The Cloud Gambit

Leadership, Decision Making, Work-Life Balance, and Everything in Between with Kendall Miller

May 21, 2024 William Collins Episode 22
Leadership, Decision Making, Work-Life Balance, and Everything in Between with Kendall Miller
The Cloud Gambit
More Info
The Cloud Gambit
Leadership, Decision Making, Work-Life Balance, and Everything in Between with Kendall Miller
May 21, 2024 Episode 22
William Collins

Send us a Text Message.

Kendall Miller is the Chief Extrovert for Axiom, Co-Founder and Chief Operating Officer for CTO Lunches, Co-Host of the Authority Issues Podcast, and serves on the FusionAuth Board of Directors. In this conversation, we discuss Kendall’s background, the shifting sands of leadership, making work-life balance a reality, and everything in between.

Where to find Kendall
Podcast: https://authorityissu.es/
LinkedIn: https://www.linkedin.com/in/kendallamiller/
Force Push: https://fridaydeployment.co/

Follow, Like, and Subscribe!
Podcast: https://www.thecloudgambit.com/
YouTube: https://www.youtube.com/@TheCloudGambit
LinkedIn: https://www.linkedin.com/company/thecloudgambit
Twitter: https://twitter.com/TheCloudGambit
TikTok: https://www.tiktok.com/@thecloudgambit

Show Notes Transcript Chapter Markers

Send us a Text Message.

Kendall Miller is the Chief Extrovert for Axiom, Co-Founder and Chief Operating Officer for CTO Lunches, Co-Host of the Authority Issues Podcast, and serves on the FusionAuth Board of Directors. In this conversation, we discuss Kendall’s background, the shifting sands of leadership, making work-life balance a reality, and everything in between.

Where to find Kendall
Podcast: https://authorityissu.es/
LinkedIn: https://www.linkedin.com/in/kendallamiller/
Force Push: https://fridaydeployment.co/

Follow, Like, and Subscribe!
Podcast: https://www.thecloudgambit.com/
YouTube: https://www.youtube.com/@TheCloudGambit
LinkedIn: https://www.linkedin.com/company/thecloudgambit
Twitter: https://twitter.com/TheCloudGambit
TikTok: https://www.tiktok.com/@thecloudgambit

Intro:

Kendall Miller is the Chief Extrovert for Axiom, co-founder and Chief Operating Officer for CTO Lunches, co-host of the Authority Issues podcast and serves on the Fusion Orth Board of Directors. In this conversation we discuss Kendall's background, the shifting sands of leadership, making work-life balance a reality and everything in between.

William:

Kendall, welcome to the show. How are things going?

Kendall:

Thanks for having me, I'm good.

William:

I'm good. How's that?

Kendall:

weather in Denver. Treating you Well, it's the, it's nearly what. Oh, it's it's middle of May. Um, school is almost out and it is not warm yet, which is very irritating. We've had some warm days, but I think we had more warm days in February than we had in March, which or maybe April, which is normal for March but isn't normal for April. It's been an irritating. It's been an irritating little while, but and it's cold as heck right now it's going to be cold tomorrow, but it's supposed to be nice on Saturday that's nice.

William:

Yeah, it's. We get a lot of rain here in the Ohio Valley, like a lot of rain in the spring, like sometimes. I think last year we had like a straight, I want to say 10 days of just rain, and it can really. I mean that's, I'll tell you. That's what wrangles with my mental health is rain and, you know, not seeing any sunshine. It kills me. But lately we've had a little sunshine, so I'm happy.

Kendall:

Yeah, I've lived dark, gray places. It makes me miserable. I'm shocked how much it affects my mental health, but it does. I get super grumpy, like two days without sun. I'm miserable.

William:

So anybody listening, it turns out the sun is good for you. Go take a walk, stretch the legs, get some steps in, that's right, get some of that, yeah. So tell me a little bit about yourself. What do you do day to day? Um, you know what? What is a day in the life of? Uh, kindle all about?

Kendall:

yeah. So it's hard to know where to start. I I do a lot of things. I have two companies that I run myself and then I'm involved in some capacity officially with three and then unofficially with a few others, the ones that I can talk about. So the things that I do myself I run a network of CTOs called CTO Lunches. That's worldwide about 1500 CTOs. We do local lunches in different cities throughout the world and we have an ongoing list serve and a paid tier. That's a Slack community for a tiny niche group of people to have conversation.

Kendall:

I have a liquor brand called Friday Deployment Spirits where we sell alcohol to tech nerds and our first liquor is Force Push Gin. And our first liquor is Force Push Gin. It's all going to be tech jokes. We set out to make some tech jokes, thinking people buy this as swag for their people, and then we partnered with a distillery in Denver that makes a just unbelievable. I mean, it's made for us. It's not like white labeled something else, it's contract distilling. So it's our gin. It is so much better than I thought we were going to get. Like I would have been thrilled selling this if it was a terrible product. It just turns out as a fantastic product. So that's one of the things I do is I hawk a liquor.

William:

You're going to say something about that. Wait, wait. So you're doing this as like a hey, we're, it's the weekend and we're pushing to main, we're pushing to production, and now we have this gin Friday deployment gin, save your weekend.

Kendall:

or or hard work deserves hard liquor. Or that guy that was up you know pushing all working on an incident all week and buy him a bottle and say thanks, but yeah, no part of it is like well, it's Friday, you know. Can I curse on this podcast, or am?

Intro:

I not supposed to Go for it, fuck it.

Kendall:

Let's deploy and have a glass of gin right. That's part of the thing.

William:

Gotcha Smart marketing right there.

Kendall:

That's part of the thing Gotcha Smart marketing right there. That's what we're going for is it's direct to consumer for tech folks. So it's fridaydeploymentco and then what else? So then I advise an AI startup out of San Francisco called Tensor Lake that's building a open source project right now that indexes unstructured data so you can run it on a whole bunch of GIFs or YouTube videos and it will tell you everything that's going on and a person's doing this, lifting that, moving this, and it's a very impressive. If you're in AI and you're doing RAG, you probably need a tool like Indexify.

Kendall:

And then I sit on the board of a company called FusionAuth. That's a Auth0 competitor, also out of Denver, I think, very developer-friendly auth, and then in the SCIAM space. And then, finally, I'm hands-on day-to-day with a company called Axiom. That's where I spend the majority of my time these days. Axiom's building the. It's the spiritual successor of things like Splunk. It's just logs at the end of the day logs, traces, metrics coming in the near future.

Kendall:

But the technology behind it is unusually interesting to me because of what the cloud has enabled in the last few years. So I mean the story that I tell is when I met the founders. They told me what they built and I said I don't believe you, which is something that we get a lot. And then they sat me down and told me how they did it and I said, guys, if this is true, number one, you can't ever tell anybody how you did this again. And number two, I want in. And so I've been working with them for about two years and I love what we're building. It's rare to get to work on a product that's this compelling. I love what we're building. It's rare to get to work on a product that's this compelling.

William:

It's all. Your title is Chief Extrovert. What's that all about? Chief Extrovert? Just like talking to the world.

Kendall:

I like it. So I'm a bubbly personality and there's a lot that I do at Axiom, but it's a lot of the external facing. Our CEO is super bubbly, great with people. That's unusual for a technical founder who's like deeply involved in the product right, and often I'm working alongside the like real nerdy CEO who doesn't have that skill but he's just busy because he's you know, he does everything else. So anything that's business facing, that's not the CEOs that he's not touching. So that's strategic partnerships. I help with business development that he's not touching, so that's strategic partnerships. I help with business development. I have my hand in marketing and sales and all the things, but anything that's bubbly, business facing, and then I have enough of a technical background that that's useful as well.

William:

Awesome Does that make sense it's weird it's a bullshit title.

Kendall:

that means he needs to be able to speak with authority externally and probably carry no weight internally, and I'm thrilled with that. It works great.

William:

I think it's really catchy. I like it yeah.

Kendall:

Extrovert as a service is a lot of what I get paid for. Yeah, sorry, go ahead, keep going.

William:

I was going to say glad we could connect through a mutual acquaintance. I got to listening so I didn't know about. I guess I can just go here. I didn't know about the authority issues podcast, but I have it queued up now. I've subscribed to it because it's really good.

Kendall:

Yeah, I also do a podcast on leadership, which I didn't say, but yeah keep going, definitely linking it.

William:

And I, you know, honestly, I feel like I know you and Rachel at this point because, like the last week, you know, since we set the schedule, like I've been listening to these on my morning walk, you know, catching some of the old episodes. And it's really good content, you know, and I just got to ask, you know, what was the motivation, you know, behind starting it.

Kendall:

Wow, that's first. First of all, it's been a long time it's been five years, so the motivation changes throughout. So the short version of it is I think when we started it I was running a small startup and, frankly, it's exhausting when you're at the top of an organization and it's lonely and you assume that everyone you talk to who's in a similar position knows what they're doing better than you, and so it's been very useful to me in my career to talk to very senior leaders and find out they're just people and they're insecure about what they're doing and they're wrestling with problems and they've seen some shit they wish they didn't have to see and like. So the the point of the podcast is, in a significant part, just to bring on people. We do focus heavily on underrepresented people, uh, in positions of leadership and talk about their background, their journey and leadership, the things they've learned along the way, and, and some episodes like to be clear.

Kendall:

We have like mitchell hashimoto's, like episode three or something I can't remember. You know we've we've had some big names on because it's been a long time, uh, but we've also had a whole lot of nobodies that nobody's ever heard of and some of them are by far. There are CTOs that you will hear on our podcast, or VPs or directors who, like you, listen to and you're like, how the hell is this person in a position of senior leadership at an organization this big? And part of the takeaway from that is, if they can do it, anybody can do it, and you know all of that is what we're aiming for in the podcast. That's awesome.

William:

That's really great. I love hearing stories like that. The podcast, that's awesome. That's really great. I love hearing stories like that. Just, you know when you when you haven't you know a lot of times. You know you're coming into tech, you're going into your career field. You don't know what that path looks like, you have no idea, and just hearing how other folks were able to do it is just infinitely useful.

Kendall:

Well, everybody has a weird story. Like we've had one person who's like well, I followed the traditional path and I got a computer science degree and then I climbed the ladder and literally no one else is like that. Everyone's like well, I have a non-traditional background. It's like no non-traditional is traditional. In senior leadership there's like nobody who climbs the ranks through what everybody thinks people climb the ranks through yeah, yeah, yep I was listening to the the a I think it was like ai hype.

William:

So you know something about ai hype from like earlier this year and you're you had this like bit about. I was laughing my head off because I'm going through it right now, but you had this bit about your, your complex summers and like shipping your kids off to like school and camps and things and um, I was like I was walking and I like it was like an over-exaggerated head nod.

Kendall:

I was like yes, yes, wait, how was I using ai to solve that problem?

William:

I don't understand well so they would I guess the episode. Yeah, you could use ai to solve that problem maybe. But probably not, but yeah, I think AI was towards the end of the episode, oh okay, this was just like a personal update.

William:

Yeah, I have a ridiculous complicated family life with four teenagers so it's messy, yeah, just managing. So my oldest plays travel hockey, which is very time consuming. My youngest is getting into like lots of exciting things that require lots of driving and you know we have a third on the way. And one area that I know I can improve in Kendall I know I can and honestly I work on it day in and day out is this work life balance stuff? How do you manage your time? And or do you manage your time, or do you manage your time, or does your time manage you? How does that look?

Kendall:

I mean I'm pretty strict about it. So, first of all, gosh, I mean, there's always ups and downs and if you're a parent and you care about your kids and you want to spend time with them which not every parent fits in that bucket but if you are, you're going to always be wrestling with am I doing this right? Right, because there's the pressure of I need to hustle so that I can provide for my family and I have to keep hustling so that I can provide for my family, because I can't afford to not be employed. Right, like we're fucked if I'm unemployed. So there's that bit. And then, with the but also, I I'm not making money so that I can, you know, buy gigantic yachts and peace out and never see my kids. Like I want to be there for my kids, I don't want to be there with my wife and I want to go do the shit that excites me now. I don't want to wait to live, I want to. I want to live right now. So if you're not in that tension, you're definitely doing it wrong, because there's no way that you're not in that tension and meaningfully employed. Probably right, because you're either way over-employed or way under-employed. And so I mean I'm pretty strict about.

Kendall:

I drop my kids off at school in the morning and I start work around 830 and I log off at five. The work is never, ever, ever done. It's never done, it's not even close to done, it's so far from done, it's unbelievable. So I might as well just walk away at five and I, you know, prioritize, prioritize, prioritize, and I get the most high priority things done every day and some things fall off my plate, and I mean my to-do methods. I have like 12. But one of them is I write down on a notepad the things that have to happen that day and I turn the page and they disappear forever and they never come back. And if I didn't get it done, I probably don't even know, and it must be low priority because it didn't come back up.

William:

Yeah, that's great. That's such a good answer. Totally, that's yeah, I'm going through and exactly what I'm trying to do the best thing you can give your kids. You can buy them anything in the world, but what they really want at the end of the day is your time. They want you to be there. They don't want you to be distracted. They want you to do things with them. That's one of the hardest things to give, also because we're all so busy all the time.

Kendall:

Yeah, I'll say I'm pretty good at this now for the most part. There's times where I wasn't and and I I have a specific memory of taking my kids up in the mountains. You know, I live outside of denver, um. There's a little town called idaho springs, 20 miles west of me that there's this amazing little tiny pizza place there that's well known in the area, um, and we drove up the mountains, had dinner, had a. We drove up the mountains, had dinner, had a beer, drove down the mountains and on the way down my wife turns to me and says figure this shit out or get a different job. I don't care which it is.

Kendall:

And I realized I'd been in my head the whole time, like I was there, I talked to my kids like a little bit, but I was somewhere else and I was so stressed out about work that she's like it's just not worth it to me. I don't care how much money you're making, I don't care if I got to move to a different house in a different place, like get your shit together or get out. And it was a wake up call. And she's probably had to say that to me a handful of times when I get dysregulated in my time management, but I've gotten a lot better at it as I, as I get older, for sure yeah, that's great.

William:

I mean getting a, you know, because you, it's like one of those things where you know it chips away a little bit over time, over time, over time, and it gets worse and worse and worse and worse. And then, hey, one day you wake up and you know, you're just like how did I, how did I get here?

Kendall:

you know, how did that happen? You know, vacation is a tool that reminds you that you're not as important as you think you are. Even you know this. This week I was at, I was at RSA. I just I just flew back yesterday.

Kendall:

Uh, I don't know how long till you ship this episode, but I was just at RSA yesterday and that's three days away from my desk, and when I come back, the world didn't cave in. Did I get as much done that I would normally get done at my desk? No, because I'm doing completely different work, you know, hobbing every knob I can find at RSA. But I come back. It didn't cave in. The world's not over, it is still running and it's going to be fine. And that's actually a helpful reminder to me, like I can slow down a little bit where I need to.

William:

Yeah, awesome. So how was RSA? Did anybody mention AI, by any chance?

Kendall:

reports. You know. So company writes you and says, hey, we want to work with you, but we need the security documents from you that prove you're secure. You know, here's a questionnaire and it's 5,000 pages long and it's it's unbelievable how often you can respond hey, I'm not going to fill that out, but here's what I have and they're like great, just need something needed to check a box. You know, or or sometimes you spend three weeks filling out this questionnaire. Well, this, Well, this company has figured out how to use AI to scrape your Slack, to scrape email, to scrape every previous report you've ever figured, filled out and then fill in this report. And I was like, guys, that scares the shit out of me. No-transcript, that I am not ready for and that's anyways, there's a lot of bad applications of api.

William:

Yes, yeah, short term win of a term failure is what? What? That is right short, oh gosh it looks.

Kendall:

It sounds so good on paper for anyone who's never done a security questionnaire.

William:

Yeah, so one of the strong themes or I guess maybe even the main theme, I suppose, that you discuss on authority issues is leadership. And so what does leadership so like? In the scope of, like, say, a large matrix organization, what does leadership mean to you and how do you like, how does that differ from management? I?

Kendall:

guess we can start there. Yeah, I mean. So. Leadership differs from management, because when you're a manager of somebody, that means you're directly in charge of them. In some sense, it is their job to make you happy in management. But you can be a leader even when you're not in management. And for the last five, six years I've had with a few on-off exceptions where I take something over for a brief period of time, but for the most part for the last five, six years I've had zero reports. But it's still my job to be a leader in the organization. So what that means is building relationships across the organization so that I can get the kinds of things done that I need to get done.

Kendall:

And that's not. That's not go make friends with the designer so that when I need a flyer for a conference I can go lean on that designer and fuck him. He owes me. You know that's not what that is. It's having good enough relationship that I can ask hey, how do I get this thing done? Is this as hard as I think it is? Who do I talk to to get it done? Where do I go to get it done? What's the highest priority? Hey, I need to yield to you on making this decision. You have to decide when this gets done, but here's my priority and can we fit it in there? Um, mostly now.

Kendall:

You know I work with tiny startups and or small startups. Not all of them are tiny, um, but you know sub thousands of people, all of them and 10 years ago I worked for, you know, a 30,000 person organization. That's a very different feeling, but the, the, the, the lessons are the same. I build relationships across the organization, including up, um, you know, all the way up to the right hand of the CEO and, uh, you know all the way up to the right hand of the CEO, and I know the VPs that can get things done or at least even help me understand why things don't get done Like in a really big organization.

Kendall:

Sometimes you got to talk to somebody at the top who's like you know. I had this happen. Hey, kendall, you think this is a problem at your level. This is a problem going back 60 years, and let me tell you the story of why. The old CEO was on his deathbed dying, and the new CEO was in the room and asked him a question and made a promise to the CEO that he would never change this thing. And so, kendall, it doesn't matter what you do, this will never change and it's like, oh that's, it's good for me to know that I should not be spending time on that. And so leadership is the ability to build those relationships you know, manage across the organization, understand what can and can't be changed so you can prioritize the right things. And then you know gather people around you who want to follow after you and help you get things done, who aren't all your reports a lot of times.

William:

Right, yeah, that's a good distinction that you don't have to be a CEO, you don't have to be a senior VP to be a leader. Anybody can be a leader and anybody can influence change. One thing that I've learned over many years is, like the I'd say that the manner in which, like an organization approaches decision making, you know it can be a titanic sized road. Well, actually not like maybe I should have led with iceberg there, but anyhow, the organizations that have gotten into a stride and how to approach efficient decision-making seem to really thrive. How important is the act of how decisions are made, and what part do you think leaders and managers alike have to play in that success there?

Kendall:

Oh man, that is a massive can of worms. I mean, where do I even start? So I've seen let me talk about the failure modes I've seen the failures where a leader who's responsible for making a decision doesn't feel like they can make a decision out of fear, right? So, lack of confidence, I don't want to make this decision, because what if I'm wrong? You're going to be wrong, especially in executive leadership. You're going to fuck up sometimes and so sometimes that's going to everybody and saying this is the direction I think we should go. Is everybody with me on this? And some people push back and wrestle with it, poke holes in it and at the end of the day you're like I'm not sure this to make a decision. So the failure mode can be insecurity, inability to make a decision. It can also be you know you make a decision and somebody overrules you and that happens a lot and like nope, ceo said you know, ceo approved this. I started shipping it. He told me I'm shipping it wrong and now I can't get anything done.

Kendall:

I worked at one organization where the entire organization, nobody, worked on anything. Everybody worked on working around the CEO From the day I showed up. It was Kendall, you want to work here. You got to know he doesn't like this, he doesn't like that. Oh, this isn't going to get you where you think it's going to go. Let's, let me help you rework that. I'm like guys. Nobody's doing their fucking jobs, like what? We're spending a hundred percent of our time working around a person. How are we not? How are we getting anything done? So there's lots of ways that can fail. Clarity on who owns things, who gets the ultimate decision, who's held responsible for it, and even a sense of safety for mistakes are going to be made, is absolutely essential to the velocity at which an organization can move. There are some organizations where every single decision has to come from the top. There are some organizations where the senior leadership is really good at pushing those decisions down, and the latter moves a lot, a lot faster, especially as the organization grows.

William:

Yeah, those are some great points.

William:

I was actually so I interviewed for a job many like several years back I can't say the company, I'm trying to get someone to come on and actually talk about this because it was really successful.

William:

But they had, like you know, like multiple tiers of you know, managers managing the managers, managing the managers, and then they had like three or four big towers in the organization and what they did was they actually flattened it down and so they had like basically one layer of actual management. It was almost like a team of teams approach, where the teams had the autonomy to actually drive and do things, you know. But then, you know, they they removed, because what was happening is, every time a decision would have to be made, it would have to go up to their manager and then their manager would have to take it up and then decisions are made by committee at the next level and then somebody above them would have to make a decision and then they'd need buy-in from a separate tower and it just took forever. So they flattened this down and they had it. It was like it was like they reinvented the company, like it's just so much better now.

Kendall:

Well, that's interesting to me because I think I think it can be done well and it can be done poorly, no matter how hierarchical the organization is. And at the end of the day, probably the reason it worked to remove that layer of middle management was there was major dysfunction in that layer of middle management, was there was major dysfunction in that layer of middle management that that was unable to empower their lower levels right. And so it sounds like somebody at the top knew how to empower people lower down and just got rid of everybody in between. And I think that does have to happen sometimes. But I I think people really actually appreciate hierarchy when it's done well and it's done wrong, a lot like don't get me wrong, the number of good leaders I've had is wildly smaller than the number of bad leaders I've had.

Kendall:

But when you feel like when you go to your boss and you say this needs to get done, here's why it's a priority and the boss can say, hey, I agree with you, or here's the business reason why I disagree with you, and turn, turn the tide and then say, but I need you to go solve it, or I need you to go solve this other thing and you have some autonomy to go figure out how to solve it.

Kendall:

That is amazing. But the hard part from the top is pushing down the business priorities because it's you know CEO has to say it 15 times for the COO to know what the priority is, and then they have to say it 15 times for the VPs to know what it is. And I mean it's real easy to get problematic. But if you're good at pushing that context down and giving people freedom to make decisions and how they solve those things, you can be a highly efficient organization with tremendous amounts of hierarchy, and there's nothing wrong with that. Flat organizations can also be just as dysfunctional. It's just how much they're actually empowered to understand what the priorities are and act upon them.

William:

Yeah, I mean, I'm a living example of that. So I worked for a pretty big company a while back where I actually had I reported to three different leaders when I was there and like the first leader was really awesome, let us run, and very little micromanagement. Like we really only heard from them when we needed to be informed of something important and we got a lot done. But then the next leader I had was just really big on micromanagement. We would have so many unnecessary meetings. It just clogged up our calendar. We just couldn't get anything done and yeah. So that kind of goes to show you that the person that you report to, and sort of just what you outlined, is, yeah, very important.

Kendall:

Well, so Leader 1 and 2 there, where one is hands-off and allows you to get things done the way that you think need to get done, and Leader 2, who's micromanaging. Which one did you feel like was more confident at their job? Not better at it, it's obvious. Who you think was better at it, who was more confident in their job?

Kendall:

the second one probably the the one who was the micromanager well, no so you can micromanage out of one of two ways yeah, one one can be the uh, I'm so insecure like I have to make sure it's done the right way, and I don't think it can be done the right way unless I'm touching you every moment of every day while it gets done. And the other way can also be the I'm just way fucking better than you william. Why the hell are you gonna code this when I could code it, you know? Like nope, you put that bracket in the wrong place. I mean, I I worked once with a cto and I actually love this guy. He wasn't the best cto, uh, who one of the engineers had spent a week built, automating something that the company really needed automated, and he did this entirely in his free time. It was like I mean 40 hours of time doing this, probably over a couple months automating this thing. And he did it all in Python. And he came to the CTO and he said I built this thing that solves a problem because we have to redo this every week. And look, you click this button, it automates the entire workflow.

Kendall:

And the CEO, instead of saying dude, this is amazing. There's some ways. I want to iterate on it. I can't thank you enough. This is incredible. Paused and said why the hell did you do this in python instead of ansible? And the engineer just burst into tears and just cried and cried and cried and then that was the end of it. I mean, he, he didn't last much longer after that and I remember being like the fuck right, like, and the cto wasn't wrong, it should have been done in ansible. But also that's on him for not setting that context, you know, and uh, or on the cto for not setting that context is what I mean, but anyways, yeah, it's, it's messy yeah, so I guess another, another observation that I just kind of lived through a few times, especially like when working in enterprises like, there's always plenty of like vision.

William:

You know lots of vision to go around. Typically, additional visions get added through turnover of like, maybe certain like high ranking positions, you know, which lead to new visions coming into the fold. You know, and I think execution obviously is where the rubber hits the road and of course, um, unfortunately sometimes where disparity usually kind of sneaks in and takes the steering wheel, um, what do you think about large organizations with leaders that maybe even have competing strategies? How do they um like, how can that type of organization become better at like the executing part? Because it's all about the vision get the funding, we have this much money to do something in this amount of time, and then it's like, oh, everything will fall into place, but a lot of times it doesn't.

Kendall:

So well, I have a couple of thoughts on that. And let's talk about the stereotypes, because I have not worked at Microsoft or a Google. I've been deep in both of them through friends and partnerships. But Microsoft has this reputation for pointing guns between departments. Right, like I'm out to kill you, I will destroy you.

Kendall:

And I remember there was a product that came out from Microsoft I won't say what it is, it was an open source product that I thought this is going to change everything. This is huge Open source. And it took me about a month to rally my engineering team to go look at it, dig in and and hey, I want to build something on top of this, cause this is, this is big. And when I went to look, I couldn't find it and I was confused and I went back and I found the press release and I found the link to get hub and I went and it had already been shut down, no-transcript. And he shut it down and the competing product that was being built, piece of shit, not going to change anything. You've never heard of it because nobody uses it. Um, and I think this one other thing would have been a game changer. So that that does happen and it definitely causes problems. You're, and then you know. On the other side of that, I think about Google, pms, which are infamous for saying no, and you've got to say no. Pms, product managers in particular, have to say no to things, and the best product managers are great at saying no. What Google's infamous for is building the whole thing, getting ready to ship it and then saying no, which is a bad idea, like don't wait till the fucking end to say no if you, if you get by and to build it, fucking ship the thing. So you know, you can fail in a lot of directions. I think. I really think one of the keys to it is saying no, but it's also, you know, back to the microsoft.

Kendall:

The culture of an organization being willing to encourage one another, row in the same direction is really important. Like there are loose organizations, good and bad, that have a very clear goal. Some of the most evil organizations in the world have a very clear goal and it doesn't matter that there's no hierarchy, it doesn't matter that person A is not even on the same continent as person B. They're working towards the exact same goal and they are incredibly, incredibly effective at accomplishing it Because it's very clear and you can meet somebody you never met that has the same goal and you're all in on it and you're going to help each other out, and you can use that for good or for evil, and all it takes is one asshole to get themselves in the organizational change. Who's like no, I'm here to build a name for me, fuck this company, and I will burn down everything in my wake if it, if it helps me get to that next. You know title? Uh, and those people exist. I've met a surprising number of them yeah, yeah, good points.

William:

Hey, I've talked to lots of folks like over the years about, like how it's funny, like how they perceive leadership, like there is definitely a striking difference between, like the generations that predated me and like the newer generations, and, you know, one thing that I hear just a lot from the younger crowd is leaders need to focus, like, more on empathy and integrity, which I think are two things that you want in your leader. You want them to have empathy and you want them to have integrity for sure. The moment that integrity is questioned, though, is like okay, trust is completely lost, and the challenge, I think, for many in leadership, especially up the org chart, they may have to make a decision. Maybe they have three options, and none of those options are good options. They're all bad options, but they have to be the one to choose. Yet, when they choose, they have to pay for that loss of integrity and subsequent fallout.

William:

Um, do you think the perception of leaders like, especially today, 2024 and beyond, from the bottom up, like needs to change a little bit, because, you know, can we all again like? We all make mistakes, we all fail, um, and there's definitely some leaders out there that have screwed lots of things up and they need to have their feet held to the fire, obviously, but yeah I mean, I always am gonna think it's leadership's responsibility and not their reports.

Kendall:

Uh, it's our job to set context, communicate reasons and execute in a way with integrity. Um, are we going to fuck it up 100%? Does an apology go a really long way? Also, yeah, and a lot of people are real shit at apologies. So, look, I'm going to go back to.

Kendall:

I'm apparently enjoying talking in failure modes. One failure mode that I've seen a lot in this is the new, younger generation leader who takes over a group of people and they're there to be the shit umbrella and protect them, no matter what. I'm going to get you raises. I'm going to make sure you can work hard. I'm going to protect your calendar so you don't get meetings. I'm going to make sure you work on the shit that excites you. So you last a long time and they completely disregard the business needs. And, frankly, if you completely disregard the business needs, eventually you fire all the people because the business doesn't go. And so is there a balance? Hey, y'all, you want to work here? We got to ship some fucking product and it's got to be the right product, or we're not going to have a job. Like there's a reality to communicating, that that is not unfriendly and is not without integrity. Like, is capitalism the world's answer to everything? Probably not. Is it the world we live in? Absolutely. And so if you're going to show up at a job, expect to get paid, you need to understand some of what's going on in the business.

Kendall:

Some leaders are bad at communicating that down. Hey, everyone, we're doubling down on this. Here's why. Here's why we think our buyers are going to react well to this. Here's why we think this is going to help us grow or get to our next round or whatever it is. And I need everybody to buckle down and focus on this one thing and I know you have a whole bunch of pet projects. You got to put them aside for the next three weeks or we're fucked. And people appreciate that kind of honesty. And it's also you can say hey, everyone, I asked you to go double down on this thing. Guess what Nobody bought. I screwed up. So here's how we're going to respond. We're doing the best we can over here. We are open to input. I may not take your input, but here's the direction we're going to go and here's why. And I think communicating that is effective and I think it's fine you are.

Kendall:

You know I have been in situations where I have said to people hey, I know this decision looks really hard and I know it's frustrating to you and honestly, there are reasons that I can't share for why it was decided. And I'm sorry, like I wish I could because I know that you would have more empathy for me and the decision that was made if you understood. But I can't share. Sometimes that's an HR reason, sometimes that's a financial decision going on in the background. You know there's there's all kinds of things that can go with that. But you can be honest. Even if your honesty is I can't tell you everything in this situation Right, and that helps. If you just bullshit, this is the right decision, get the fuck out of my way. That doesn't get you anywhere.

William:

Yeah, all great points. Yeah, it's just it's complicated and the thing is like one if you've had success at one organization and you go to another organization, it's a whole different thing, it's a whole different culture, it's a whole different set of problems. It's just very different. I like what you said about. Essentially, what you said is taking responsibility and accountability and being transparent. Any leader can do that, no matter where you work, there's nothing stopping you from doing those things, and that's something that seems to be lacking a lot of times.

Kendall:

I don't have all the context. I trust that they're making the right decisions in this and so we're going to go do the best we can to support them in it. Or if your answer is, this was handed to me, I have no idea why and frankly I think they're all motherfucking liars. You should get a different job, because there's a lot of dysfunctional companies out there and you being, you know, a voice that just communicates down that everybody at the top is an idiot is one maybe true, but two not very helpful to anybody.

Kendall:

It's not helpful to your reports, it's not helpful to the leadership, it's not going to get the business anywhere and yeah, I don't know. I mean, I'm also like there are different cultures all over the place and I regularly encourage people who are job seeking or who are miserable in their job, like the only reason you're here is because you don't believe something better exists. And there is things out there that are better, and it might involve a pay cut, but it's worth getting paid a little less money to be a lot more happy and uh, there are cultures that are wonderful and there are cultures that are terrible, and I like to fiddle around until I find the ones that I like. And I also recognize that at the top sometimes I'm blind to what's going on at the bottom, like I can think this is the most wonderful place and these people are the most wonderful leaders, and sometimes that is not what's happening and I hope that I know about it and I hope that people tell me about it, but they don't always. And there's a leadership.

William:

You know there's a power differential and you can't always make that go away, even if you try right, yeah, so it's like it's been great having you on. And before we go, are you in a gaming mood? Do you want to play a quick game?

Kendall:

sure, I mean, I'm not much of a gamer, but I'm assuming this isn't, uh, you know, what? What are all the cool kids playing call of duty or something like that?

William:

I'm not a gamer in that kind, okay, so the only thing I play is games with my kids. These days I don't have time ticket. Ticket to Ride child edition. It's pretty fun, okay.

Kendall:

Board games require a certain level of focus that I don't have. Anyways, go ahead.

William:

So I'll name a technology or a thing, and I just want you to say the first thing that pops into your head.

Kendall:

First thing Okay, this is exciting. It feels like the kind of game I can't lose, but maybe I can surprise myself.

William:

Everybody wins. Okay, everybody wins, all right.

Kendall:

Artificial intelligence Lots of power consumption.

William:

I like that. Actually, that's a good answer. A lot of folks don't think about that.

Kendall:

Real quick, I will say I spoke to an AI company today who was asking me for feedback on a product and I was like what you have built is exactly my expectation. You have replaced a very junior hire with a first draft, and that doesn't get me very far. Anyways, keep going. Blockchain Distributed databases that are auditable. I actually think there's good uses for blockchain.

William:

Keep going I do too, actually, I do too, um, especially in health care, actually, um, uh, so last, I'm gonna do one more technology and security.

Kendall:

Wow, I think actually, what I think of is we are right at the beginning of the hockey stick. We have just begun to see technology affect our lives and security as well. It feels like we're living in a technology age, but I think we are clueless to the number of ways that it's going to affect us. And we're just beginning.

William:

Yeah, yeah, I yeah, totally with you on that one. Well, so it has been a pleasure talking to you. This has been a very fun conversation and, uh, can can you let the audience know where to find you LinkedIn Twitter Are you are you making? Dancing videos on Tik.

Kendall:

TOK or what to find you LinkedIn Twitter.

William:

Are you making videos on?

Kendall:

TikTok or what. I'm not on TikTok, I'm not on Twitter. I pretty much spend most of my life removing social media from my life. I am very active on LinkedIn because I have a liquor brand I'm trying to hawk. There's a couple other places on public slacks and such, but LinkedIn is probably the easiest place to find me.

Chief Extrovert
Balancing Work and Family Life
Building Relationships and Decision-Making in Organizations
Leadership, Culture, and Stereotypes in Tech
Leadership Communication and Transparency
Blockchain and Technology Impact Interview