Strong Leaders Serve with Teri Schmidt

162. Little Changes, Big Gains: Accelerating Team Decisions & Personal Fulfillment with Jason Silver

• Teri Schmidt

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Do you get frustrated by how slowly decisions are made at work? 

Our guest today has a solution for this AND practical insights from his newly released book "Your Grass is Greener" on finding joy in your work journey and boosting productivity, even in tough environments. 

Resources:







Connect on LinkedIn: https://www.linkedin.com/in/teri-m-schmidt/

Get 1-on-1 leadership support from Teri here: https://www.strongertoserve.com/coaching

Set up an intro call with Teri: https://calendly.com/terischmidt/discoverycall

How many of you get frustrated by how slowly it decisions are made at work? Yes, me too. That's why when Jason silver reached out to me to be on this podcast and talk about how we are unintentionally building teams for slow decision-making. I was intrigued. And I invited him on.

Teri Schmidt:

And we do get into his really simple tips. For speeding up team decision-making. later in the episode. The episode is about so much more. We focus in on the many topics and tips in his book titled your grass is. greener. Use what you have, get what you want. At work. And in life. I love the idea. That we can make. Work work for us, regardless of what role we're in. A little bit about Jason. Jason is a self-described multi-time founder of kids. Two boys. And a multi-time founder of companies. He gets his biggest thrill, helping other people enjoy the hard things in their lives. And for him, surfing is a close second to doing that. He was an early employee at Airbnb and he helped build an AI company from the ground up back before AI was the cool thing to do. Today, he spends his time advising a startup portfolio value. Uh, startup portfolio. Valued in the billions on how to build great lasting companies that people actually enjoy working for. We cover so much in this episode, and I know that you are going to enjoy it and find it at least one thing that you can start using today in your leadership. And make sure you access the bonus clip in which Jason and I discuss his unique view on the imposter syndrome. Have you ever heard anyone call imposter syndrome a superpower before. Well, Jason explains why he believes that it is and how you can use imposter syndrome to your benefit. So be sure to grab that at the link in the show notes. If you don't know me, I'm Terry Schmidt. I am an executive leadership coach and podcast hosts at strong leader serve. Where I love partnering with caring leaders and teams to accelerate their impact. And this is the strong leader serve podcast. Hey, Jason, welcome to the Strong Leaders Serve Podcast. I'm really looking forward to our conversation today.

Jason Silver:

Me too. Thanks a ton for having me.

Teri Schmidt:

Of course. Well, why don't we jump in? I, I gave a little bit of your background on the intro, but I would love just to hear from you more about your story and some of the experiences that led you to write the book. Your grasses greener. Mm-Hmm.

Jason Silver:

Yeah, sure. You know, it's, uh, depends how far back we want to go, but, uh, you know, 50, 000th of view is pretty technical coming up. Like I did two engineering degrees, thought I was going to be technical, got really interested in business, founded a couple of companies, you know, hit like a double, you know, no one was going to retire off of it, but pretty, you know, fun for my first couple tries. And then I was very fortunate to wind up at Airbnb in the earlier days there, which was an incredible experience. Got to see what it was like to have like true global up into the right growth. Uh, then went from there to founding, uh, uh, an AI company. This was back before AI was the coolest thing on the planet for everyone to be doing. It was really fun to be in on the very early days of that. And, I then hit a pretty hard moment in my life. I lost my sister. She passed away from cancer, and that news was obviously very hard when it hit, and it flipped my life upside down. I was building a company at the time. My sister was very sick. She eventually passed away. I had a young kid, um, and it was bad for all of the reasons that you could imagine it would be bad. And at the same time, it pushed me in a direction that has really shifted my life in a positive way that I think my sister would be proud of. And that was to really look at the way I was living my life and how I was working. And, uh, I went down this path of trying to understand. You know, why do people talk about work life balance? What does that even mean? Why am I working on the things I'm working? How does it fit into my life? Am I truly prioritizing my family in the way that I want to be day to day? Um, and I went down a very like Tim Ferriss y experimentation pathway of, I started with my life. Um, and it started with like, I was just trying to cope, you know, I, I didn't know how to go through something like this. I don't know that anybody does. I was pretty shattered. You know, I could see that I was bottoming it out, but I didn't know what to do. And so I just started reading tons and tons of books. And if someone out there said, this thing will help you feel better. Yeah, I tried it. Everything right. Like. Polyphasic sleeping, cold plunges, know, hanging from my arms for three minutes every day, you name it. I tried it. I tracked it all. And, uh, some things helped me feel better and other things were no good. So I, I scrapped them. and after time, I, I, I really felt like I was getting better and it was great. And, Hey, this, this is helping. And I could feel finally that it was slowly reversing the trend. And then I plateaued. And I tried to figure out why. And what I eventually realized is everything I was doing was focused on my quote unquote life outside of work.

Teri Schmidt:

Mm-Hmm.

Jason Silver:

And I realized I'm not really changing anything about work. I'm not doing any of this experimentation at work. I'm spending so much time at work. It's such a big part of my life. It's such a big part of who I am. I took the Tim Ferriss method that had worked in life and I applied it to work. And that's when things really started to take off. You know, I, I, I, Set more goals, less goals, no goals, work five days a week, four days a week, work really early in the mornings, work really late at night, no meetings, only meetings, like you name it, every productivity hack on the planet. I think I've probably tried some version of it. And over time, the same kind of thing happened, uh, that happened with the life hacks, plateaued. It's just been getting like better and better and better and better. And my team started to take notice, started to help them, tell them what I was doing. They started to, uh, you know, really get interested in it as well. And I made the choice to shift, to do this as like a full time focus. You know, I, I, always enjoyed building companies as a way to help people achieve and be the best versions of themselves, but profit was always there. Profit's always king. And I wanted to see, well, what would happen if I put all my energy into like, Can I help people who. Our overachievers are really care about achieving in their careers and don't want to sacrifice everything outside of the office, uh, to, to make that happen. You know, how do you still have that ambition, but have more space for the rest of your life, enjoy the rest of your life a little bit more. And I learned a lot of interesting lessons coming out of that. So I told you 50, 000 foot view. That was probably more like a five foot view. So I'll stop and

squadcaster-80gb_1_07-25-2024_101029:

No

Jason Silver:

see what way you want to go from there.

squadcaster-80gb_1_07-25-2024_101029:

that was great. And there, there are so many different directions that I would love to go. Um, first off, I just want to say as a data person, I love the fact that you did all these experiments and tracked how they are impacting you and not just on kind of a one off, but you were looking at trends as well. So speaking to that, I'm curious, why do you think it is that you plateaued in what you were doing? And, and the changes you were making in your personal life, but, and the results that you were seeing, but not so in those changes and the results you were seeing in your work life.

Jason Silver:

Yeah, it's a great question. I, I don't know for sure.

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

my best guess is there's only so much time that I'm spending, you know, on, I don't even really like having the distinction between life and work for me now, it's just

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

bubble, but there's only so many knobs you can tweak, right? You can do things with your body, what you put into it, you know, what kind of exercise regime you have. You can, you know, do things with your mind. What kind of meditation you do. Going to therapy was a big, helpful thing for me that I always had some stigma about, and I'm glad I got rid of that. But there's only so many knobs. And I think what I found at work is I haven't hit that ceiling yet of, I feel like I've tried all the knobs,

squadcaster-80gb_1_07-25-2024_101029:

Interesting.

Jason Silver:

there's just, there's so many of them. And each time a new project comes up or a new direction comes up or a new thing that I get excited about that I want to work on, it opens up a whole whack load of new things that I can experiment with, try with, et cetera. And so it, I haven't hit the ceiling yet. Will I? I don't know. You know, it's possible that there's some stuff, you know, outside of work that I just, I'd never heard about. And I still find out about that stuff, but it's just, You know, there's only so many big life changes that I can have that open up the doors to more experiments. You could try to run at work. It feels pretty endless. You know, I get to talk to you right now and that's going to create a whole bunch of new ideas for me and we'll see where it goes from there. And it's just new projects, new people, new places. There's more stuff to always be tinkering with.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. Yeah. That's, that's fascinating. And two points. I think your point about, you know, we spend so much time there, I, I always get a little sad. When I do see people kind of, you know, just right off work and, and say, it's going to be terrible, you know, there's nothing we can do about it. Let's just enjoy the time that we don't have to be there because, um, like you did, you know, I lost people very close to me early in life and kind of had a similar, um, effect of life is way too short. to live that way. Obviously, this is a, you know, could be considered a position of privilege in that, you know, if you have a choice to make work better, but I would argue that no matter where you are, there, there are knobs that you can tweak to make work better.

Jason Silver:

Yeah. You know, I think it's a. It is a good argument to make. And I think it is accurate to say that for some people in some situations, you can't do anything. Uh, and I think that's very hard, you know, and, and, and I feel for those people deeply and it's very challenging. And there are some like systemic changes that need to be put in place to help in those situations. Uh, but what I've found kind of walking the path I'm on now is that is the minority. You know, that, that's not most people, at least in the space that I walk, you know, and I, I work with a lot of folks who are in some version of knowledge work, working on their laptops, on teams, whatever. But what I found is a lot of people who have much more agency than they think, you know, they, they have this agency, but they're not looking at it in the, uh, in a, in a way that's going to give them that agency. And as a result, they think they have none.

Teri Schmidt:

Mm

Jason Silver:

I have to do the work that I need to do. My boss gave me this stuff. I have to get it done. I can't get this promotion. Um, because you know, my boss hasn't given it to me yet. I can't go and get that job because I haven't been able to land it yet. And those things are true. Uh, but what I learned is that you mentioned a point earlier about, you know, what is happening in your day to day and do you have to endure it? you instead say, yeah, it's true. These are the tasks I need to get done. What would need to be true for me to enjoy them? Right. Rather than like, I'm just going to endure it. There's nothing I can do. And when you take that mentality of, well, what would need to be true for me to enjoy them? This is for me, what opened up all the doors of, Oh, wow. Like I just assumed that I had to go through by like, this sucks, grit your teeth and bear it. I'm like, well, I don't want to. You know, grit my teeth and bear it for 40 years. You know, that's, that's not what I want. Nor is the future guaranteed. Like, how do I enjoy it now? A little bit more. Right. And it just kind of went that one day would be better than the previous day. The next day would be better than the last day. You string together a week of five days that were better than the previous five days. Next thing you know, this month was better than last month. Then the quarter, then the year. And you look back and you're like, wow. You know, it didn't take a promotion or a new job to make this happen. It just changed some, frankly, very small changes in my day to day approach that has led to a really big shift for me.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. Yeah. That's, that's excellent. And I, I do want to dig into that next, but before we go there, one more question related to your story, um, and it relates to a question I asked earlier about kind of plateauing and some of the changes you were making in your life and your personal life and, and not plateauing in the work life. I've been thinking a lot recently about, um, kind of the, the self help, um, world and the fact that. Often, it can be kind of a selfish endeavor, um, you know, definitely I, I believe we need to put on our oxygen masks first, but that's for the purpose of being able to serve others. That's for the purpose of being able to put that oxygen mask on someone else. And um, This is kind of reflected in our leadership model here at Strong Leaders Serve, it's ground, grow, give. So it's about grounding yourself in your strengths and values, and then growing the skills you need to grow. But what I argue is if that doesn't have an outlet of some sort, it is going to become stagnant. Um, and you do kind of plateau there. And I wonder, If one of the factors of your continued assent at work has to do with the fact that those changes you're making are not just for yourself. They have an outlet of impact and results on people around you and people that are impacted by your business.

Jason Silver:

I'd like to think so, you know, I, I hope, I hope you're right. Uh, I think too, one of the, one of the things that I learned was, you know, that. Maybe this is obvious to everyone who's listening. And it was maybe a thing I might've like understood, but not really like grok the concept, uh, because of how much time we spend at work, an improvement at work results in an improvement in your life.

squadcaster-80gb_1_07-25-2024_101029:

Mm. Mm

Jason Silver:

And I just started noticing a huge change where, you know, I've impactful with a unit of time than I am now.

squadcaster-80gb_1_07-25-2024_101029:

hmm.

Jason Silver:

what I've noticed is I end my days. Uh, what's the right word, like tired, energized, you know, like I'm

squadcaster-80gb_1_07-25-2024_101029:

I haven't heard

Jason Silver:

I've, yeah, like I've done a lot of stuff and I'm tired from doing it, but I'm not exhausted. I'm not drained,

squadcaster-80gb_1_07-25-2024_101029:

Uh huh.

Jason Silver:

know? And so then what happens is because I've completed a work day and I'm fired up, but a little fried, you know, Then I go get my kids from school and they come home and I deal with quote unquote life at that point. And I'm rolling into that with a different kind of energy. And then that experience is better. And when that experience is better, I go to bed at night and I wake up in the morning, like ready to go. And it's just this, like, when work is better, life is better. When life is better, work is better. And it's just this never ending cycle of positivity. If you can nail that initial, just get the flywheel going. And I think that that has made such a big difference that You know, you don't have to like lean back from work to create more space for your life in order for everything to balance out. You know, I don't really believe in the

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

thing. Again, if you just change how you're working, you can lean into work. You can still be as ambitious as you want to be, but it can become such a positive driver for everything else going on in your life. And it just becomes, you know, the high tide that floats all boats. And I think that's the thing that I learned is actually sure. When I, you know, when my mind's not right. I'm not going to show up really, you know, the way I want to at work, but when work's not right, I'm not showing up with my life very well either. And living the life I want to live is kind of the most important thing for me. So I've found that like the root cause is a small change at work can have a big impact on, you know, the entirety of my life, which has been a really cool unlock.

squadcaster-80gb_1_07-25-2024_101029:

Yeah, that's so true. And, and what a motivating factor to improve things at work. You know, it's, it's not just about being more productive at work. It's about that compound effect on the rest of your life.

Jason Silver:

Yeah, that's I think that's exactly right. The compounding nature of it is, I think, is what I've really seen is because I'm ambitious, you know, because I care about having an impact because I care about helping people professionally, because I care about accomplishing things. I get a big boost when I do those things. And if I can get a boost from the doing of those things and the accomplishing of them. You know, it really just spills over everywhere and there's a ton of research that shows. You know, the happier you are, the better you perform, the better you perform, the happier you are. And it's this like incredible flywheel of positivity that

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

I was not tapping into. You know, I was in the zone of like, put it on my back, I'm getting crushed, just like slog through it. It'll be great when you get to the finish line. I don't know what the finish line is, but like, when you get there, it'll feel amazing, you know, and my mindset has totally shifted more towards, you know, You got to have some of it flowing now, otherwise it's, I don't know why I would believe it's going to flow later.

squadcaster-80gb_1_07-25-2024_101029:

Yeah, exactly. That's a great point. And you know, I think the approach that you take that really drew me to your book and, and wanting to have this conversation with you is that, you know, when you're talking about people being happy at work, you're not saying, Well, you need to find the perfect job. You need to leave that awful job you're in right now and find a different job. and you're also not saying, well, you just really need to be clear about, you know, hitting specific milestones. you even mentioned that those are kind of two fallacies that people fall into, and that, that leaving the job could be cutting back on their hours, or it could be finding, you know, another, Quote, unquote, perfect job. Why do you feel that those two strategies kind of missed the mark?

Jason Silver:

Yeah. They're the most obvious to try. And I think that's why we all try them myself included.

squadcaster-80gb_1_07-25-2024_101029:

Mm

Jason Silver:

you know, on the milestone one, I think there's a couple of challenges with it. One is the nature of the way the world works. And the other is the nature of the way our mind works. I

squadcaster-80gb_1_07-25-2024_101029:

hmm.

Jason Silver:

you know, and the way the world works is, You can set all the goals, all the goals that you want to set. Whether or not you achieve them is largely out of your control.

squadcaster-80gb_1_07-25-2024_101029:

Mm-Hmm.

Jason Silver:

You can do all of the right things in all of the right ways and not hit some goal that you want to hit. Uh, and that's not because you didn't do a great job. You know, something could have just happened in the world. We all remember the pandemic that blew up a lot of

squadcaster-80gb_1_07-25-2024_101029:

Mm-Hmm.

Jason Silver:

right? You know, you could be working on something in all of the right ways, and all of a sudden the market shifts on you, a competitor changes, something in your life shifts, and you have to out of your control. And so placing your happiness on a thing that you have no control over, for me, is, uh, you know, not the world's greatest idea. Um, and with respect to the way that our minds work, uh, there's something called hedonic adaptation, which is basically like, The whole idea of keeping up with the Joneses, or you're like running on a treadmill, basically. And what that means is our minds are really good at setting baselines. So I have some baseline experience in my life. And what happens is I always return to this baseline, which is good and bad. Okay. So the, the good news is if something in quotations, bad happens, you will dip and usually you will come back to your set point over time. The challenge with that is when something good happens, promotion, raise, so you hit some giant milestone, you'll spike, it'll feel great. And you'll come right back down to that set point.

squadcaster-80gb_1_07-25-2024_101029:

Yeah.

Jason Silver:

And so the goal we're trying to do is to basically change this set point. But when you rely entirely on a milestone, uh, you know, my experience was I accomplished a thing I enjoyed for 15 seconds, and I'm thinking about the next thing I need to accomplish right after it, I'm always chasing, right? We're always running towards something. And. You know, for me, that didn't result in, in a perpetual state of feeling the way that I want it to feel.

squadcaster-80gb_1_07-25-2024_101029:

Mm-Hmm.

Jason Silver:

and then the next strategy that you mentioned is, you know, cutting back. We see people quiet quitting. There's all sorts of stuff here. This is the work life balance concept of like, I'm just going to carve out more time for my life. And of course there are times when you need to do that. But the challenge with that strategy, if you care about achieving, which in my experience is most people, you know, most people want to accomplish something. Whatever that bar is, whatever that goal is, maybe they want to feel like they're contributing to a team. Maybe they have some big goal that they want to whatever it is. Achievement is the thing that I think is just like naturally baked into us. And essentially what you're saying is just lower your standards. Don't care so much about achieving things and feel okay with that. And again, because of the set point that we have, that might work for a week or two or three. That's why vacations are awesome.

squadcaster-80gb_1_07-25-2024_101029:

Right, right. Yeah.

Jason Silver:

But if you're trying to take your base nature and just say, I no longer care about achieving it, I'm going to underachieve by my own definition, I'm going to underachieve, I could do more, I'm not going to, and I'm just going to be happy with that. It doesn't usually last, you know, after some amount of time, you're like, I need more. I need, I need to, I think I, I'm not living up to my potential, so to speak. And so in that way, cutting back is, it doesn't help us either. And what that left for me was the Venn diagram of, okay, well, I'm not going to cut it back necessarily. And I'm not going to only focus on milestones. What I need to focus on instead are my moments, right? The moment to moment. What can I be doing to enjoy what I'm trying to accomplish a little bit more? Great example. I love talking to people. Something I love doing. I love meeting new people. I love having conversations with people. I have a book launch coming up. There are a million ways to promote a book launch, but when I build a strategy, I think about two things. Number one, what do I need to accomplish? Whichever one thinks about usually, and then I carve out a thing, uh, space to do a thing that's not often done, which is like, how do I want it to feel while I accomplish it?

squadcaster-80gb_1_07-25-2024_101029:

Mm-Hmm.

Jason Silver:

And so when I do the first job, what do I need to accomplish? I don't got to get this many impressions and drive this many yada, yada, yada, whatever. How do I want it to feel? I want to enjoy it as I go through it. So one of the tactics I lean on quite heavily is meeting people like you, having conversations like this, because it both accomplishes or takes me on the way to my goal and I deeply enjoy it. And it's fun for me. And I got a lot of energy out of it. So I haven't changed the goal. I haven't changed the thing I need to do. I haven't changed my job, so to speak. I've just shifted the way I'm doing it so that I enjoy it a heck of a lot more as I'm going through it. Yeah.

squadcaster-80gb_1_07-25-2024_101029:

you say to someone that says, yeah, that sounds great. You are an entrepreneur. You have a lot of flexibility. I am in a job with a boss telling me exactly what to do, um, kind of looking over my shoulder about how I'm doing it. How could they employ that same strategy? Mm hmm.

Jason Silver:

And this goes back to the point from earlier of it probably feels like you don't have the agency, you know, and it's easy for someone on the outside to look at what I'm doing and say, well, it's easy for you because of X, Y, and Z. You don't see the challenges with it in the same way that, you know, I look at your life and I'd say, well, you know, it's easy for you. And you're like, well, you don't see the challenges I'm dealing with. So it's easy and it's hard. It's just different, easy and hard. And I think the, the kind of key call out here is like, no matter how micromanagey your manager might be. There's only so much that they can micro on you. Right. And what I learned is that in a lot of cases, the things that made me feel better were not additive. Meaning it wasn't about adding more to what I was doing, right? It wasn't about like getting a new project, a promotion, whatever. It was about removing an impediment to me. Enjoy myself more classic example, slow decision making inside of companies is incredibly frustrating. You sit around, you wait for a decision. Okay. And that is very frustrating. It drives me nuts. You know, I used to work in jobs with bosses, et cetera. It's very, very frustrating. And you might think there's nothing I can do about this and you'd be wrong. Right. And the, the, the lessons I've learned is that the solve to a problem like this is a very small thing that you say in meetings and a micromanaging boss is not going to prohibit you. From saying something in a certain way, when you're interacting with people, that, that would be an example of a highly toxic environment that you probably should leave. But in the vast majority of cases, your boss is not following you around being like, you just asked somebody this particular question. That's going to rapidly increase our decision making speed. You can't do that anymore. If they're censoring your speech to that level, it's probably the right time to ask, like, Is this really where I want to be, where I want to be spending my time. But that is something you can do. And the genesis of the book was, Holy Jesus, I have these tactics, which no one's talking about. And literally if you can talk or type, you can try every tactic in my book. And I don't know how your manager would stop you from doing the things that are in the book. It would be very, very challenging for them to do that. And so I think that's why it might feel like you're sitting in a spot where you really don't have agency. And I think that's because. You're looking at the problem in a very understandable way that a lot of people have, and myself included, we're looking at it before. And my hope for the book is I'm going to flip your understanding on its head. And you'll see, wait a second. There's this whole avenue down here that I've never really thought about. I can try these things. I have agency to do these things. And the impact I could tell you from experience, both mine and folks I work with, it's massive when you try them. So you might be in that spot. The challenge would be. You know, read the book. And if it has zero impact for you, send me an email and I'll pay you back for it. You know, I think, I think that's, that's a good argument. And I just don't think it plays out that way. I think that's how it feels when you're in the zone. You need something to shift your perspective in some way, shape or form so you can see a path that is available to you. And that's what I hope the book accomplishes for folks.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. It, I think the point about shifting your mindset, around the agency, around the fact that you do have agency and you were generous enough to, to share an advanced copy with me of the book. So I was able to see that even the playbook that you have at the end of the book, I just love because you take all these strategies that you can try and, you know, put them in a very condensed way. Form. so highly encourage everyone to go out and, and get it and, and try out some of these strategies, but you mentioned something about slow decision making, so I'd love to, to dig into that because that is a pain point that I have experienced myself and I hear from my clients, you know, how we're in unintentionally building teams that slow decision making. So I'd love to hear your experiences about where you've seen that happen.

Jason Silver:

Sure, and this was a big, you know, light bulb for me, and I'm going to explain this whole story and yada, yada, and it's going to all come down to a tactic that anyone could try, and everybody is going to think, that's not going to work. Uh, and that's what I thought too. And I'll just encourage you to try it when we get to the end, like humor me, you know, suspend your disbelief, give it a shot and see what happens. Cause it's really shocking when it

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm, mm

Jason Silver:

honestly. And what happened was I kind of figured out the hack and then I reverse engineered, like, why is this working? I don't really understand. Uh, and what I realized is we're building teams for diversity, which is by all empirical metrics. An incredible thing to do. And if you don't believe in that, probably people should go and listen to a different podcast, but there are reams and reams of research about it. The right way to accomplish it is very challenging. Um, but when I say diversity, you know, I'm not thinking about what's your background, what do you look like in my mind, I'm thinking about like diversity of thought. And when we have diverse thinkers on a team and access to that diverse thinking, we get better results. But there's a fundamental challenge that we don't often think about when we're running a team. And what winds up happening is we build a diverse team with diverse thinking, and we get very few of the benefits and all of the drawbacks, and we don't spend a lot of time talking about the drawbacks and a critical one in my experience is human beings are wired to agree with each other. And yet the more diversity we build, the more diverse thinking we have, by definition, the more disagreement. We will be creating.

squadcaster-80gb_1_07-25-2024_101029:

Right.

Jason Silver:

And the challenge in most workplaces is to make a decision. We usually have to agree. And the argument that I will make is stop trying to agree. The desire to agree is what is creating all of the slowdown. I have to go and talk to so and so in marketing and get them to agree and such and such in, uh, finance and get them to agree and so and so in product. And they have to agree. And once all these people agree and sign on the dotted line, meanwhile, it takes me two weeks to lobby that person. And then once I have their signature, I have five weeks to lobby that person. A decision I can make in minutes winds up taking me months. And so the question boils down to actually less about how do I make faster decisions and more about how do we disagree better? And the number one way that I've found to disagree better is be clear about who gets to decide who they're disagreeing with every

squadcaster-80gb_1_07-25-2024_101029:

simple.

Jason Silver:

It seems simple. It's so hard to actually implement, right? Like it's just, you have to remember to do it and to do it. And like, for me, I started paying attention to this and the number of times that I slipped until it became a habit was really hard. Was shocking to me. Um, and when I teach people, they're like, uh, this is too simple. I can't possibly work. I'm like, just go do it. I come back, talk to them in two weeks. And like, how did I make decisions? You know, before this,

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm,

Jason Silver:

I had a workshop I ran, uh, not too long ago. We had 70 managers on a zoom call and we took a meaningful business decision and we made it in 20 minutes

squadcaster-80gb_1_07-25-2024_101029:

hm,

Jason Silver:

and the 70 people on a zoom call. Okay. And they didn't all agree with the decision.

squadcaster-80gb_1_07-25-2024_101029:

hmm, mm

Jason Silver:

they were all aligned.

squadcaster-80gb_1_07-25-2024_101029:

hmm.

Jason Silver:

And that's the point we're trying to seek alignment, not agreement. Okay. So like the step one, the tactic that, you know, literally everyone can do, I don't know how your boss would stop you from doing this is before you debate any decision, decide who's going to decide. Meaning we have to make a decision. You and I are driving in a car. We got to, you know, turn left or turn, right? Well, okay. Who's going to decide? What usually happens in most work settings is we will just start talking about the merits of turning left versus turning Right. and we will debate the decision. But we do that with no clarity on Does Jay get to decide that he's going to turn left because he's driving the car or does Terry get to decide that we're going to turn right because she's holding the map and she's the navigator.

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

So before you launch into that debate, and this is kind of the trigger that you pay attention for is when you're in a meeting and you hear people starting to debate a decision, you raise your hand and say, quick question, who will make this decision?

squadcaster-80gb_1_07-25-2024_101029:

Hmm.

Jason Silver:

Oh, it's Terry. Okay, great. Now let's have a vigorous debate about it, knowing That when Terry's heard what she's need, she needs to hear, she says, All right, everybody, I heard X, Y, and Z. This is how I'm thinking about it. This is what we're going to do.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. Yeah.

Jason Silver:

Without that, we have no way to break a disagreement until you and I just argue, argue, argue, argue, argue until one of us is beaten to a pulp and we agree to disagree or we don't even agree at all and it just spins and cycles and never really gets made.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. That's interesting. And the, the driving analogy brought up a question for me because I, I think it's about assumed decision maker, um, and you know, in a car, obviously you're, you're assuming the driver's going to make the decision about which way to turn the car. And I think that happens a lot in meetings where you assume that the person with the Is going to make the decision becomes a problem. Particularly like you were talking about, you know, getting agreement with marketing, getting agreement with everyone else. You know, I was just in a job where. Basically everyone gets thrown into a meeting and you have multiple people at the same level. Um, and you just talk back and forth and back and forth and back and forth. so I think that's a key point of asking the question and getting clarity around the decision maker, even when it's assumed.

Jason Silver:

especially when it's assumed, you know, I tell a story of in a book, in the book of a COO, similar, uh, story to what you just described, they have to make a big important decision. They've been debating it for weeks. It wasn't moving forward. Hey, just, can you ask who's going to decide? Well, it's obvious. It's so and so just. Let's see, he pauses a meeting who's making the decision. Multiple people put their hands up. Okay. And his first inclination is I just made everything worse. And my first inclination is you just started to make everything better

squadcaster-80gb_1_07-25-2024_101029:

Mm hm.

Jason Silver:

now we're going to have a debate about who's actually making this decision. And the three people who put their hands up have to figure this out. Even if they decide we're going to take a vote on X day, so be it. There are three of us on this day, however much debate we've done, we're going to stop debating. We're going to take the vote and that's going to be the decision. Fine. Or we're going to say, well, I thought it was me and you thought it was you, which one of us is actually better? It turns out like, yeah, I'm driving. The kids are screaming in the back. Like,

squadcaster-80gb_1_07-25-2024_101029:

Hm.

Jason Silver:

I just want to focus on driving. You tell me whether to turn

squadcaster-80gb_1_07-25-2024_101029:

Mm hm. Mm

Jason Silver:

You know, I, I don't have an argument with Google Maps. I don't see, I don't need to have an argument with you. I'm going to trust you to tell me left or right or whatever. Now we're clear, right? So if you're assuming this is like the whole problem, you're assuming, you know, who's making the decision. Don't do that. Just raise your hand. Who's making the decision. Let's get it clear. It's very common that multiple people will think it's them and you will have to have a debate. Oh, this is a thing. This decision is going to impact what we do on product and what's going to happen to our revenue. So it's, it's finance and product. Okay. Who gets to make this decision? Let's have that debate. And it's a great debate and it takes 10 minutes to figure it out. And that 10 minutes will increase your decision velocity. I mean, I don't really want to stick a number to it, but like, there's a lot of zeros behind it, like much, much, much, much faster.

squadcaster-80gb_1_07-25-2024_101029:

Definitely.

Jason Silver:

the other thing that it does is it lets you get to a spot where, you know, we talked about, we don't have to agree. There's another kind of key question. So there's two, the first is like, who's making the decision. And the second is whether you're the decision maker or not, but let's just pretend that I am in this situation. And you and I have argued about turning left or right. And at some point we got to decide I'm going to hit a brick wall. That's in front of us. If we don't like,

squadcaster-80gb_1_07-25-2024_101029:

Mm

Jason Silver:

go one way or the other. The key question here is what needs to be true for you to support my decision, even though we can't agree.

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

there's two key words in there. Number one, support. I'm not asking you to agree. And number two is can't. I'm telling you, we can't agree. I don't want to spend any more time debating or trying to get you to agree. We've debated, we've recognized that we're not going to agree on this.

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

And we just put away the point of, you know, We're not going to agree here. Let's not talk about it anymore. We can't agree. How can I help you support my decision? And usually what that comes down to is people just want to feel heard, right? They want to know that their input was considered, even if they're not getting what they want. And that's what leaders are usually afraid of as well. I have a team of 15 people and they all want different things. That's great. What's not going to feel great for them is if you unilaterally make a decision, you don't tell them how you made that decision. They have no idea if their input was considered. They don't feel part of the process. People usually have no problem. If you're like, Terry, I hear you. You think I should turn right for reasons X, Y, and Z, right? I'm really hungry. And I know that there's like a stop to the left. I can see it. So I'm choosing to go that way, even though I think right might be the shorter path to go.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. Yeah. And that gets at what, yeah, exactly. That, that gets at what you were talking about or what you've alluded to that, uh, we're naturally wired to want to agree because we want to belong. But if we are it in a way that people are heard, they then have that sense of belonging.

Jason Silver:

That's right. You know, it's hugely beneficial to have people on a team who are dissenters, who don't

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm. Mm hmm. Mm hmm.

Jason Silver:

a problem if they don't support the decisions that are

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

You know, I don't need to agree with every decision. And if I'm on a team, I think the only way that I agree with every single decision is if we have, uh, like a very non diverse team. Because the only way I'm going to agree with every decision we make is if everybody on the team thinks exactly like I do. That's wholly uninteresting to me. Right? So I get way more interested and way more excited when there's disagreement happening. It's like the sign of us making a good decision. When everybody is in the room nodding their heads, that's when I get worried. You know, there's this thing called the Abilene paradox. If you heard about, haven't heard about it, it's a good one to look up. And that's basically where a group. We'll make a decision collectively that none of the individuals think is the right decision. Right. And so it's very possible it's well studied it's frequently happening that people will be agreeing and nodding their heads up and down and in their heads, they're thinking, this is not a good idea. isn't what I think we should be doing in this particular situation. So what I want, uh, is if I'm the person making the decision, Until someone's disagreeing with it in some way, shape, or form, I don't think I've done my job very well. But I've flipped the script for myself of, I'm not trying to get agreement. I'm not interested in agreement. I don't want consensus. What I want is alignment. And if you disagree, I want to hear that. I want to hear why you disagree. I want to hear how you're thinking about it. I want to hear what I'm missing that you know that I don't. And then when I get to the end, I'm like, it's time to make that call. All right, Terry, you don't have to agree with me here. Here's how I'm thinking about it. This is the stuff you told me that is part of the decision I've made. This is the decision I'm making. Can you support this? Most often it's like, I got it. I'm good. Let's go. Let's see what happens.

squadcaster-80gb_1_07-25-2024_101029:

Right. And your key question of what would need to be true for you to support it, I think opens it up to, Oh, let me explore that. Let me explore what's really behind my support of your decision that I don't agree with.

Jason Silver:

Most times it's like, help me understand how you made the decision. That's what people will tell you. Most times it's like, even though we can't agree, what needs to be true for you to support my decision? Most times it's Jay, help me understand. How did you get from A to B here? I don't quite understand how you were arriving at this conclusion. That's the vast majority of cases. Then outside of that, uh, there's sometimes something else will come up. I need to know that we're putting in something to track the impact of this thing so we can check in on it in a month or two, right? Or I'd like to book a meeting in a quarter for us to review whether this is still the right decision going forward. Sometimes it looks kind of some version of something like that. Um, it's usually one of those two. And of course there are times when you fundamentally can't agree. But that's like, you see, you can't align, sorry. You can't support a decision. That's like I'm willing to die on a hill moment. And those are few and far between. You know, I'm not saying you should like drop all your ethics and values and let someone make a decision that you fundamentally can't support, but then you can communicate that to them and say, Hey, I, I cannot in good conscience support this decision. So we got to figure this out now. That is so rare. It is like a fraction of a fraction of a fraction of the percent of the cases overall.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. Yeah. I would, I would imagine so. And you know what I love about these two questions is that I think they work just as well in remote and hybrid teams, maybe even better, you know, have even more of an impact in remote and hybrid teams as they would in a, everyone in the office situation.

Jason Silver:

Yeah. I mean, being remote gives you a bit of an out if you feel awkward asking, and you probably will to be clear, like it's a simple question. And that's why I say simple question, but implementing it, like you got to get over, I guess, yourself a little

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

uh, when you're on a remote call, you can use that as an excuse. Hey folks, I know we're all remote on this one. I just want to make sure we're on the same page. Who's actually making this

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

And so it gives you a quick out. It can be a little bit harder in a room full of 10 people to be the person to raise your hand and be like, Hey, everybody, look at me. Like

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

And you disrupt in that way. Um, you'll find pretty quickly that it, it does usually add a lot of value, but. You know, trying it out first on a remote call is a great, easy way to just dip your toe in because everyone knows that, you know, communication, it can be more challenging when we're remote. And so you're kind of doing everybody a favor here, but more often than not, even in a group setting with 10 people. You'll ask, who's making this decision? Somebody at the end of that meeting is probably going to say, Oh, Terry, thank you for asking that question. I didn't know which way I, I didn't know who was deciding this. Like, I'm glad you asked that someone else is probably thinking about it. And it's about who has the courage to kind of raise their hand and say, you know, just help me quickly understand who's actually the person making this decision. They're often not even in the room and that's a quick fix there. It's just like, it's Terry. Where's Terry? Well, she's at lunch. Well, could we have this meeting right now without her? Nope. Perfect. We don't have to waste an hour, you know, talking around in circles. Let's get back together when Terry's here.

squadcaster-80gb_1_07-25-2024_101029:

Yeah. Excellent point. Well, there's so much more that we could talk about, um, but I know we're running short on time. So I do want to ask you one question that we ask most of our guests, and that is, what does Strong Leaders Serve mean to you?

Jason Silver:

You know, to tie it into what we were talking about earlier, if you're going to be a strong leader, your goal is to build the strongest team you can possibly build. And if that's a knowledge work, you know, that means a diverse team. And if you have a diverse team, they're going to have diverse needs. And that's going to require you to think a lot about what are the people on my team need to do the best job that they can possibly do.

squadcaster-80gb_1_07-25-2024_101029:

Mm hmm.

Jason Silver:

you know, a bad A bad leader is thinking about what's best for them. I don't really love the monikers good and bad, but like, you know, a leader who's not serving or a weak leader, in my opinion, is someone who's, you know, primary objective is, well, what's best for me and how do I get this group of people to accomplish this thing that's best for me?

squadcaster-80gb_1_07-25-2024_101029:

hmm.

Jason Silver:

And I think a strong serving leader, a strong leader period is thinking about what's best for the group. I'm one of multiple cogs in this group. How do I get us to a spot that's, you know, best for the group overall? And that just requires you to be looking at, thinking about, and serving the group to get to that greater good rather than just, you know, well, this is what I want. Let's go do that. You know, everybody line up behind me and do the thing that's good for me. So more focused on the group.

squadcaster-80gb_1_07-25-2024_101029:

Very well put. Thank you for sharing that. So I know you have your book, actually, when this is released, your book will have just come out. Um, so encourage everyone to get that and we will include the link in the show notes, um, as well as your LinkedIn profile and website. Is there anywhere else that you'd like us to direct people to go?

Jason Silver:

I would love folks to just pick up a copy of the book, like you said, you know, the website will be in the show notes, but it's, um, yourgrassesgreener. com. Um, and through that, if you pick up the book, it comes with a bunch of bonuses that you get that will help you walk through a bunch of these things. And when you do that, you'll get access to me via email. And I would love to hear feedback from folks. Like I'm a big, You know, one to one conversation type of a, of a guy. Like if you read a thing in the book and it really resonates, I'd love to hear it. If you read a thing in a book and you, in the book and you try to implement it and it flops on its face, I'd love to know and try to help in, in, in whatever way I can. So, you know, the gateway would be, uh, please do check out the book and then don't be shy about getting in touch. I'd, I'd love to have a direct conversation with folks.

squadcaster-80gb_1_07-25-2024_101029:

Well, excellent. Well, thank you again, Jason. I, I really appreciate you coming on.

Jason Silver:

Thanks, Terry. Really appreciate you allowing me on.

Teri Schmidt:

What a great conversation. I hope you found one thing that you can take and try out today in your leadership. And make sure you go listen to the additional conversation that I had with Jason about imposter syndrome and how it can actually be a leadership super power. You can find that at the link in the show notes. And until next time. Lead with this quote by Jason in mind. How you're working. might be the only hurdle to enjoy your job more. Your dream job. Isn't a position you get one day. It's a job you practice every day.