B (2:34)

Well, and, and, and you're healthy, so you must have been somewhat successful because you've eaten and so for the rest of the entrepreneurs out there, there, there is some success out there, right? Don't give up. Right?

A (2:46)

Absolutely. If you're comfortable with uncertainty, it's a great life choice because even if you don't, you know, win the lottery, so to speak, you'll have a lot of growth and personal challenge in all of those great ways on your journey.

B (3:02)

So right, right now, Jeff, you help other startups build successful teams and get them moving and things like that. Let's talk a little bit about that. And then how do we apply that to big corporations? Because yeah, I see weird things going on in big corporations right now. They're the CEOs and executive management, they're all frozen. Yeah, it's because they're not, they're not.

A (3:27)

Frozen in a defensive. Yeah, yeah, they're like frozen in this defensive posture is what I see.

B (3:32)

Yeah, that's what I'm seeing.

A (3:33)

Really uncomfortable. Really uncomfortable. So yeah, I, to answer your question on the intro, better. So I'm, I'm working on my fourth tech company now. I've been at tech company founder since I dropped out of college in the early 2000s and I've, you know, had some good success with that. And, and what I do now is, you know, working on this fourth company is primarily focused on using technology to help other businesses, often smaller businesses, but still, I've had quite a lot of interest in the beginner town as well in improving their performance of their organizations. But I generally reserve about a day, a week to be an early stage advisor, mentor and investor for startups as well. It keeps me sharp. And honestly, the number of times I'll get off these calls or meetings with great folks and have to look in the mirror and say that great advice you gave Based on your 20 years of experience doing this, you need to remember to take that advice yourself. Is worth every minute I spend on that, on that kind of passion, if you will.

B (4:34)

You know, people, people always say to learn something and internalize it, you can read it, you can listen to it, but once you start teaching it yourself, totally.

A (4:45)

And that my dad was a teacher and I think that really underwrites a lot of what I'm doing now is, is really focused on trying to, to help and teach because you know, as you know, someone who's been part of, you know, the peak performance organizations and trying to drive things forward, the impact you can have by being able to teach other people to, to fish as opposed to giving them fish is just so tremendous. The, the geometric progression there is a, is A sight to see. Sight to behold.

B (5:14)

Yeah. Okay, so let's talk about when you approach. When. When teams approach you and you're all about helping them be more successful in, In. In the eyes of uncertainty, which, frankly, that's all we have right now, it seems like, is uncertainty. In every industry I talk to uncertainty in healthcare, in high tech. So much uncertainty in high tech. In education, there's uncertainty.

A (5:41)

Yeah.

B (5:42)

The only certainty I see out there is if you're a plumber or an electrician, because we need more of them.

A (5:48)

We do.

B (5:49)

And those jobs, Those jobs are essential. So. But all this uncertainty, how do you approach that with a company?

B (5:59)

Teach me.

A (6:02)

So I think when I, When I was first starting to work as a. As a mentor and investor with startups, often the question would come from whether it was government or other places, having been part of accelerators, they would say, hey, what. What is it? You know, what does it mean to be an entrepreneur? And often folks have this perception of it being very centered around risk. And you're a risk seeker.

B (6:24)

You.

A (6:24)

You're a daredevil, if you will. You jump out of the. Jump off a big cliff and build the airplane on the way down. And while there is some truth to that and a bit of romance, I think the deeper truth is entrepreneurs are individuals who are comfortable with uncertainty, and most of us as people are not comfortable with uncertainty. And so the answer to your question is, I think what these current times are really providing a massive opportunity for is a lot more entrepreneurship. I think that's really what it comes down to, because if you're comfortable with uncertainty, then what you rely upon is your skills, your wits, your experience, and your ability to create something with a future that we cannot predict and an inability to defend the castle that we have just by sort of building a bigger wall or a deeper moat. We really need to change our attitude from being defensive to more offensive, but doing that in an entrepreneurial way as opposed to that person who just, you know, says, hold my beer and does something crazy.

B (7:44)

Well, I've seen organizations that tried to be offensive in these times of uncertainty. Some succeed and some fail miserably. Is it because they put their ladder on the wrong wall, or is there some other thing that's causing that?

A (8:00)

I. I think it's going to vary, and obviously there's lots of case studies in business schools, but I think in my experience, it's a combination of inflexibility and being offensive from the position of fear as opposed to a position of genuinely based confidence. So if you're like, you know, a cornered wild animal, then you go on the offensive. You don't, you don't have, you know, you haven't got your thoughts together. You're, you're not centered at all. You're off balance and it's just a really risky proposition. Whereas if you are on offense because you've centered yourself and you've got a plan and you're also constantly prepared to, to live in the uncertainty that it might not be the perfect plan and therefore you're going to change it based on what changes in the future, I think you're in a much better position. So it's really that difference between kind of wild offense versus, you know, stepping forward in a darkened room, knowing that you're feeling the way down the walls and you know, if you stub your toe, it'll hurt a little bit, but you're not going to die.

B (9:11)

Well, but you're not. I, I like that. Right. So offensive with confidence.

A (9:17)

Yeah. And I think that's essential really because the, the ability for the current wave of technology to disrupt entire industries is like something, you know, the closest I can come up to is, you know, 25 years ago with the Internet really starting to go mainstream. And this feels an order of magnitude bigger than that in terms of its impacts. It's also going to take a while.

B (9:42)

Yeah, I'm feeling the same thing. I was in Silicon Valley during the dot com boom and bust. Yep, it was a major change. This one feels, this one feels even more so. Yeah.

A (9:55)

The one I was thinking about the other day as well, Darren, is, you know, this is a change that is going to be different for our psychology. So when Internet arrived and enabled a higher degree of speed of communication, universality of communication, almost universality of information, those were things that were a really big change. But we already understood newspapers, tv, telephone, faxes, you know, there were already the modes for us to have as a proxy and we would just multiply the speed of them and the, and the ubiquity of them. But this transition for sort of universal intelligence is like nothing any of us have ever thought of before. We've always tied intelligence, if you think of it as the knowledge piece, not the kind of raw iq. That's something that's acquired incrementally through trial and error, through book smarts and, and, you know, all of those things. And this is going to be, I think, a really massive change because we don't have a mental framework to understand this in the same way that we just thought, well, email is like A fax that doesn't have the screechy sound and is a lot faster, you know, like, it's just a bad analog. Right.

B (11:10)

Yeah. This is. This is a major shift. All right, so I'm a startup. I got all this uncertainty. You've come in to help me. What? All right, no more. No more pontificating. Yeah, because that I. A lot of people pontificate about this. We've done pontificate. What do I do? What do I do? Jeff, Help me.

A (11:31)

So there's a psychology piece around the uncertainty. We'll put that to one side because we've covered that. Then from a tactical point of view, it's to really unburden yourself from the limiting thoughts of what you can do. Because what you can do now versus what you could do a year ago or two years ago is different order of magnitude. Right. So that means you can go a lot faster with a lot fewer people, which also means that the people you do have are so much more important to your success compared to a competitor who's similarly funded with a similar size team. So the expectations from a talent point of view are dramatically increased. So that's where, you know, the product I'm working on now, Team Score comes in. Is trying to understand what the performance of your team is, because frankly, over the past 5ish years, and maybe going back a bit further, there has been a general sort of slippage in terms of intensity because obviously we had to get through crazy times five or six years ago. And before that, there was still a whole lot of, you know, extra turbulence and cheap and free money. And so it allowed organizations to get bigger than they probably needed to be with more duplication than any did have. And in those environments, you end up with places that end up having people and roles and responsibilities that you wouldn't create or hire or have if you were starting again fresh. And so the consequence of that is you need to get in shape. There's metaphorical, you know, sort of, whether it's building strength or losing pounds, whichever your metaphor is, I think the defining characteristic of success, whether you're a startup or a big company in the transition we're going through and thinking about coming out the other side in 5, 10, 15 years, is actually mostly going to come down to your performance and your fitness. Because it's all well and good to have a great idea, but if you don't have the strength, if you don't have the endurance, if you're not in shape as an organization to take advantage of it, then I'VE got some bad news for you. There's somebody who's a tenth your size using the new technology that is going to come and eat your lunch.

B (13:52)

I love the metaphor of losing weight because we're seeing that with big corporations right now. They're shedding people, but I don't think they're building strength, too.

A (14:02)

I think that's the big risk is that people assume that they can reduce headcount and put more pressure on and then just throw in some tools. And it's a bit like that Austin Powers scene where he has him tied up and he closes the garage door and his son says, oh, why aren't you going to watch him die? He's like, oh, no, I'm just going to close the door and assume everything went according to plan. It's just, you know, like you, you watch these big orgs and. And they'll come up with a plan and then close the. Close the door and not see that. That it didn't go according to plan.

B (14:45)

Okay, so losing weight is getting rid of people. Building strengths in my organization is that skilling up my people, reskilling my people, building more cohesion in my group. What, what, what tips do you have for me there on. On building strengths in my team?

A (15:01)

So I think there's probably a couple of analogies that folks listening and watching may be able to take on board. The one that I've had a lot of resonance with when I've talked to folks is the way that the military looks at having sort of this special forces organization, which is set up with less hierarchy, more permission, and a lot more responsibility. And it's small. If they tried to make it the whole size of the. If they tried to make the Rangers, like everyone in the US army become a Ranger, it would fail. It would fail, right? Like, it has to be Special Forces. That's where the special fit comes in. And so I think there's probably an opportunity to do some of that in organizations around this technology change. To do what sounds kind of a bit rote, but is internal disruption. Because you're better off having internal disruption than having someone else come and, you know, Kodak, you. That requires probably doing what, you know, Xerox did with Xerox parc, but then continuing to stay out of the way so it doesn't become Apple, who commercializes the PC or the Mac and the Gu. The gui. It could have been Xerox the whole way along, but it was too much coming out of Rochester. You know, once they found out that Menlo park in California was starting to get some attention. Then there was a smothering effect going on in the crib there. So I think that's part of it. You want that special forces play, but then you actually need to be able to protect them and allow them to do things that are uncomfortable. The other option, which has probably some similarities, is after there's been, you know, if you think back to 08 in the financial crisis, but it happens in other, other kind of games as well. There's this sense of a good bank and a bad bank. And I know it's very pejorative and no one wants to be put in the bad bank. But the good thing about separating your operations into kind of the good bank, which is the, the future and this is the seeds after the fire. They're going to, you know, continue to germinate and grow and carry you guys forward.

A (17:06)

And separating that out and then having what could be another, a great business for another decade or two live in the quote unquote bad bank is potentially what's needed. No one wants to be in that. So you have to kind of come up with a better name for it. But I do think that the fact that you can do 10 times more per person with the new technology, if those individuals are empowered, empowered.

A (17:29)

And frankly, you know, expected to do it, then, then you effectively can like carve off 10% of your org and expect that to actually be the size of the current org that you have in 48, you know, months or something like that. Like it's not overnight, but it's, it's, I think, probably the right answer because everyone I talk to in, in whether it's medium sized or large companies, the number one thing that keeps coming up like in my, you know, I'm part of ypo and there's a lot of really big company presidents involved in a bunch of these events that I'm part of. And, and it's always about culture and culture change. And what I end up hearing from them is that they're kind of stuck in stasis because they can't get everybody to hold hands at the same time and jump in the pool all at once. And all it takes, if you're trying to get everyone to jump in the pool together for one of those great photos at a party is one person say, I'm not jumping in. Next thing you know, people have got cuts and scrapes and you know, it's just, it's, it's impossible. Right? So I just think that you can't make 100% of people change. So you're better off creating a self selecting good bank, bad bank or special forces group and empowering them.

B (18:40)

Yeah, I'm glad you said that. Not everyone can be in the special forces whether. Because there could be a desire thing, there could be a skill thing. Yeah. And I think part of the problem that we've had in corporate culture, frankly over the last I don't 10 or 15 years is yeah, everyone should be the same.

A (19:00)

Yeah, yeah, everyone's the same.

B (19:03)

No one's better than another. We've seen that by getting rid of annual reviews or organizations have gotten rid of those. No more stack ranking. No. There's some employees that are far better at their jobs than others.

A (19:16)

Yeah.

B (19:16)

They're just. Everyone is different. Right. Putting them in the right position is, is critical. So I like what you said there. There's some self selecting. I want to take the risk. I want to, to getting engaged in something that may take more than 40 hours a week because yeah, I have a passion for it and I want to be held accountable for it. There are people like that.

A (19:39)

Yeah, yeah. And it's, it is about the passion. You know, it's, it's a lot of goes back to some of Simon Sinek's work around start with why, you know, and any folks are. I'm here because I, I want to just keep doing the same thing I've been doing for the past 10 years, for another 20 years and gradually increment up the corporate ladder. There's nothing wrong with that. Like we got to take the value judgments out of this and there is a place and a role and a need for that. Like AI isn't going to change everything overnight I think because there isn't the mental framing to understand what this is going to be and the uncertainty is so much higher that it could take twice as long as the Internet to play out. But you don't want to find yourself, you know, as a CEO of Borders, you know, six. You know what I mean?

B (20:22)

Yeah. No, no, there's, there's some great examples.

B (20:36)

All right, get fit. What's next? You told me to get fit. I've, I've, I've got my, my special forces. I've decreased. I lost some weight. I got rid of some of. It's not just people I'm getting rid of. It's process.

A (20:50)

Process is huge.

B (20:51)

Is, is huge because that slows me down. Right.

A (20:54)

Yep.

B (20:55)

What's my next step? I'm fit now. I think I'm fit.

A (21:01)

Well, being fit as you know is it never really stops. Right?

B (21:06)

That's true.

A (21:07)

Special Forces are training all the time. So it's not quite like I did this. The box gets checked and then I go on and do that. No, that's actually, it's actually like an ongoing thing. And for some organizations it's going to be a culture change. That is a change and that's okay. But then the question is, all right, if I've got that as part of my routine and I've made a commitment and I'm going to be making incremental progress there, like nothing is less likely to succeed than a crash diet. So, all right, I'm making, making steps that are thoughtful and deliberative to get fit and get in shape and not doing massive wholesale reorgs or firing or whatever else. You know, like, don't, don't do those things. But you make those incremental steps, building out your Special Forces capability. And then really it comes down to constantly asking not just what can the new technology let me do, but also asking what's going to stay the same. So it was a guest you had a couple of weeks ago now who was really talking about that sentiment of, all right, what is, what does the customer really want? Like, what is the business you're in? And, and not asking it in a porter's five forces way, but more a deep fashion, like, what why do you exist as an organization? You might have lost that why or it might have been a bit smothered or hidden under the how and the what that everyone focuses on around their oil structure or their budgets or their accountability lines or whatever other internally navel gazing focus goes on. But if you can continue to focus on that and ask the hard questions, like, does the world really need somebody who's focused on maintaining typewriters? Well, I think you can probably answer that question pretty clearly now, but it may not have been so clear 50 years ago to pick an extreme example. So, you know, really, I think the, the step that I would encourage next is to actually focus on the things that aren't going to change.

A (23:11)

And the.

B (23:12)

Things that are not going to change. Right, you said.

A (23:15)

Yeah, I think so. Like, Bezos said something great a long time ago. He's like, yeah, you know, all of this changes a lot, but the thing that I'm pretty confident is, is people are going to like to have more selection. They're going to like stuff cheaper and they're going to like it faster. Those three things seem pretty universally like, that's not going to change. In another, you know, sort of five or 10 or 20 years, lots of other things will. And so being able to then identify in your business what are the things that are going to, you know, be consistent. So in my business, one of those key consistencies is you want to be better at whether it's serving your client or running a business next year than you were this year. So how do you get better? Right. And what does your customer want? That's going to vary. Obviously. Bezos example is very B2C. Pretty much everyone I work with is B2B. But even in that B2B context, there's still this aspect of, okay, what does the customer really want to do? They want to make better decisions, but they also realize they generally lie to themselves when they say they want to be data driven. Because 90% of our decisions come from words like gut or heart or, you know, like the things that don't have words associated with them. Right. That limbic brain is where the decisions really come from. So, you know, they're actually saying, I want to be data driven. They're really saying, I want to be data justified. So it's just like, okay, what do you really want to do? You want to have better understanding to feed that limbic brain. You want to have, therefore, and then make the decisions and, and then work through the outcomes of them. Those things are pretty relevant.

B (24:53)

You just said something that just makes me think that AI will never be able to run a whole business because AI doesn't have that intuition, that gut feeling.

A (25:04)

Right. Yeah.

B (25:04)

That we base a lot of our big decisions on. In fact, you could probably look at the richest men in the world and women in the world.

A (25:11)

Yeah.

B (25:12)

And I bet their gut decisions that they made, they. Right. With data justification. I love that term, by the way. Yeah, that was so that's really interesting that you said that because I, I, I think that too, your gut tells you, let's do this. The data may the, and then I go find the data to justify why I did what I did.

A (25:33)

Yeah. And yet what's interesting is we need to have the inputs. We need to think and see. And in certain environments, smell, taste, touch, we need to have those inputs to inform our gut. Right. So we still need to.

B (25:50)

Yeah. But ultimately there's something inside us, and that's why I don't think AI can handle that.

A (25:56)

Yeah. It's going to be interesting too, because, you know, if AI is able to trick us with those things, then maybe it can have effect. But I think if you wanted to imagine someone's literally driving A company or a team or an okr. Like I don't know that that's going to be something. Whereas using the AI to augment that. So what I found to be incredibly valuable, building my latest company was being able to use AI as a thought partner and tell it. Look, you're a McKinsey consultant who's been doing this for 20 years. And now you're my co founder who's put everything, everything on the line. And here's a starting point for a product and a plan. And in a 90 minute drive to the mountains earlier this year when I was taking my kids up to learn how to ski in Breckenridge, managed to do more in 90 minutes than I would have done pre AI in a whole week. Sitting around in a conference room with whiteboards and sticky notes. It's insane.

B (27:04)

I, I had the same thing happen to me for Thanksgiving. I drove out to Utah. So it's a 10 hour drive. My wife and kids are asleep in the car. And I pulled up Chad GPT and we had an hour long discussion on what we could do to improve the show and to get speakers engaged. It was incredible. I was like, this is great because I could say, give me a different angle, give me this angle. You know, it was awesome. But ultimately it was my, it's your.

A (27:37)

Decision and my decision.

B (27:39)

Right. It was regurgitating back to me what I was telling it. Right. In a different way that spurred on more brain thought.

A (27:46)

Yeah.

B (27:46)

How do you do that with. With a team? Because that'd be great to add to your special Forces team and AI that's sitting there with you saying, hey, you know, I want you to take this position that us as humans sometimes have a hard time doing. Especially if I don't have a team that's balanced.

A (28:06)

Yeah.

B (28:07)

With diversity of thought that I can bring in another, another diverse idea without having to hire someone or, or vet them and then then become. What's the right word? Indoctrinated in team. Yeah. Because that's a problem, Right? Yeah.

A (28:25)

It is a really interesting point I found with the right kind of prompting and frankly being pretty spicy that I can get some of those contrarian thoughts to the surface pretty quickly and eliminate the sycophancy. And so that's where it's like telling it. It's a co founder who's put everything on the line like that. Those sorts of sentiments have actually been pretty effective at creating an adversarial conversation in a very constructive way. But I think AI as a tool for teams is actually a really big challenge like that shared knowledge, that shared context, being able to make sure that you build upon it, the context piece and having that shared in an org continues to be a really big challenge because most of the stuff that I'm seeing in the field is variations on a search engine. You know, like I'm going to use Rag and it's going to do this and it's like no, that's not quite right. But the context windows are increasing significantly. And then the other thing that I'd say is at least for the foreseeable future, it's still, you know, businesses are going to move forward based on those people to people relationships and interactions. And so the ability to pull in a metaphorical McKinsey consultant and instead of having to sign off and a six figure purchase order and realize you're dealing with three months of all of the drama, instead being able to spend 20 bucks a month and get going is sure. Is it as good, Is it as unique? No, but it's many orders of magnitude more accessible. So say thank you and get on with it. And I think that having that advantage than amongst a team like a group of people all sharing and thinking in that way, I think is going to be really beneficial. I don't see the tech actually disintermediating the human to human connections. I think what it's doing is it's allowing each of us with those thoughts that are running around in our head all the darn time to be able to make a lot more of that. So then when we do have those human to human interactions which hopefully are more frequent, not less that we're actually, you know, the creams rising to the top a heck of a lot faster now.

B (30:33)

I, I like what you're saying there. I actually think the same way. I think that Gen AI will increase the human to human interaction.

A (30:41)

Yeah.

B (30:41)

And get, and get rid of some of the miscommunications that happen because we can articulate our ideas so much better now than we could in the past where they're. I, I can't explain it. I can picture it in my head but I can't, can't get the words out. Yeah, that's difficult. But because I'm also afraid that I'm going to say something stupid. Does that make sense?

A (31:03)

Yeah, no, true, you've got, you've got a trusted place there. You can say something stupid and realize it was stupid. And when you go to share with your team, you've actually got a much more formed thought.

B (31:15)

Yeah, no, very, very interesting stuff. All right, Jeff, if people want to find out more about you and what you're doing.

A (31:22)

Yeah.

B (31:23)

How do they reach out to you?

A (31:25)

Yeah. The best bet for now is go to Team Score IO. So Team Score is the product I built because of what I needed in my last company, which was a better way for managers to have that peripheral vision as to what their remote and hybrid folks are working on. But I refused to roll out the spyware technology that's common in the space because I was, like, not doing it is going to mean the 40% of really awesome team members that are, like the top contributors, let's say, are going to feel really, really cheated and distrusted. Just so a 10 or 20% that I need to sort of work through and manage to a better place. I have visibility there, like, so that was a bad trade. So I think Team Score IO, check it out. It's a free product. Obviously there's paid tiers, like any freemium products, but if. If you've got remote or hybrid folks, check it out and love to hear what you think of it. You can also find me on LinkedIn.

B (32:20)

All right, Jeff, again, thank you so much for coming on the show. This has been a great conversation. I love to. I love talking to. To new people. That's why I do the show. Thanks, Darren. It's been great. Thanks again for coming on.

A (32:32)

Excellent. You're most welcome.

B (32:36)

Thanks for listening. Listening to Embracing Digital Transformation. If you enjoyed today's conversation, give us five stars on your favorite podcasting app or on YouTube. It really helps others discover the show. If you want to go deeper, join our exclusive community@patreon.com embracingdigital where we share bonus content. And you can always connect with other change makers like yourself. You can always find more resources@embracingdigital.org until next time, keep embracing the digital transformation.