drive? Do you want to take the most economical route, the most scenic route, right? We can go from A to B, the point is to get to B, but the way we get there is kind of up in the air, right? And so your boss might say to you, let’s take you and I as hypothetical examples. And I’m the person that you just described who really likes spreadsheets, and you’re the person who threads them.
Maria Ross 31:01
I’d rather poke my eye out with a sharp stick. Yeah, exactly, you know, and you want
Jason Silver 31:05
to go give a big presentation. I also love presentations, but I’m going to play the spreadsheet guy for the purposes of this conversation, as long as there are no follow up questions, okay? And we both are handed the same task, okay? And the task is, we got to give a project update at the end of the week. My version is the like analytical spreadsheet guy is, I’m going to go collect a bunch of data, I’m going to crunch it in a spreadsheet. I’m going to send around an email to the team in advance with everything I found, and say, come to the meeting with any questions. We go to the meeting. They ask their questions. I get back the answers. I updated everybody on the project. Objective accomplished. You are going to go talk to a bunch of people on the team, see what’s going on. You’re going on. You’re going to build a beautiful presentation that tells a really nice, engaging story. You’re going to stand up in front of the team, give your presentation. People are going to ask questions. The meeting will end. Both of us accomplished the same objective, yes, but we did it in two completely different ways. And if you gave me your version or vice versa, we would be miserable, right? And so the whole point of the book is, it’s about how, right? Yeah, I’m not telling you that you have to change your to do list. We still have to deliver the project update, right? But if you change the way you’re accomplishing it, you can enjoy it a heck of a lot more, especially the exercise, which is the major problem most of us. We talked about knowing yourself and self reflection stuff, most of us don’t know that much about what we enjoy doing, so I’ll give folks an exercise. They can try. You can try too. If you’d like to, you need a piece of paper and a pencil in your calendar. Pretty simple, okay, on you’re going to take the piece of paper and on the left side of the page, you’re going to write a list of activities at work that you enjoy. You know, I really like brainstorming sessions. I really like crunching numbers in a spreadsheet, whatever it is, these are things I enjoy doing, right? And if you’re like most people, your list will be more than four things, less than 15 things, you know, a handful of items. Okay, then on the right side of the piece of paper, you’re going to open up your calendar, and you’re going to look at last week, and you’re going to write down the things that you did right? I went to this meeting where we did this thing. I talked to this customer about that thing. I worked on this HR problem. And when that’s done, you’re going to draw a line from the things you enjoy on the left to any of the things that you actually did on the right. Oh, and if you’re like most people, you will have few to none, few to no, lines, right? And then you will think, Well, why don’t I enjoy my day to day job? Look at your piece of paper. It will tell you why. Yeah, right. And if you want to do one thing to make your job more enjoyable tomorrow. Look at your list when you’re given a task and find a way to accomplish it that incorporates at least one of the items on the list right, and that will result in you enjoying the process more, and it will very likely result in it being a better work product at the end of it. And so the to do list doesn’t change, no how you talk. It’s
Maria Ross 34:02
the how. So, okay, first of all, I love this idea, because best practices are really just ideas. They’re suggestions that might work, might or might not work for you, right? So I love that point, but it’s also this point that you know, I’ve done with my clients when working, you know, a lot of my clients are doing their own marketing, and I’m like, Okay, your goal is to generate leads. Your goal is to generate revenue and get customers. If your solopreneur as an example, why on earth would you engage in a marketing tactic that you hate? Because it’s going to be clear and obvious when you’re engaged in it, that you’re not nuts about it, that you’re throwing it in. So there’s lots of different ways you can actually reach your target market. Do you like podcasting? Do you like speaking? Do you like writing emails? Do you like being on Facebook or Instagram or Tiktok? Like find the intersection the then. Diagram of what will effectively reach my target audience, and what do I enjoy? Yeah, and only engage in the things in the middle. So I what I hear you saying is the same thing for your job is find a way to engage in the work you need to get done, and make the Venn diagram of the things that you enjoy doing, and try to find ways to accomplish the work that needs to get done by enjoying it, if you can. If that’s in your control,
Jason Silver 35:27
it’s the silliest thing, right? But like, if you want to enjoy your job more, do more work that you enjoy. And what that usually gets translated as is, go find a job that you enjoy overall, but Right? Or that you’re only doing things you’re you enjoy. That’s right? And that’s so rare, you know, I think you practice a job, you practice enjoyment at work. It’s not a thing that exists, right? And so, like, what you’re saying is, you know, hitting home, obviously quite a lot for me, because you’re kind of, you’re preaching the language. But the point really is just, you have to accomplish some things, and you’re looking for that overlap. But what I see a lot of teams do, and the way that I think we’re all kind of hardwired at work is we spend all of our time thinking about what needs to be accomplished, what are the goals, what’s the Gantt chart, whatever. And we think that because something like enjoyment is fluff and it doesn’t matter, you don’t carve out any time to think about it. And so what I’m suggesting is spend this 95% of your time on all the stuff you’re currently doing. What do I have to accomplish? What’s the Gantt chart? What’s the backlog? What’s the whatever structure you use? Take 5% small amount, and just have your list and say, I know what needs to be done. Now I’m going to spend a little bit of time being intentional about how I’m accomplishing it. And you mentioned, you know, if it’s in your control, if you know it is possible that you have a boss who is so micro managing that they will literally stand over your desk and tell you what keys to press on your keyboard. That’s very, very rare. You might have a boss who’s controlling and likes you to do things a certain way. Yeah, the best thing you can do in those situations, it’s not easy to go to your boss and say, I want to enjoy my job more. What can I do? But if instead, you go to your boss and you say, Hey, I know I have this project update at the end of the week, and I know it’s usually done in a presentation format, I’ve done some thinking, and I would really enjoy doing it in the way I described earlier, and ask them this question, what would need to be true for me to try it that way, and the wording of the question is very intentional. You’re not asking them if you can, you’re asking them to list the factors that would need to be true in order for you to try it that way. And that makes it a very productive conversation, because you’re giving them something very specific that they can measure the risks against. They can articulate the risks to you. Hey, I need you to make sure that you include this in whatever your email is that goes out in advance, and I need us to check in afterwards to make sure that you landed what needed to be landed. Since you’re asking you to do it anyway, great. I can do that. That means I get to try it this way. I want to do it. Let’s go from time to time. Obviously your manager is going to tell you, no, sorry, Jay, you can’t do it this way, and that’s okay. But by asking this question, you’re going to show your manager that you’re thinking about this, and maybe they don’t let you do it your way this time, but the next time, or the time after that, or the time after that, they’re going to and they’re going to start to see the result, and it will kind of build over time from there. So what would need to be true for me to try it, insert the specific approach that you have. I love
Maria Ross 38:25
that so great. Okay, let’s talk a little bit more about the book in the in the short time that we have left. You know, you’ve done a lot of research and coaching around things like imposter syndrome and also about how empathy is the key to helping folks deal with that specific brand of self confidence or anxiety, because that can actually take away a lot of our enjoyment in our jobs, because we’re dealing with imposter syndrome or self doubt, or, you know, whatever you want to call it. So what is the role of empathy in helping us deal with that kind of lack of self confidence or anxiety about our job. Yeah,
Jason Silver 39:02
so imposter syndrome is this interesting one. I think it’s poorly branded, is my opinion. And it’s kind of the question and the answer all rolled into one. So the first thought in it is, if, like, we all feel it, if I’m an imposter, you know, the stats are something like 80% of people feel imposter syndrome at some point in their lives, in their careers. If that’s true, we’re all imposters, and we can’t all be imposters. So this thing just needs, like a fundamental rebrand. And the idea is that, you know, I don’t feel like I can fit in with this group of really great people. They’re better than me. I don’t have enough or whatever, whatever it might be. And the common advice here that I see is, I think, wholly useless. Believe in yourself. You can accomplish anything, right? Like, just don’t have self doubt. It’s not a light switch, right? I’m not just like, Oh, I feel like doubting myself right now. I’m just gonna stop doubting myself, right? I. Yeah, it’s gonna go great. That doesn’t work. And I think it actually makes it worse, because you had a little bit of totally normal self doubt, then you label it as a syndrome. Now you have something wrong with you that you have to fix, right? You feel bad that you can’t fix this thing about you and you can’t get the job done. I’m like, I think it’s really corrosive. It doesn’t help Great. Rather, I think there’s a way to flip it on its head and turn it into a superpower. Lots of great research coming out of a bunch of different schools. One of the ones that I think is really interesting is some work that was done at MIT. And what they showed is they took they took doctors, and they put them into two groups, and let’s call them the the confident group and the not confident group. And then they had them go into these kind of mock physician visits, where they have to diagnose what the patient is presenting, and then they have the patients rank the doctors afterwards. Okay, so what they found is the folks who felt imposter syndrome performed equivalently in terms of their diagnostic capabilities versus the self confident ones. So they went in with self doubt, and they did just as well. So imposter syndrome isn’t hurting our ability to perform. But when they followed up with the patients afterward and asked them to rank folks, what the doctors what they found is consistently the folks in the self doubting group showed up as more other focused as they cared more. And so what’s happening is because you feel like you don’t belong, it makes you think more about how to help and show up well for others, which is in turn, making you more empathetic and you’re paying more attention to them, and you’re actually increasing the probability that you fit in, because you’re trying a bit harder. The question then is, well, what do I do about this?
Maria Ross 41:41
Because, because I’m like, I don’t want this to be the solution for how to be more empathetic in your job is to doubt yourself. Yeah,
Jason Silver 41:46
I’m not saying. What I’m saying instead is recognize the imposter syndrome as a trigger moment for something that can lead to a lot of greatness, right, right? If you go down the spiral of self doubt, and there are a lot of you know, if you have very severe imposter syndrome. It’s a very real thing. And if that’s where you’re at, I am not a psychiatrist. You should go and seek you know mental health for sure. It can be very, very effective if you’re not in that zone of debilitating it’s just it comes up for you regularly. It’s getting in your way. What can I do about I can’t make it go away. Recognize it as a trigger. I’m feeling self doubt in this moment, don’t turn it off. Instead, turn it into what will make you most belong. And there’s tons of research, mostly out of Harvard. What it shows is, if you want people to like you and you want to fit in, the number one thing you can do is ask them questions, very simple, so you don’t have to be like I’m an imposter syndrome. Let me flex with all this knowledge that I have and show them how smart I am. That is the anti solution. The better solution is I’m feeling imposter syndrome in this moment. It’s not the moment for me to show off what I know or really push myself out there. Instead, it’s an opportunity to learn. Do I actually have a knowledge gap? What is that knowledge gap? How can I go and figure that out? Okay, and so the antidote, or the thing that flips imposter syndrome from a syndrome to a superpower, is questions. The question is, what kind of questions and where? So I’ll tell people this, and they’ll say, Oh, God, I can’t ask questions in a meeting. It makes me feel very nervous. My colleagues are all around, yeah, and the research backs this up too. If you and I are in a meeting, talking a lot, and there’s five other people around listening to us. I ask you a lot of questions, you will be biased to like me more. Everybody listening will be biased to like you more. And
Maria Ross 43:29
oh, 100% curiosity is the number one trait of empathic people. Because you’re take you’re focusing on someone else. They always talk about when you know you meet someone for the first time, ask them about them. Don’t talk about yourself the whole time.
Jason Silver 43:41
Yes. And the tricky thing, though, is that in a meeting of 10 people, you will think, oh, Jay’s great. He’s so engaged. He’s listening to me. Everybody else be thinking that guy, Jay’s an idiot, like he doesn’t have any answers. You know, it’s all coming out of Maria. He’s just asking questions. Nobody’s hopefully, nobody’s consciously thinking this. But right, your brain is going through this bias, right? And so the findings from this work out of Harvard is the most effective questions are in one on one situations, and they’re follow up questions, which is great, because one on ones are the least risky environments, and follow up questions are the easiest, because you don’t have to know anything to ask them. You just have to listen, right? And so if you’re feeling imposter syndrome, the whole kind of gamut of the solution, there is not a problem unless you have a, you know, severe mental health problem. And I’m not trying to belittle that, right? For the for the average person, it’s an opportunity to create something really amazing for yourself. Recognize the imposter syndrome. Don’t turn it off. Pick somebody from the team, one human, get them on their own book. A coffee meeting with them. Grab them at lunch, whatever, and ask them follow up questions. Help me understand insert thing that they said in the meeting here, right? Help me understand that thing you said about the presentation you were. Yeah, help me understand what you meant when you talked
Maria Ross 45:02
about, I’m laughing, because this is part of the whole thing about finding common ground is the three magic words of Tell me more, right? Tell me more about that. Tell me more about and also, because then I can understand your point of view, and I don’t have to guess what it is. So from a from a linking it to empathy standpoint, I love this. So how does this relate to
Jason Silver 45:21
enjoying your work more? So imposter syndrome is one of the most commonly felt things at work. Like I said, 80% of people get it, and it is a huge detractor to your experience at work. If you’re constantly walking around with feelings of self doubt, you can’t get it done. Why am I not good enough? When that goes away, it is very, very freeing. And for me, what I found is there is no magic wand to wave to become more confident. It’s actually chipping away at removing the self doubt. And this tactic is a great way of just it comes up for me. I don’t get caught in it. I know what to do. I have a formula. I get somebody in a one on one, I ask them follow up questions, and all of a sudden, yeah, the self doubt becomes a thing that I’m looking for. Because I’m like, oh, when that crops up, it’s it’s telling me that I have a moment when I need to go and do a thing that I know works. So just feels great overall. So that
Maria Ross 46:17
sounds like that’s one of the most common workplace challenges, really briefly, because we want people to check out the book why your grass is always greener. What are some of the other common workplace challenges that we might be dealing with as you know, human beings in the workplace trying to interact with each other?
Jason Silver 46:33
Yeah. Sure. So the books divided into thirds. The first is all about freeing up more space and time for yourself. The second is about changing the way you work so you enjoy it more. And the third is about accelerating yourself without having to wait around for a promotion. So first third of the book, it’s all about how to do five days of work and four without changing your job at all, without working until midnight. The things that we talk about there are miscommunications, and how to stop them, because they’re costing you a full day every single work week, slow decision making and how it’s not just your boss’s problem, you can help make a big difference on it with some key tactics and effectively distractions and prioritizations and why that’s a psychological problem, and how to help yourself on them. Got imposter syndrome, which we talked about, how to measure your joy on the job, which is not something that’s talked about very much. You got to measure a thing before you can feel like you can move it. And then how to enjoy your job more, which we talked a little about, bit about earlier, the last third. All about how to progress faster without waiting for a promotion. There we talk about how to make better decisions. Feels great when you’re making really high caliber decisions. How to get more feedback, which is like the rocket fuel for that’s key yourself, yeah, and how to see opportunities that everybody else misses. Love it. I love it
Maria Ross 47:47
so much. I mean, yeah, that is really so much of this overlaps, because this idea of ego kills empathy is so huge, because when we are so focused on trying to play the expert in the room, that is when we overlook risks, when we miss opportunities, and, more importantly, when we miss that opportunity to connect with someone else and maybe find out what their experience is or their perspective is. So you know, this idea that leaders have to have all the answers, or that if I want to be a leader, I have to pretend I have all the answers, is such a false narrative, because we can be confident and say, You know what, I don’t know, but I’m going to find out, or I don’t know, but we’re going to find out together, or I don’t know, but here’s what the next steps we can take are to be more sure about this. You can say that in a confident way and let people know that you have a mastery of the situation, even if you don’t have the right answer in that moment. And so a lot of what you’re saying ties so much into that of being able to sort of take the focus off you and be observant about what’s going on for you and take a beat, and then being able to ask questions and interact with people in a way that you’re actually sharing your problem solving collaboratively versus like you as a leader or an aspiring leader, think that you have to show up with everything baked.
Jason Silver 49:12
I mean, totally agree. You know, I think, yeah, I know it’s not great to judge people, but we all do it. And like I judge people on the quality of their questions, not the answers. I think we live in a world where, you know, almost every answer is at the tip of my fingers. You know, I can go and ask chatgpt A question, as if it’s like the person sitting in the desk next to me, you know, I can Google things, yeah, but all of those things only work if you know the right question to ask right same thing at the office as well as I think great, the best leaders, I know, they ask the best questions to the right people. And those are the things that are very unlocking. Is you’re thinking about it this way, rather than jam my different idea down your throat, like, right? Here’s a question that will broaden your perspective, and then, oh, look at that. Yeah, we come up with an idea that. Better than both of ours combined.
Maria Ross 50:01
Yeah, clarity is not about asking. It’s not about having the right answer. It’s about asking the right questions that’s right and being able to spark that problem solving and spark that innovation. So I love it. Well, Jason, this has been such a great conversation. Thank you so much for your time. Today, we’re gonna have all your links in the show notes, including your link to your book, which I hope everyone will check out. How your book is called, your grass is greener. Use what you have, get what you want at work and in life. And for anyone who’s exercising while they’re listening to us, what’s the one best place they can go to to find out more about you and your work?
Jason Silver 50:36
Yeah, you can go to your grasses greener.com. That’ll take you to my website. You can see the book there. You can see me. If you really want to look me up, you can do it through the website. Find me on LinkedIn, but your grasses greener.com. Is the simplest, easiest thing folks can remember. I love it. Thank you so much for your time today. Thanks for having me, and thanks for everybody who is still jogging and listening to us and
Maria Ross 50:57
everyone. Thank you for listening to another episode of the empathy edge podcast. If you like what you heard, you know what to do. Please rate and review and share it with a friend or a colleague until next time, please remember that cash flow, creativity and compassion are not mutually exclusive. Take care and be kind. For more on how to achieve radical success through empathy. Visit the empathy edge.com there you can listen to past episodes, access show notes and free resources. Book me for a Keynote or workshop and sign up for our email list to get new episodes, insights, news and events. Please follow me on Instagram at Red slice. Maria, never forget, empathy is your superpower. Use it to make your work and the world a better place.
