Digital Wisdom™

The 3 Leadership Styles That Decide the Fate of Every Tech Project

• Richard White • Season 1 • Episode 3

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Why do 70–95% of digital transformations fail? 

In this episode of Digital Wisdom, Richard explores why leadership, not technology, is often the deciding factor in digital transformation success. Drawing from over 25 years of consulting experience, he unpacks how different leadership styles — visionary, structured, and empathetic — shape outcomes in complex tech projects.

Through real-world stories, he shows how missing even one leadership element can derail delivery, culture, and impact.

🟠 Book your complimentary 30-minute leadership coaching session with Richard  here 🟠


What You’ll Learn:

  • The three leadership styles every transformation needs: visionary, structured, and empathetic
  • Common pitfalls when one leadership style dominates
  • How to balance your natural tendencies with complementary team strengths
  • Practical ways to identify and fill leadership gaps before they cause failure

Whether you’re leading a digital transformation or steering a project team through change, this episode will help you build balanced leadership - so your next initiative doesn’t just deliver, but lasts.. 

🟠 Book your complimentary 30-minute leadership coaching session with Richard here 🟠

Gain clarity on your leadership style, uncover the gaps holding your projects back, and walk away with practical steps to strengthen your impact.


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About the show: 

Digital Wisdom is the podcast for leaders driving complex digital transformations — and determined to get it right. Hosted by Richard White, a trusted advisor to billion-dollar businesses and CEO at 365 Inhouse. Each episode unpacks proven strategies, hard-earned lessons, and real-world insights from the front lines of enterprise technology. If you're navigating chaos, aligning systems, or scaling with purpose, this is your blueprint for clarity, momentum, and results.

Richard White:

According to the likes of Forbes, KPMG, Boston Consulting Group and Bain Company, digital transformations foul between 70 to 95% to meet their objectives. And in my experience, leadership is the biggest determining factor. Now, whether you are a business owner, an executive, A CEO, a director or manager, the good thing is we don't need to be amazing leaders. It's about drawing on the strengths of the team and understanding our own weaknesses in order to be successful, to make sure that we do our projects on time, on budget, delivering what was promised and leaving our reputation stronger than before. I've also seen the other side though, where projects struggle, derail, turn up late, go over budget, and teams just lose trust and faith. And it's heartbreaking because it's often not about the technology. In fact, I often say technology in tech projects is only 10%. The other 90% is everything else, and leadership is a huge part of that. It happens to also be a big passion of mine. I've been a consultant for 25 years plus in tech projects. And in fact, my biggest passions are tech, business and people. So this kind of, for me, comes right in the center of all of that, I've spent a lot of time analyzing books, self-analysis, a lot of self-exploration, and working with leaders on multiple large scale projects. To see how we show up in projects impact the success of those projects, and I genuinely care about delivery a little bit too much. Sometimes a weakness is mine is I, I find it hard to separate work from, from home life, as my wife would attest, but fortunately, she's very forgiving. and for me over the years, I've generally been able to categorize leadership styles into one of three different areas. One is the visionary leader. Two is the structured leader and three is the empathetic leader. Now, of course, we are all complex human beings and there's probably a lot more than that, and I don't mean to simplify it. there's probably frameworks that could mention other aspects as well. But for me, I found all of these three have to show up in projects. In order to ensure they're successful and broadly, people will fit either into one, two, or more of those categories. And in fact, here's the truth, we don't have to be as leaders, we don't have to have all three of those styles to be successful. But the truth is we do have to have. All of those styles in a project for it to be successful. Therefore, it's about understanding as leaders, what are our weak points and what areas do we need to draw in from other people to be able to compensate for those. Now the structure of this episode is I would like to talk through each one of those styles starting off by giving a bit of an intro and an outline to the style questions to help self-identify. But then also telling a story from my own experience, a real life example of someone. And I'll change the names and the details so that it is not so obvious. Uh, 'cause of course I care about confidentiality and even if we work together, I don't want you to feel, oh, am I gonna appear on a podcast with Richard sometime in the future? No. so I'll cover up the details, and then I'll provide a summary wrap up to each of those styles, and then I want to just add a few questions, common questions and answers that I get asked usually when we are talking about these kind of leadership styles. So let's start off then with the visionary leader. So visionary leaders, they're big picture thinkers. They build solid directions. They're inspirational. They see possibilities where other people can't, and actually they're infectious to be around. But vision without structure or empathy can often overwhelm teams, and sometimes those visions foul to land with the team. Now, how can we self-identify? So are you excited by big goals and new ideas? Do people describe you as inspiring, but sometimes may be hard to pin down? And do you get frustrated when other people don't necessarily see the vision that you have? Now, the story I would like to share with you is one. Let's call him John. He was a senior director of one of my clients, a fantastic visionary. His aspirations were so high, he was inspiring. he could see the industry from a very blue sky thinking it was inspiring to be around and he could talk for hours and he could go into a huge amount of detail. And one thing He was good at was talking through the entire customer journey. Now I wanna spend a little bit of time talking about a customer journey because it fits in really well with this visionary style, but as you'll see, it becomes applicable as we start to go through this episode. So a customer journey is essentially an end-to-end entire process of your business and how customers interact through the various different stages of the business. It includes different client personas 'cause often we do deal with different personas. But it also has the touch points. Starting from the very point of awareness of where they first hear about your company or your organization through to then how do they consider working with your organization, or taking on your services, the decision points they go through. Then becoming a client through to retention and then through to advocacy. Literally, we know everything and we start to look at how do we want that person to fill or those people to fill through every one of those different touch points. So it gives us a really good view of the organization and the customer journey. But, the result of that is we also see what are our true aspirations. Then we can start to see, okay, so how can we now get tech to match at those various different points? So I often have conversations, and one of my biggest conversations with people is that they usually start off saying, I need this piece of tech. Let's say it's a CRM system, or an ERP system could be anything. In fact, I've got a call the other day just from someone who was saying, I want to make the most of ai. How can I do that? And often it's about stopping and saying, okay, let's take a little bit of a step back. Do we know what our customer journey is right now? Because once we know that customer journey, we know exactly the points that we could bring the technology in and how it could make an impact to make sure that we bring that customer journey to life. someone may pick for example, an ERP system and go for that. But then later on they realize, oh no, we need a CRM system. And then they bring it on and then they think, okay, how is that now gonna map to my ERP system? But if we had that full customer journey, we would know what we would need that would allow us to start to look at, okay, so. is there one system that can allow us to do the CRM and the ERP together, for example? So the customer journey is a massive part of what we usually advocate for, and it's a huge part of bringing a vision, a visionary leaders vision to life. but the thing is, when structure is not incorporated within that vision, then. What happens is that people start to become lost and frustrated and the visionary leader starts to get lost and frustrated because how do we then start to move people from A to B? How do we start to get there and prioritization starts to get lost. So the structure is, really needed empathy as well, because. Everyone has their day jobs, right? And sometimes people may not care so much about that vision because they need to be taken on a change management journey. So what is actually in it for them? What is a benefit for them to be able to get them to care as much, to be able to change then, or give up some of their day to day, in order to put towards making that vision come to life. So what we did with John is that we started to document that entire customer journey, got everyone involved, so they felt a part of the process. We started to break that customer journey down into high level components. We then started to do costings and time boxes and understand, how it would all come together. We then set a realistic roadmap of how that would all play out tied with budgets and resources, and we incorporated change management aspects to help everyone see their own part in that journey, the benefits to them, and how will they manage their time with bringing that vision to life. so what, so what happened in this instance is that John, the visionary leader, started to see. The reality of the vision and actually how long it would take and what would be needed. So actually his vision started to get tempered. Now it is not that, that vision obviously wasn't applicable because it is, you need to have that vision and the blue sky thinking, but then we need to bring it down to a realistic level and temper it and make it a bit more realistic. So he became a little bit more realistic. People started to get aligned. Work was focused, the progress actually started. Toge begin, and that company did start to change their industry one component at a time. It was quite incredible to see and witness. So in summary, vision is powerful, but vision without structure or empathy is just a dream. If you bring three of those together, though visionaries are unstoppable, but let's now look at a structured leader. So a structured leader, all about foundations. They plan, they organize, they prioritize, they look at systems, they look at efficiencies, and they give teams clarity and security. But. Structure without vision or empathy can just start to feel like bureaucracy. Just red tape. So let's look at a bit of self identification. Do you naturally create processes, frameworks, and order? Do you like, do you feel comfortable in plans and roles, knowing who has different roles and how they're structured? Do you struggle sometimes to inspire change? And do you sometimes get caught so much in the weeds that it's often hard to come back up and Take a look at the bigger picture. Now again, you could start to be saying, actually, I do identify with parts of vision, parts of structure, but that would just help identify those aspects of you that could be the structured part. So in terms of the story, the real life story, and again in this example, let's call her Jane. She was a C-Suite executive of one of my clients that I worked very closely with. Now, Jane was incredibly structured. She had process after process, lots of processes. All of them were documented, and everyone knew what their part in the process was. The missing aspects is that there was no real vision, so there was no customer journey in place, and it felt like to some degree, that people were running around like headless chicken chasing their tails because there was that lack of vision. There was lots of competing technology decisions were being made very quickly and not tied to a vision. So, of course there was lots of rework because a decision was being made, progress was being made towards that. And then we realized, oh, actually no, we wanted to go in a different direction because it wasn't tied to a vision. So therefore, let's rework that and we'll go off in this direction. So lots of processes, but actually not the right ones. And in terms of empathy. There was actually so much internal frustrations of people not feeling heard because people could feel and see that whilst the structure was there, it wasn't necessarily the right ones. And sometimes they were doing a lot of overwork and working late because they were following these processes. There was a lot of frustration and they were fed up with change being the wrong change and, and a feeling that it was overly engineered. So what we did is we started off having just open conversations to draw out the views, and if I'm very honest, that was one of my most heartbreaking projects that I've worked on. Because to hear those kind of views and to hear the level of frustration, it was quite heartbreaking. But it had to all come out in the open in order to then start to move towards aligning everyone. So that everyone can feel like they had a voice and we started to move in that direction. And again, we created a customer journey. We took time. To rebuild, to start to understand what are those various different components as I mentioned before, what's the costings, the resources that's required, the time boxes. Let's place that now into a roadmap. Let's set structures to help make sure we can get there. And as a result, some great vision work was done and accepted throughout the organization. So some solid foundations were set. They nailed the structure going forward. I wish I could say that was a happy ending, but it wasn't. Sadly. In this instance, the empathy wasn't truly embedded. So decisions continued to be made based around speed, cutting corners, saving money and missing how decisions were landing with the teams. And in the end it showed. The plans looked great, but the team unfortunately weren't on board. So it's just a reminder that empathy is not a soft skill. It has to be incorporated with structure and with empathy, because essentially structure and vision without empathy means it's just not reality. So in summary, structure is essential. Can't run projects without structure, but structure without vision and empathy is just dead weight, red tape bureaucracy. So all three means that structure becomes the scaffolding to true digital transformation. So let's look at the empathetic leader. Empathetic leaders always put people first. They listen, they connect, they make other people feel heard, and they build trust very quickly. They're great people to be around. The thing is empathy without vision or structure. Often just translates to stress competing priorities and projects that just stall Now, empaths usually know that they're empaths. So you probably already know if you are an empath or not, but are you a great listener and a supporter? Do you build trust very quickly, but actually get caught between competeing visions from different people? Are you a people pleaser? Now, I know this because I'm a bit of an empath, so I know I'm a bit of a people pleaser. I've tried to work on this over the years. And trying to keep everyone happy. So in terms of the real world example, let's call my example Jim. Jim was a project manager. Now Jim was incredibly empathetic and he was given the entire project, and realistically, he was given the role of being the visionary and the structured leader as well as the empath. But he had empathy in abundance. He was very approachable. His team felt heard, and everyone felt involved. What was missing was a vision. So there was too many competing visions from others because he was listening to the various different opinions of others, and often they were competing. Visions and plans were constantly in flux as a result of that, and teams had to down tools to change their focus very quickly. When there was a new direction being set. So it's very hard for them to stay on board as well. So structure was also missing because it felt like red tape and because it felt like red tape, there was resistance. So naturally for people pleasers, it's hard to push against that resistance, and therefore there was not a lot of structure put in place. And as a result of that, just like vision structure can change very quickly. So what did we do now? We started off again, you'll hear me talking about this a lot. It's one of my big favorite things. We did a customer journey. Let's map out what that vision is for that organization. We involved everyone. We started to prioritize together as well as a team. 'cause what I find is if we get everyone together as a team and we start to talk about those priorities together, then actually what starts to happen is people will intuitively know what's more of a priority than others. Even if it's their own, they would realize where it actually comes down on the order. So they would likely give up some of their priorities 'cause they can see that others actually in the organization need it more. We set direction for the year, so we set a roadmap based on what came out of the customer journey mapping. What we did in this organization is that we then installed an executive to act as the visionary leader, the one that would own that customer journey and own the roadmap. So that took it out of the place of Jim because actually if he wasn't naturally good at it, you bring in someone that is to incorporate those skills into the team. We set up structures, we set up governance frameworks. In fact, if you have a look at the blog on our website, we talk about 10 different governance, structures to put in place that can really help create good foundations for any project. So we installed some of those, but then we also installed an executive to act as that framework owner. Again, so this is now the structure and we are now pulling someone in that is really good at that structure and can then help take that away from Jim to make sure that they maintain the governance and then Jim can get on with what he's actually really good at. The results of that is that built a really strong team. Jim was able to work to his strength. He was able to manage the project, adhere to the standards that have been set up. He was able to listen and bring everyone on board. Now, in this instance, we didn't set up any change management capacities because he was so good at it himself. So the whole business started to be aligned. Great foundations were set. Everyone was aligned, people were working to their strengths. There was a sense of shared ownership, everything, and everyone was working like clockwork. So in summary, empathy is a true superpower, but empathy without vision or structure is actually just like having a spreadsheet with no data. It has no meaning. 'cause realistically people wear everything in tech projects. We've looked at now all three of the styles. So which style do you feel you are? Now again, you could go broadly across one or more of those styles. In fact, I unusually sit within all three. And honestly, it's probably why I do what I do. I love driving through vision. I'm absolutely obsessed by structure and I have quite a deep sense of empathy. But having all three doesn't make anyone any better. In fact. Much better leaders than me aren't all three. They just know their own strengths, their own weaknesses, and they know how to bring people on board in order to be able to compensate for those weaknesses and make the team flourish. And it's really about staying conscious is to which part is needed in any moment. Sometimes the visionary leader is needed. Sometimes it's the structure, sometimes it's the empathy. In fact, just a side note, I remember one of my clients that I went into, I went in as a COM manager and they had, it was literally the perfect vision structure that I've ever seen. The system was almost impeccably managed. I was so impressed. Yet as I started to talk to people, I started to hear that actually. People really weren't happy from various different departments. And the more I sat with them, the more I started to realize it's just because they wasn't involved in the process and they needed to be brought on board. So at that moment, it was the empathetic leader that was needed. So it's just trying to understand at what moment. Which is needed, but all three of them are needed. That's the thing. Once we have all three of those roles filled, whether it's by one leader, by two, or by three, that's when projects succeed. It's when you take one of those out that the project starts to fail. So let's look at some common questions that I have coming up over the years when I talk about these various different leadership styles. So can one person realistically develop all three styles, or is it better to build a team that balances them? Now? I think this is an important question because for me personally, whilst you can go out and build or learn those skills, actually I think it's probably better just to understand what is my weaknesses, what are my strengths? Let me play to my strengths and let me bring in people to help. compensate for my weaknesses, you know, 'cause often as leaders we can often feel to ourselves, I don't necessarily trust to hand over this to someone else, but I actually recently brought someone on board, on my team to take over for me, on a very large project. and actually they've done way better than me. They were brilliant. It made it so easy to just start to hand over. So. I'd say just trust the team and to trust the strengths that we can bring in. 'cause ultimately, we are better when we're working in a team with multiple different skill sets and trusting those people. Another question, how can structured leaders avoid becoming too rigid? I think this is a great question because in some projects You need to have huge amounts of structure and it works well for those organizations. But then if you was to pick up that same structure and put it into another organization, it doesn't necessarily translate. And actually for them, it could just feel a bit too much like red tape. So it's actually about taking a step back, reading the room. I, I have one example where. I went into one organization. They're a huge organization, a billion pound company. So in my mind I'm thinking billion pound companies usually like to have a lot of structure, but actually this one doesn't. And I can kind of sense that. So what I try to do is to say, okay, here's a structure that I think could work with well for you. Here's the reasons why I think it could work well. Here's the downside, you know, here's the process of setting out. What do you think? Would you like to have that? Would you like to give it a go? Some they've accepted and they've worked really well, but others they've resisted and actually that's fine. And I think as leaders. Especially within large scale tech projects, and especially if we get used to certain structures, knowing that they work really well, but it doesn't necessarily work for someone else. It's about readily being able to step back, be flexible, allow it to unfold and actually see what happens. It also has actually started to work really well, that even though they don't have the structures, that would work for other organizations, it actually works fine for them not having it. So I think it's just about being flexible and not becoming too rigid. Another question, what happens when the wrong person is leading a transformation? In truth, it can be devastating. Right? And sometimes, you know, I think that's why 70 to 95% fail. And it's why I think the biggest reason is leadership. And in fact, this isn't just me saying this or my experience. So I travel around to conferences as many of us do, to conferences all around the world. And I. Started to ask other speakers in forums, what do you think is the reason why 70 to 95% foul and unanimously the answer came back leadership. And one of the biggest issues that I, I see is when it is given ownership and leadership of a tech project, it feels logical, right? To give an IT project to the IT team. And it is not always the case, but it's often wrong to give it to them. And again. I'm not saying that against every IT director and IT team because I've also seen some very successful, projects being led by it. The reason why I say that is it should be about frameworks signing off management, not system ownership or leadership. Because often, especially when we're talking about business critical systems like A CRM, because they're often about people and about processes, and it often lead it with a technical mindset, whereas what is actually needed is a business mindset. Now, again, here's where we talk about those different leadership styles, because often IT leaders. Tend to be a bit more towards the structured leaders, but it could also be that it could be a combination of both. If you bring in the business leaders shared with the IT leaders, you could then potentially bring in the vision and the empathy. So because a business mindset is needed or an em, certainly an empathetic leader is needed to connect the tech with the business outcomes. So one final question is if a transformation has already gone off track, what's the first step to rebalancing leadership and rebuilding momentum? And I would say honestly, it's having an honest, hard look at ourselves and each one of those three styles, who is leading it and which ones are we lacking? Are we lacking a vision? Are we lacking a customer journey, a roadmap? Are we lacking some structure in place or are we lacking some empathy? And usually you can feel the empathy side because people just aren't on board. They're not happy. Sadly, there's no quick fix. However, it is almost like if you had a tree that had some kind of illness and to treat that tree, the best approach wouldn't be to treat the leaves. If you did, I mean, you'd fix maybe some of fewer of the leaves, but it would just quickly come back again when we actually come down. To the roots and we treat the roots. that's essentially the effect when we are looking at the customer journeys, the roadmaps, the structures that we are putting in place, and the change management or the empathetic sides of what we're incorporating within these tech projects. Those are the things, the core elements that start to completely change the entire path of the tech project. So it's like we are treating the roots of the tree. As opposed to, uh, the leaves. And it does start to have quite major impact when we do look at those aspects. So I absolutely love working in this area. I love helping leaders lead. I like helping leaders find their natural zone of genius whilst helping to close the gaps that could potentially make them fail. and from my experience, these large scale tech projects are not luck. And it's why at Digital Wisdom, we offer our right first time commitment. Because for me, if you have all the right aspects in place, it's like one plus one equals two, you will be successful. But it's what, knowing what all of those variables are. Otherwise, it's just like algebra A plus B equals C, so we can figure this out together. So if this does resonate with you, I'd love to talk to you. I am offering a free 30 minute consultation where we'll look at your leadership style and any gaps that may be holding you back. Absolutely no pressure, just a safe space to reflect and explore. The link will be in the show notes, or you can go to Digital Wisdom Group slash leadership. Remember, digital wisdom is not about tech. It's about the people and the leaders who have the courage to grow. Thank you.

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Richard White

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