EntreLeadership - Improve Your Decision-Making Skills Using Rigorous Thinking with Wes Kao

Episode Date: March 14, 2022

Join us as our host, George Kamel, talks to Wes Kao. Wes co-founded altMBA with our friend Seth Godin. She is also a co-founder of Maven. Wes talks about the power of rigorous thinking and the transformational impact it can have on your culture and your team. Later in the episode, George chats with Kacy Maxwell, the executive director of ramseysolutions.com. Kacy shares how you can use a few frameworks as your guide to encourage your team to think critically.   You’ll learn: How to tell if you’re a lazy thinker Why lazy thinkers are followers not leaders The type of thinking that can transform your culture The two keys to critical thinking   Sign up for The EntreLeadership Podcast Takeaways—a weekly email where you’ll get three tangible takeaways and a tactical action step related to each week’s episode: https://bit.ly/podcast-takeaways   Support our sponsors: BELAY: https://bit.ly/33SwBlO Hite Digital: https://bit.ly/HiteDigital NetSuite: https://bit.ly/NetSuiteEntre Exodus 90: https://bit.ly/Exodus90Entre Kyro Digital: https://bit.ly/KyroDigital   Links mentioned in the episode: The EntreLeadership Podcast: https://bit.ly/TheEntreLeadershipPodcast Wes Kao’s website: https://bit.ly/3IMB7C3 Maven’s website: https://bit.ly/3hCUGAK altMBA’s website: https://bit.ly/3sFRriw Download the Critical Thinking Cheat Sheet: https://bit.ly/3hIiWlf Schedule a call with Tim, our producer: https://bit.ly/3bJOSmi   Learn more about EntreLeadership Events: EntreLeadership Summit: https://bit.ly/EntreLeadershipSummit EntreLeadership Master Series: https://bit.ly/EntreLeadershipMasterSeries   Learn more about EntreLeadership Coaching: Elite: https://bit.ly/EntreLeadershipElite Advisory Groups: https://bit.ly/EntreLeadershipAdvisoryGroups Executive Coaching: https://bit.ly/EntreLeadershipExecutiveCoaching Workshops: https://bit.ly/EntreLeadershipWorkshops Weekly Report Tool: https://bit.ly/WeeklyReportTool   Listen to all the Ramsey Network podcasts anytime, anywhere in our app. Download the Ramsey Network app: https://apple.co/3eN8jNq Learn more about your ad choices. Visit megaphone.fm/adchoices

We all know Apple's famous tagline, think different. And while Apple was talking about innovation, the principle remains true if you want to grow as a leader. Now, you might fancy yourself a critical thinker who asks the right questions. But let me ask you a question. Are you seeing the results that you want to see? Are you raising up new leaders in creating a thriving culture? From the Ramsey Network, this is the Entree Leadership podcast, where we help business leaders grow themselves, their teams, and their profits. I'm your host, George Camel.

and today's episode is all about rigorous thinking and the result that it can create for your team. Our first guest today is Wes K.O. Wes co-founded Alt MBA with our friend Seth Godin and more recently co-founded Maven, a platform that helps creators build cohort-based courses and deliver an incredible learning experience at scale.

We'll talk about the power of rigorous thinking and the transformational impact it can have on your culture and your team. In our second conversation, I sit down with Ramsey leader Casey Maxwell, and we talk about how to encourage your team to think critically using a few simple frameworks as a guide. Up first, my conversation with Wes K.O. Wes, it's so great to talk to you.

It's great to be here, George. You have quite the resume, and you've worked closely with one of the marketing legends, some may say that Goat, Seth Godin, and your work is really inspired by this concept of rigorous thinking. And rigorous is a $10 word, and so I'm hoping you can break it. down for us today and show us the difference between plain old thinking, which some leaders out there may be doing, and help us get to that rigorous thinking. So what's the difference to you? Yeah, rigorous thinking is the opposite of what I call lazy thinking. So lazy thinking is assuming that you're going to try a random tactic that you see your competitors doing and assume

that it's just going to work for you. It's making assumptions that you don't even know that you're making, kind of going through life, just going through the motions. Rigger's thinking, on the other hand, is having a systematic way of making decisions. It's thinking about the upside and downside. It's thinking about tradeoffs if you take a certain path. You're thinking about what success looks like before you even start. You're thinking about implications that your actions might have down the line for yourself, for your team members, et cetera. So it's really a way of, uh, questioning your own thought process and decisions to make sure that what you're about to do actually make sense. So this is a much deeper level of thinking.

Most people, it's a little bit of gut. It's a little bit of some group think. But you're saying we've got to really think through every facet and kind of get a 360 view of a problem as we're thinking through it. Yeah, exactly. And I think the thing that trips some people up is they think, well, rigorous thinking sounds hard. It sounds like it takes too long. I don't have time to think rigorously, but the ironic thing is that thinking rigorously actually saves you time in the long run. Because what ends up happening usually when you think in a lazy

way is you jump straight to taking action. And you realize, you know, a week in, two weeks in, a month, a couple months in that something goes wrong. There's an avoidable mistake. And usually in those situations, if you had just taken five to ten minutes to think about your situation a little bit more jumping straight into action, you would have realized that X or Y was going to be a problem. And so rigorous thinking is actually a way of saving yourself time while still acting quickly, shipping quickly, and staying on your feet. So what does this look like in your day-to-day life as someone who practices rigorous thinking? What does it look like to make that shift in just the everyday?

Yeah. In everyday life, it looks like thinking about what next steps would look like if we decided to do something. So as a leader, as a business owner, as a creator, you're making a lot of decisions on a daily, weekly basis. And you don't always have full information. You're often working with imperfect information. And rigorous thinking means thinking about if we were to go ahead with this idea, what would we actually do? What are the distinct steps that we would take that would get us to our goal. And what's the hard part? I think a lot of times we think about a grand plan and it all kind of, it's kind of vague and all kind of mush together. We're like, oh, we'll figure it out when we get there. But thinking about what that hard part is before you start helps you think about whether or not

you have the assets and levers to be able to tackle that hard part. What you don't want to happen is to distract yourself with busy work. So you feel like you're making progress. You feel like you're taking action, doing a bunch of these little things that are actually pretty easy if you kind of, you know, dig down deep. You know that, you know, I can do this part. But the part that you're not sure about, you kind of put off, right? That's very normal. We're kind of afraid of it. We're not sure to figure it out. But that's the part that you really should figure out because it might mean doing or not doing the thing in the first place. So we tend to do the easy things that don't take a lot of thinking. And then we procrastinate on the stuff that takes the deep work because we want to

make sure we get it right. And so rigorous thinking can help us get there. And you mentioned this can help us save time. It's going to help us make better decisions. And it helps us think through the impact it has, not only on the business, but on the team. That seems to be a big part of this. As a reactive leader, you're not always thinking about, well, how is this going to make XYZ feel over here and this person over here? Is that part of it? How does this connect with the team that you're working with?

Rigors thinking is a huge part of building culture and building a strong team. So usually if you're in a position of leadership, you got there because you're good at both strategy and execution. But if you are now a leader and you're managing a team, you can't do everything yourself anymore. Your effectiveness is directly dependent on how strong your team is. And so what ends up happening, though, is that because leaders are usually so good at doing everything themselves, their team member will come to them and say, you know, George, should I do this? Or Wes, you know, I want to do this.

Do you approve? And our instinct, our reflex as a leader is to answer that question. We say, no, don't do that because X. Or, no, that's not a good idea. Let's not try that. But what your direct reports end appearing is a lot of no, no, no. Why is George always telling me know? Why is Wes always telling me no?

And, you know, in our own heads, we have the reasoning. We have the rationale. We have the thought process. But we don't always have time to explain it to our direct reports. So rigorous thinking is actually going one step beyond just explaining it. It's actually letting the direct report think for themselves. So instead of answering the question, the next time your direct report comes to you with something, ask them, what do you think?

How do you think this could work? Right? If you automatically have an answer of, you know, oh, I totally know this wouldn't work because X. Instead of just saying that, help them come to that conclusion themselves. Ask them to think through, well, how would this part work, right? Through the part that you think, you know, might be a little bit difficult. Ask them for examples of how something like this has worked elsewhere. And it doesn't mean we have to have done something before to be able to do it.

But if this is a behind-the-sky idea, it's not rooted in anything, it's harder to imagine that this might work for us. But if you say, oh, like, this company in a different industry or this other individual tried something and I see patterns, I see rhymes of how it could work for us in our situation, then that makes the whole team more confident that this tactic is worth trying. So instead of just saying no all the time, it teaches your team to think for themselves and helps them assess a situation so that long term, they become more independent. They're not always needing to come to you. They actually can ask themselves a lot of questions that you would have asked them anyway. And so by the time they come to you, they've already asked themselves this initial set of questions, so they're more likely to come to you with higher quality ideas. Yeah, it reminds me of when you're in school, the best teachers always led you to that insight and you have very, the light bulb moment. And that was always the best learning experience. And the same thing

feels true in a business setting. As a leader, instead of just telling them the answer, when they get there themselves, they feel empowered. And that changes the posture, it changes the culture on a team. And so it's a really powerful thing to try to get back to that rigorous thinking. Do you think as a culture, we've just gotten lazier because we just have access to information more readily? Where do you think the lazy thinking is coming from? That's a great question. I think the lazy thing. I think the lazy thinking is coming from a couple areas. One is that humans, our brains are inherently lazy. And that's not a bad thing, right? We're trying to conserve energy for decisions that matter most. And we pattern match. We look at what other people are doing. We look for clues for what feels safe based on what others are doing. And so this whole idea of seeing a shiny object and then wanting to chase it. And I think the modern day equivalent in business is seeing a competitor or a colleague, or a different company doing something and then immediately thinking, oh my gosh, we're behind.

We need to be doing that too. Why didn't we think of this? Let's get on it immediately. Without really thinking about what are their assets and levers and constraints. What is unique about their situation that allows them to pull this off? You might have similar assets and levers and constraints that allow you to pull this off, or you might not, right? If there is a creator out there or a business owner and they have a huge audience,

they're able to do certain things that you might not be able to with a smaller audience. But let's say you have a stronger community. You are able to do things that they can't, right? Or if you have more capital, you're able to do things that they can't. Or if you have a team of specialists versus their team of generalists or whatever, right? So it's just looking a couple layers deeper to think about what is unique about my situation that allows me to do certain things and gives me a competitive advantage and not just kind of jump. jumping on, you know, whatever is the next shiny object. So, and the shiny object syndrome is

is one reason lazy thinking happens. And I think the other is rigorous thinking takes practice. It doesn't necessarily come easily. You know, I think a lot of people are excited about trying rigorous thinking, but aren't really sure where to start. So I have a list of questions in an essay that I've written on lazy thinking, 20-some questions that you can ask yourself. So we mentioned a couple here with what's the hard part, what are second-order effects, what does success look like? If you were to, you know, instead of jumping straight to prototyping, you know, most people think prototyping is the minimum way that you can try something. If you actually just think about it for 10 minutes, like, don't prototype anything yet.

Don't get your hands dirty yet. Just sit and think about how would this actually work? Like if I got approval from my boss right now, what would I do next? What would I do for the next couple of weeks? What would I do between now and this finished project, right? And whatever part that you are unsure about, talk to your boss about. When you bring a more specific question that hones in on a part that you've already thought about a little bit, that actually gives your boss, your partners, your colleagues more ways for them to be thought partners for you. So I think those are two ways that, you know, lazy being kind of areas where it kind of rears its head in ways that you can combat it.

Yeah, I think there's in leadership culture, it seems like you're kind of rewarded for being the loud one in the room with all the opinions. But what I've seen in my career is the best leaders are the ones who sit quietly, and then they ask a question, and everyone's mind is blown at the end. They're like, oh, my gosh, we didn't even think through that. That's a great call-out. And so it just brings me back to rigorous thinking is really pointing to important questions to ask ourselves instead of just leaping to action, which is probably a go-to move as a leader. That's why you're there.

As you're action-oriented, you can execute, you can get the team to rally around something, but it's so important to sit back and ask those questions. So I want you to help leaders start thinking this way. How can they begin to make this shift from lazy thinking and lean into rigorous thinking? I think one big way to do that is a little bit indirect, but I think you'll see how it's connected. I think the biggest thing that you can do is have the humility to admit that your initial idea about something, that your thinking might not be as rigorous as it could be. this is actually a lot harder than it sounds because I think most of us like to think that we are

sharp people who know what we're doing. We consider ourselves reasonable. And it can be pretty unsettling for someone to tell you that you're actually not as rigorous as you might think you are. But I think accepting and embracing that there are areas where you're thinking might not be that rigorous is the first step. So rigorous thinking isn't a blanket. Like are you rigorous? Are you not? It's not binary. There are some areas where you are more rigorous than others. And then there are some areas where you might be newer to the topic or you might not have thought about it with as much nuance as someone else has. So there are moments all the time where I talk to my co-founders and they point out gaps in my logic. And there are a lot of times when I point out gaps in their

logic. Or we look at the same primary data, right? We look at the same recording of an interview with a candidate where we look at the same email from a creator. And we come to different conclusions. And that's a good thing. You want a team where you have people who are seeing different things. You're not all just noticing the same thing because you can fill in each other's gaps and you can make each other more rigorous. So I love when my co-founders, Shreans and Gagin, point out, oh, like, I'm seeing the same thing as you are, West, but here's the conclusion I come to. It's actually the opposite conclusion that you come to. And half the time I think, you're right. You know, strong opinions loosely held. I give up on mine. I agree with you. Right. So this idea of being able to be flexible

in the face of incoming information, in the face of new inputs, new data, I think that's very, very important. And I think the other thing is always reviewing primary data yourself. What I mean by primary data, I remember this term. I think I learned it in, you know, social studies or something, in junior high, but primary data is, when I say primary data in a business context, I mean assessing a situation for yourself, not just listening to it or getting a secondary account through someone else. So a lot of times someone, you know, a team member will come to me, you know, for example, and say, oh, you know, I, you know, had this scuffle with a customer or client or with a colleague and they said this, I said that. And, you know, and before

I come to a conclusion, I'll say, can you send me the email thread? Can you send me screenshots of what you guys talked about in Slack? I want to see the actual data myself. And there have been times where I have agreed with that person, whatever their account was. And there have been times, many times where I've come to the exact opposite conclusion, where that person had a certain lens when they were describing what was happening. And in their mind, they were respectful, They were friendly, they were warm, they were justified in saying what they said. And when I saw the actual words that they used, I came to a different conclusion and said, you know, this did not come across the way that you thought it came across.

And I will explain to you why. So that's the other part of rigorous thinking is you want to explain why so that they can then come back and say, oh, yes, actually you missed this thing, right? Maybe I miss something and then I changed my mind, right? But if I'm talking to a direct report and explaining why what they thought was warm and respectful didn't actually come across that way. I want to be able to point to specific words where, you know, you said this thing and that sounded a little bit abrupt, or this person, you know, the person we were talking to was trying to give you a bid. They were giving you an opening.

They were trying to, they were trying to make peace with you. And you kind of slapped down that bid when you replied with this thing. Right. So I want to break down the line by line of here's exactly how the conversation happened as you're showing me in your screenshot so that we can both learn from it. and you can learn how to, you know, translate your intent more accurately with words, right? And so it becomes a learning opportunity for everyone involved. And so that levels up the rigor for the entire team. Wow. A lot of nuggets in there that we could unpack.

I'm seeing themes of, number one, having an emotional intelligence, and that's something to work on as a leader of the nuance of communication and perceptions and looking at that primary data. But there's also a level of humility that you need to start with. of going, you know what, maybe my way isn't the only way. Maybe I could bring others in who have different thoughts who could make this better and help see the roadblocks that are ahead that I can't see. And so that does take a level of swallowing your pride and having some vulnerability to let others speak into it, even if it doesn't align with your own conclusion of where you think we should go.

And that really also points to having healthy conflict and learning how to do that really well with the team. It's not just about asking questions. It's how you communicate it and the nuance of that and being winsome in that way. So there's so many aspects to this rigorous thinking that are super powerful. So I want you to speak to how this type of thinking can transform the culture of a team. And we've touched on it,

but I want you to just speak directly to what this looks like. I think for the right team members, rigorous thinking is a really exciting part of a culture. I had an early team member who came from a fang company, so Facebook, Amazon. what is it, Apple, Netflix, Google.

And she was there for five years. And at her three-month mark at Maven, she said, I learned more in three months working at Maven than in five years working at the fame company that I was in. Wow. And she said she didn't know if she was sleeping through it or if people just weren't giving feedback or they, you know, what was going on. But she didn't realize the level of intensity and rigor that could happen in the process

of making decisions. So I think for, and she was excited by this. So I think that's the positive, the positive version is you find the right kind of people who want to be challenged, who are looking for juicy challenges with non-obvious solutions that they really want to dig their teeth into and find it intellectually stimulating to work on. And they want to improve, they want to sharpen themselves. They already believe that iron sharpens iron and they want the people around them to level them up and to challenge them. And they are ready for that discomfort. I think that that is, that is the best case scenario. On the other hand, I think the worst case scenario or, you know, not ideal scenario is someone comes in and they are used to being the smartest person in the room

or one of the smarter people in a room. And all of a sudden, when you enter a really rigorous culture, it's a high likelihood that you are no longer the most rigorous person in the room. And I think all of us say that we don't want to be the smartest person in the room, But when it actually happens, it can be really disconcerting. It kind of, you know, if your identity is I am a smart person, I know what I'm doing, I add a lot of value, I'm a high performer. And all of a sudden, the environment that you're in challenges that worldview and challenges your identity and your view of yourself, that can be really upsetting in many ways. Yeah. And so I think from a team perspective, you know, that's something that at Maven, we've started to talk about in the interview.

process. So I'm hiring for four or five different roles right now. And up front, I tell candidates that we are rigorous culture. We give a lot of direct feedback. And especially in your first three months on the job, you are probably going to get your ass kicked. Even if you were the highest performer on your team before, even if you're amazing, we know that you are amazing. This is why we're hiring you. We would not hire someone who we didn't think was amazing. So us giving you feedback is not a sign that you are not amazing. It means that we are leveling you up. We are helping you understand our culture, our internal bar for excellence, our speed and quality of decision making. We are sharpening you, essentially. And so that, I think, has become a really important part of,

one, being transparent with candidates as we're interviewing, because it's as much about whether we think the candidates could fit as it is about them wanting to be a part of this culture and thinking that they're going to learn a lot and contribute and have fun in this, you know, in this new role. So I want candidates to have that full information. So they can decide for themselves, is this something that I want to be a part of and not be blindsided when they join and think, you know, wow, like this culture is not what I expected. Yeah. Well, there's a big takeaway I'm hearing is that a culture of rigorous thinking equals growth. And I think everyone who's listening to a podcast like this, they're growth oriented. They want to grow. They, you know,

may not desire the discomfort and all the challenges, but you love to feel like you're growing. And I think the lazy thinking is where people get stagnant, they get complacent, and rigorous thinking says, man, what's ahead? What could we build together? How can we level up as a team? And so I love what you're doing. I love what you're doing at Maven. It's been called the University of the Future.

So what is the elevator pitch for those that aren't familiar with Maven that you co-founded? Maven is a platform that makes it really easy for creators to build live co-based courses. So court-based courses are the opposite of what you usually think of when you think of an online course. So usually think of LinkedIn learning, teachable, Udeme, Skillshare. So these are basically a bunch of pre-recorded videos that you watch on your own time and there's no interaction, there's no community. I personally have purchased a bunch of courses, I think, One on hand lettering calligraphy, another on classical music appreciation, where I watched maybe a couple minutes of the first lecture and said I was going to come back to it, haven't gone back in seven or so years.

So the completion rate is super low. That's a very common story. The completion rate is anywhere between 6 to 10 percent. And a recent MIT study said it's anywhere between 3 to 6 percent completion. So if you flip the model and kind of look at the opposite, it's court-based courses. So Seth Godin and I created the Alt MBA in 2014, 2015, and really kicked off this category of court-based courses. And what we discovered with launching the Alt-MBA is that if you create an online course where you offer community and you offer accountability, and you have set start and end dates that create a sense of urgency and encourage your student to focus during this amount of time,

and you bring a bunch of like-minded people together from all over the internet. and you give them projects and you give them hands-on activities and exercises and opportunities to debate each other and role play and actually put their lessons into practice, you create a much more engaging experience that results in better student outcomes, better engagement, and a much higher completion rate. So the Alt-MBA had a 96% completion rate versus a 3% to 6% for the average for most evergreen courses. And what we're seeing now with Maven with the hundreds of cohorts that we've launched is

around a 75% completion rate on average. Amazing. Wow. You guys are doing some incredible work, and clearly that level of engagement and connectivity to what you're learning changes the game. And so I love what you're doing to help leaders out there, small business owners, creators. It's absolutely incredible. So as we wrap, leaders are listening and they want to step into this. They've admitted maybe they're not as rigorous as they could be. What encouragement would you give to them as they step into this difficult process? I think most leaders are probably more rigorous than they might think. So I would say that the biggest step is to train your team to be more rigorous. So if you ever thought, you know,

I wish my team would stop coming to me, you know, with half-baked ideas that really don't make sense that are kind of distracting, I wish they would, you know, think a little bit further, right? Instead of asking me things that were easily findable on Google or easily findable if they just, you know, searched in our Google Drive, you know, for a little bit, right? So, I think most leaders have had this thought. And so one of the first things you can do to start adding rigorous thinking to your organization is the next time that your direct report comes to you with a question that you think is, is something that is within their capacity to figure out.

Give them a chance to figure it out. So don't just answer. Ask them, how would you figure this out? If I weren't here, what would you do? And give them a chance to answer. Wait for them to answer. You will often be surprised that they will say, the thing that you would have said a second later, and there you go. So they'll say that and you say,

awesome, that's exactly right. Go do that. And that also builds their confidence that, you know, they thought they didn't know and had to come to you. But when you say, you were spot on, like, you got it. Like, that's exactly what I would have said. That makes them feel really good. Wow, that's good. And that empowers a whole new generation of leaders as leaders begin to do that. So it's an incredible tool, a great place to start. Wes, thank you so much for being on the podcast. and sharing so much wisdom with our listeners, appreciate you and all that you're doing with Maven. Keep going.

Thanks, George. Thanks so much, Wes. You have given us a lot to think about. See what I did there? I thought that was pretty good. Well, if you want to learn more about Wes and what she's up to, check out her website, westk-o.com, and check out Maven at maven.com.

To make it easy for you, we've got some links to those in the show notes. Now, rigorous thinking comes down to asking really good questions. So what are some methods, frameworks, and questions that can help you and your team step into more rigorous thinking. We'll have a conversation about that right after this. All right, coming up, I talk with Casey Maxwell, our executive director of Ramsey Solutions.com. We're going to sit down and talk about how to encourage your team

to think critically using a few frameworks as a guide. Here's our conversation. Casey, thanks for coming back on the podcast. Yeah, glad to be here. So we are talking about how to encourage your team to think critically today. So I want you to think long and hard about this topic. so that we can dish out some wisdom for our listeners today. That's good. That's good. I actually did think a lot about it. So I think it's a good start.

Good. So most people would consider themselves a critical thinker if you ask them. They said, oh, of course, I think critically. But I've met most people, and I can assure you that is not the case. So what does it actually look like to be a critical thinker? Yeah, I get that a lot. Like people are, hey, do you think critically about this? And they're like, yeah, yeah. But honestly, most people just shoot from the hip. And so when they think about something for 30 seconds, they feel like, man, I feel like I really critically explored that topic. But what I've realized is that when it comes to critical thinking, it's not a, hey, I need to go lock myself in a room for hours and hours and hours to really think about this.

There's two key things that I've realized when it comes to critical thinking. It's knowing the right questions to ask and then having the right frameworks to use that information in. Because questions and frameworks help you get out of your own head and help you think about things more objectively. So it's not just going with your gut and thinking about that for a second and then spewing out the answer. We've got to ask some really good questions. Exactly. Not surface level. We've got to go deeper than that. So I know you, in your leadership role here at Ramsey, you've been challenged in a lot of ways to think more critically. Can you give us like a recent

example of where you had to do this in practice? Yeah. So I had a leader here at Ramsey. Talk to me about a thought exercise. So typically a thought exercise, again, is just a way to sit down and think about a project objectively. And so what he did is he said, hey, sit down for 30 minutes. I was about to take over this project. We already knew that I was going to lead it. And it was a big project. It was migrating 23 domains into one domain.

So that's a lot. And I had never led something at that scale. And so the project, as I sat down and thought about it, he said, okay, sit down and say, if that project is successful, what is true of the person leading it? So what are the skills and attributes that that person had? Now, the key is I took myself out of it. You don't think, what do I have to bring to this? You say, what needs to be true of that person?

So you write down all the different attributes. So there were things like needs to understand our marketing technology stacks, so very specific skills. But there were also things like needs to be their A1 priority. Once I had that list, I then said, okay, what's true of me relative to this role? So I went through each of the things. Is this a strength of mine?

Yeah, great. Okay, I have that. Is this a weakness of mine? And then once you realize these are the things that I have a deficit in, you can say, okay, I'm either going to fill that where I'm going to level up or I'm going to bring somebody into the team to help me out with this. To fill in those gaps. Exactly.

But that took a level of deep thinking instead of just going, all right, I'll figure it out. And then you realize, I don't have it figured out. You haven't got the right team in place. So this is really important to ask these questions right up front. Exactly, because it didn't solve all my problems, right? But it set me up to make decisions that made the project better. I realized the key things that I was deficient in, I brought key people and added them to a core team.

I knew that communication was going to be important. So I spent time on figuring out, how do we communicate this across the organization? So you mentioned frameworks up front, and there's a relationship between asking good questions and having the right framework. which ones have you found to be the most helpful when you're trying to get your team to think critically? Yeah, one of the best frameworks you could use is called the five whys.

So when your child asks you for something, typically if you say no, what do they respond with? Why? Yes, and then you answer that, and then what do they respond with? Why? And then what do they respond with after you give the next answer? Yes. To the point where finally you go, because I'm your parent and I said so, right? But there's something in that of continuing to ask why that will help you understand what you need to do.

So a lot of times we start solving a problem. We have a problem that comes up and we start solving it. But when you ask why, why is this a problem? Then once you get that answer, you say, well, why is that true? And then why is that true? And what happens is you ask that enough times and you get to the root problem. And that's what you actually need to solve, not the thing that you thought was the problem. Interesting.

So you're kind of getting way below the surface. And most leaders, they're probably looking at it and going, why? Okay, let's move forward. Let's just go do the thing, Casey. We don't have time to sit here all day and ponder. What do you say to that person? Well, a lot of times when people say, no, no, I want action. I need to do this now.

What you're saying is, I just want to do this action multiple times, right? So if you go and don't do that five-wise and you solve that symptom, you're going to have to solve a different symptom later because you never address the root. problem. So there may be more time at the beginning, but it's going to save you more time in the long term. Yeah, that's good. Five-wise. Any other frameworks that you found helpful? Yeah, there's a thing called a pre-mortem. So you may have heard of post-mortem. Yes, you've heard of post-mortem. This is the prequel. Yes. So a post-mortem for people that don't know is after a project is over,

you look back and say, hey, what worked, what didn't. A premortem is where you sit down and say, it's another thought exercise. If this project or this thing I'm trying to do is successful, right? You don't want to look at that. That's what everybody thinks. No, you switch it and you say, if this thing is a failure, what are the potential things that caused it to be that way?

And then you sit down and go, okay, well, now, keep that in the realm of possibility, right? Because you want to say things like, oh, a shipment didn't arrive on time, or we didn't calculate, the estimates or something like that. So you want to keep it in reality. You don't want to say, oh, a plane fell out of the sky and smashed my van. You can't deal with all of those sort of things, but you find a set of things that are possible things that could derail, and then you put things

in place to make sure that those don't happen. Yeah, that's smart. I mean, it feels like premarital counseling. It's important, right? You want to put yourself in a good spot and have the team prepared so that when something does go wrong, it doesn't throw the whole thing off and it becomes a failure. Exactly. We're just thinking through it ahead of time. Yeah. That's great. Because when it comes to the way we approach things with our gut,

one thing we don't realize that we always bring to the table is bias. So a lot of times we have hindsight bias. So we think, oh, we did this in the past. I'm sure it's going to be true the same in the future. And so we go about it, even though variables have changed. Or we have things like confirmation bias, where we have an outcome that we really, really want. And so then we just kind of handpick almost subconsciously.

the information that supports that, and we ignore warning signs. So these frameworks and these questions will help you get out of your head, help you identify some of those biases, and help you make better decisions moving forward. Yeah, and that every person on the team probably has their own biases they're bringing to the table. So what is the conversation like? If you're in the meeting with the team and you're working on a project,

how do you kind of circumvent that? How do you ask those good questions to weed all of that out? Yeah, some of it is just continuing to ask questions. I think a lot of people share opinions as facts, right? And so if you take everything that everybody says as a fact, then what's going to happen is you're going to end up making poor decisions based on those biases. But asking questions of like, well, what data supports that?

Where did that come from? What are the variables that are different? What could go wrong? Do we even want to do this? It's just slowing down enough and asking the questions that is going to help set things up to be better in the long run. run. So the theme I'm hearing is add less, say less, and ask more. Exactly. That's the key here. Okay, so this may sound overwhelming. A lot of frameworks, questions to ask, what is one small tweak that the

leaders listening can start doing, can create that habit to form critical thinking amongst their team? Yeah, I would say set aside time to think. Most people are just running and gunning. They don't have time and they're just making decisions as they go. If you are, are setting aside specific time to think you're going to actually do it. It's not something that we naturally do. We don't naturally sit down and say, hey, I want to ask questions that are going to get me out of my own headspace, right? But setting aside time and putting together a set of questions, like the ones we talked about today, to help you kind of get out of that space. The other thing is, before you make any decision, there's another framework out there called halt. And it says,

don't make any decision or do anything if you're hungry, angry, lonely, or tired. Because those are emotions that will cause you to skew in a certain way. So if you have any of those, halt or stop and take a step back until that emotion has passed, and then you can lean in and start making better decisions. Yeah, that's a great reminder to actually schedule the time to think. It feels strange to have that on the calendar for thinking time. But, man, the power of just being still for a second and not being in another meeting and responding to an email, creating that space to think more deeply, to have some prompts that can help you get to the right answers.

That is super critical. So I appreciate all these questions, the frameworks that you've given us, Casey. Always love having you on the podcast. Yeah, thanks for having me. Thanks so much, Casey. Always love having you on the podcast. Now, Wes and Casey both talked about

how rigorous thinking is a hallmark of great leadership and strong teams. And a big part of that is asking yourself and your team a lot of questions. So if you need even more ideas on what questions you should be asking, we've got you covered with our free resource, the critical thinking cheat sheet. To download this free resource, just use the link in the show notes. Hope you enjoyed today's episode of the show. If you did, I want to challenge you to share this with three people on your team or in your circle. And if you really enjoyed it, leave us a review and tell us what you love about it.

And there's one guy in particular who would love to hear what you think about this podcast. And his name is Tim, and he produces this show. He wants to know what you like, what you don't. like and what improvements we could make. Your input helps shape what you hear on this podcast. I think that's pretty cool. So go ahead and use the link in the show notes to connect with our producer, Tim. If you want to keep up with us on social media, you can follow us at Entree Leadership. This episode was produced by Tim Hull, edited by Jacob Harrison, and mixed and mastered by Will Rutter. I'm your host, George Camel, and on behalf of the entire Entree leadership team, thanks for listening.

Until next time, keep learning and keep leading. If you enjoy this podcast, you'll be should check out other great podcasts from the Ramsey network, like Borrowed Future. Not so fun fact, America has a $1.6 trillion student loan crisis and it's out of control. I'm George Camel, host of the Borrowed Future podcast where we uncover the underbelly of the student loan industry and show you what you can do about it. It'll inspire you to see that it is possible to avoid student loans and graduate college debt-free. Listen to Borrowed Future wherever you listen to podcasts.