247. Million-Dollar Misunderstandings: How to Fix Tech-Business Disconnect

Companies invest millions in tech projects every day. Some deliver remarkable returns while others crash and burn, wasting fortunes and careers.

The deciding factor? Rarely the technology itself—it's the disconnect between technical implementation and business objectives.

In this episode, you'll learn a proven system for bridging this expensive gap.

You will see how to diagnose misalignment, quantify its impact, and implement frameworks that create genuine understanding between technical and business teams.

You'll get lessons you can use at work today.

This episode is for you if you:

• Want make sure you get the best ROI on your tech innovation projects 
• Need to become the translator who can align technical realities with business goals
• Work in tech and are tired of business stakeholders changing requirements every week

Timestamps

00:00 Introduction

00:56 Digital Transformation Failures

02:50 Tech and Business Misalignment

06:09 Diagnosing the Disconnect

09:03 Importance of Communication

11:59 Creating a Collaborative Culture

15:11 Taking Action on Survey Results 

Resources mentioned in this episode:

• Harvard Business Review: Coding Isn’t a Necessary Leadership Skill — But Digital Literacy Is
• FREE download: Anonymous Survey on the Tech–Business Divide 

For more career & tech lessons, subscribe to Tech for Non-Techies on:

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Transcript

Sophia Matveeva (00:00.215)
Every day, companies invest millions in tech and digital transformation. But did you know that most of that money actually goes to waste and 70 % of digital transformations fail, according to McKinsey. And usually technology is actually not the problem because it is the disconnect between business goals and technical execution that is usually the issue. And in this lesson, I'll show you how to uncover.

the hidden and expensive misalignment, sabotaging your digital project and what you can do to fix them. And you will learn a proven system to align your clever strategy with what actually happened so you can avoid costly delays and finally get ROI from your innovation investments. So if you're a business leader or you're an innovator who wants a better result from tech teams, then this lesson is for you.

Welcome to the Tech for our Techies podcast. I'm your host, tech entrepreneur, executive coach at Chicago Booth MBA, Safiya Matheer. My aim here is to help you have a great career in the digital age. In a time when even your coffee shop has an app, you simply have to speak tech. On this podcast, I share core technology concepts, help you relate them to business outcomes.

And most importantly, share practical advice on what you can do to become a digital leader today. If you want to a great career in the digital age, this podcast is for you.

The way I'm making it is so basically you can listen so you don't actually have to watch the lesson without the visual simulation of slides and my face. You can still learn quite a lot. And also this lesson is going to have a really, really handy handout. It's a free survey that you can do with your team. And the link to that is in the show notes if you are listening and it is just below in the comments on YouTube. Okay. So now.

Sophia Matveeva (02:21.152)
I'm going to get started, share my slides with you. Let's do this. So for those of you who don't know me, hello, wonderful to meet you. I run a company called Tech for Non-Techies and we are the leading strategic advisory firm empowering non-technical leaders. And we've been featured in the Wall Street Journal. Our work has been in Forbes, actually we started by being in Forbes. That's another story, BBC and so on and so forth. And our main thesis is

in really encoded in this Harvard Business Review article that I wrote a couple of years ago. And basically it's about the fact that if you are a business leader, know, if you are a CEO of a company, if you are a non-technical founder of a company, then you don't actually need to be a coder. You don't need to learn how to code, but you do need to know something about technology. And we call that learning to speak tech, learning the language of technology.

So you can collaborate with technologists and link your business strategy to tech goals. And so if you don't want to go on a coding bootcamp, you are free. Okay, so these are some of the organizations that we've worked with, the University of Chicago, Constellation Brands, governments around the world, Royal Bank of Canada. Anyway, so this lesson today specifically is about million dollar misunderstandings.

and how to fix this disconnect that happens between the tech side and the business side. And you know what? This disconnect happens pretty much in every company. I've seen this through my work, through the work of my colleagues at Tech Fun on Techies, through my conversations with people. These conversations really happened when people, especially after a couple of glasses of wine. Anyway, so I'm going to tell you.

how to fix these disconnections without having to go to bars and have late night drinks with people. Although you can obviously do that if you want to. Anyway, so the tech versus non-tech tension is actually a $2 trillion problem. Here is why. So as I mentioned right at the beginning, 70 % of digital transformation projects fail to meet their goals according to McKinsey. Okay, so that problem, obviously I think.

Sophia Matveeva (04:43.438)
The average digital transformation project is about $30 million. So if 70 % of that goes to waste, that's a big problem. So there's another study that basically says that by next year, by 2026, there will be $2 trillion in waste and investment into digital transformation. So what on earth is going on? So most studies show that basically it's kind of what I said at the beginning of the episode. It is not the technology that's the problem. It's culture.

say another McKinsey study says that 62 % of failures cite culture as the biggest obstacle and that that's basically employee resistance and poor change management. Okay, well, what does that mean? I'll tell you that in the next slide. But basically, happens when you have culture as the biggest obstacle? What happens when you have employee resistance? Well, digital transformation investments don't have the ROI that you want. So you waste money.

Basically people hate each other, so team morale goes down. You know what happens when team morale goes down? People leave and then you have to find new people and you have to onboard them. you know, like right now my company is actually scaling, which is wonderful. So I'm having to hire people for good reason. And you know what? I'm really not enjoying the process. It's wonderful when you have a really productive employee already working with you.

you know, writing job descriptions, interviewing people, then onboarding them, that whole thing, nobody likes doing it. So if people leave, because basically you've created a culture of employee resistance, you can have an unpleasant problem, not just an expensive problem, but an unpleasant problem. So obviously your execution goes down, like you can't work as quickly as you would have done if you had a full and happy team.

And as a result, businesses' reputations suffer, you know, with the media, with their customers, with investors, which basically means that CEOs can get fired and they lose their competitive edge. So have I got your attention now? This is bad. You do not want this. Why does this happen? So basically there are theories into why this happened. And I think a lot of the theories are kind of misguided and most leaders assume they know where the problem is, in my experience, they're often wrong.

Sophia Matveeva (07:06.802)
So why is there this misalignment? So often business leaders, like tell me in the comments if you have experienced this and your comments can be anonymous. So only I will know. So business leaders think that tech teams are too slow. So if you've ever worked on a project and the minimum viable product is late, the engineers keep on pushing deadlines, might've had this experience. What about if...

tech teams think that business leaders don't understand what's possible. maybe you've got engineers watching this. I'm sure that some of them have been in a situation where a business leader tells them something and they're like, okay, we could do that if we had Instagram's budget and three years to execute this. We are not going to be able to do this with our team of three people in six weeks. And so as a result, as a result of this, both teams blame each other.

Projects still get delayed, projects still go off track, ROI is still not what you want it to be. Everybody hates each other. This is a problem. So what do we need to do? First, we need to pretend to be doctors. Put on your white coat. But anyway, seriously, before you start trying to fix any problem, you've got to work out what that problem is. So, and this brings me to Leo Tolstoy.

so Leo Tolstoy, the first, the first sentence in Anna Karenina is all happy families are alike. Each unhappy family is unhappy in its own way. That is also the same with tech teams and business teams. So there are some where they don't have this tension. Most do have a business and tech tension, but some, some don't. So the ones that don't, they're all alike. But each tech.

and business tension, they're different in all sorts of companies. They're because this tension arises for different reasons. So just like Leo Tolstoy spoke about families, we have the same thing in business. So what do you need to do? First, you need to figure out exactly where is the problem? Who is the most unhappy? Why? Because most of the time it's actually fairly easily fixable. You've got to diagnose the correct problem.

Sophia Matveeva (09:32.934)
What you need to do is to run an anonymous survey. And actually you can get a free anonymous survey that we use with our clients. So you can basically take what we use, either just send it to your people and see what results you get or tailor it. But if you're listening to what I'm saying, and this really resonates with you, just take the survey that we use with our clients and send it out to your people. in this anonymous survey, you need to segment

tech and business responses. And we have that in the server that you can download and you can download that at techfinantechies.ca forward slash survey. The link is just in the show note. So segment tech and business responses. Make sure to ask about real work and not just opinions. like actual real stuff, like things, know, tell me about a particular project, what happened on this project, not, you know,

I don't like it when Bob doesn't listen to me. That's an opinion, so I'm going to be very helpful. Make sure that your survey isn't too long because we've all done surveys that you start doing it with the best of intentions and then you realize it's super long and then you give up and you can't be bothered. So I've definitely done that. So make sure your survey doesn't go above 10 minutes. Our survey is about eight minutes and kind of that's the optimum. And also my advice is

don't just make it this HR thing because if HR sends out the survey and people actually honestly do it and they spend their time and they give me their effort and then it's just this HR initiative and you get some metrics and nobody does anything, you will have even more unhappiness and disillusionment. So this has to be really from the leadership. This has to come from the top leadership of the company or of the department, of the unit.

It can't just be basically a middle management HR exercise. So ensure leadership commits to action. So there are five things that you need to have in your survey. Again, we've divided that in hours. You can just take this lesson, do it yourself, or you can download our thing. I said, so number one, you need to figure out what do your teams think about your strategy? Do they actually know what your strategy is?

Sophia Matveeva (11:59.056)
Because often we find that, you know, even when you think, like if you are the business leader and you think, okay, I have been saying the same thing, I've been saying what our strategy is and what our goals are over and over and over again. And you might think, you know, I'm like, I shouldn't keep on saying this. You might be surprised. You might still be surprised that people still don't really understand what your strategy is. And often we see that this is one of the biggest disconnects when the tech team

either doesn't understand your strategy because they've never really been told or they misunderstand it. So you have to understand, well, you have to find out what do people actually think your strategy is. Then number two, you need to figure out what are the decision-making processes in real life? Not what you have in some handbook, but how do decisions actually get made? How do decisions get discussed between the tech team and the non-tech team? You know,

If the business side asks for something and the tech side pushes back, what happens? What happens in real life? Because this is like, you're really getting into the nitty gritty. Okay. Then the third area is communication effectiveness. So how, I mean, how often do the two sides talk to each other?

Is it a regular thing? it because it's in the calendar, they have a weekly meetup. Who goes to that meetup? What do they talk about? Who participate? Is it just a business team meeting where essentially they give a presentation, they just tell the engineers what to do? Is it the other way around where essentially engineers completely dominate it? I've seen this in some companies where engineers completely dominate it and basically the business side is kind of too intimidated by the engineers. That happened.

And in the company where I've seen that happen, they had a really, really, really serious delay with releasing their product and some very, very unhappy customers. communication effectiveness is important to understand. So then you also need to talk about your survey, the project execution realities. So when a project is actually being executed, inevitably some issues will come up like, you know,

Sophia Matveeva (14:19.206)
How do you issues that come up with quality assurance? How do you fix last minute changes that business leaders want to put into the sprint? how does, what actually happens when a project is going from idea to reality? And the final thing is kind of, it's a bit more willing, but super important, trust and psychological safety. And this is important for both sides. So think about this, the business side has

They're in jargon. right, like I went to business school, I worked in private equity. We talk about ROI, we talk about margins, we talk about equity and so on and so forth. We've got all of these words. And you know, when you are hanging around with people like you, you assume that everybody just knows what these abbreviations are. You assume that everybody knows what these things are. But actually.

On the tech side, they make the same assumptions, right? They talk about APIs, they talk about backend, they talk about Ruby on Rails. And if you don't know what that is, you might think, okay, should I know this? Is it okay that I don't know? If I ask, am I going to get fired? If I ask, am I going to get ridiculed? And essentially, really good collaboration, like in places where I have seen where this really works well.

is when essentially both sides have a learner's and a teacher's mindset towards each other. When both sides have the psychological safety to ask for clarification and say, I don't know what a freeze is, can you explain to me what it is and why we need one? Or I don't know what a technical debt is, can you tell me? So if you have this kind of, and equally you want that from the tech side too.

It is especially for the senior leadership. It's super easy to think that you're really approachable and really lovely and really kind and there's loads of psychological safety around you. Often that's not true and often people are actually really terrified. So this is why you need to basically survey them anonymously. Make sure it's anonymous. So basically you send out the survey.

Sophia Matveeva (16:39.698)
Use hours, create your own customized hours, whatever you decide to do. Give people some time. Make sure that they understand that this is not just an HR initiative, but this is something that actually the leadership is going to take seriously. And whilst the results are coming in, whilst people are doing it, here are some things that you can do that will A, increase your team effectiveness, but also B, show to your

team that you're actually taking this really seriously. So first of all, just break bread together. It's so simple. It is so simple. I don't know why people try to do it. Literally just book lunch together. I would suggest go outside, know, don't just bring sandwiches into the office because like the sandwiches, the sandwiches often end up being soggy and it's just not that nice. But you know, just have a lunch.

where you have the tech side and you have the business side and they just talk about everything and anything, not necessarily work. So schedule a no agenda lunch. Then another thing that you can do, a quick win, start joint planning sessions. So this is when the business side starts really explaining what they're working on and why and asking the tech side, well, okay, do you have any ideas for what you guys could do to make it better?

so equally the tech side could tell you what they're working on and the business side could say, we don't understand why you're doing this. Can you explain it? And this is how you start beginning your collaboration and your planning sessions. And what I would suggest for the senior people watching this is you need to create a clear escalation path for when priorities conflict, because this is really where issues happen. So basically who is kind of like.

King Solomon, who is the wise person that people go to when the business leader is like, okay, our biggest customer wants this thing and they say they want it now and they're not going to prolong our contract if we don't do it. And the tech side is like, okay, but we've got so much technical debt, if we don't figure this out, then our entire product is going to collapse. Both of these things are problems, right? They're both priorities.

Sophia Matveeva (19:07.686)
There has to be a clear path about, okay, when something like this happens, who do you go to? How do you have that discussion? Okay. So this is the end of our lesson. If you want the survey, just go to techfornontechies.co forward slash survey. Here's a quick recap of what we covered today. So this tech business misalignment that I have shared with you, it costs trillions of dollars. So two trillion.

dollars are projected to be wasted by next year by failed digital transformation projects. So this is really, really serious. This isn't just some sort of nice like kumbaya thing, like projects get stalled, careers get ruined because of this. So take it seriously. So the first thing you need to do is diagnose the problem and understand what flavor of the problem that you have because

Each company is different. Each unit is different. Even if you're in the same company, one unit is going to be different from the other. So you need to do a diagnosis before you take action, analysis before action. Then you can have a data driven approach. Right? So how do you do that? You run an anonymous survey. That anonymous survey has to come from the top leadership, not just from HR. You have to use structured questions and you have to have some questions that are

only for the tech side and only for the business side and some that are for both. And most importantly, you actually need to act on the results. So when people pour their heart out to you and they really believe you that, you want to listen to them, then they need to see you taking some action. And you know, most people are reasonable. They realize that you're not going to just wave a magic wand after a survey and everything is going to be great.

But if they see you making effort, then people start having hope. And hope is a wonderful thing. Hope is basically what gets us to walk through walls and to achieve the impossible. Okay. So I hope that you have found this lesson useful. If you found this episode useful and you're watching on YouTube, then please leave me a comment or like this episode. And if you haven't yet subscribed, then what are you doing? The lessons here are amazing.

Sophia Matveeva (21:31.858)
And if you are on Apple or on Spotify or any other podcast player, thank you very much for being with me, for having me in your ears. And if you haven't subscribed, come on, you got to do this. And I would really appreciate a rating and a review. So thank you very much for being with me and I shall be back in your delightful smiley tears next week. Ciao.