Adaptive Software Development with James Hammack

Jay Bradford: How’s it going? This is Jay and Michael here on the IT Directors Podcast with our guest, James. James, what’s going on?

James Hammack: Oh, it’s been a good day thus far. I’m glad to be here. Thank you for having me. 

Jay Bradford: Yes, hello. Look, hey, we are so excited about this episode. We are talking about adaptive software development. And look, what better guy to talk about it with, Michael, than James.

Michael Thomas: This is the guru right here. Not only does he embody the beard, but also the knowledge of software and adaptive software development. I’m feeling it.

James Hammack: I’m not sure what’s taking longer to grow — the beard or the knowledge — but, yeah, thank you.

Michael Thomas: Simultaneously, nonetheless.

Jay Bradford: Yeah, that’s right. So, James, just for our listeners and viewers, James is our Director of Software Development here at Clear Winds Technology, and man, this guy is super talented and just super knowledgeable. You have a fantastic team, and I’m excited for this episode because I really think our listeners and viewers are going to gain a lot of knowledge from this. So we’re going to kick it off. James, just tell us a little bit about what your role is, what you do, and your background and how you got into this role.

James Hammack: Yeah, my background and how I got into this role — and even software development as a whole — was simply that I needed a [00:02:00] job, and that’s always a good thing. It does help put food on the table. And so in thinking through what is really going to be around for a long time, the idea was definitely given that website development is going to be around for a long time. And of course, as technology has increased and changed along the way, it went from not just websites but web apps, which was not really a thing at that point in time. So we’re talking over a decade ago — web apps weren’t really something that was on the horizon. So I’ve kind of grown with the role and with the industry from when I started and further into where I am now. It’s taken a while, and it has been a wild ride along the way to learn all these things, but it’s been a fun one.

Jay Bradford: Man, that is fantastic. I mean, you talked about web apps and just the transition and how technology has grown in the development role, right?

James Hammack: Mm-hmm.

Jay Bradford: And you know, that leads into what we’re wanting to [00:03:00] talk about, Michael — kind of this big picture of how technology never stands still. You know what I mean? And if you’ve been around technology, you know we’re doing this podcast for IT directors to network and to help them gain knowledge. But technology really never stands still. And in the programming world, James, that has never been more prevalent than right now.

James Hammack: Absolutely. Yeah, it changes fast, and sometimes it can be overwhelming.

Jay Bradford: Oh, look, I can imagine. Just being in it for many years myself, I’ve seen how software has radically changed.

James Hammack: Oh, yeah.

Jay Bradford: We have AI — everybody’s talking about AI and all these buzzwords — but software has just grown so much over the last five years, you know, for web development and all these things. But hey, we have some questions that we want to ask you, and Michael is going to get us kicked off here and talk about some of these things. I’ll let Michael fire our first question at you.

Michael Thomas: Yeah. And even as we’re going, my thoughts go to — I’m curious — what do you do to stay on top of those trends and stay in front of them? You said it’s overwhelming, but what do you actually do? How do you stay in front of the trends? What’s your process?

James Hammack: Yeah. I read a lot all the time and am constantly doing market research, all of that. But really, for that to work the way it does, I have a really great team.

Michael Thomas: Mm-hmm.

James Hammack: Being able to have a good team on board, being able to manage them, and then being able to stay ahead of the trends, make sure we’re heading in the right direction for our products, making sure that it is actually serving people, but also having some form of anticipation of what’s coming next — that’s a huge part of it. So if I’m not really looking forward, then I’m constantly playing catch-up. And that’s really the goal: how can you look forward rather than just playing the catch-up game? Because the catch-up game is the overwhelming part.

Michael Thomas: Mm-hmm.

James Hammack: But once you get up to speed and you spend time — like I said, a lot of reading, a lot of video [00:05:00] watching, this sort of thing — then you’ve digested a lot of material and you can begin to anticipate what’s coming up next.

Michael Thomas: Okay. No, that’s — I think you’ve got to stay in front of it because if you don’t, it’s one thing to perfect your skill and your trade, mm-hmm, but if you stay in that moment, someone else is going to pass you.

James Hammack: Oh, yeah.

Michael Thomas: And I think we end up seeing that. So in all of these different areas, it’s like, hey, how are you growing? How do you continue to sharpen your own skillset? And kind of one of the questions we’re talking about — hey, rigid project management, what’s the problem? What is rigid project management, and what’s the problem with it?

James Hammack: Yeah, so the idea of rigid project management isn’t necessarily called that, right? No one wants to be called rigid.

Jay Bradford: Yeah, that sounds bad. When you asked that, I was like, man, James does not come to mind as rigid, right?

James Hammack: Uh-huh.

Jay Bradford: That’s a great question.

James Hammack: Uh-huh. So the idea is really applying [00:06:00] rigid standards to various types of project management. It’s really more about seeing the framework and identifying, hey, is this really set in stone? Is there a set-in-stone process for each thing that you’re doing, and what does that look like?

Michael Thomas: Mm-hmm.

James Hammack: And so there are several different frameworks that are more rigid than others, and then there are some that are far more agile than others. So when you’re talking about rigid project management, you’re talking about things that are very set, and there’s a process that you have to follow every single time. If you step out of the process, then you’re seen as stepping outside of the project altogether.

Michael Thomas: Mm-hmm.

James Hammack: And so that’s really what we’re talking about when it comes to this rigid aspect. Traditional — and this is probably a better term and a little more palatable — traditional [00:07:00] project management is much more rigid. You sit down, you try to plan out everything you could possibly think of that’s coming, and then you fit those into neat little boxes. This is how we’re going to tackle this, and then you do it. And regardless of feedback, regardless of new understanding, it’s like, this is the project we put into place, we’re going to follow it, and it’s not going to move. In certain industries, that is exactly how you want to do things.

Michael Thomas: Mm-hmm.

James Hammack: So this isn’t a one-size-fits-all solution. In anything where you’re literally moving physical objects and there’s logistics involved, rigid project management is probably really key for success.

Jay Bradford: Mm-hmm.

James Hammack: Because there’s already a ton of logistics going into it and you’re doing the same thing — you are moving things from point A to point B and then installing those things there.

Jay Bradford: Mm-hmm.

James Hammack: You want rigid project management, so that’s actually a really good thing for that scenario. The problem comes when you’re trying to apply that to [00:08:00] fast-evolving technology and the landscapes that we have today. That’s where it gets hard.

Michael Thomas: Yeah, I can appreciate having a measuring stick and knowing, hey, this is what we’re doing, this is how I know I’m meeting my objectives, my goals, my different stages, and those types of things. But yeah, if all the other variables are constantly shifting —

James Hammack: That’s right.

Michael Thomas: — and outgrowing your measuring stick, then you can find yourself in a problem.

James Hammack: Oh, for sure. And quickly.

Jay Bradford: Oh, 100%. And so, James, this takes us right into — from rigid project management — what we’re talking about: adaptive software development. We talked about the rigidness and how you have to be agile. So what does adaptive software development mean, James? What does it mean to you?

James Hammack: Yeah. This again gets into more of a philosophy behind how you do things. The idea behind adaptive software development [00:09:00] is an agile mindset. When you think agile, think flexible — you’re able to really make changes on the fly. And Agile and Scrum are tightly woven; they’re built on top of one another. I really like Scrum a lot.

Michael Thomas: Mm-hmm.

James Hammack: When I was introduced to Scrum — and therefore Agile, so keep these things together in some respects — I was like, this is the way to do this.

Michael Thomas: Hey, tell us what Scrum is real quick.

James Hammack: Yeah, so Scrum — you would start at the beginning of, let’s say, a particular week, this iteration. In your project planning, you meet together, you go over the tasks, tasks are assigned out, and then you work through them. Then you come back together for a retrospective. Sometimes, especially for larger companies, people will do these things every day — a 15-minute meeting in the morning and 15 minutes in the afternoon. That’s kind of your bookends of the day. Others will do it on a week-by-week basis, and others still will do it even further out. But if you get too much further out past about two weeks, it’s really not as helpful of a framework. It’s really about taking [00:10:00] extreme ownership of what you’re doing and making sure that the way you’re doing it keeps change in mind — and that’s where the agile aspect comes in. So you can really pivot well. Adaptive software development has a different approach in some respects and a similar approach in others. It is meant to be agile, it’s meant to change fast, but there’s an acceptance of risk and of the fact that things simply won’t happen the way you plan — which, in the technology world, is all the time.

Jay Bradford: That’s real life.

James Hammack: That is real life —

Jay Bradford: Every day, right, in our IT world.

Michael Thomas: Exactly. Hey, that’s every day in parenthood, man.

James Hammack: Oh, for sure.

Michael Thomas: You don’t know what’s happening. Absolutely.

James Hammack: That’s right. So it sometimes feels, when you’re doing software development and working through problems, like raising a child. Random things pop up and you think, I wasn’t expecting that at all, and there’s no reason why it should have happened. So that is a huge thing. The idea is to speculate and — I like to [00:11:00] use the word anticipate when it comes to this.

Jay Bradford: Yeah.

James Hammack: And I didn’t even realize adaptive software development as a framework and a philosophy even existed until very recently. As I was doing Scrum, it felt a little boxy for me.

Jay Bradford: Mm-hmm. Mm-hmm.

James Hammack: It’s not crazy boxy, but it felt a little too rigid for my own personality, so I kind of adapted it and used the Scrum agile mindset and made it fit for how I typically like to lead. I took what I felt was really strong from that and applied it. And then, as I was talking about this with someone, they asked me, “Hey, are you familiar with adaptive software development?” I said no, and looked it up, and when I read it, I said, this is exactly what I do.

Jay Bradford: Yeah.

James Hammack: This actually fits a lot of the problems I had personally. Not saying Scrum isn’t good — it works for hundreds of [00:12:00] Fortune 500 companies and they’re doing amazing things using it. It’s super helpful. But it just didn’t fit me a hundred percent.

Michael Thomas: Mm-hmm.

James Hammack: So I prefer — to get back to it — adaptive software development. Rather than speculate, I like to use the word anticipate. I really seek to anticipate what might come up. But in that anticipation, I know things aren’t going to go the way I want. Things are not going to fit together perfectly. We might have extra meetings that week because there’s a client we have to step in and help, and there’s a kind of crisis mode that throws off our planning. Or even within software development — one of the key things we talk about all the time, and a core part of our products, is being customer-driven.

Michael Thomas: Mm-hmm.

James Hammack: So we want to be customer-driven. Well, if we’re customer-driven and we have this massive roadmap that has no flexibility in it, and then we get [00:13:00] customer feedback that throws off our product roadmap — what are we going to do?

Jay Bradford: Yeah.

James Hammack: Mm-hmm. Well, you adapt. You speculate — you say, hey, there’s uncertainty involved in the project. I’m going to own that uncertainty and not let it throw me off.

Jay Bradford: Man, James, as you were talking about that, I’m going to give our listeners and viewers a real-world example.

Michael Thomas: Mm-hmm.

Jay Bradford: So just yesterday, I was on a call with James about this very thing — software, and what we’re talking about: adaptive software development and the management skills and the project management around it.

James Hammack: Mm-hmm.

Jay Bradford: So James is very unique, for our listeners and viewers, in the software development role in that he is not rigidly set in his ways. Most software developers and programmers are very rigid, and when they write applications, they don’t want to change, because they’ve written it and they think, okay, this is the way it has to be. So James, we had a call, right?

James Hammack: Mm-hmm.

Jay Bradford: And I was giving you feedback from my role as an IT director about what I would like to see in a software tool that we’ve developed at Clear Winds. James, you used this very same framework about being adaptive, because you took our feedback — you didn’t say, “Come on, guys, that’s not what it’s going to do.” You said, “Hey, I like this. That’s great. We hadn’t thought about that.” And that is being agile.

James Hammack: Yeah. Mm-hmm.

Jay Bradford: And I think that’s why you and your team have been very successful and why the product we’re developing — School Manager — is such an adaptive tool

James Hammack: Mm-hmm.

Jay Bradford: for our end users, right?

James Hammack: Yeah.

Jay Bradford: Because you’re taking in all these different inputs, and while you started down one runway, it’s gone in a different direction.

James Hammack: Oh no, it’s different more than you realize. Because of the feedback we’ve gotten, we’ve pushed back entire chunks of where we thought we were going to be growing with School Manager in particular. We’ve pushed them down the roadmap. They’re still on the roadmap because we know we want to do them, and we know people are asking for them, but what people are asking for right now is different than what we thought they would be. So hearing that, we’ve got to do something — we’ve got to pivot.

Michael Thomas: That flexibility [00:15:00] is key. I think that flexibility is why you can continue to grow. It’s one thing to be so centered and focused on whatever your deliverable is that you miss all the different

James Hammack: Yeah.

Michael Thomas: feedback and what’s taking place that can actually help you get to a better place overall. But it’s that aspect of being forward-thinking, trying to anticipate, and I think that allows you to roll with the punches, roll with the challenges, those types of things

Jay Bradford: Yeah.

Michael Thomas: and continue to build something that can be a much more effective tool.

Jay Bradford: Oh, a hundred percent. And James, I mean, I think you embody adaptive software development and the management philosophy around it. From an IT director’s perspective, and as someone who has been on the customer side and is now on the client-facing side helping our customers — I see both sides, and it’s very interesting. Because a lot of people don’t want to change. Number one, they don’t want to change their project management approach, [00:16:00] and that’s hard. But number two, when you’re developing software, that’s your baby. That’s your thing, right? You don’t want anyone saying, “No, change this.” But we are adapting as a company for our clients.

James Hammack: That’s right.

Jay Bradford: I think that’s why software companies that have thrived are using this methodology, right?

James Hammack: Oh, for sure.

Jay Bradford: And those that aren’t — they’re not thriving. You have AI, you have all these different tools, and you have to be able to adapt. You have to be agile. And look, in life in general, you have to be agile, right? You can’t just go down one path.

Michael Thomas: Mm-hmm.

Jay Bradford: And so, as I mentioned in the meeting yesterday — I was thinking about it because I knew we were recording our podcast today — and I thought, this is incredible, this is exactly what we’re talking about. So look, you were talking about adapting, learning, being agile, and how important learning is, James, for you as the director of our development team but also for your staff. Can you expound on that?

James Hammack: Yeah. So one thing — and this is something I think is important for a software development team when it comes to learning — [00:17:00] is you actually need to set aside time each week to learn as well. If my team isn’t setting some time aside for that, it probably won’t get done, because everything else seems to take

Michael Thomas: Mm-hmm.

James Hammack: precedence over it. Each one of the team members has different ways in which they like to learn and different resources they prefer. Really, the key is to make learning a part of your weekly schedule and then actually do it. I’m reading things all day long, constantly. I’m doing a lot of research. I’m trying to figure out problems and anticipate future problems. I like to look at the landscape as it stands and then see — what are some upcoming things that look like they’re taking off? Then I research them and see whether they’re actually going to take off. And I’ve been really blessed in a lot of ways to have that forward-looking [00:18:00] instinct, and it does very much happen. I’ve seen companies start small, and we’ve used technologies they provided that they really championed, and then it grows into some pretty significant things along the way.

Michael Thomas: I think that aspect of being a lifelong learner — I love that phrase.

Jay Bradford: A hundred percent.

Michael Thomas: And I think it’s key. Even if you take three to five minutes in the morning — hey, there are a ton of newsletters you can

James Hammack: Sure.

Michael Thomas: subscribe to in different fields and different areas. And if you take just three minutes, even three minutes, when you arrive, you’re sharpening yourself, getting the juices flowing, and you’re in a much better position to respond and proactively tackle what’s in front of you.

James Hammack: Yeah, for sure. And then there’s the aspect of coming together weekly and talking about what we’ve learned. Because we ask three main questions at the end of every week: hey, what went well, what didn’t go so well, [00:19:00] and what did you learn from it? And it’s really a forward-facing aspect — what are we going to do now that we’ve learned this? We don’t want to repeat the same things. The definition of insanity, as the saying goes, is doing the same thing over and over again expecting a different result.

Jay Bradford: Yeah.

James Hammack: Well, that’ll kill a software product, period. It’ll kill a company, period. Any of this sort of thing. So learning and vocalizing that to one another — to the point where we’ve celebrated failures — and that sounds so weird every time I say it.

Jay Bradford: That’s good.

James Hammack: And people say, “What do you mean?” But that’s where you learn. That’s where you learn in life.

Michael Thomas: Exactly right. If you’re afraid to fail, you’re not going to try. And you have to try, because you won’t find what works just by doing that one thing. That’s right. And the — I mean, it’s the same three questions. I ask two out of the three the same, but I say, hey, what’s worked well, what hasn’t, and where is my room for growth?

Jay Bradford: Mm-hmm.

Michael Thomas: And those are the three questions.

Jay Bradford: And that’s the key — the room for growth, right? Both of you mentioned that. [00:20:00] And as a division lead, you’ve got to be willing to accept your failures and say, hey, what did I learn from that? How do we grow from that?

James Hammack: Oh yeah.

Jay Bradford: Being rigid is saying, we’re going to do this project this way, and we don’t really examine our failures or successes — this is just how we’re going to do it.

James Hammack: That’s right.

Jay Bradford: And sometimes you do have to have that rigid mindset, but we are talking about the adaptive software development mindset.

Michael Thomas: Mm-hmm.

Jay Bradford: And I think it exemplifies what we do as a whole and as a culture in our company, but especially what you’re doing in our software team. So as we close this episode — I really think this is going to be a great episode for our IT directors. Number one, they’re going to learn that things don’t always go as planned.

James Hammack: That’s right.

Jay Bradford: And if you’ve been in technology for more than three weeks, you’re going to learn that things don’t always go as planned. But in the software development world, if you want to be relevant and if you want to stick around — I mean, with AI, I now have an 11-year-old who [00:21:00] can develop applications that would have taken me weeks to build

Michael Thomas: Mm-hmm.

Jay Bradford: by using some of the large language models and tools available. And so we have to learn to adapt. And it’s so refreshing to see, from my level, how we do that as an organization and in particular in our software team.

James Hammack: Yeah.

Jay Bradford: And I think our IT directors are really going to gain a lot from this, especially if they have a development team. You know what I mean?

James Hammack: Yeah, that’s right.

Jay Bradford: You nailed it, James. And Michael talked about it too — learning to accept some of those failures, learning from them, adapting, and cultivating your staff around that mindset. And celebrating the wins and the losses — that’s how we grow in life. So I think we have a lot of great takeaways for our IT directors in this episode. And Michael and I are just pumped to have you on here, James.

James Hammack: Yes, sir.

Jay Bradford: Great episode. So look, everybody, go follow us on LinkedIn, go follow us on Instagram, go follow us on Spotify — IT Directors Podcast, powered by Clear Winds Studio here. And just a fantastic episode. We thank everyone for listening and joining today, and this is Michael and Jay. We’ll be back next week.