Build an AI Leadership Team with Keith Wasserstrom

Welcome to the Artificial Intelligence Podcast with Jonathan Green! In this episode, we delve into the nuanced world of leadership amidst technological advancements, featuring our special guest Keith Wasserstrom, a seasoned business coach and former general counsel with a rich background in corporate strategy and management.

Keith offers invaluable insights into the intersection of leadership and AI, emphasizing the importance of clear communication and adaptability in the evolving tech landscape. He discusses strategies for leaders to effectively integrate AI into their operations without overwhelming their teams, advocating for a balance between technological efficiency and human oversight.

Notable Quotes:

• "It's a challenge... you need to learn how to research and find the answer. AI doesn't replace the critical thinking process, it enhances it." - [Keith Wasserstrom] 
• "When everything's an emergency, nothing's an emergency. It's about prioritizing and managing real-time pressures." - [Jonathan Green] 
• "One of the biggest challenges is navigating the AI bubble strategically, ensuring it reduces stress rather than adds to it." - [Keith Wasserstrom] 
• "So if I can find someone who does the task 75% as well as I do, I delegate it, freeing up my time and theirs." - [Keith Wasserstrom]

Connect with Keith Wasserstrom:

Website: https://corporatecounsel.com/

Connect with Jonathan Green

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Transcript

0:02

Is it possible to build an AI leadership team? Let's find out what today's a special guest, Keith Strom. Welcome to the Artificial Intelligence Podcast, where we make AI simple, practical, and accessible for small business owners and leaders. Forget the complicated T talk or expensive consultants. This is where you'll learn how to implement AI strategies that are easy to understand and can make a big impact for your business. The Artificial Intelligence Podcast is brought to you by fraction, a IO, the trusted partner for AI Digital transformation. At fraction a IO, we help small and medium sized businesses boost revenue by eliminating time wasting non-revenue generating tasks that frustrate your team. With our custom AI bots, tools and automations, we make it easy to shift your team's focus to the task. That matter most. Driving growth and results, we guide you through a smooth, seamless transition to ai, ensuring you avoid policy mistakes and invest in the tools that truly deliver value. Don't get left behind. Let fraction aio help you. Stay ahead in today's AI driven world. Learn more. Get started. Fraction aio.com. Now Keith, I'm excited to have you here because you're just a master of translating the technical into the understandable, because so many lawyers feel like they speak in calligraphy and a little bit of Latin and a lot of times. People have the same approach to artificial intelligence. There's a lot of different keywords that we use to sound smarter. It's like I'm a prompt engineer. It's it's a lot of words to say. You're good at asking questions of Chat, GPT, and we have a lot of this technical jargon. And one of the challenges that happens as you work further up the hierarchy is that you can't afford to seem dumb. So you can't admit, you don't know what a word is or what things are, and it becomes the emperor's new close where nobody knows what it means, but nobody wants to admit that they don't know what it means. And this happens to me all the time. I'm in meetings constantly where I'm looking up what terms mean and double checking it, and there's always a simpler name for it. There's either an acronym or something else. Just starting from that point, how could someone in leadership. Is there a way to, to, without seeming dumb, say you don't know what something means. First of all, I think I remember it's, it reminds me of an experience. I was general counsel at family office and we'd had quarterly meetings with all the presidents of all the different companies that the family office owned and. The chairman, president of all the companies, I guess whatever, he owned all the companies. He would lead the meetings. And most of the people around the room were, I don't wanna say yes, men and women, but they just nobody wanted to because he got very, I don't wanna say hostile, if you challenged him, whatever. So he was using a term wrong and everyone in the room knew it. And, it was just funny 'cause people are looking at each other and little s murky and whatever else. And finally I just corrected him after several times going around using that silly word. And he's, he got embarrassed, but he started laughing and da. He says, why would if I had whatever, broccoli on my teeth, why wouldn't somebody say, whatever kind of thing. It made me look stupid longer, so he appreciated. And the only reason I did it is because. I felt extremely comfortable in my position. I was not worried about getting reprimanded or fired, anything like that. So I said it and I said it in a funny way. So not to embarrass him, I hope, hopefully not to embarrass him, but everyone else cracked up because they were all thinking the same thing. So it is, it's a challenge. And it's funny, I. I was a m and a lawyer, securities lawyer and all kind of stuff, dealing with the SEC and they all have their different languages and sometimes I didn't know, and you try to pick out, figure it out in context. I remember when I was a, an associate, I. You just, you figured out based on the context of the conversation, what they might be talking about. You hope. And this, when I started out, there wasn't Google, so I couldn't, today it's so simple. In the middle of our conversation, I could just Google those three letter words that you gave me and figured out exactly what I'm talking about. But back then it was a little more challenging. Yeah it's really interesting how now. There's no longer a period of not knowing what something means or what something is. You no longer have to wonder anything you, no matter how random the thought is, you can look it up and know within a few minutes. And one of the other challenges I've noticed in leadership is that there tend to be two spectrums. One end of the spectrum is the leader who is trying to do everything self trying to get in there. And this is something I deal with in the CTO roles. There's a temptation to be the one coding, but if you're coding, you're not, you can't. Do both, right? Because you need to be available and it's 90% meetings, , which is, I'm not a meetings guy, but now I'm in meetings all the time and they all, it's different when you're the one running the meeting, suddenly they feel a lot more important and then you're ones sitting there silently. But it's at the other end of the spectrum though, is the leader who's hands off and trusts everyone. But then when something's wrong, they find out really. Farther down the line, it takes'em a lot longer to problem. How can a leader find the happy medium where they're not putting in a hundred hours a week, but also where they still have the finger on the pulse of the business. So I I'm a business coach and one of my platforms that I work with is called System and Soul. And the system is very much if you're familiar with the entrepreneurial operating system, I. It's EOS. It's been around for a long time. So System and Soul is newer, maybe five years or so. And they really added the soul part of it, which is really dealing with employees and purpose and making sure people are happy and fulfilled at work. But the, on the system side, on the so we have, I think ES calls it like a level 10 meeting. We have a. Weekly sync and the idea of the weekly sync is it should be quick meeting. Sometimes they do it standing up to make sure it's quick. And the idea is you go around the room and again, every week you're meeting and so you say, these are the things I need to accomplish this week and at the next meeting. You just say, these are the three things. Yes and no. I did number one, I did number two. I didn't do number three. And then if that goes on for a long time, you're not getting to number three. At some point the leader has to realize, okay, what's problem, what's the problem with number three? Is it a personal problem? Is it we need that done. And you're, you said, gonna do it last week and the week before that. Why aren't you getting to it? And it could be there other, like sometimes the leader puts on other priorities on top of those things. And I know that happened to me and I would sometimes ask, I say, okay, you wanted me to do this. Is this more important than this? And you having that communication, which a lot of times there does not exist. So the, these weekly sinks. Are really good. Just make sure everyone knows what they're supposed to do this week and if they're accomplishing it, accountability.'cause that's the thing that the leader needs to see who's doing what and who's not doing what. And if they need help, a good leader would say, how can I help you with that? You're I see you haven't gotten to three, three weeks in a row now. How can I help you with that? What do you need from me? What resources need or something like that. So those kind of a, if you have that kind of a quick meeting,'cause nobody likes meetings. And there's a funny thing we talk about how if you look around the room, that eight people in a room all making,$200,000 a year kind of thing, you're spending a lot of money on meetings. So we try to cut those out as, make it more efficient. You literally med my mind. Every time I'm in a meeting, I look around thinking about how much does this meeting costing me? And I, that one of the, that's one of the big differences between an entrepreneur and someone who's gone up through the ranks, right? Because when you're, it's your own business, you're thinking, I'm spending, this meeting's costing me $2,000 a minute or 2000, even $2,000 an hour, and it's. Is it worth it? And it changes. It's so different than when it's not your own money or when it's like the corporate credit. So it's like people spend more on the corporate credit card than their own credit card. Yep. And it's amazing how much your mindset shifts when you start thinking about rather than, is this meaning worth my time? Is it? It's everyone's time. I've heard this saying that if someone's not allowed to speak at a meeting, then they don't need to be there. Because I do see some of these meetings that are just too many people and it's is the purpose of all the people there just so someone has to listen to you. And one of the kind of challenges to navigate is, which also you brought up, which is great, is like knowing the real priority tree because I've seen some businesses where everything's an emergency. And when everything's an emergency, nothing's an emergency. And I see there's another version of this where there's multiple scales. Like sometimes it's a scale of one to 10, and sometimes it's a scale of cold to hot. And it's can we just use one scale for everything? Because I am , I sometimes work with clients and I don't understand their emergency scale. So I'll say on a scale of one to 10, how big a deal is this? If they keep giving me tens, I know something's wrong.'cause it's not, I'm like, here's a 10, there's a tiger in the room with you is a 10. If you're a tiger in the hallway, that's a nine. Talk tiger. Outside the house, we're talking seven. So there has to be a scale because Tiger, the room has to be worse than Tiger outside. And this is something where, 'cause I feel like this can actually establish a culture of like red alert. You know when a ship's in trouble, they go, okay, we're battle stations. Red alert. You can't be at red alert all the time because people's nerves get afraid. People can't be giving a hundred percent attention. And this is one of the struggles because as a leader you wanna get everything done. And I've been there too, as a leader myself, sometimes I'm like, I want everything to get done on time. And one of the things you have to deal with is that it never gets done as fast as you want. Something always happens, and sometimes it's your fault. You say, work on this brush or you distract someone. All you have to, all you have to do is give one wrong hint about a future project and you can throw off everyone. So you have to, I've done this myself recently. So just realizing that now as we enter this world of artificial intelligence, a lot of CEOs and a lot of leaders know they want it, but they're not sure why. We've gone through this a few times. We went through the phase of I need a cell phone. Why? Maybe even before that, I need a car. Phone, . My kids can't believe a car phone's a thing, or, I needed a pager and I need this. I need to be available. And the question is why I. We jump over it 'cause it's exciting. Or I need a website. So many people go there. I need a website 30 years ago. Why do you need a website? I'm not sure, but I've heard I need it. And we're going through that now with ai. Everyone says I need it. I don't, and they go what do you mean? They go, I don't know. And it's a real challenge for CTOs, for tech teams, even for myself, when I do consulting on projects, it's that I have to dig in to figure out what exactly Do you want the AI to do? When you say ai, what do you mean? And the definition is very broad. No two people mean the same thing when they say ai. So for people from, I try to approach it from a problem solution, tell me what the problem is and then we'll figure out if AI is the solution. Because if you buy a hammer, you're gonna start looking for nails, right? If I, when I buy a tape measure at the store. I come home, I have to start measuring stuff to show to my wife that I didn't waste the money. Like you start using whatever tool you bought, and we see this where people do make a major investment, whether it's AI or another tool, and suddenly they want everyone to use it because otherwise they have to admit they made a mistake and it's like good money after bad. So how can leaders from the top down navigate this world and possibly build out some of their team using artificial intelligence or some of the modern tools, some of the technologies. First, I just wanna mention, as you were talking about the emergencies, I remember I had declined that everything was an 11. So it was like exactly what you're saying. Okay, obviously it's not a big deal if it's everything's an 11. I, I had this experience, SEO is just completely foreign to me, right? I understand what it's supposed to do and everything else. And I remember I had a friend who. Did SEO when I, we were actually good friends, so I, he convinced me, to give him $25,000 instead of me paying for leads, with $10 for every lead. He would create the SEO for my website so that I wouldn't have to pay for leads anymore. So it sounded like it made sense because I was spending, like probably$20,000 on lease every month. But after, three or four months, nothing happened. I apologize for. But and eventually he's six months later, he came to me and he says, listen, I apologize for you. I owe you $25,000. I did nothing. And I was like it was good to hear, but I never got the 25,000 a diff different issue. I just think that the AI is similarly like that black box. People really just don't know what it is. And I tell people every once in a while are you using chat GPT? Just ask it a question, and and I, you, I get them to do something with chat, GPT, you give me a headline for a new commercial or something like that. And it will, you tell what the issues are and it's that's cool. That's amazing.'cause you might sit there and. Think about all the thing, different ideas of a commercial and chat could give you 10 ideas just like that. So it's it's that easy aspect is something to just make them understand exactly what's. AI is to, to a very low, sim, similar extent sim easy extent. I guess they could under at least understand and appreciate what that does. But think people are reluctant to use technology. I remember when I started as a lawyer, we just got emails, and my boss, I was a new associate. He was a senior, partner at the firm. And he. Used email 'cause it, everyone leaves email, but he did not want, and he was upset about it because normally somebody would a client who wanted a project done would call the lawyer most of the time, not get 'em, leave a message. The lawyer would call back when it was convened for the lawyer and maybe not get the client, so it could go a week or two before he has to address that issue. Now with email, he says, I get the message that I, they're expecting me to do something right away. So he said, because I wanted to give a client his text message or his phone numbers for a text message. He goes, absolutely not now. I guess this is 1992. He said, then everyone just could demand it immediately, so he said, forget that. So he he refused to hand out. He was very reluctant on emails by the way. But text message was absolutely not just, it just . Changed everything, whatever the, everything's now. So I think there is some concern and fear, clearly I know employees at, in certain things that they're doing. They're, especially on the research side, if you could just ask chat, GPT or whatever the other perplexity, the other ones what you're looking for, you're gonna get it a heck of a lot quicker. Which actually reminds me of another quick story as again, as a first year associate, I went, walked into my partner's office. He called me into his office. He asked me a question, and as I was leaving his office, I walked by another partner's office and I just poked my head in and asked her to answer to his question. She knew right off the top of her head, so I went back to him and I gave him the answer and he said. He got up, he went and slammed the door shut and he said, Keith, how are we gonna make money if you can answer the question like that? And also I want you to learn, I, I could have walked in next door and asked her myself if I needed to know the question. And I probably knew the answer anyway. So he said, you need to learn how to research and learn and get, you need to learn how to find the answer. So he was just very upsetting. And the other point, I guess his point was when you could have spent an hour on and we could build something and again, you get better and you get experience and I get pit paid. So it was a learning experience as well. Yeah. One of the challenges that happens is once you do it fast, they expect it to be fast every time after that. And there's this idea that I've thought about a lot, which is that we got watches so that we could be on time. But all it does is means you fill out, you bill out more of the day, right? Lawyers bill out in 6 15, 3 minute increments, and now you have to get more and more strict. And the same thing happened to each time. We have a technology that says, oh, you're gonna get all your time back. Once we got email, did we get our time back? No, because people expect icy, like your boss was saying. Same thing with cell phones. And what's interesting is that. We see more and more of you have to work when you're on vacation. You have to work when you're here. You're always available. Your boss will call you on the weekends. This when I was younger and we, my family would go on vacation. That was it. You would, you knew what city we were in, but like you would, you'd have hotels asking for the names to try and find. Right now you could. You still have that? Immediate access and it actually has this negative effect. I see this with a lot of employees. Would you do something fast with ai and now rather than you getting more breathing room, there's just an expectation for you to deliver 120%, 130% every day. So it doesn't make things better. And I see this a lot. We talk about efficiency. Like you're not really, if I help you with AI and I can get you to be . More efficient to where you can get three days, five days of work done in three days. You're not gonna take a four day weekend good , or you can make a little bit more money. And that's one of the challenges is that with all of these tools, that's what we promise. More free time. We have this drive that causes to put in more time and still put that pressure behind us. Is there a way to navigate that because. I see one of the challenges that you get, your employees get burned out or they feel that too much pressure because really you did it in one minute. Once. You can do it one minute again. Yes. One of the things I sort of coach on is the sort of the work-life balance. And we try to use these, new technologies, which is today ai and also a lot of people. There's this whole thing that, my old boss at the family office, he would write, he would spend his entire Saturday signing checks for every single money employees. He had a thousand employees, and one time I remember I used to be one of the last people at the office, but every once in a while he would, he'd be in the office when I left and I always say goodbye. And I'd say, listen, why are you working so hard? He guy's a billionaire. So he said, Keith, I have a thousand people that are counting. And he, he really felt that pressure of if something happened to him or one of his businesses, people would be unemployed and not get checks, not feed their families. So he really felt that pressure. So something I really try to focus on is if you, you think you could do everything the best in the office, but if you could find somebody else that does it, 75% as good as you delegate. Take that task off of your plate and now you've more free time. Now again, trying to convince people to do the right thing with that free time is a challenge. I had one client who hired me because he was very successful, business was phenomenal, but he just had a wife and two kids, and one on the way, and he says, I wanna spend more time with my family. I, I said, I can't do. There's this whole idea of having a visionary and an operator, somebody that actually gets stuff done. The guy who has all the big great thoughts. So he was the visionary, but he was also the operator.'cause when you start your new business, you're typically both. So I found him an operator, somebody who manages the medical office.'cause he was in the medical field, she took off. Took half of his plate off, things task off of his plate, and he had more time on his hands. The problem that he had was he started opening up offices in other cities. So I joke with him, like after the first year, I said, look, it's a good thing you hired me and not your wife because for you I might be successful. But your wife, I complete failure. You're not spending any more time with her. I only used to speak to him when he was in, in in, it's a hundred percent a problem. I guess that's maybe a different problem. Like you said you choose, I wanna make more money versus I wanna spend more time with my family. So that's a choice thing that we never even got into with that conversation with him. But I'm sure his wife's gonna have the conversation with him. Yeah. I thought you were gonna say that he realized he doesn't like his family that much. I don't wanna go there. My wife doesn't like it. It's I think that. We, as we get more technology, we keep getting this, the promise never comes true though, that we'll have more free time because the time always fills. There's more meanings now than before. I I went through this phase where like I, I started getting imaginary buzzes from my phone 'cause I was expecting messages all the time. And now I I realized something. It took me a long time. It. It's always an emergency until it's on their desk. So I have had projects where they go, this is an emergency, I need it by next week. And they don't look at it for 12 months. Yes. Kills, kills you. And I've started to realize that like my phone, I leave it on silent all the time. Like I never turn the noise on my phone. He goes, if it's an emergency, you'll find me. I'm an easy, I'm easy to find. I work from home, and all the people that need to find me can walk upstairs because unless you're, a fireman doctor, a police officer, it's never a emergency to the minute, it's never that level of an emergency. And it just, we think it, there's this feeling of importance that comes with being available. I'm available all the time. I must be important because doctors have pagers and now I have a pager, so I'm important like a doctor. And it creates this I think this kind of self-fulfilling prophecy where you start to feel more importance so you become more available. So you become busier, but you never, it's not really true. It doesn't really make you more important. It just makes you more stressed out or more like less because people that are really important. They're hanging out in yachts all the time. They're flying around in private jets. They're, they don't have cell phones. I don't think the cell, I don't think the president, any president has a cell phone. If they wanna do a phone call, they say, Steve, gimme your phone.. That's how I imagine it. Like I feel like when you're at that level, it's like, why would I have a phone? I'm surrounded by people who have a phone for me. So it's that level, like how can someone. Approaching this next technological revolution. We're in this AI bubble. There's a lot of this pressure. Use these new technologies. Actually be strategic and say I'm technologies in a way. That don't increase the pressure on my team, that don't increase the demands, but instead give us the benefits and actually do lower our stress, lower amount of time and let us get more done with less pressure. Is that even possible? Yeah. So I think for an hourly work or somebody who works, I. Nine to five, and that's their job. If we do make their eight hours, really four hours because of AI or any other great technology, they still have to sit in the office for four hours. Now again, maybe we can give them twice as much work and now they're twice as efficient and we're making the company's making twice as much money that's possible, but there's not always that much. Work for them to do. So theoretically then, you run it, the employees worry about losing their jobs because they're doing everything in halftime. They don't need me the full time. So that's so I think one of the challenges of all these things, even with my client that start opening up offices instead of spending more time with his family, it's the why he hired me, because he wanted to spend more time with his family but that. Disappeared as soon as I solved his immediate problem and gave him the ability to spend more time with his family. And again, maybe you're right that there's like an excuse. I know, I have five grandkids now, so going, when I spend a day with them, I'm exhausted. It is tiring. I go home and rest from that. So you wanna do it, but it's also a challenge. It's if you find out exactly what their goal is, whoever's in, suggesting this new technology, this ai, or whatever it is if the goal is to make the person work twice as hard or get twice as much done maybe that just puts more stress on the person. So maybe if there's some kind of, happy medium, where instead of working eight hours, you are only gonna get six hours worth of work to do, but I'm gonna still pay you because you're getting eight hours of work done. So that is like a win-win. Again, I don't know a lot of. Owners that might wanna do that, especially not my old boss, but I think there are people out there that would recognize the efficiency benefit from it and also share that benefit. And that probably is the best way to have a really engaged workforce force. All looking for ways to cut. Cut corners and be it more efficient and be it more effective and everything else to, for the benefit of the company. So I think that there are ways, if it's managed properly, I think that's brilliant. I think that's a really strong perspective because especially as we have more and more people working from home, working remotely, we have to find systems where we track value rather than time. With my employees, and I'm glad you brought this up. I say, here's what I expect you to get done in a week. Here's a week's worth of work to me. If you get it done in two hours, I don't care. I can't see you and you can't see me, you don't know. I'm in the swimming pool during this phone call, and I don't care if you're in the bathtub, and that's really freeing. Once because it's . When you try to do this time tracking boss, now you're, you have more work.'cause now you're checking their screenshots and checking their mouse activity and you create the culture you don't want, you've given yourself a ton of extra work and I don't want any of that. So as long as, and I had to make this transition because it just, I've not able to run a team that way. Whenever I've tried to run a team that way, it's been ineffective me from what I've switched to, here's the number of tasks I want done, here's how long it should take. Or at the beginning I say, here's what I want you to do. How long will this take you? They have to estimate their own time, and that gives me a sense of, do I feel like I'm getting value? Are you getting enough done in this amount of time? That removes all of these other pressures, and it also lets them do what they want. I have people who work for me. I have one lady who works for me. I suspect she works one hour a month. Her results are so good., it doesn't matter. She doubles her. Her numbers double every month. I go, I don't know what you're doing, but I also don't care. Why would I look inside that magic box? It's it's always double. That's great. So I think you've ended on a really great point for people who wanna know more about what you, doy, they're interested, maybe they wanna lower their pressure in their own lives and they're feel a little bit of that stress. How can they find out about you, connect with you online and maybe just learn more about the things that you do. Appreciate that. Yeah. Again, it, Keith Wasserstrom, I'm at corporate counsel dot com. Corporate counsel. It's C-O-R-P-O-R-A-T-E-C-O-U-N-S-E l.com. As a former lawyer, that's where the council comes from. And I have a lot of really good tools. I learned I have a call right now in 15 minutes with my lead, my assistant and soul team, and every week we get together, all the coaches and we learn a new tool, which are really. Help us on the culture side, the purpose, and the making sure people are happy going to work and all kind of stuff. So I love to share those with people and free consultation. Happy to see if I can help before we, get engaged. But I also love, just love helping people. Amazing. I'll make sure I put the links in the show notes and below the video for people watching on YouTube. Thank you so much for being here for another amazing episode of the Artificial Intelligence Podcast. Thank You Jonathan. Thank you for listening to this week's episode of the Artificial Intelligence Podcast. 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