New School IT ™
Is your enterprise struggling to reap the full benefits of AI at this stage of your Digital Transformation? You're not alone, and we can help!
Old-school IT philosophy is to treat the AI business transformation as a one-time project, and unfortunately, that just won't work.
Welcome to New School IT, a Podcast dedicated to the conversation that will set your Data and AI journey on the right course.
Join us and learn the power of how a systemic approach to disciplined agility can drive game-changing Data and AI digital transformations!
New School IT ™
¡¿ŞKǏBIDÍ-WÅRE?! – your own software is your only option
Digital transformation isn't just an upgrade—it's a full-scale business shift requiring trust, discipline, and cultural alignment across departments. We break down why software development is so challenging and what makes the difference between forgettable tools and those that become indispensable.
In this revealing episode of New School IT Digital, hosts Roland, John, Nasheed, and Ryan tackle the uncomfortable truth about why digital transformation is so difficult. Through candid stories and real-world examples, they uncover how even the most well-intentioned software projects can fail when developers lose sight of the actual humans who will use their tools.
The conversation moves beyond technical challenges to expose the cultural and organizational barriers that derail transformation efforts. We learn how departmental silos create language barriers, turning what should be simple collaboration into a game of corporate telephone. The hosts contrast "old school" IT mindsets focused on project completion with "new school" approaches that embrace continuous evolution—revealing why companies stuck in delivery-mode thinking struggle to create software people actually want to use.
What makes the difference between software that gathers digital dust and tools that transform how work gets done? The answer lies in trust, discipline, and a willingness to connect deeply with users' needs. Through examples of software that gets it right (and some that miss the mark), the hosts provide a framework for evaluating your own company's digital efforts.
Whether you're a business leader frustrated by failed IT initiatives, a technical professional trying to bridge the gap with business teams, or someone caught in the middle of a transformation gone sideways, this episode offers both validation and practical guidance. Join us on this journey to reimagine how your organization approaches software development and digital change.
Share the knowledge, share the Podcast!
We give these examples of software that gets it right:
ZoomInfo (https://www.zoominfo.com)
Perplexity (https://www.perplexity.ai)
Miro (https://miro.com)
Tableau (https://www.tableau.com)
Hello, it comes along. Digital is a dance, not a maze. Feel the rhythm, come a play.
Speaker 2:Hello, this is New School IT. How can I help you?
Speaker 3:Hi, welcome to the second episode of New School IT Digital. Exciting right, or maybe a bit of a chaotic mess. Skibbity-ware anyone. I'm your host, roland, a 30-year veteran digital transformer and founder of Soda, a system of disciplined agility.
Speaker 4:Hi everyone, I'm John.
Speaker 3:My co-host John was a senior corporate executive who retired after successfully selling his software startup to a Silicon Valley unicorn. Hi, I'm Nasheed. My co-host Nasheed is an accomplished data engineer and entrepreneur. Hi, I'm Nasheed. My co-host Nasheed is an accomplished data engineer and entrepreneur.
Speaker 5:Hi everyone, I'm Ryan.
Speaker 3:My co-host, ryan, is an enterprise sales executive for a tech company in the Silicon Valley. We can help. In our first episode, we talked about why digital transformation isn't just an upgrade. It's a survival strategy. We urge those who recognize the struggle in their company to speak up, because change starts with a voice willing to say this is not working Before we dive into fixes and solutions for the rest of the season. Today's episode is about why transformation is so difficult. We break down the real challenges. First, good software isn't just about slick features or perfect code. It's about trust. The truth is, if people can't rely on the tool, they will avoid it. Second, digital transformation isn't just an IT project. It's a full-scale business shift. The companies that truly succeed don't just add new tools. They change how they work. Leaders need to champion it and every department has a role to play. Third, the transformation takes discipline. One has to be brutally honest about what could happen, what should happen and what's actually occurring right now to drive real innovation.
Speaker 5:Yeah, that is good.
Speaker 3:Finally, we'll share some examples of real-world software we feel got it right and not. Don't worry if you miss the names. We'll provide the links in the episode description. More than just technology, this conversation is about people, culture and the way we work together. So, whether you are technical or not, hop on this train of thought to see your digital transformation in a whole new way. Let's get started.
Speaker 2:Please hold.
Speaker 3:Before we even start with the meat of the conversation, who wants to nutshell what the digital transformation actually is?
Speaker 6:By digital transformation, we're simply referring to organizational enablement using technology or software. It's as simple as that.
Speaker 3:Okay.
Speaker 6:Business leaders, regardless of the industry, are in the software business, whether they realize it or not.
Speaker 3:Yeah, I like that, though I would say it's not just the business leaders, it's everyone in the company. Oh, there you go, nasheed, can you give a real-life story to start the conversation of? Why is it difficult to develop good software?
Speaker 6:I was at a large restaurant company and we built a pricing tool for franchisees. We didn't talk to the franchisees, we just wanted to build a menu level pricing tool that gave them pricing guidance to either raise price, keep price the same or decrease price. And we had this whole algorithm on the back end. It was amazing. We loved it, we're celebrating, we're high-fiving. And then we put it in front of the franchisee. They look at it and say what am I supposed to do with this? They're like it's very intuitive. You adjust the weights. If you care more about competitive pricing, you can just change that. And we're going through it because it's intuitive to us from an analytics perspective.
Speaker 6:But we're analytical and the franchisee said all I want to know is what price it should be. That's exactly what he said to us. He was like I don't have time to play around with the weights, I don't have time to figure out. And he was like I see colors that indicate good or bad meaning. We can move price up. Is that moving up a dollar? Is it moving up 25 cents? And I was like we didn't think about that. We just thought, hey, this is going to be a great tool to tell you hey, you have room to move price. We didn't tell him how much, so it wasn't for him.
Speaker 3:You built a research tool. You got it. That wanted instruction.
Speaker 5:Yeah, that's a great point. Yeah, that's a great point.
Speaker 3:If we take Nasheed's story as a single but salient example of how easy it is to get software wrong, what would you suggest to individuals in a company, in a company that may have a myriad of these stories, whether told openly or kept hush-hush?
Speaker 4:My advice to folks would be, as you think about software is, get very intimate with the people who are going to rely on that software, what actions they're going to take, what decisions they're going to take, and make sure you understand that incredibly well before you start to develop up the software. And, alongside that, think about the ways of working that need to be established to deploy the software effectively. And my final point would be be curious. Be curious all the time about is there a better way of doing it? Is there an improvement we can make that will make us either more productive or generate more sales or more revenue? The thing I love about the world that we're living in is just how dynamic it is, and celebrate that and leverage that.
Speaker 3:Great Machine. What would be your advice?
Speaker 6:My advice would be targeted towards those leaders within the organization who are responsible for delivering these types of initiatives and developing software as a business tool Number one. Reach out, get some help, because it's a very difficult thing and I've watched leaders who are great leaders struggle and many times lose their opportunity within certain companies because they hesitate to take the risk. They hesitate to move, not because they don't want to, but because-.
Speaker 3:They're not the first to dance.
Speaker 6:They're not the first to dance. I was trying to avoid the reference again, but the reality is, in some cases they have justification for not being the first to dance because they don't necessarily see how to connect the dots. They may not have the training to develop a roadmap, they may not know how to connect these departments, they may not know how to get the organizational buy-in and it's a very difficult undertaking when they may see their job as something much simpler. I think that's the advice I would offer.
Speaker 2:Please hold.
Speaker 3:My advice today would be use disciplined decision-making to determine how best to go about your transformation. Three elements that come together. One is think about what I'm emphasizing could what the transformation actually could do for your company Be very specific. The more precise your vision, the more concrete the goals, the clearer the purpose becomes. Yeah, the next emphasis is going to be should Think about what should happen, whether your employees and your partners will think of your intentions as truthful. I've been part of companies where management says we want to do this, but then everybody does the opposite and nothing bad happens. What should happen and what could happen are two really important parts of discipline when you're making decisions.
Speaker 5:Yeah, 100%, I like that.
Speaker 3:The third element is radical honesty Facing the truth of what really is happening and asking yourself what would I say if I were completely unfiltered? This is not easy. It takes courage to speak up, even being honest with yourself. Most people hesitate to be the first to step forward, to challenge the status quo, to overcome the fear of being judged. I know firsthand, creating this podcast is stepping into the unknown for me. I'm just a guy who learned, sometimes the hard way, how to build great software and companies where tech wasn't the focus. Putting myself out there is scary, but I'm doing it because this conversation needs to happen. It's also why I didn't do it alone. I have the help of three co-hosts and their support gives me confidence.
Speaker 5:Absolutely yeah, I'm with you on just the new school IT team.
Speaker 4:I'm just glad everyone was paying attention. That's great.
Speaker 3:I'd like you to feel that too. You may be listening alone, but you're not alone in your company. If your team is thriving, celebrate it, but if you're feeling frustrated, if there's tension around the tools that IT is providing, that's a signal that a conversation is overdue. We started this podcast to spark that conversation, because once you connect with people who believe in the same change, everything shifts. What starts as a timid hey, am I crazy? Can build into something unstoppable. It can start with a whisper, but as the choir grows, it becomes a roar. That makes sense.
Speaker 5:I like that. One of my old mentors actually used to say Ryan, be intellectually honest with yourself. Is it real or is it just something you're just pushing? It's like a goal that's not really happening. Can this happen? If not, move on.
Speaker 2:Please hold Soda, mixing it tight right into soda.
Speaker 1:soda, Please hold.
Speaker 3:I'd like to introduce the idea that systems thinking can help cut through a root cause of difficulty in good software development.
Speaker 6:Okay.
Speaker 3:You might ask a system of what it's? A system of cultures? Right now, your company already operates one, whether you realize it or not Marketing, sales, finance, hr, it. Each has its own culture and, as a result, each speaks its own language that is shaped by its functional concepts and ideas.
Speaker 4:The challenge, roland, is that within each function, we tend to have developed our own vocabulary and language. This acts as a useful shortcut when we're communicating with other members of the function and, frankly, it also makes us sound more professional.
Speaker 3:When these cultures collaborate, they have to convey the meaning of their concepts and ideas in terms that the other team understands. This isn't about converting German to Japanese. It's about making ideas understandable across teams in plain English, so that knowledge spreads, not just specs and jargon.
Speaker 4:The challenge is to speak very plainly so that everyone who's working on the software truly understands the needs.
Speaker 3:When you add software development to the cultural mix, it gets really interesting, because suddenly ideas also have to be converted into artificial language. So what starts as a tool that is needed in sales is expressed through conversations in plain English, including body language and gestures, emphasis, analogies, whiteboard drawings, and then all of that has to be explained to computers as binary instructions. So imagine all the cultural wiring needed to connect business teams who need software, finance and leadership who approve and fund it, and developers and product teams who build it. Wow, this is where old school and new school comes in. Think of old school like FedEx, they don't make the product, they just deliver it by following a delivery process. When you do this for very large numbers of employees, it requires a lot of skill Deploying software, maintaining it and the computers and the networks that everyone uses, supporting all of that, keeping the company's data secure. When you have thousands, tens of thousands or even hundreds of thousands of employees, these are all very important skills. But developing software is different than delivering it.
Speaker 3:Old school mindset revolves around delivery projects, resisting change in the interest of speed towards the finish line and a post-mortem culture where the project dies after delivery and the team moves on. New school IT has a constant evolution mindset. It understands that change isn't a disruption, it's the job. Innovation isn't a one-time event. It's a continuous operation, like how Excel has evolved since its first version many years ago. If your IT culture expects software to stay the same, they are already behind the difference. Old school asks for completion. New school embraces iteration. Here's a couple of other language clues whether your IT department has older new school culture. Old school thinks handoff. New school thinks feedback. What is scope? Creep to old school is a backlog to new school. Going digital isn't just about adopting new tools. It's about shifting mindsets. Software must evolve at the same pace as your business or it becomes obsolete.
Speaker 5:I like this. It's really making me think about how important mindset is. You have a smartphone, but you're using it like an analog phone. You're just using the phone. Get a flip phone, which is two bucks a month probably, and you could just dial out. Don't pay extra for that smartphone.
Speaker 6:One thing that I heard from what you said, roland, is the market has shifted on all of these employees, but also those who are in leadership positions throughout the organization. When you're talking about new school IT, it begs the question where do you find these champions? And I ask the question because where's the training ground for that type of individual? In this podcast, exactly, yes, people ask me all the time is it a technical skill? It is technical, but it's a blend of art and science and the technical resources are not the best suited to drive these types of initiatives. In most cases.
Speaker 3:The digital transformation goes to die in an old school culture.
Speaker 5:Absolutely. It's a funny role in Kai, my eight-year-old. They have this. What is it? Skibbity, ohio? I don't know what, whatever.
Speaker 3:Skibbity. I've been reading about it.
Speaker 5:Okay, it sounded like that for me. So once in a while I just say skibbity to them and the kids just laugh and I'm like I don't know what I'm talking about.
Speaker 2:Please hold.
Speaker 3:Rashid, you were talking about what we all call the user experience of software earlier. John, do you have any additional thoughts on that?
Speaker 4:You can define a user, but there will be all sorts of people in that job role, some highly analytical, some conceptual. Your software has to meet the needs of both. Then you have this additional element where power users, who can probably describe what your software can do better than the original designers can. But you'll also have a large base of occasional users and they may be more senior management who are looking at sort of I want to see a boil up reports, for example. I think that's quite a challenge meeting that broad range of people types.
Speaker 6:How did you do it, john? That's my question, because you're here. You've actually developed software. You sold it. How did you do it, john? That's my question, because you're here, you've actually developed software. You sold it. How did you do?
Speaker 4:it. We put some simple rules in place. So we said, look, let's make some promises to our users valuable, actionable, relevant, If you had to do it again, what would you do differently?
Speaker 4:As a founder CEO, you start your your business or I started my business championing a set of ideas about what our service would look like. What I would have done differently is I would transition from championing to discussing and engaging with customers much, much faster. Yeah, because there there were. There were ideas that I had which I still think were fantastic ideas. There were bits of the software that got almost no visitors which I loved and adored and spent money developing, and I think that's a problem that you get when you're developing up or applying software corporately. You know I'm the project leader. This is what I think you have to set that aside and actually build a picture of what these different user types think and need. You can only do that by working with them and talking with them.
Speaker 3:Machine any other points that make it difficult.
Speaker 6:The last piece would be when you're talking about a corporate software development initiative, is it's really about a workforce, is a workforce transformation project? So it really depends on the speed at which you can transform the way the work is done. So those are the only pieces I would.
Speaker 3:I would add Please hold please hold any other thoughts on why it's difficult to develop good software the biggest thing about software nowadays is the is the speed of change.
Speaker 4:When we first came to market, there was a great deal of interest in the fact that we could collect data from hundreds of retailers all over the world very quickly. That became table stakes, and so the next level was can you build insights on that data in terms of showing where the opportunities are? The next iteration was can you prioritize those opportunities and tell us what to do to take them? What was the actions? And then where I think we're heading is can you do the work, and I think that a lot of software is developed and gets to the point where it's doing a good job at a particular stage, but isn't ready to adapt into the next stage.
Speaker 4:A lot of businesses build point solutions. I think, increasingly, though, there's massive economic value in creating solutions that are designed to connect to other solutions, and I think that's a very different set of skills and mindset that needs to be applied. I think people have such high expectations of AI, for example, that that automation bit is going to come a lot faster. The danger is, if you haven't got the ways of working right and you automate, you're going to have a real problem because you don't automate bad practice.
Speaker 2:Please hold.
Speaker 3:Ryan, let's start with you. Your job is to sell software. I'm curious what your take is on what makes software good and what software do you like? Which ones do you think are maybe not as good?
Speaker 5:Yeah, first one comes to mind, it's Zoom Info.
Speaker 3:For everybody who's not aware of Zoom Info, their main product is a commercial search engine that is specialized in contact and business information.
Speaker 5:And Zoom Info is 100% accurate. Some software you click and you check on LinkedIn and like this person hasn't been here three years. Why isn't their database updated? And that's so frustrating. When it's not accurate, it's like my kid doing chores. You know, if they're not going to do it the right way, I might as well do it myself. You know, if you're going to feed the dogs and there's dog food all over the kitchen floor, you know like I'll do it myself. You know like.
Speaker 3:Totally All right, ashid John, do you guys have a similar perspective on something that makes you feel really good when you use it, or something that is just horrible?
Speaker 4:I was thinking through this and a lot of the software I use. I use it because it works. Software that I love is more to do with things that make my life more productive. So Perpexify, for example, I just love working with. It's almost like an interactive sort of experience in building up some ideas and thoughts, and I like that a lot.
Speaker 3:Nice. My example of that would be Miro. Miro has allowed me to free myself off the 8.5x11 PowerPoint slide and to tell stories with an endless canvas, and it's amazing what it does to the mind.
Speaker 6:For me, tableau. Tableau really unlocked the whole ecosystem, yeah, and changed the way organizations look at data.
Speaker 5:Skibbity, skibbity.
Speaker 1:Please hold so that makes any type rain to sold out soda.
Speaker 3:Thanks for tuning in. If I could suggest a takeaway from this episode, thanks for tuning in. If I could suggest a takeaway from this episode, it would be that it's really easy to get software wrong, and people do not have a lot of patience for tools that don't work or that don't keep their promise. Likewise, if the tool exceeds its expectations, people will fall in love with it and this too, the difference between employee frustration or delight with your company's digital transformation comes down to deeply connecting a cultural system, being disciplined and being receptive to change. In the next episode of New School IT, we'll move from the what and why to the how, breaking down practical steps to make transformation a reality with a system of disciplined agility. The next episode will drop in two weeks.
Speaker 3:If you like what you hear, if you feel it can help you start an important conversation with your friends, if this way of looking at your digital transformation could help another team in your company, share the podcast. Remember, the more we share knowledge, the more of it exists. We look forward to seeing you again in our next episode. Untiloda soda soda soda, soda, soda.
