Episode 042 – Future Proof Your Career w/ Scott Drake

Scott is a Tech VP in Medical Education. He is the author of “The Programmer Hiring Playbook: A Crash Course in Interviewing and Hiring for Your Real-World Needs,” and he is also the founder and curator of LearnLeadership.org.


The world puts unrealistic demands on your time.
Do you have the skills to manage your time well?

Scott Drake – 01:06 – I got started back in the mid-90s, kind of, kind of sideways. I kind of backed into it. I was um, working for the student newspaper of the University of Kentucky as a subpar graphic designer and a sometimes writer. Uh, it was not a very good graphic designer, but the uh, advisor approached me and said, hey, check out what Tennessee is doing with their newspaper. They just put a version of it on this thing called The Web and I didn’t know anyone that was and so I bought the one book I could find the handyman to do with, it was a book on Mosaic, web browser, Mosaic and over Christmas break taught myself how to do html and came back in mid-January, built the site for The Kentucky Kernel which is the student’s paper there, and quickly got tired of manually producing sites.

Scott Drake – 01:45 – So I started, you know, writing code to, to convert content from newspaper, from QuarkXPress the program we’re using and to html. And so that kinda got me into programming and then it just kind of snowballs from there. I just kind of rode the wave, the wave of the web as it kind of started there in the mid-90s and in, you know, crashed out in the. I guess it really hasn’t really stopped in that point. But uh, so yeah, I kinda came into, came at it from sideways that don’t have any formal training just so I’ve kind of learned as I’ve gone along.

Jon Ash – 02:16 – So what do you do today?

Scott Drake – 02:18 – About two years ago, I joined a company called ScholarRx, uh, we build software tools for medical students um mostly medical students that are preparing for their boards, which is a very stressful time for med students. They had a, they’d been in business for about eight years with their software product that had kind of gotten to a point where the, the team they have of contractors working on that just wasn’t the greatest need. And so they brought me in. They said, building a team, building a team that can build this product better. And uh, so over the last, the first year I built out a team of about now 12 people and we’ve rebuilt the entire platform in the last week, last I don’t know. We started launching in about six months ago when it finally fully got it done. So, so now I, I’m not on anymore. When I took this job I said you can be hands on or used to be hands off. And I said, I think it sounds a step back and let some other people a deal with the next javascript framework.

Scott Drake – 03:10 – So, um, so, uh, pretty well stayed instead of stepped back, stepped up, totally leadership role at this point.

Jon Ash – 03:18 – So, so how have you enjoyed that transition?

Scott Drake – 03:21 – So for me, I enjoyed a lot because I’ve always been kind of a tech nerd and a business nerd and a leadership nerd. I kind of like all of those disciplines, so I like to build things. So that’s a, that’s a great fit for software people, you know, I enjoyed building software and writing code for so long, so I’d like to build things but to also enjoy building teams and I enjoy building organizations and building companies. So to me it’s this year kind of exercising the same mental muscles, you just using different tools and different technologies but you’re still building things and that’s what I get out of bed everyday to do this, is to do that. So I enjoy it a lot. It’s people is challenging, but you know, in general, I enjoy it a lot.

John Callaway – 03:58 – You kind of have a, a varied history in your career. Everything from Microsoft, uh, Silicon Valley and now in Louisville, Kentucky. You’d want to kind of walk us through that career path.

Scott Drake – 04:09 – Yeah. So, uh, as I said, I got started in newspapers and uh, first at the collegiate level, but when I started the professional newspapers I hadn’t touched the web at all. So we won some awards, some of the first awards they gave up for, for, for websites and college media. And that got me recruited out of school into professional newspaper. So I started working professionally for a couple of bigger newspapers around the state, worked for a couple of other things. I was mostly consulting, so, so again, I was kind of an entrepreneurial thing at the same time, but uh, early on when javascript was first taking hold is with back into the late 90s, there just weren’t a lot of us around who have done a lot in javascript and started looking around thinking maybe I’ll go out west and then they’ll go someplace different.

Scott Drake – 04:51 – And a recruiter from Microsoft called and said, hey, you know, you should really, you know, send us your resume. And I’m like, look, I’m self taught, I don’t know a thing like, um, um, you know, can barely stand up and walk. I’m a toddler at this. And they’re like, yeah, give it a shot. So I sent, I sent, I sent my resume and what I learned is that though they’ll give a lot of people a shot, you may not stick around if you’re not good, they’ll send you back home. But, um, but I got up there and it was, it was kinda strange because when you come in green or you come in without the biases of the education, then you can sometimes be a little more creative because you’re not, you’re not thinking of how things have always been done. You’re thinking, how would I solve this problem from scratch?

Scott Drake – 05:30 – And so you ended up coming up with some unique things in that fit well in a, in an environment like Microsoft. So I stayed there for about a year. Uh, they, I had a chance to stay on, but I didn’t really want to stay out west. Came back to Kentucky. And then maybe a year later, my boss from Microsoft had left and gone onto a valley, start a company, he called me up, said, hey, why don’t you come out here and run a team out here for me? And I’m like, sure, that sounds like fun. So I went back out to California for a while and eventually came back here and I’ve been back here since, I don’t know, about 15 years, I hear being loyal and uh, and I, and I like it here a nice if you’re closer to the beach. But other than that it’s a, it’s a nice place to live. So I enjoy it.

Jon Ash – 06:07 – And so you recently gave a talk at a Code PaLOUsa, believe it had something to do with future proofing your career. Could you tell us a little bit about that?

Scott Drake – 06:17 – I’ve run in quite often to programmers and didn’t happen a few years ago. Um, I had someone who approached me who was, he wanted to change teams. And his reasoning is that he was working on a team that was working, was still mainstream technology just wasn’t cutting edge technology. But he felt like if he didn’t shift to a team that was working with cutting edge technology, he was going to get left behind, he was going to become obsolete. And if something happened, you know, with, with this job, he wouldn’t be able to get another job because his skills, he didn’t feel like it would it be, would it be up to up to speed.

Scott Drake – 06:44 – And I’ve heard that a lot that people have approached me a lot, but the reality with him and I pulled him aside, I said, you’re not going to struggle to find another job in this industry because you become obsolete. Secondly, you’re going to struggle because you’re not a good problem solver and you don’t manage your time well. And there’s this handful of skills that kind of go along with the technology. So we focus so much on technology and often we ignore these other skills that make us a complete developer. But those are also the skills that often keep us employable. Right? Um, most organizations don’t care if you’re using mainstream technology or cutting edge technology. A lot of times they’re happier if you’re using mainstream technology or they’re happier if you are come in and work on that a five-year-old .net app, right? But if, if you don’t know how to solve problems or you don’t know how to learn new technology as well, or you don’t know how to play well with others or you don’t make good decisions, there’s these, these, there’s seven or eight skills that I, that I lumped into that end of that talk that if you don’t do those well, you’re going to struggle to have a long career in this, in this industry.

Jon Ash – 07:47 – So how did you come up with basically finding out those seven, seven or eight skills?

Scott Drake – 07:54 – So as I kind of sat back and I talked to quite a few people and I put together some and some other people put together a few and we kind of put our heads together and that’s kind of where we got. Um, there’s really, there’s eight. I mean, does that kind of rattle a few how to learn? How do you solve problems? Well, there’s a lot of techniques and learning. There’s a lot of techniques and problem solving. It’s a lot of techniques in decision making, playing well with others. Do you manage information well, like we’re just completely bombarded with information from all these places, whether it’s bugs or whether it’s feature requests or whether a support request or whether it’s, you know, things from slack or things from this or whatever.

Scott Drake – 08:28 – How do you manage that information flow? Well, you manage your time well, right? Burnout is a time management problem, mostly caused by the developers like the world puts unrealistic demands on your time. It’s always going to do that. The world is always going to ask more of you from your time and you can deal with, so can do. You have the skills to manage your time well. Habits and routines is another one, and then self marketing and those tended to cover the gamut of what just that core kind of skillset. I’m sure a few other ones out there, but we were trying to limit ourselves to maybe seven or eight that we felt were really core to having a good productive value. Creating career in the industry.

John Callaway – 09:09 – The old cliche of the developer that you can just feed Mountain Dew and pizza and slide it under the door and never have to interact with them as is really proven to not be true anymore.

Jon Ash – 09:18 – Yeah. Developers are expected to have people skills. They’re, they’re expected to have soft skills are expected to be able to gather requirements and, and go through problem solving and deliver solutions. Not just break fix.

Scott Drake – 09:33 – Yeah. I had, it’s funny, I was having a kind of a one on one, kind of a, a half year check in with somebody I hired. He’s one of my younger, younger guys. He’s maybe five years into his career and um, he said that he, a pivot point for him in his career is when he went from being a maker to being a problem solver and he had really approached his job early on as I’m a maker, like I’m a tech guy. I’m going to sit and play with, you know, with, with the hardware and software. I mean, he’s all over the place with data sciences, all this kind of stuff.

Scott Drake – 10:01 – But he’s got all these things sitting up on a shelf that nobody ever uses and at a certain point his career, he pivoted and he goes, okay, making is fun, but it’s more fun to solve problems for somebody in a way that somebody is going to use it. And it was kind of fun. I’ve been trying to figure that little piece that I keep talking to them about him because I liked the way he put it, that he kind of went from being a maker to a problem solver. And I think we all have to make that transition at some point.

Clayton Hunt – 10:27 – So when you make the transition from a maker to a problem solver. So as a maker it might be fairly simple or fairly easy to come up with a new thing to make, right. So you can sort of feed that desire, that hobby. Um, when you transitioned to a problem solver, a, how can you sharpen the saw as they might say, how do you, how do you in your own time get better at the problem solving?

Scott Drake – 10:54 – It’s, I think it starts with getting good at, at understanding other people. And what other people’s expectations are for the things that you’re building. Um, I think, uh, I don’t want to go straight to empathy, but it gets a little bit to being able to see the world from the perspective of other people, especially the perspective of your users. The problem solving in general. I mean there’s, there’s a lot of times we have different expectations or different outcomes as developers. Like we see the need of the solution to be able to do these five or six things. Would you go talk to the customer? They just really want to do these two things right?

Scott Drake – 11:31 – We think, oh, it’s got to scale like early on, every, every young developer thinks everything has a skill giantly. But then you get into understanding what are all the actual pieces that go into what does the customer really want. And a lot of times they might not want them. There’s like 14 things that came up with. And I don’t ask me to rattle them off on my head, but I can, I’ll put it in the show notes of when you make a decision is like just what technology to use. There are actually 14 things that came up with and, and they ranged from how complicated is the problem, uh, how innovative you know, is, is, is this something that requires an innovative type of solution or is this pretty routine, uh, what does the team look like, you know, is this going to be a huge team or a small team?

Scott Drake – 12:09 – How much turnover do we think we’re going? There’s all these little bits and pieces that go into just some basic decisions around what technology is used or potentially how to apply them, but early in a career and you just don’t have that experience to, to understand that and make those better decisions as far as what is a good solution to a problem versus, you know, what, what, uh, what do I think coming into it, purely looking at it from a developer’s perspective.

John Callaway – 12:33 – It’s interesting you said maker and in my head I’m picturing more implementer because early on in my career I was working for a company that they were implementing. They brought in some consultants to help them define their software development lifecycle and they, they defined an eight week cycle for a project and the first six weeks were all project planning and documentation and putting together very detailed functional specifications and then they handed that out all the details and all the paperwork off to developers at week six and that’s when they started to work on the project.

John Callaway – 13:10 – Yeah. And, and that was kind of the picture I had in my mind was, you know, many years ago developers or at least in my role at that time in my career it, it felt very much like here are the instructions but the instructions into the computer and that’s, you know, maybe with the advent of, of, or the popularity of agile and that that’s just not the case anymore. That’s not how software is done.

Scott Drake – 13:34 – Yep. Yep. Agree. And that becomes particularly important. And we’ll talk, we’ll talk leadership a little bit. When you transitioned to leadership as developers, I like to be given problems, right? I don’t want to be handled a solution. So for a long time you’re right. In certain situations, in certain environments, the business would come to you with all of this stack of documentation and say here’s the solution, go code it. Right.

Scott Drake – 13:55 – And that’s not as much fun for me as a developer. Right. Bring me a problem. So even if they brought me this big stack of stuff, I would say, okay, let’s, let’s back up what’s the problem and is this really a good solution for that problem? And that’s really popular. Like that works well with some environments in some environments are like, you know, don’t ask just code it. Right. And I didn’t do well in those environments, but uh, yeah, so it, it’s, it is, it’s, it’s, um, much more, especially as the industry has shifted more toward agile. Even with those big waterfall type projects. Like we, we embarked in the last two years on rebuilding an entire platform. We’ve completely replaced product and all the management stuff. This was a huge waterfall like project that we still treat it in an agile way that we still presented to the development team as problem, problem, problem, problem, and help let them help us solve those problems instead of trying to sit down and figure everything out and they give it to a developer. So even in these big, big you a gigantic project, she could still break it down into a way that you’re working more problems than you’re working in solutions. Just hand it off to somebody.

John Callaway – 14:59 – That’s interesting. Did you. Did you set to deliver MVPs?

Scott Drake – 15:04 – So the market was already proven, so did you do MVP for a couple of a few reasons? Do you need to get something in front of a customer so the customer can tell you you’re right or wrong? Right. We didn’t need to do that. We had a working functioning product at market with thousands of users and we weren’t going to make significant changes to how the, the, the, the problems that the, that the, that the software solve for the students. We were going to improve it, which we did significantly improve it, but we weren’t trying to solve the problem of will the market adopted. There weren’t technical problems that we were trying to. So sometimes you might do an MVP just to say we don’t know technically how to do this. So we didn’t feel like we did some early PLC work to make sure that we were in the right area for technical, but we didn’t feel like we had those kinds of problems either.

Scott Drake – 15:46 – So we, we did some early work to say, you know, technically we’ve proven that we can do it this way. Uh, we did do some stuff and some prototyping. I’m a big fan of prototype and even before you get to MVPs of two that we could put in front of students and some of those things that make sure that we were still going in the right direction. But ultimately we had to get eight months in before we get started to take parts of the platform down and replace it with new parts of the platform. We couldn’t just build something in six weeks later, hope to plug in and it’s just, we just couldn’t do that, but we still were able to organize and structure parts of that project in much more of an agile way.

Jon Ash – 16:20 – So let’s, uh, talk about kind of growing into leadership. So when, when a developer ready to kind of urban, is that the right question to ask? I mean, is there a set of skills that someone needs to acquire or is it just the person who doesn’t do well at coding? We’ll put them in people?

Scott Drake – 16:38 – I mean it could be, it could be that I enjoy being in tech, but um, I don’t enjoy coding or I’m not good at it. So here’s another skillset that I can try to develop. Um, no, I mean it’s, it’s when you go into leadership you have to say, you feel like maybe I’m going to take control of the situation, but a lot of ways you have to be prepared to give up control. Okay. Again, as a developer, do you want somebody to bring you problems or solutions? And what a lot of us do as leaders is we go in and we go, okay, my job up to this point has been to solve problems.

Scott Drake – 17:12 – So when I see problems, my instinct is to try to solve them myself because that’s what got me promoted. Okay? But if you, if you sit there and you continue to try to solve the problems of the team and handoff solutions to all your, to all your team members, then they’re going to get bored and they’re going to be unchallenged and eventually you’re going to be the person with all the problems on your plate. Uh, and you can’t do that. You can’t function that way. And that’s the mistake I made when I first got into leadership. But when I first went out to silicon valley, uh, I had eight developers and they were all bored and I was overworked because I had no idea how to lead people. Um, so the, it’s a very hard transition just because most of us aren’t trained that way.

Scott Drake – 17:53 – Nobody teaches us this. Nobody says, you know, hey, this is, this is the way you need to approach it. But yeah, you really do have to learn how do I set vision, how do I communicate a vision of boundaries? Okay, where are we trying to go? What is the problem we’re trying to solve, but what are the boundaries we’re going to put around this so that we don’t go into completely left field. So boundaries might be we’re going to work in.net, we’re going to use angular to like, like help me make these decisions of what we’re going to do, but then we’re going to establish boundaries. But within those boundaries I’m going to give you problems and let you play this game yourself in a way. A lot of us, when we first went to leadership, we want to play the game like where the coach player and it’s hard to be the coach player and the coach, right?

Scott Drake – 18:31 – I’m your team, just just, it’s it, it’s too confusing for the team. So yeah, if, if you. To go back to your original question, when do you know you’re ready or when you want to do it? A lot of people do because they get more money, right? It’s a good or bad reason to do it. I think it’s a terrible reason to do it. Uh, just because again, if you’re not, if you’re not ready to do it, you’re not good at it. You don’t want to do it for the right reasons, then it’s not a good reason. Um, for me it came down to I can have a bigger impact if I can learn to work through other people with 15 people on my team, I can accomplish much bigger goals than I can if I’m doing it with my own two hands. So if you get to a point where you want to work on bigger problems, then leadership might be interesting.

Scott Drake – 19:14 – If you get tired of learning javascript, the javascript framework might just knock you out completely and you can, you know, you can maybe go into leadership. For me, it, it, it really is about, with some of my organizational stuff, I want to change the world, right? I can’t change the world as easily as a single developer is that can, as a leader who can, who can inspire and bring people on board to help solve problems. Whether it’s for a med students or whether it’s for great technologists who want to become great leaders, I can do that better through leadership than I can through technology. Not gonna have a bigger impact that way.

Clayton Hunt – 19:49 – Right? So you’re still solving a problem. You’re just not solving the same problem that a developer is supposed to be solving.

Scott Drake – 19:49 – It’s true.

Clayton Hunt – 19:59 – Um, if, if someone is trying to make that transition is, is there any kind of a hallmark that they can pay attention to that will let them know that they need to stop because they’re trying to solve the wrong problem

Scott Drake – 20:11 – It was a couple of ways I can take that. So yes, I am solving problems today. My, my biggest problems today, what I do today as a leader more than anything is I try to get agreements okay. It’s not as, not as sexy or fun sometimes is, is programming, but that’s, that’s the problem I’m trying to solve today is how do I get whether it’s people on the tech team disagreed on stuff, whether it’s business, you know, to different stakeholders in the businesses agree on stuff, whether it’s the business and the tech team disagrees. So my job right now, the problems I’m trying to solve is how do I get agreement, says the bulk of what I’m doing today. Um, I would say as much as possible, like if you’re, if you’re straddling, if you’re sitting in that point where you’re a tech lead, where you’re hands on contributor and a leader, you’ve got to try to find ways that you can isolate.

Scott Drake – 20:54 – If somebody comes to you with a problem, you’ve got to find a way to, to help them think through that problem that coach them through that problem, but you’ve got to give it back to them. And if you find yourself not willing to do that or, or. What I would do back in the day is after about three minutes, I would be frustrated. I could see the solution and, and they’re struggling, so eventually I’d be like, just give it to me. Right? Which is the worst thing. You can do this, the worst management.

Clayton Hunt – 21:17 – And you’ve got your, your, your face in your palm and the palm of your hands and, and their lost.

Scott Drake – 21:17 – Yes.

Clayton Hunt – 21:26 – So how do you, how do you combat that issue?

Scott Drake – 21:26 – You hire better

Clayton Hunt – 21:34 – Let’s say we’re already past that point now.

Scott Drake – 21:36 – It is. So, so, um, so it’s coaching problem solving. It is. I’m making sure that they’re clear on what the outcome is, make sure they’re clear on what the problem is that we’re trying to solve. Are they clear with where the, where we’re trying to go now that we have some clarity as to where we’re trying to go, what are our options? Then if they’re struggling with options, you can help them with the options. Uh, how do we pick an option? Okay. Ask. It’s an issue of asking them these questions, not telling them. Okay. And it is an issue of having the patient, uh, and you have to learn your team, you know, some, some people on my team, I can take a much higher level problem and in five minutes we can figure it out and I trust them and they can go and some people and I’m just gonna have to spend a little more time with um, but it, it is an issue as a leader that you have to learn how to do that.

Scott Drake – 22:25 – You have to number when you have to, went on to become a good problem solver yourself. But then you have to. We’re not a coach problem solving, which is one of the first things I think you should learn when you go into being a leader. But nobody taught you that. Nobody taught me that, right? This is just something you just have to learn. So that to me, that’s, that’s the way you have to handle it. You just have to get better at coaching pumps off.

Clayton Hunt – 22:44 – I, I’m, I’m asking specifically about that one because I find myself in that kind of situation. I’m technically a while. I’m on the front end tech lead and you know, sometimes you’re just like, oh, we’ll just do this because it’ll fix it. But you know, you wanna you wanna like, you know, guide them but not tell them. And uh, sometimes it’s uh, it is a struggle.

Scott Drake – 23:05 – So one of my, one of my favorites was a, we had a team, so, so this was years ago, so 15 years ago, 15 years ago, we had built, um, there was a team in India that have built up the data entry port of an app and then a US based team built than analysis in dashboarding, part of an app and it was SQL database dinette front end on our side, but they were using Java because they were a Java shop and they were normally a job at Oracle shop and Oracle SQL. At least back then you had it, you couldn’t just interact with them the exact same way. Like with Oracle, you have to be very handsy with the transactions in SQL. You pretty state state pretty hands off with transactions, with SQL take care of itself.

Scott Drake – 23:46 – Well they were trying to interact with SQL, the way they would interact with Oracle and it was just messing everything up and then for like this one on for like six months and we would just have the app would just crash and it’d be deadlocked and all this stuff going on and, and we’d go, our stuff was fine, throw walking the database, why the blocking? So eventually it came down to the point where I said go fund me three articles on interacting with SQL from Java. Okay. And then the next day they came back and they go, breakthrough, hey, we had the breakthrough. We figured this out finally, and it’s in its. But it really came down to, I didn’t want to read the articles but I just wanted to make sure that they were doing the things that they needed to do to learn and discover these things on the road.

Scott Drake – 24:23 – So it really was as basic as that, like, you know, to go to Google and just google it and figure it out. Sometimes they might not even be thinking that way. So you just have to point out the obvious at times, but like I said, you can’t treat everybody the same way, but if you don’t do that, you’re just gonna you’re going to frustrate yourself and burn yourself out there as a leader. So you just have to learn how to do that or get a, get a better team.

John Callaway – 24:48 – I’ve found that dealing with my five year old that if, if I’m starting to get frustrated it’s because I’m failing to communicate in a way that he can understand what I’m trying to ask him to do or to stop doing. And then I really just need to adjust my approach. And then sometimes I just needed to take away the toy or whatever.

Scott Drake – 25:07 – Yeah. I’ve heard that a lot. Yeah, I hear that a lot of the leadership is a lot like parenting. I mean, it’s true. It’s a lot like.

Jon Ash – 25:14 – In your future proof talk or I believe it was the one at Code PaLOUsa, you talked about the different levels of leadership. Uh, I don’t recall what they were, but would you share what those are?

Scott Drake – 25:25 – So, so what, what really to me when I got into leadership and what really frustrated me is that I studied to be, I studied hard to prepare myself to become a leader and when I get out there I’ll fall on my face. Right? And the reason being is that I studied the wrong things. There’s, when I sat down and kind of broke this apart, there’s actually 28 topics in leadership on four different levels. So it’s not hard to pick their own topics if nobody points you in the right direction.

Scott Drake – 25:53 – Okay. So the four levels are lead yourself, which is a lot of the future proof stuff is how do I become the role model for my team? How do I become what people should, should model themselves after, which is problem solving, decision making, time management, those things lead yourself as level one, lead a team level to uh, getting good at coaching, getting good at delegation, getting good at understanding how culture and purpose drives engagement. A project management, hiring, how do you lead meetings? So those are some of the core things in the lead, a team level and you might get to that level and you may stay there your whole career because that’s where you’d love to be. Nothing wrong with that. If it is the case, there’s 14 topics to study instead of 28. Okay. Um, lead a department is, is a third level where you get into much more.

Scott Drake – 26:40 – I think that’s probably part of my time at this level in the next level where you’re, a lot of your job is, um, is resource planning, personal development, getting agreements, negotiation. Negotiation isn’t with vendors. Negotiation is enter in your company with your bosses, with your team, you spend all your time negotiating and getting agreement. So that’s a lot of a job of a, of a departmental leader as a manager or director level. And then the fourth kind of level is organizational leadership, which again is people who are there kind of have to change the world. That’s their mindset. Their mindset is, is to do that, they have to get good at what is our vision, what is our vision strategy, what I would call vision strategy, uh, which is how do we want to change, who do we want to help, how do we want to help them?

Scott Drake – 27:22 – A cross discipline, leadership, business development, marketing, sales, you know, high level operations, uh, partnerships and relationships is really big at the organizational leadership level. And you can’t change the world by yourself. So how do you bring in the right partners and people to help other organizations potentially help you do these kinds of things. So there’s really those four levels in. The problem I had is I did a lot of organizational leadership stuff when I should’ve been doing team level, you know, I should’ve been studying the lead a team stuff and I said to organizationally, so, so I studied hard, I just started throwing things. And, and so what I hope to do with, um, with leadership that org and some other stuff is to, is to help people not make the mistake in, to have a more realistic track of what they should study, when, you know, based on where they are in their career, where they want to go.

Jon Ash – 28:09 – So what can people find @learnleadership.org.

Scott Drake – 28:12 – So right now it’s pretty thin, we’re just kinda getting started and I’m, and I’m working with, with a, with a handful of other people just trying to figure out where we’re going to go with it. Um, the, the, the, I think the kind of the vision. I’m trying to answer two core questions which is what should I study 20 topics and what should I study? So let’s answer that question. If I want to help great technologist become great leaders. There’s 10 different ways I could do that. So I think I’ll learn the two things. What should I study when and what are some, some high yield resources for each of those topics. And um, that may be that we do book and resource recommendation pocket where podcast recommendations things along that line. There’s a lot of different stuff out there people will follow.

Scott Drake – 28:52 – Like if you want to become a better learner, what are some good resources to help you become a better learner? Well here’s some high yield stuff that we’ve curated, enlisted out. So if you’re working through these things here, some things you can do. I would like to do some interviews. So again, I’m a, I was talking with another guy, speaks a lot on hiring a. He would explain and teach hiring a little bit different than I would, but we all learn differently. We learn by what we can relate to. So some people are going to relate to him and some are gonna relate to me. So if we can both put up a 15 minute quick start guide on hiring, then as you get into hiring, one of those is going to resonate more than the other. So can I bring together some people like that and do some, some interviews?

Scott Drake – 29:32 – So we’re still trying to figure out exactly what we’re going to do with it. It’s definitely kind of a pre mvp that’s out there now. It’s not even really a total product, but we’re, but it’s mostly so I can, talking to people, I can start looking for the other people who want to help champion the cause and the cause of helping technologists become better leaders. And uh, so we’ll see where it goes in the next year or two. Um, it’s been kind of fun to, to, uh, to get it to this point, but we’ll see where it goes.

Jon Ash – 30:00 – Is there anything that any of our listeners could do that, that might help you with your efforts?

Scott Drake – 30:06 – Yeah, I mean it’s, it’s, um, if, if people have an interest in leadership, if people have an interest, if there are resources that they found valuable, if they have a particular topic so they have an interest in. They don’t have to be an expert. Like I wasn’t an expert at hiring when I started putting stuff together on hiring. That’s how you learn, right? You learn some things about teaching. Uh, so are, if there are specific things that they are interested in, they can, there’s, there’s, uh, uh, get involved section on the site and you can fill that in and uh, and I’ll reach back out to them as we get into audio and potentially video production. There’s some stuff even on that side. So even if you’re not content centric but you’re more technically centric then there, there may be some ways like that that I can help let people in as well as just general technology. I think there’s some other things that have been kind of floated around, um, groups, you know, being able to group people together under cohorts to help them learn together.

Scott Drake – 30:58 – So there’s potentially even some technology things that we might want to try to build into it. But I would like to do that in a much more like an open source community produced way as opposed to, you know, try to build out some, some company around this. This is, to me, more of a, more of the, the, the community getting together and trying to solve this problem collectively is what is, what I hope I can take now where it was going to go out and you know, it’s like any other startup, it’s, it’s, uh, it’s, uh, you, you started to get on the path and you find people who may be helpful and you see where you ended up. So that’s kinda where we are.

Jon Ash – 31:33 – So obviously you gave the talk, future proofing yourself, which is very, you know, I’m a very specific advice for people that are kind of the technologist. But do you have any specific advice for people getting started in the industry?

Scott Drake – 31:47 – So I would say be yourself. Uh, there’s no, there’s, there’s no single one way to do this, right? There’s not a super developer’s going to come behind you every five minutes. I’m bagging on everything you just did right? There may be, but they’re, but they’re jerks to the industry. They’re not the average people in industry. So, so go forth and do your best. Don’t be afraid to make mistakes. Uh, don’t feel like you have to do it this one certain way and it’s going to be perfect. As I said, when I got out the Microsoft, I was bringing ideas and concepts that were somewhat novel and unique and that was very well appreciated. Okay. So even in places that you would think as rigid and as a academic at times is someplace like that can be, that’s not always what, that’s not always what’s valuable then you’re just another voice, you know, you’re, but you’re not really standing out to me in any way.

Scott Drake – 32:35 – So definitely, um, be yourself find real problems to solve. Like I talked to a lot of people coming through through code camps and doing things along that line and they keep waiting for the next class and waiting for the next class and I’m like, just go build something. Right. Is there something that’s kind of interesting? You know, I learned how to code because I thought it would be cool to have some kind of photo sharing site. Okay. So I just started coding stuff out and it never went anywhere. Right. It’s set up on a shelf. That was the maker version of me, but that’s how I learned the code is so I’ve built like Flickr before there was Flickr and I built a Facebook before those are Facebook and that they’ll all these things before they ever existed and they never saw the light of day, but what they helped me do is learn how to code better.

Scott Drake – 33:15 – So if you’re just getting started, uh, just code, just build stuff, um, that’s how you learn. Um, so yeah, I mean I think those would be, you know, those would be probably the two biggest things that come to mind that I would suggest.

Jon Ash – 33:31 – Awesome. Well that seems like some sound advice. Do you have any upcoming events, speaking engagements or kind of any other announcements that you’d like to.

Scott Drake – 33:39 – Yeah, I’ll be. I’ll be at a Pittsburgh Tech Fest June 2nd, which I’m not sure when this will air. That’s the only. I’ve got books so far this year. I’m starting to put some stuff together. Some of the talks I’m doing, I’m going to start trying to go to some of the meetups around the Midwest and deliver some of those talks as well. So if, if, um, you might keep an eye out on, on some of those things as well, you can also follow me on Twitter, which I’m not super active on Twitter, but you can definitely catch me on some of those on where I may end up.

Jon Ash – 34:07 – Okay. And that was the next thing I was going to ask you is was there any other place the listeners could keep up with you?

Scott Drake – 34:18 – So yeah, I’m on Twitter at, at @tscottdrake and tscottdrake.com. There’s a, there’s a sign I just put up that I’ll also post the upcoming speaking in some of this stuff as well.

John Callaway – 34:23 – All right. Thank you Scott. We appreciate you taking the time to speak with us today.


“Tempting Time” by Animals As Leaders used with permissions – All Rights Reserved


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