Tech Scenes Unplugged with Brian Wang

Speaker A: It's interesting to think about how many conversations people try to avoid.

Speaker B: When you work with someone long enough, you'll notice if there's like a recurring complaint. And to me, when someone's like recurringly complaining about a thing, that's a pretty big sign that there's some blind spot that they're missing. They're either not taking a specific action or they're avoiding that particular issue and kind of like recycling internally by complaining about it. But that's a blind spot. They're avoiding some discomfort they can't see see in the system that they're actually contributing to the situation they complain about because they're refusing to feel something really uncomfortable in that conversation.

Speaker A: Let me say something that will probably be the worst marketing for me ever. Uh, I feel like part of the work that I do is creating those conversations that they don't want to talk about. Brian, welcome to tech scenes.

Speaker B: Hey Jeff. Great to be here.

Speaker A: Well, it's been a long time coming. We've had a couple conversations. We've been trying to schedule this. I'm, um.

Speaker B: Yep.

Speaker A: What is your.

Speaker B: You're going to today.

Speaker A: So between our calendars, I'd like to say, but mine has been kind of the, the problem, uh, I have to admit. But yeah, I'm so happy that you're here. And you know, let's just start from the top. Tell people what you're up to right now. Coaching CEOs and founders. And why did you decide to do this?

Speaker B: Crazy to say. I'm hitting seven years now of coaching, uh, early stage founders and CEOs of startups, um, full time. And, um, yeah, the way I describe my work often is I'm often helping founders make that transition from that sort of builder identity to leader. So a lot of times when founders and CEOs decide, uh, to hire me, it's because they've reached a point where the product or service that they're building is starting to work. They're building traction, um, and the demands of the business are just evolving. And a lot of that means, you know, recruiting the right team and um, setting them up for success and, uh, in a lot of ways dropping a lot of what you used to be doing as an early stage founder, um, building and selling all day into someone who's actually creating the conditions for a group of people to succeed really well. And in my experience that's really hard, both in terms of like, recognizing when that shift is necessary and also the skill development and the identity shift that gets involved there. So, um, I've been doing a lot of that now for like uh, I said last seven years. And prior uh to that uh, I, I myself was a founder, ah CEO. I ran ah a startup for about five years. Spent some time in, in VC and project management as well. So I've spanned a few different roles um, in, in uh tech startup land. Um, and, and uh, coaching is really where I've found my home now over the last uh, several years.

Speaker A: Well I think that makes a lot of sense that parallels a little bit of my background too is and I think it helps to have that relevant experience right that have a ah, variety of roles within kind of that venture world. Especially if you're coaching and helping executives within that world. And um, being a CEO, founders can be a lonely place. You know, you want to make sure that you're always you know, presenting yourself well to all the different stakeholders and oftentimes it doesn't leave a lot of room for being completely transparent. And I think the role of a executive coach, I think everybody should have a coach. I think it's a really important element. I mean based on your background it makes complete sense what you're doing, what drives you and makes you really want to do this.

Speaker B: I'll start from kind of maybe like at a system level and then I'll talk about the individual um, at a system level. Uh, something I often think about is the fact that especially in the modern age, there's so much power that actually comes with a role uh, like this when your company's actually working and it's scaling. Especially in technology, right? When we consider how much leverage and impact technology, uh, especially frontier technology can have on um, our lives, everyone's lives, there is huge capacity for benefit but also harm in terms of what people are building and putting out in the world. I'm a strong believer in the idea that uh, leaders often they might be coming uh, to the work from a couple different orientations. But one is often they might be coming from a place of insecurity or lack because we're all vulnerable human beings and we're always dealing with that. When we do that, when we're leading from that place of insecurity, it can have I would say somewhat predictable consequences. It creates a certain environment where people can't do great work or maybe there's um, a lot of conflict or there's a lot of avoidance, a lot of withholding, um, or a lot of fear, uh, which can then kind of go downstream into everything the company does. And even if the company is successful, um, it Might lead to like a, like a carelessness or thoughtlessness around the way that these products are, um, being deployed out into the world. Um, and so the flip side of that is I think a lot of leaders out there, especially if they've done work, they develop a certain type of maturity, they recognize that there's a way in which they can transcend that sort of sense of insecurity and then actually go into more of a stance of contribution and their values. And um, what do I really want to see in the world, um, in terms of a positive vision for it? When I think about coaching, coaching often can work across both of those ends. I think when you help a leader recognize when they're in that place of lack or insecurity or fear which all humans are subject to, then, um, they can start to have a chance at operating from a different place. As they do that work, they can almost inoculate themselves a little bit against those sort of traps and then find ways to move towards that positive contribution. Uh, which I think in practice means healthier cultures, happier, more motivated teams, uh, and ultimately, um, better products and services for the world. And then of course downstream, all the way to the end users and the customers. Um, and so coaching as a support structure can really help people kind of hold up the mirror and recognize when are they in those, those particular stances and when those patterns are coming up. And so going back to this kind of leverage point, you know, I often think about this idea that like, if, if I can help a leader really, um, I use the phrase like clean up their consciousness in a lot of what they're doing, then that has huge downstream effects on the company that are building and ultimately the impact on society. So that's one way I think about it from a systemic level. But I'll just also say if on a personal level, the why. So I was a founder myself, right? And as you were referring to Jeff, it can be a very lonely, isolating place to be. We need support. We need support. I had a coach when I was a founder and I found it incredibly, uh, invaluable. And uh, it takes a village. And so for someone to be in that position where there's a lot of pressure, they have a strong need to perform well, to, uh, show up in a certain way. Um, it does a lot to a human being, um, and it can make it hard for them to be at their best. It can also be hard for them to take care of their own well being just on an individual level. And so I also often look at Coaching as a way in which a leader can really take care of themselves through that journey. Um, again, just both on the individual level, but also that systemic level.

Speaker A: As someone that's coached teams for a long time within, within business. But I also coach outside of um, the workplace. I coach, I've coached hockey for I think 16 years now. I coach wrestling and jiu jitsu and um, I just can't imagine any high performer not having a coach. You know, think of it in the sports realm, imagine any team not having a coach and how bad that would go. It just wouldn't work. Right. Yeah. And uh, it just makes so much sense to me that you have a support system, you know, any sort of team needs, like clear roles and responsibilities. Like if, if you think of like, let's just use the hockey analogy, like if you're offensive people, your forwards, you start playing defense, um, because the defenseman's not doing their job or the defenseman decides to go uh, up, up the ice past the, than someone to have to pull back. But if they didn't, like, it all fall apart. And so, you know, I really think like, like you must play your role, you must know your role, you must know your lane. Um, and then you think of sports too. There's a system involved, there's, there's a system across the sport where they know if someone's here, another person is going to be here without even looking up. Because there's like a system involved in that. And I think um, there's a lot of elements of teams across, outside of the workplace that really shows the need for that in the workplace. And one of those elements I think it's really clear is coaching and having a clear leader.

Speaker B: Yeah, I would just say it often doesn't come on its own.

Speaker A: Right.

Speaker B: Like a lot of times, especially when you're like a first time founder, you often don't come into that position having a playbook or having the experience of like how do I actually build and structure a team? How do I set up uh, people in specific roles with their responsibilities and what they're supposed to own. And you know, the other part of coaching that you uh, know this is so much of it's around feedback. Right. Like feedback is the way we learn and we experiment and we get more feedback and then you know, we learn, you know, what to do, what not to do, et cetera. And that's the other thing I also uh, consider around coaching is, is sometimes you're just too close to what's happening. Um, which makes it really really hard for you to either learn from what's going on or even notice that there's a particular thing that's happening, um, in that situation. And so, um, you know, one part of the role as a coach is to be able to point those things out, to be able to, to surface and notice, hey, I noticed there's this pattern, uh, or dynamic happening, um, you know, between you and this other person or you and the team or, you know, whatever it is. And, and then, um, can we actually learn from that? Can we reflect on that and notice, like, is that actually the result you're trying to create? Or, you know, can you, can we recognize, like, how, you know, you're having a part in this situation that maybe you're complaining about? Um, and then, uh, can we learn from that?

Speaker A: Kind of reminds me of within our peak system is like, I call them learning loops. And so annually, every teen does a survey, asks, uh, a variety of different questions, basically getting to like, what's working, what's not working at the end of the day. Right. And reviewing that together as a team, as that team, you know, if it's the leadership team or sales team or marketing, whatever team, uh, that's doing it is it allows them to kind of get some feedback and hear what other people are thinking, what's working, what's not working. Um, and then we do that quarterly or if it's semiannual. However teams are structured, it's kind of a little bit different than like an annual or quarterly review, but it is that learning loop and getting that feedback and consistent on a cadence. And so doing that individually for people I think is really important. You know, you do have your reviews of people are organized and doing that, but not. It's. I think it's different when it's a coach that is really trying to strive to make you better. Not. Not all leaders or managers are also coaches. Right. I think there's a difference between that.

Speaker B: Yeah. Like when you go into a role like that, you, you do wear a lot of hats. There's the, the manager who is responsible for results. And then oftentimes there is like the coach role where it's like, if I'm on a team and I'm coaching my direct reports, there's. There's an element around just like, how do I develop this person and give them feedback? And I think that that's. There's like some non zero amount on that that's always necessary when you're managing people. But yeah, to your point, I think as an external coach, Like I, you know, I kind of offer the benefit of like being able to in some ways, not always but like, but like offload a little bit of that to somebody else and hopefully that also like gets infused into, you know, the culture in some way as well. Just do, just like do modeling. Right. Being able to experience that and see what that's like and how can I, how can I take that um, you know, into, into my everyday and I guess like, you know, you just actually made me wonder about a question. Jeff is, is when it comes to teams and they perform really well and in particular they learn really well. Like what have you seen the teams that, that perform well do differently compared to those who maybe sort of stay in the same place for a long time.

Speaker A: That's a long question or long answer. Here, just read this. Um, there you go. I, I would say that probably start at the highest level. The teams that perform really well. I think there's five behaviors. One symbiosis. They are not that they, they work magically together but they are trying actively to work well together. I think the second one is communication we were just talking about that is having the right level of communication but also having like the right cadence of communication. It has to be a cadence you can't just rely on. Oh, uh, making sure we were at Slack. You know, I mean like you have to have like a structure. I think for communication alignment is super important, important. And I like to think of focal points like are we clear about our mission? Are we clear about our three year vision? Are we clear about our one year plan? Are we clear about our 90 or 100 day OKRs? We clear about our roles and responsibilities? Those are focal points across reverse engineering back to where we're going and then also who owns what. I think having that clarity and not only that clarity but alignment that we agree upon what those things are, solves so many things.

Speaker B: And then learn some questions on that one. So I'm going to pin that one for later. But I have a question.

Speaker A: That one, I love talking about that one. And then I'd say the next one's learning. And that's what we were just talking about. Those learning loops. Are we always trying to get better and do we have the feedback and learning loops to actually learn, uh, what's working, what's not working. What's not working is awesome because we can flip. We don't have a sales process and to create a sales process and so we always have a bias to action, always moving forward. Um, and then the last one I really think is just empowerment. And that magically, magically, uh, spells scale. Ah, by the way. Um, but empowerment, yeah, it's very convenient. Um, empowerment is really important because once you get those other things right, it unlocks the team just to run. And not wondering about, like, when we go through roles and responsibilities with the team, and I just did this leadership team last week, we walk through their role, we do it once a year. Um, and then we ask questions. Is there any questions about, you know, what they do? Is there any, you know, um, overlap? Is there any gray areas? You know, what are things that come up often around this person's role and their responsibilities? Um, and then I asked the person themselves, is there anything that's holding you back from doing what you need to do? Is there lack of clarity that you have about your role? Uh, and so we do that with leadership teams once a year on, on their annual session. Um, we do at the leadership team level. We get each of the. The teams, but I think that's really important. And knowing that empowers them just to run. Now we know where we're going, what we need to do, how to do it, who's doing it, when it's going to get done by. Um, and a lot of times when that is not clear, you're not using the full leverage of your team. And it can be very frustrating. Right.

Speaker B: Well, it also sounds like in some ways, I don't know if this is the way you've set it up, but, um, like there's like a sequence to that. I would imagine empowerment's great, but it kind of is not so important if people are not clear on their roles and responsibilities. Um, ah. Or if they're not aligned, like, we can all feel empowered on what we think our jobs are, but if we're not actually on the same page or like, what our jobs actually are and what they're not, then empowerment is kind of like the wrong part of the process to focus on. Am I reading that correctly?

Speaker A: Yeah, I wouldn't order those, but I definitely always felt like. I'm glad that when I came up this analogy of scale, that E was the last one, because I really think you have to get these other ones right to make that. Make empowerment work. But also I also think about empowerment as, like, are we doing what we need to do to empower our people? Just like symbiosis. Are we trying to become a team? Right, right. Uh, but yeah, I really think, um, if I had a narrow, nail it down to one, and then maybe I only had like a couple hours of one team. I would try to get the clarity around mission 3 year, 1 year and okrs, which takes more than a couple hours. But we need to get clear on those things. Right. Um, and start in that order too, to really reverse it back, I think.

Speaker B: Yeah. So that's really foundational.

Speaker A: Yes, I think so. I think it's hard as a team to know where to go and what to do if you haven't talked about it and had those conversations. And if they're isolated of a CEO just telling different people to do things doesn't work. You have to get the team together. We have to talk about it. So it's similar, I guess, analogy. Um, and I want to use this jiu jitsu analogies with you because we love to, um, but I'll use hockey right now because it's easier if we didn't know the goal was to throw the puck into the net. Right, right. We, we need to know that. We need to know, um, what's the system in order to get it there and what's the plan? And if we didn't know and there was no net, we could be empowered as we want, like you said, but what would we be doing? And we'd, uh, you know, and oftentimes when I work with teams for the first time, they think, oh yeah, we do have some clarity and you know, we kind of know where we're going. And you get in there and you ask a few different questions, like simple question, like what are the top five most important things to accomplish by the end of the year as a team? And you'll get 30 different answers.

Speaker B: Yeah, that's a red flag.

Speaker A: Right. And, and, but it's also common. It's, it's not, it's not uncommon because they just haven't had that conversation. And sometimes if you ask them and you get to those like 3 to 5 and you ask, okay, how are we actually going to do that? That oftentimes is missed too. Like they may define like the revenue goal or they have some financial, uh, elements that they usually take onto but they haven't really talked about, like what do we actually really need to do? And then that how question is really important too. A lot of them haven't really gone through the how. And that's where the cross functional elements of teams, like the work that they're actually doing, needs to have clarity. And if that doesn't have clarity, that's where it gets real messy. And you hear like, you know, uh, we don't have Good handoffs or there's gaps or we don't. They don't know. They can't tell if they have the right people or not because they don't know how they're connected well together. It's a whole nother kind of element. But yeah, um, changing gears a little bit, I know we pinned a couple of things. We absolutely come back to that. I'm curious, as an executive coach, how do you identify those blind spots and how do you address those?

Speaker B: Uh, there's a couple things that come to mind. One is just a simple process. Like sometimes when I'm working with a new client, um, for the very first time, I like to front load a little bit with just some assessment work. So actually um, just like run a360 and go and um, do a bunch of surveys, do a bunch of interviews with the folks who this person's directly working with across different levels and try to synthesize something and do some pattern recognition around. Like what's, yeah, going back to what you were saying earlier, like what's this person doing well, what are they not doing well and what is there to look at? Right. And so that, that's a super helpful practice because, um, it allows you to get, ah, ah, different perspectives on you that maybe, um, you wouldn't normally get. And ideally for me, I can help that person funnel that into this notion of the one big thing. So there's a great book called Immunity to Change, which you probably know. And they talk about this idea around. Look, we all have things to work on. We all have, uh, growth edges to push against. Um, but the trap is to try to go do too many things at once, try to change too many things at once. Um, and so what they really encourage folks to think about is what is the one big thing that if you really started to make improvements on that, it would have the highest leverage, the highest unlock, and maybe even like have impact on the other stuff that you've identified. So that's one way of, uh, helping someone kind of notice those blind, uh, spots or patterns is let's just get feedback, right? Going back to feedback in the room and try to synthesize and make meaning out of it. Um, and then, uh, start to identify what are the areas that we want to start to commit to changing. Um, so that's one way. The other way that comes up is talking about blind spots. When you work with someone long enough, you'll notice if there's a recurring complaint. Um, and to me, when someone's recurringly complaining about a Thing that's a pretty big sign that there's some blind spot that they're missing. Um, because people complain repeatedly, I. E. They're not resolving a thing or, you know, over time, um, because there's some way in which that person's keeping the thing going.

Speaker A: Right, right.

Speaker B: They're either not taking a specific action or they're, they're avoiding, uh, that particular issue and kind of like recycling internally by complaining about it. Um, but, uh, you know, they're in a system. The complaint keeps recurring. When we recognize that that person has some agency around that, then again, there's some blind spot. They're not, they're not actually exercising their agency around that. So, you know, an example of that might be, you know, if, let's say I'm working with a founder and they're complaining about their co founder, they feel like their co founder is not working as hard as they are or something, you know, which is a common thing.

Speaker A: Very common, right?

Speaker B: Yeah, super common. And so if I hear that a few times, like, hey, like, I've heard you mention or share this complaint that you think your co founder is not working as hard as you are or as much as you should, um, the first question I might even ask is, have you had a conversation about that with your co founder? And they might say like, no, that's crazy. Like, I don't want them to think that I'm like, just complaining about them or like that I'm ungrateful or, or there's gonna be a really hard conversation or whatever. Um, and so there, there might be some, you know, reason they have for avoiding the conversation, but that's a blind spot, right? Like, the blind spot being like they're, they're avoiding some discomfort they can't see in the system that they're actually contributing to the situation they complain about because they're refusing to feel something really uncomfortable in that, in that conversation, or they have some story about how that conversation is going to go and they're very certain about that. And, you know, so things, things keep on going. And so, yeah, I would say that that's also a good marker of blind spots. If there's something that keeps repeating. Um, and I'm picking up on that, and I'm picking up on that nerd energy. Then I'll often just like hit the pause button and be like, hey, I noticed that you've brought this up a few times now. Here's how I'm receiving it. And I want to, I want to like, just check and see, like do you. Have you noticed that?

Speaker A: Right?

Speaker B: And then like, what do you, what do you make of that? As I share that reflection, it's interesting

Speaker A: to think about how many conversations people try to avoid. And, uh, let me say something that will probably be the worst marketing for me ever. I feel like part of the work that I do is creating those conversations that they don't want to talk about. And it's probably a real unpopular thing for me to say about what I do. But, um, it's not that I enjoy conflict. I dislike it so much that I feel compelled to walk right into it to try to help teams solve it. And there's a lot of times people, what I find, and we kind of talked about this already and maybe it's coming back to that question that you have is a lot of times when there's disagreements, it stems from that lack of clarity. And I'll give an example. I was working with a leadership team last week, um, and the question came up of international expansion.

Speaker B: Yeah.

Speaker A: And they said, I really think we should start thinking about international expansion. And the two co founders just went at it, went at it. And I said, pause, pause, pause, pause. I'm like, when you say we need to start thinking about it, when do you actually want to do it? Like, is that three years out? Is that one year out? Is that right now? And, uh, the person that brought it up said, oh, that's like five years out, but I just want to start thinking about it. The other co founder is just like, oh, the way you said that made me think we need to start doing stuff with this right now.

Speaker B: There's like assumptions flying around here about what that meant.

Speaker A: A bunch of assumptions, what that meant. And oftentimes, I won't say always, but more often than not, if you ask the time in which we're going to do this and get clarity on that timeline, that solves it often. Or if we say who should, who would we have do that? Right? You know, like so just trying to get it like the where, the when, the what, the how, the whole. Right. Those kind of discovery questions. Just getting clarity on that often just brings everything back down and just very common. And uh, yeah, like part of what

Speaker B: that made me think about is like, yeah, when, when it's so common when you're in a team meeting, someone says, I think we need to think about X or what about, you know, this particular goal. Uh, and when we as listeners often end up assuming that that means right now and oh, crap, I'm going to be on the hook for some of this, in some way, or the thing that they're mentioning is going to cost me something because his resources are going to go away or whatever it is. So there's like a whole bunch of uh, assumptions that go in, but they almost always get tied back to like, but this is going to cost me something right now. Right. And so then that triggers a defensiveness, which is why then there's like now we got to like argue about it, uh, rather than like taking the time to, to get curious and just be like, okay, so like, what do you mean by that? Timeline wise, what does that actually entail? What do you have in mind? Even just a little bit of, um, just like open ended curiosity. Can I think to your point, we solve a lot of these tangles, um, that people end up in.

Speaker A: Yeah, the why question's great. This, uh, happens. Here's another one that happens a lot with teams I'm working with. We'll do some prep work ahead of the session, kind of try and nail down some of the biggest priorities. You know, maybe let's say on the year. And this one happens very often is I'll say, um, at the top line, what, what's our revenue goal? And the CEO will provide a number.

Speaker B: Yeah.

Speaker A: And the CFO looks a little different. I can tell in the room based on that number. And then the head of sales has a look on their face. And then I'll say, you know, like, Tim, do you want to say something? And he'll be like, yeah, well, we gave the board this number and m, we're sharing this number internally. And then the head of sales is like, and I have this number. Let's just start with what is the right number?

Speaker B: Right.

Speaker A: And you know, it might be 20 million. And this one had 25 and this one had 16. And uh, just I typically right away start and say like, why do you have 20? Tell me why you have 25. Why did you put 16? As they talk about it, typically within 10, 15 minutes, we decided it's 32. You know, it's like the. Often times it's even bigger and it's because things float around. One conversation gets marked this way, this one gets marked this way. Um, put them in the realm, talk about it and then get context. Uh, and this is real quick on this is like context and numbers is really important. Is this like shooting for the moon? Is this minimal? Uh, what is this? And define that number. And once we define that number with that team, we have that conversation. We put the context to what that actually Means and give the team the context of what that means. Cause that's really important. I mean, it's hard to uh, as humans to align around letters and numbers, right? At the end of the day we're writing down numbers and letters and we're like. And that's giving us the power to do what we need to do.

Speaker B: There's so much meaning that gets tied up in that, right? Like we're naturally meaning making, um, creatures. And so we can't help but make meaning which is informed by assumptions which are often hidden and so on. Um, part of what you're bringing up makes me think about the book, um, Crucial Conversations. You're probably familiar with it in the book. Uh, this is coming up because I've kind of borrowed this a little bit in some recent conversations with folks, but um, they have this great phrase in Crucial Conversations, um, called uh, the pool of meaning. And so the reason why these like, maybe high stakes or like emotionally charged conversations can go off the rails, or the reason they kind of go into this high stakes sort of feeling is because people are not sufficiently adding to the pool of meaning.

Speaker A: Right?

Speaker B: So if you've gotten multiple people in a group and they're all trying to align on something, there's like, like, you know, you've been talking about. There's all these hidden assumptions and, and ideas and implications around what's getting proposed and um, which need to be uncovered through clarifying questions like where did that number come from and what's going to be required to get that done and is that higher, low, et cetera, all those things. And so what the authors in the book talk about is, you know, effectively these conversations can find resolution as long as people can stay in the conversation long enough to uh, add sufficiently to the pool of meaning. And once that pool of meaning is sufficiently large and shared, then it's like, uh, okay, I understand actually what, what we're all saying here. And now we have a road to actually get to alignment because we've laid out all those things in front of us both in terms of what we're cognitively meaning, but also even just like empathetically what's going on for each individual person. Um, and then the reason why this is maybe a little bit of an aside, but like the reason why people fail to get to that, that point of the pool of meaning being, you know, sufficiently contributed to is that um, a lack of safety. Like, people get like triggered, they get defensive, they, they, they kind of get into like an us versus them sort of, um, uh, state and then it kind of falls apart and then dialogue shuts off. Pool is no longer actually being added to. And then, and then you're kind of like in, in a stuck place.

Speaker A: Yeah, yeah. I think it, I think I boil that down to fear. I think a lot of times people respond in a fearful way. Um, one of the things I try to do, and this kind of goes back to what you were saying a little bit earlier. It's like showing up in kind of that. Right. Mindset. Showing up kind of grounded, I think is really important. When I bring teams through an annual session or a quarterly session where we're there together, we usually go through kind of like session expectations. I call it simple, like open, equal, transparent room. We're all on this team together to win. If we win together, we all win. Um, and really try to get like a baseline of like, togetherness. And like, the more that we can put out on the table and solve, the farther faster we're going to go, the more that we are keeping these stuff in our rucksack, kind of hike up the mountain together, it's going to weigh us down and it's just going to tire us out. Um, I always feel like dealing with the things earlier is better than. And having it wear on you. And I try to get them in that mindset and I think that's, that's really important, um, to allow them feel like they have the right to have some of these conversations that they maybe wouldn't normally have. The other thing I think is really interesting and you made me think of this is oftentimes when I'm in a room with a team, the conversations are the most important element. I mean, at the end of the day, we are trying to. I usually have, um, an objective for every piece of the meeting that we're trying to do. You know, define the five objectives or whatever that might be. Right. But the process to get there creates this conversation that creates this kind of, um, mental connectiveness, um, that you were talking about or like I'd like to say the context for helping us make these decisions. And it's kind of reminds me of like a brain and synopsis. Synopsis. Right. Like these conversations are like triggering all these different things and creating these pathways to understanding. And it's, we're going to give them the AI next. But I think I don't see today probably something in the future how, you know, technology is going to help us with that. Maybe technology can help unearth more information and data amongst what everybody's thinking about. To have this group consciousness. As of right now, the best way I find for teams to get in alignment and get clarity and have that context is by getting together and having the right dialogues in the right environment and actually pausing to spend the time to do that. Um, how are you seeing that play out in your work? Sitting individually with somebody, are you often coaching them? But the coaching them or to help coach other people, do you find that

Speaker B: in your work that does some. Specifically on that last point that does come up sometimes, you know, especially when it's like, hey, I have someone who I want to help them perform better or there's, um, you know, feedback I want to offer them because it's important, you know, for the company and for that person. But the other thing that I was really, um, sitting with as I was listening to you, Jeff, is yeah, this whole idea of like humans coming together and talking, I. E. Sharing what's, what they're thinking and feeling with the other person so that they can, that other person can grock it. And there's this exchange that happens between people so that they can, um, create more of a shared reality. And like that. I mean, that is, you know, to be a little bit overly simplistic, what a team is for. Right. Like a team exists because you can achieve a lot more with this group of people than you can with any one individual or these, you know, individuals who are all separate. Right. There is a shared consciousness that, that does take place, that does get formed or emerges when the conditions are right. Um, and yeah, for sure there, there is like a necessary amount of time spent together in order for people to drop into that. Um, and I think in the best case, you know, you talked about mindset or mentality. It's like, you know, if you're not careful, you can be in a place where it's like, let's just say like you and I were on like a two person team, just for argument's sake,

Speaker A: and I are right now on a two person team. Right.

Speaker B: Yeah, we're trying to create a great podcast. Right. And so there's two ways that I might approach that. Um, I could say, hey, it's Jeff and it's me. It's you and me. If I view us as separate, then I'm going to be more naturally predisposed to think about what's good for me, what's in it for me, and I'm probably going to be more likely to consider, um, trade offs in a way that's like highly individualistic versus can I actually be in the place of we. And can I actually tune my attention into the we? Can I actually put my attention into what is it that we want collectively and am I committed to that and to extend that into the team side of things? Like in that shared consciousness, the, the word that comes up for me is um, attunement. So can I actually attune to the needs of the group? And what is, what is it that the group wants to create here and what is it that the group needs in order to create? Uh, to do great work. Right.

Speaker A: Yeah.

Speaker B: And that's a very different form of consciousness compared to me versus you or me and you. Right. Like everyone is probably experiences where they're on a team and they've had a teammate who's like, they're just self interested and you can energetically, you can feel that and you can feel like we're not going to do great work here because I mean this is getting political or uh, this person is wanting to like, you know, maintain their own resources or their own reputation or whatever it is. And there's like friction in that. But if it's, oh, we can all feel collectively that we're committed to each other, to this collective and we're taking care of it sufficiently, then I think then you, you, you, you have much more of a chance of people, um, making decisions faster, they get to alignment faster. Um, people are able to go into their areas of strength much faster and they're clear on what they, what they're doing, what they're not doing. Um, they know what the goal is, et cetera. But it's all because they've um, almost like subsumed their own interests to that of the group.

Speaker A: Yep.

Speaker B: Which there's pros and cons to that. But that's, that's a bit of what came up for me there.

Speaker A: There's running close on time already. This gone so fast. Um, let's, let's shift gears and talk about AI.

Speaker B: We can't leave this without talking about AI.

Speaker A: Right. So what are you seeing and how do you feel like teams are adapting to this new autonomous workflow?

Speaker B: One of the things that I'm seeing is, you know, like if I've worked with someone for a while and they've been, you know, um, working on their company for let's say a few years. Um, I'm noticing a tension where they, let's say they have a team of like 20 people, let's say, um, and because they're starting to adopt modern uh, tooling agentic workflows, cloud Code, all this sort of stuff. They're noticing like, whoa, we have a lot more leverage here, um, into what's possible and conversely some sense of like, like their team is a little bit too big. There's like too much going on. I'm noticing some leaders are like, I really want to spend more time with cloud code to build because that's faster than having to be in these like five one on ones or this, this next team meeting. It does feel at times that people are in this, this thinking of, well now that we have autonomous uh, workflows and these AI tools, what the hell do I have my team for? This team is feeling like more of a burden. There's too much drag here. There's human messiness which is true to a certain extent. Um, and so as a result I think that I'm just without judgment, I'm noticing like, okay, people are starting to hire a little bit more slowly. I think they're feeling maybe a little bit um, more comfortable reducing team size because it kind of makes more sense for them. I think. You see there's a lot of public examples of that now with like larger companies. Coinbase just talked about that, um, obviously Block did that uh, publicly, um, not too long ago. But even in small companies I'm seeing that in small startups where there's a little bit of a, hey, uh, with all these great um, uh, bots and AI, what do we have all these people for? Um, and I'm of two minds of it. I think one, yeah, it's incredible that these technologies exist now and wow, imagine what people, people can accomplish now like you know, on any individual basis. At the same time, how do we actually find the opportunity to take an existing team and make it that much better with these new toolings? There may be the case that you know, you discover, yeah, like we're way more efficient with fewer people now, um, or that maybe some of these workflows are revealing some of the like the core inefficiencies of ah, a team, the way it's set up. My counsel would be, hey, can we investigate what this is revealing for the current team? Maybe there's some dysfunctions and are there ways we can address it? Because wouldn't it be great if you had a team that was actually on top of its game? Because we were able to take the time to notice what's not working and really address that and equip uh, them with these new tools which does require a new way of working. Let's just be clear. Um, there's a little bit of this black and white, you know, either or thing going on. I can understand it. But at the same time, um, I think there's a little bit maybe m reactiveness happening with it. Um, and I would really want to see people explore a little bit more deeply like what's possible with existing team now with the new tooling rather than like, let's just kind of like get, get rid of all this like human messiness because it's uncomfortable.

Speaker A: What I've been noticing is I think you'll find this interesting coming because you're some of your product background. We used to only worry about the founder, like running after shiny objects. Right. Like, oh, I want to do this now and I want to do this now because they're kind of typically a, you know, visionary type person. Right. Um, now we just equipped everybody across the organization with tools that are. Can speed up their work.

Speaker B: Yes.

Speaker A: And everybody now, not everybody, a lot of people. And I'm even seeing at the leadership team level, companies between 25 and 500 employees at the executive level, um, across the board developing things. So now your head of marketing is in Claude or your head of sales is in Replit and they're building these things and they are getting sidetracked and they see all this possibility. But they've never managed a product before and defined a M project before. They don't know exactly. They think they know what they want, but they don't know what they need. Right. Like all the things that a product management, product manager knows what to do. Um, and I, I'm seeing teams get very distracted and what I like to bring them back to is like, again, what do we want to accomplish by the end of the quarter within this team? What's success look like or by the end of the year? Right. How are we going to do that? Now I do believe the world is going to still have. We're going to define objectives of what we want to accomplish. We're going to have humans and technology helping us achieve that. Like we always have. Agents are a little bit different than our standard CRM system. Right. They're actually doing work. But I do think we'll still be organized around trying to find where we want to go and how we're going to do that might change. Um, but right now it is a little bit of the Wild west. And I feel like a lot of teams are starting to do things that, uh, spending a lot of time on things that they'd never spent time on before. And it's getting distracting and it's actually slowing them down in many ways. But that's just kind of like the stage.

Speaker B: Can I just add something to that?

Speaker A: Yeah, yeah.

Speaker B: The thing that came up for me as I was listening to you is that there's like, ah, a lot of potential for incoherence or a lack of coherence in an organization. And so if you've got everyone equipped with an agent and they're building their own products, then all of a sudden you can end up with like a dozen things that have sprung up and they make absolutely no sense, um, because there's nothing tying them together.

Speaker A: Right.

Speaker B: And so I think the job of a leader is to, you know, as, as always recognize the reality for what it is and what the implications are. And how do you actually get ahead of that and say, okay, we are in a new world and there is a possibility for us to become like doing 50 different things right now, which is not what we want. How do we actually, um, I mean this, this actually makes the importance of leadership even greater. How do we actually rally people around a unified direction? And how do we actually build in this new era? Um, and can we actually have guardrails or at least like rules of the road? And how are we going to actually use these things in a way that again, goes and serves the team rather than, you know, the head of marketing or the head of sales, like their particular agenda.

Speaker A: Right. What outcome do we want?

Speaker B: Correct.

Speaker A: Collective.

Speaker B: Right, Collective.

Speaker A: Collectively, what outcome do we want? And it's interesting because a lot of these things that are being built, it's, you know, incredible saving time. But now we actually also, uh, have to maintain these tools that we built. And with the speed of which these tools we're using to build these new tools is changing. Ah. And it's going to become more and more complex. We're going to end up with a lot of tools in every area of the organization. It's going to be interesting. It's going to be really interesting. Uh, but at the end of the day, I do believe, um, that answer the question around, like, where are teams going with AI? I think as long as humans are involved, I think humans will want to be making decisions. Now how we gather that information and that data to make the decisions, definitely going to change and is changing. Um, but I believe we'll still see like a human chain of decision making. Uh, analogy I like to use is, uh, I can put my car on a variety of different levels of autonomy. Right? I can say, hey, stay in this lane and start and stop and just Stay in this lane. Or I can say, like, bring me to Starbucks. Um, same with my business and other businesses. We have different levels of autonomy that we're building in the business. Um, but I'm never going to get in my car and just have it bring me to wherever it wants to take me. Um, same with my business. I don't want to wake up tomorrow. And Collective Genius is now an insurance company. Um, you know, I think we're. I think as long as humans are involved, humans are going to want to make. Make those decisions of where we're going. The end goal, the vision. Yeah. Um, but I do believe how we do it, it's rapidly changing.

Speaker B: It's going to change, yes. Rapidly, radically changing. I don't think I've seen this much change in the landscape in my entire career, frankly. I think it's like the fastest change.

Speaker A: Why do you think CEOs and founders should do Jiu Jitsu?

Speaker B: Yeah, that's. I love that question. Why should founders and CEOs do Jiu Jitsu? Um, well, if you have a taste for pain, that's always, ah, a good outlet for it. Um, what's really interesting about Jiu Jitsu is that it really forces you to learn how to learn. I think a lot of times you go into, like, a new endeavor and you're convinced you know how to approach it, and maybe you're, like, grabbing different skills that you've collected along the way, and you, um, sort of approach it intuitively. Um, and with Jiu Jitsu, at least in my experience. But I think this is true of other people I know too, when they go in, especially when they're a newbie, they're just like, completely, utterly lost. Just like nothing makes any sense whatsoever. And there's like, a huge amount of overwhelm that I experienced when I was. When I was first starting out. When you start to get through that, you have to kind of confront this reality, which is like, you don't know anything. You really don't. Like, you're forced to be a lot more humble, maybe than you're used to. And, um, you are recognizing all these gaps. And then, so, um, from that place, what I've learned, at least in Jiu Jitsu, is that, um, there's something around one, um, not just knowing where you are, but figuring out, like, what do I need to focus on? For me, that's just like, fundamentals. Right now, I'm just like one year in, so it's like, how do I actually start to understand these fundamentals? Um, how do I maintain focus? That's a huge one too. I think that, you know, and you've seen this, I'm sure it's easy for someone to start doing Jiu Jitsu and they try to do like all the moves, they learn all the techniques. They spend like two weeks on this position, then two weeks on the next position, and so on and so forth, and they're spread way too thin. And so really it's like, how do I actually maintain focus so I can get really good at this one position or this one escape?

Speaker A: Right.

Speaker B: Um, and then once I've gotten really good at that, now I'm going to move on to the next thing and I'm going to start to build the chain so that my competence grows over time. But I'm not trying to do 50 things at once, which you talk about shiny object. A lot of companies do that. And so, um, yeah, so so many reasons when you, you're, you have this humility of, uh, knowing that you don't know anything, um, uh, being able to focus and also going back to feedback. Um, you know, for me, with Jiu Jitsu, it's forced me to analyze, like, what am I not doing well, where am I getting caught in bad positions or giving things up and how do I start to then, um, iterate on the next role or the next class so I can start to practice that and drill it and then see if I can correct that. Right. And so it's a slow process. It's slower than I would like. But that's kind of the nature of learning. And uh, to me, you know, going back to founder CEOs, like, so much of their job is learning so much of their job, um, iterating and improving on their end and for the team. Um, and so, uh, yeah, uh, for all those reasons, I would recommend Jiu Jitsu.

Speaker A: Yeah, there's so many elements to it. Um, and you even awoke a couple in me that I hadn't thought about before. And I literally could probably write five books about this. But the, you know, the quote of a black belt is a white belt that never quit. I really like that. I think that's part of my philosophy on life, is that unless you quit, you're done. You know, that's the only way you're done. But if you keep on going, it's probably the best advice I was ever given, uh, in my first startup was don't quit. And that's why I always in peak and all that is a bias for action. Always learn, absorb it, do Something different. But always take action and keep on moving forward. The other thing that you said, and it's actually advice I give a lot of white belts and early Jiu jitsu people, is like I say go home and write down that one move you're going to do from your guard. Mhm. Your closed guard. Go home, write down that one move that you're going to do. Every time you get into open guard.

Speaker B: Yeah.

Speaker A: Every time you have someone internal, what are you going to do? You know, so there's only a few different positions, but just start with one and then try that one. And then when it doesn't work, come ask me, show me what, tell me what happened. And uh, and we can figure out why it didn't work. The next time you're in that position, you try that one move again, they, you maybe do it a little bit different, you get more feedback, maybe it works, maybe it doesn't work. And then we, we keep to keep uh, on fixing it, keep on fixing it every single position. And then what happens is one move and then they do this. And now I have a second move over time and then I have a third move. And the highest level guys, it's not that they have all the moves, it's that they master a few moves. I mean like, master like no matter what the person's going to do, they've seen every single defense and they can play off of that defense and do

Speaker B: something, respond down the chain, they know

Speaker A: how to respond and then it's all interlocked together. Right. And then, you know, I'm in Mount and I do my one thing in mountain and maybe I ended up get rolled and I'm in closed guard again and I do my thing. So it's just, I like to think of it as a path, uh, through the forest that you're chopping and then all of a sudden, all of a sudden you'll come across your other path that you see and like, oh, now I'm. And the more that you take those paths, the wider they get. I think the wider they get and I think it's the same, um, with learning, being a CEO, being a founder, learning how to work with your team. The more times that you go down those paths and you know the what to do, they just widen and become easier and better. Uh, the short answer though is grit. You get frighted. High press, acceleration. Yeah. Uh, you need to, you need to be calm, you know, you know what it's like, probably like I remember when I first started out and black belts would Just destroy me. And they just looked like they didn't even know. Like, like I was trying everything possible and they just, like, slowly. It was a slow death and I could see it coming and I couldn't stop anything.

Speaker B: I want to just add something, if I may, on that one, because I think that what that reminded me of was the, what I mentioned around humility, um, and grit. Um, I think there's a connection there. Because what I notice is a lot of times when someone is getting burned out or they're really, really frustrated, um, about something that's not working, um, uh, oftentimes they're banging their head against the wall and, like, reality is just telling them this thing is not working, but they keep going. And I think a lot of the times the reason that happens is because they are personally identified with their approach. They're personally identified with the strategy or the thing they're trying to make succeed or whatever. Um, and there's ego tied up in that. And the reason I don't feel bad if someone smashes me in Jiu Jitsu is because I don't have an ego about it. Right. I know I'm a beginner, and so, like, I have nothing to defend there. And so I'm perfectly fine getting smashed or passed or just like, learning from that process. But I think when you have some ego, and most founders I know have ego about what they're doing, that gets in the way of them recognizing, like, oh, reality is telling me something that I'm not listening to, and it's telling me I need to respond in a different way. But again, they have this ego that they're trying to defend, and there's this lack of humility. So going back to the question, I think Jiu Jitsu is a great way to start to find the ways in which your ego's getting in the way. And can you allow that to soften a little bit? And, um, that allows you to learn. It's the same thing with startups. Like, people who, like, take way too long to pivot or, or they take way too long to go fire someone. All these things often get tied up in this ego identity component, which is preventing them from recognizing reality.

Speaker A: And then as you scale or as you grow in your belts, that ego does will start coming back. You build this confidence. And so, you know, you might have this, this training partner, you're both black belts, uh, but you like to smash them and you get smashed by them. You're like, okay, what did I do wrong? You know, it never ends. You know, it never ends. You hire a bunch of people, you get better at it, and then all of a sudden you make it a wrong hire again, you know, and they have to reabou.

Speaker B: But I was past this.

Speaker A: Yes. And so keeps on coming back. I have to end with one last question I'd like to ever ask everybody. And, uh, so the question is this. Um, it's more of a scenario. Brian, you are on a desert island the rest of your life. You have everything you, you possibly could need. You have food, healthcare, water, everything you need. The only thing you don't have is entertainment. There is no entertainment on the island. And you're there for the rest of your life. However, luckily for you, an old 80s boombox drifts ashore with unlimited batteries. But you can only bring one album of any era, any time frame, one album to listen to the rest of your life. What are you going to bring?

Speaker B: Blackwater park by Opeth. They are a, ah, fantastic Swedish death metal band. And they're way more than just a death metal band. Uh, that album is extremely special to me. And, uh, it's such a journey. And uh, yeah, I would say that's the one. That's the one I'd pick.

Speaker A: Wow. No one's ever said death metal ever out of desert island to me, ever. That's a great answer. I love the first. All right, man. Thanks for joining me on the show. I appreciate it.

Speaker B: It was a pleasure. Thanks for having me, Jeff.