Never Stop Asking Why

Never Stop Asking Why When Designing Human-Centered Digital Transformation

Podcast Show Notes

When it comes to digital transformation, so many organizations are getting it wrong. They’re doing digital for digital’s sake, and they never stop to ask ‘Why?’ Only after fully understanding the ‘whys’ should organizations then build solutions rooted in human-centered digital experiences.

Join us for our second podcast with experience expert, Diane Magers, CCXP, Threadfin’s Experience Practice Lead (and well-known Founder and Chief Experience Officer at Experience Catalysts), as we discuss meaningful digital transformation. If you hear something that especially sparks your interest, contact us for deeper conversation tailored to your company’s needs. You can always find us at





Podcast Transcript

Intro (00:07):

Welcome to Experience Threading: The Podcast where we discuss human-centered, outcome-focused digital transformation. If you’ve ever wondered…How can we make it easier for people to get their work done? How can I move to the cloud and then stay in the cloud? What’s the best way to handle risk in this work anywhere world? Then we invite you to listen in for the tools, techniques, and best practices you need to overcome these challenges.

Sara Keeney (00:43):

I’m Sara Keeney at Threadfin. Joining me today is Diane Magers. Hey Diane, thanks for joining.

Diane Magers (00:51):

It’s good to be with you today. I am the experience advisor at Threadfin and I am super excited to talk a little bit about how digital transformation can actually take that next leap.

Sara Keeney (01:03):

Thanks, Diane. To get started, I want to just to be really clear when we’re talking about digital transformation, in terms of today’s conversation, digital transformation would be a process and a culture shift that uses technologies to create or modify business processes, culture and experience to meet changing needs. Now with successful digital transformations, there’s clear definitions, there’s clear targets for creating new value for the brand, for the customers and the employees as a result of the transformation. Correct?

Diane Magers (01:39):

Yes. <Laugh>, yes.

Sara Keeney (01:41):

Good. That was so official.

Diane Magers (01:42):

Yeah, I think any definition, I mean, if I ask 10 people the definition of digital transformation, they all tell me it’s something different. But I think that’s the power of digital transformation because it’s using the technology in a different way to optimize the business, to meet a certain need, and that certain need is customers or employees or the business. So when we think about why you’re doing digital transformation, it always comes back to humans. And I think that’s where people get a little lost sometimes in thinking about, well, we’re doing digital, as I call it, for digital sake, right? We’re going to digitize this, which is great. If it’s something you can automate, a form or you can bypass a bunch of manual steps, that’s awesome. But when you think about why you’re doing it and the benefit you’re going to get out of it, I think that’s what digital transformation is missing right now. The impact they’re having to the business, not just from cost savings, but also from productivity, from generating revenue, responding to customers quicker, giving customers ability to do digital. I think companies kind of miss that. They’re kind of doing the backend work, but they’re not really looking at the impact that it’s having as broadly as they should.

Sara Keeney (02:52):

That is very well said because digital transformation should be done in order to have a positive impact on the humans that are involved, whether they’re the customers or the employees. So with digital transformation, we’re really marrying technology and the experience of humans, making sure we meet those needs, and then that has an incredible impact on an organization.

Diane Magers (03:18):

That combination of those two things, digital kind of sits in the middle of those. It’s how you use that technology. It’s how you really bring what we’re learning, I mean, with generative AI and with all the things, the metaverse and all the things that are going to be happening. Remember when we were doing this all before and digital wasn’t a thing, we had technology and we had humans, and there was no way in between to really make that sync, make that relationship sync, and that’s where digital came into play and we said, oh, we can be more agile. This can be about the way that we work. It can really help us do things. So it was leveraging that, but you’re going to see it go into hyper speed pretty soon. And what I’m concerned about and what organizations should be thinking about is we don’t want that technology or digital or the metaverse or the things that we’re doing, even if it’s innovative, to overshadow the human and overshadow what those needs and expectations are and what we’re doing to really solve human problems, right?

Diane Magers (04:16):

Not just problems like solving cancer. I mean, there’s lots of things digital can be applied to, giving better care to patients, for example. But it can also solve a lot of other problems for how we get work done, how we work remotely. Think about how much we changed in working remotely. That was a culture shift, that was a digital shift. Those things that we have to do, that’s what digital really means. It’s being agile, but it’s being very much about how we do it to care for that person working remote. What are they going to be doing? How do they feel connected to the organization? What tools do we give them? How do we bring them in? So I love talking about these examples of how digital has really made a difference and always keeping in mind that the purpose of it is yes, the health of the brand, but it’s also about the health of the person.

Diane Magers (05:07):

And I don’t mean physical health, I mean the health of what we’re doing. What I find now is a lot more people are talking about this return to humanity. We think about digital and we think about all the things that it can do for us. And you know, great. You think about it today, things get so automated and it’s all proactive. It’s all taken care of for you. Well, what does that do in freeing up people’s times to create more poetry or solve world problems, you know, and have conversations and have deeper relationships. I look at it as, it’s a tool to help us really kind of cross over to that next era of humanity, if you want to say. I have these bigger dreams about where it can go and what it can do for us. But I think organization right now are just like, are we doing it? Did we do it right? Are we doing it right? And that’s where the Threadfin and the experience in digital come together in my mind. That’s why we’re huge proponents of how to do this differently.

Sara Keeney (06:06):

So we’re saying digital technology combined with the human element can be incredibly powerful. I mean, we can have more poetry in the world, <laugh>, but when we’re looking at digital technology, we’re looking at experience and the goal is digital transformation. What does that actually look like? What do leaders, whether they’re in the digital space or in the experience space, or just the CEO of an organization, what do they need to know about this? What do they need to be aware of? What do they need to start thinking about?

Diane Magers (06:37):

I think when they’ve undertaken digital or they put somebody in charge of digital, or they’re adopting digital, all those things we think about anytime you’re using the word transform, I think you have to define what that means. And we find a lot of organizations who haven’t really looked at it, they’re transforming digital by using technology and solving new problems. But what they’re not transforming is how the culture adopts the agility approach to digital. Digital is all about agility.

Diane Magers (07:09):

Digital is also about the culture of getting people to think differently, to work differently, to break those paradigms that organizations have had for sometimes hundreds of years in many instances. And to really think about how they use that on purpose and being intentional about it, that they’re considering everything that they do in the ecosystem of their company, the customer, the supplier, the partner, really the world in general. I mean, most organizations on the top of their charts is sustainability and giving back and global and, and purpose, right? Those things can be enabled by digital as well. So I think sometimes when we hear the word digital transformation, they only think about how we’re going to get the guts to work and they forget that it’s all about these other things that have to fall into place and change with this move to digital.

Sara Keeney (08:01):

Can you give me a couple of examples? Because I hear what you’re saying. When I initially thought digital transformation, when I was newer to this space, I thought, oh, it means we’re going to take our old phone system and put in a new modern phone system and that transforms something digitally, right? But this is really different. This is a lot like looking at the end result that we’re after and then working backwards to figure out how we choose and then implement and then train and continue to iterate on the digital solutions that we’ve selected. Give me a couple of examples to really help clarify what this looks like in the real world.

Diane Magers (08:40):

Well, I love the way that you started, because I think an example would, would be super helpful for people. Because they’re like, I don’t really get where you’re headed. You’re talking about all these really high level things and yet we’re really dealing with a lot of this change in the organization. I loved what you said about beginning and where you begin, because I think, I always think of Simon Sinek when I’m thinking about digital transformation. It’s why. Why are you doing it? Like if you don’t have an answer to that question and you don’t think about the multiple why’s. The way you think about if we’re going to do digital transformation, why are we doing it? Okay, we’re doing it to improve the performance of our company. Well, why are we doing that? Because we want to generate more business.

Diane Magers (09:24):

Well, why are we doing that? Because we know our product really helps. Product, service, app, whatever you want to say, can really help improve customers lives. Why do we want to do that? Because we know that’s a sustainable growth that will really drive attraction to our brand. I mean, think about the Googles and the Apples of the world, right? They know if they create something that serves a need and an expectation that they’re going to be ahead of the game. And the game is really about how they thrive as an organization. So you think about those companies and not only do the companies thrive, but their people thrive typically. And so it’s this why that you go back to and really start to understand what you’re trying to accomplish, and then begin to talk about how do we achieve that? It’s not only about digital transformation, it’s about understanding the culture and shifting the culture and helping the people in the organization see that digital while sometimes seems like a threat.

Diane Magers (10:20):

Like you’re taking my job. It’s part of it. Right? So I’ll leave that at the premise because one of the examples is if you think about a care center, I have seen so many care centers go from taking calls that really are just addressing the same issue over and over again. They’re answering the same question. Customers are having the same problem and they can’t find the information they need. So a digital transformation comes in and says, we’re going to identify the caller. We’re going to have this data. We’re going to proactively know, hey, for example, that maybe the service is going to be out for whatever we provide at a specific time. And we want to be proactive and notify the customer about that. Or shifting the knowledge base that a care team uses to understand that, hey, we have this customer who just onboarded or just got this new product.

Diane Magers (11:11):

How can we proactively reach out to them and feed them information in a way that’s at the rhythm that they need. You know and creating that content. So those things when you think about it, aren’t just technology. That’s why digital came got birthed, right? It was that technology being implemented wasn’t going to solve the problem. We had to add this human element to what does it allow us to do for the people that are in our organization, the people that are our customers of our brand. And once you figure that out, then the digital implementation becomes, we now know what our purpose is and we can move the technology and the transformation toward that goal. And I think that when we think about experience threading, that’s exactly what it is. It is starting with that human and what we’re really trying to accomplish and then saying, how do we do that? What are all the ways that we can do that using technology and using the shift and using agile thinking to get there.

Sara Keeney (12:10):

Right, because in the example that you just gave, we could start with two very simple things we want to solve for. We’ve got people whose phone time is not being used as efficiently as it could be because they’re answering the same thing over and over again. Those would be employees. And then you’ve got customers who need information and they need to get it quickly and concisely and accurately and in a timely fashion. And so from there you’re figuring out what do I need to do to solve for that? Now I want to go back just a second because you had mentioned when you said why, you asked why like five different times and you kept going and kept going and kept going. Is there any kind of guideline around that? I’ve heard something about maybe you ask why five times and you get to the root of what you’re after. What do you typically do?

Diane Magers (12:58):

I call it the two-year-old approach. Right? Because that’s what a kid does. I think why, why? And by this time you get to it, you start to realize you’ve never really had to explain it before. Like, you know, why do I have to tie my shoes mommy? Well, you <laugh> get to that point though, where you really have to think about what’s the right question we’re trying to answer. What’s the right solution we’re trying to find? And so there is a technique called the five whys. And that’s exactly why it works, right? Why-How laddering, there’s lots of insight techniques because it helps to get from why are we doing this? Why are we doing digital transformation? And then there can be multiple things that are flying into that. But if you don’t understand that, how do you really define success? And I, and I feel like when digital transformation started, people were kind of doing digital for digital sake, like I said, like automated…

Sara Keeney (13:51):

Right? It was fun. It was cool.

Diane Magers (13:52):

Yeah, which is great. It’s all fine. But now they’ve come back and said, well, we solved a lot of those problems. We kind of got the guts of our organization to really move. And we’ve done some things when covid hit, we had to move to different structures. And so those people who were thinking about digital transformations and the why and the how and looking toward the future, were able to make those moves when everybody else kind of lagged behind. And I think we’re going to see the same thing as we go into this probably down year, right? Nobody’s anticipating a great year, but it’s a down year. They think about what the new why’s are. Why do we exist now? What can we do for our customers? What can we do for our employees? Why should we be making investments in certain things today and not others? I think it’s this introspection that organizations are going to have and wisely spend where they’re going to get the biggest impact.

Sara Keeney (14:48):

So you’d never stopped asking why.

Diane Magers (14:49):


Diane Magers (14:52):

No because you’ll have multiple things you want to do. So today, if I were to ask a CEO, what are you going to do differently this year? And there’s probably four or five things at the top of his head or her head. And you think about, well that’s a lot of things, but how do you know that’s going to solve the problem? So you have to dig deep into that why of customers, employees, suppliers, a reason for the business to live, for example. And really get to the point where you understand what and why you’re doing each piece before you start to enable it with digital. It’s just a big gap for a lot of organizations. They see something and think, we’ll digitize that. And they don’t stop and think about the fact that, for example, if I’m calling in about my insurance policy, I want to talk to a person. I don’t want to have, you can put the quotes up there all day long, but I want to talk to somebody who can guide me through buying insurance and how do I optimize that? So there comes a time when you have to start with that why in order for you to really build that experience the way that it should be digital and human.

Sara Keeney (15:57):

When we’re asking these whys, who needs to be in the room or on the phone call when we’re having that discussion, when leaders are having that discussion, getting to the why’s, figuring out what it is that they need, who should be involved in that? I mean, do we want managers and above? What roles do we want to have engaged in those discussions? What would best benefit an organization?

Diane Magers (16:23):

Oh, if I could get a magic wand!

Sara Keeney (16:26):

Of course, imagine you could okay. Perfect world.

Diane Magers (16:27):

And honestly, typically when we are talking about creating great experiences, which if you haven’t heard it yet I’ve already repeated it four or five times, you have to start with the experience because that’s really what you’re trying to design. That’s the why you’re back to the human, back to the person. But ideally, what I see organizations do, and I think this is going out of style <laugh>, where the, the core team of C-Suite will make up something and say, this is what we’re going to do. This is our strategic plan. Great, wonderful. That’s worked for a long time. But what they’re not really uncovering is thinking about how do we bring customers in and ask, you know, and really understand what they’re after. How do we bring in employees from all levels of the organization? I mean, not everyone, I don’t want to discount it at all, but that really end to end and kind of top to bottom.

Diane Magers (17:21):

So the best example of that is thinking through just shifting or creating a new product. You have to have a way to understand why the customer’s going to buy it and consume it and use it. You’ve have to think about the data thats needed to do that. You’ve have to think about marketing and all the way down to care. You’ve have tothink about suppliers and supply chain. And how can you not have everybody in the room when you’re developing a product? Well, I think about the same thing when you think about a strategy. I know that the executives have the purview to be able to see things and they understand the way the organization operates. But many organizations now, we see employees contributing to where the organization’s going, getting ideas from what they see customers needs and wants are, and really building the organization more from what’s needed for the employees to serve the customer. Their viewpoint is, and the customer’s input rather than it being just thinking about here’s the goals for the organization and here’s what we think will get us there. So it’s this merging of all those things together.

Sara Keeney (18:27):

So a broad range of people involved in the discussion is really going to be the best way to go about this and get to the true why, and then start actually solving the potential problems or finding the potential things that could be improved. And then moving into that digital transformation more deeply.

Diane Magers (18:47):

And you know, I, I have a friend, a peer who was worked in an innovation lab in one company and he recently moved to a very static organization. And what he has defined and what we lovingly called design the business, what that means is you can use design thinking and thinking about the experiences and use the same technique. Like design starts with what are the needs and expectations? What do we think about that? How do we prototype things? How do we test them out? How do we be agile? How do we understand the impact that’s happening on the business? You can just design a product or service, but why wouldn’t you design the business at the same time and use the same principles, asking the why, really doing the work internally about what do all the employees think about the direction we’re headed and how can we understand all the great ideas that they have and value what they’re contributing to us. And then use that as a way to say, if that’s where everybody thinks we need to go, how will we get there? Which is where design starts to do discovery and the conceptual and kind of going out and coming back with a few ideas. I think that’s where we see a lot of organizations that work really well and are trying to figure out that new path forward, designing the business.

Sara Keeney (20:12):

So it can be really broad and also really focused depending on the need and what the organization’s trying to solve for and probably where they are in their maturity as a business, I would imagine.

Diane Magers (20:25):

Yes. When you think about the maturity of a business, if you ask executives what they want to be when they grow up, you know, it’s interesting to learn. I would ask anybody who’s listening to this to really think about your executives and if you are an executive, think about think about that why. Why you exist and what your goal looks like. What are you really trying to accomplish outside of the revenue and the cost savings? Like what is your goal and what is your goal for the organization, the way you want it to work. One of the things we find when people adopt experience as their lead, experience led customer centric, whatever you want to call it, they begin to have a different perspective of how the organization should work, what they need to be doing, how they need to be delivering that, bringing more information in from customers and employees because they understand if they don’t build for what the needs are, they’re not going to be around. And we’ve seen a lot of organizations leave.

Sara Keeney (21:26):

Absolutely. When you look at everything from the experience lens, it gives you a whole different point of view.

Diane Magers (21:32):

I can tell you I worked with an organization and they were just phenomenal. They wanted to become experience led. So that was kind of a mantra. We know that we need to take care of our customers and our employees, but they didn’t know how. We have this goal in our head, but what are the tactics and what do you actually do differently? And they committed all of their leaders and they brought leaders like from all different levels and they committed to come together. And one of the things that we did is we kind of mapped out, everybody’s kind of heard of journey mapping by now, but we mapped out really the whole ecosystem. We did kind of a customer journey, but we did workflows and processes and kind of end to end, top to bottom. And one of the things that they discovered was a lot of their issues by looking at it that way, were coming from just the onboarding.

Diane Magers (22:21):

Like their onboarding experience was not very good so they received all these other issues that were coming about because they weren’t onboarding the customer very well. And here they had been focusing all these efforts on these things when they really hadn’t figured out the root cause of what was going on. You didn’t tell the customers this, therefore they had a problem, therefore they called care and they bad mouthed you on the internet. Right? It’s this cascade of things. So mature organizations really move forward. They look upstream, I call it, for those things. And they explore all the things that are happening instead of focusing on 15 things, they’re really honed in on those things that can really make change and really answer the why question in a lot of instances.

Sara Keeney (23:12):

Well thanks so much for your time today, Diane. Enlightening and entertaining as always. I appreciate it so much.

Diane Magers (23:20):

Of course, my pleasure.

Sara Keeney (23:21):

We’ll talk again soon.

Outro (23:27):

Thanks for listening to Experience Threading: The Podcast. We invite you to leave a rating and a review on the platform you use to listen to this podcast. If you heard something that especially sparked your interest, contact us for a deeper conversation tailored to your needs. You can always find us at


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