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Your Questions Answered: “Ask Me Anything” Part 1

AI uncertainty, DX self-assessment, human-centered design, and the "Lightning Round"

Thank you for your questions on digital transformation, submitted as part of my first ever “Ask Me Anything” edition of David Rogers on Digital.

They sparked a lively 1-hour conversation, and I’m delighted to share the first half with you today, in Part 1.

(Part 2 will follow in a couple weeks, after more articles!)

A big “thank you” to my friend Clark Boyd, who pitched me your questions and acted as my foil and interlocutor.

Your Questions (Part 1):

Major topics

  • [02:53] “What do you recommend for a self-assessment before starting a digital transformation?”

  • [09:12] “How to cope with uncertainty around AI and the future? How open should we be with employees about what we don’t know?”

  • [19:38] “What are your thoughts on using human centered design as a foundation for digital transformations?”

Lightning round

  • [26:20] “Will you have a course on this new book?”

  • [27:45] “How would you recommend adopting an overall vision statement?”

  • [28:39] “What are the common pitfalls in digital transformation?”

**

Enjoy!

Click to watch the video above ☝…

…and read the transcript below. 👇

And please let me know in the comments if you’d like to see another edition of “Ask Me Anything” later in 2024!

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Transcript:

[00:00:00] David Rogers: Welcome to a special Ask Me Anything edition of David Rogers on Digital. This special edition gives us a chance to answer some of the many questions posed by readers in the last year. I'm delighted to be joined today by my friend Clark Boyd. Clark, welcome.

[00:00:19] Clark Boyd: Thanks so much, David. Delighted to be here.

[00:00:22] David Rogers: Clark has taught for several years in my online programs, taught with me for my programs for Columbia Business School online.

[00:00:29] We've also worked together on client projects for the David Rogers Group, where he's helped deliver workshops for companies accelerating their digital innovation in some exciting Asian markets. Clark is long experienced as a marketing practitioner, spent years practicing, also speaking and teaching principles of digital marketing, not just in my classes.

[00:00:54] But most recently what's really fun is, Clark is now the CEO and co-founder of a very interesting startup, called Novela. They've built an amazing tool for really learning and then testing and applying your strategy for digital advertising campaigns by using an AI and data-driven environment where you can actually run simulations and test out your actual marketing strategies and campaign strategies without spending the money yet, but getting really incredible feedback and testing and learning and then apply those decisions as you start to then put them into the actual campaigns you're running and run them side by side. So, their flagship simulations focus, at this point so far, on Google ads and on Meta ads. They're building out a lot of new products. They've had a phenomenal response in the classroom from my students. I've actually been using this as a tool in my online digital marketing class for Columbia Business School, as have some other leading universities around the world, which will go unnamed.

[00:02:00] Anyway, Novela is also now starting to work directly with enterprises and midsize businesses, basically where digital advertising is critical to their growth. So again, it's called Novela, very cool startup, very interesting to see them on that early stage, where you've got an incredible first product, but lots more to build and everything is about staying close to the customer and figuring out which problem you want to solve next, so, very cool. Great background that I think will give Clark a lot of insight into the perspective on the conversations we're going to be having today.

[00:02:34] So, Clark. Thank you for joining us. And you know, you're the interlocutor. So let me hand the microphone to you.

[00:02:42] Clark Boyd: Left a little speechless by that introduction, very gracious, thank you very much, David, and hi, everyone. It's great to be with you today. What we're going to do is work through the questions that have been submitted.

[00:02:53] I'll take a few along the way in the Q and A if they pop up, but we'll look mainly at the ones that we've prepared for already. We'll do some big topics and then some lightning round, quick fire questions as well, just to mix up the pace. So, our first section is about self-assessment for a digital transformation, and we had a wonderful question from Alice here, who asks,

"In order to transform, I understand we need to know where we are now to know how or where we can transform. How would you recommend assessing this? I'm looking at specific processes and workflows. What else would you recommend we do?"

[00:03:33] David Rogers: So how do we assess our current state as we're embarking, or maybe refocusing a digital transformation effort? Thanks for the question, Alice. First thing I'll point to is this idea that I write about in my latest book, The Digital Transformation Roadmap, about a shared vision. And that is really supposed to answer two key parts of what Alice is asking about. Part of the shared vision is spelling out, "Where are we?" "Where are we now?" And that's the future landscape, which is going to look at what's happening in terms of your customers' evolving needs and expectations, what's happening with your competition, what technologies are entering, new business models being tested in your particular space, all these factors that are driving change and shifting your market positioning.

[00:04:23] Also, your right to win is very much a part of, "Where are we?"

[00:04:28] What are our unique advantages? This is a topic I've been writing about recently in David Rogers on Digital, and also what are your strategic constraints? This is something that companies often overlook is really assessing what are the red lines, what are the things we won't do? By choice, or maybe we can't do, because of external constraints, things like existing contracts with our suppliers or partners that prohibit us from pursuing a certain distribution channel, or our legal structure that prevents us from taking a very centralized approach to something or, regulation, of course.

[00:05:04] So, again, the shared vision is partly about really getting that clarity of where we are now, but it's also about, “Where are we going next?” And that's what the North Star impact is about, what's the impact of trying to achieve, and also the business theory—what's our theory for how making investments in digital transformation is going to pay off.

[00:05:21] So that's one part of self-assessment. But Alice also touches on some other things. She talks about looking at our specific processes, our workflows, et cetera. So, this is, I think, a bit of getting a little more broadly into a diagnostic of where we are as an organization.

[00:05:41] What are our strengths and what are our weaknesses? This is very important when I'm advising companies, it's one of the things we try to do early on. As a first cut at that, I would suggest in the book, here, just pull it up here. You'll notice in the back, that's why I put these in the appendix, there's a self-assessment, a tool, there's an introduction on how to use it, and then a battery of questions that you would use for various people. Basically, you want to get input from a variety of people anonymously in the organization so that you can surface, what are some issues out there? What are strengths? What are relative strengths and weaknesses? You probably want to pair that with some qualitative interviews as well. But the quantitative will start to point you in some directions. So, I think that upfront focus is also, I have found, that diagnostic to be helpful. Really trying to identify what are our strengths and weaknesses in terms of organizational culture mindset behaviors and then also process blockers.

[00:06:45] What are the things we're better at? What are the things we tend to have trouble with in terms of whether it's allocating resources or empowering teams to move quickly or dealing with technical debt or these various things, accessibility to data, etc.

[00:07:03] The last point I would make is, as you're doing this self-assessment, you're starting to get a sense of the things that need more work and are going to really need to change the most in your organization. Do not try to fix everything all at once. The bigger the organization is, I find this, and maybe also to a degree, the older, but really size, the more this seems to be the instinct.

[00:07:27] It's okay, we understand there's all these problems and they're systematically intertwined and it's, if we're really going to, solve it, we've got to fix things on lots of fronts, so let's do a long planning process and then do a big reorganization, shake everything up and redraw the org chart and so forth, and that tends to be very unsuccessful. So instead, you want to take an iterative approach to changing the organization, just like we take an iterative approach to innovating new products and services, so that's why I advocate, always think of these, I call them the Five Steps of the Roadmap, and one flows into the next, but try to go through all five steps in 90 days. You want to start learning as quickly as you can and see what you learn by doing. It's really about learning by doing, not a lot of upfront planning process.

[00:08:22] Clark Boyd: Yeah, and I think that the benefit of people actually feeling a bit of change rather than six months of planning and thinking about it and then announcing it as a massive thing that's going to happen. And then if nothing happens in the immediate future, I've seen a lot of times where people lose faith that the plan is even going to work.

[00:08:40] So having a constant sense of the change happening and there's progress, even small. It gives a sense that, okay, we're moving in the right direction and there's momentum building here rather than waiting for the big bang. And yeah, it rarely happens.

[00:08:54] David Rogers: You set up an overly high expectation or over promising implicitly, and you also give a bigger window for the critics or the naysayers or the doubters to be, while you're waiting for months and months, this isn't going to work, or here's why I didn't think it was going to work, et cetera.

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[00:09:12] Clark Boyd: Absolutely. Tying into that, our second theme is about coping with an uncertain future, and we'll blend or at least bridge two questions here. Our first question is from Kamal and the second one is from Alice. So, the first question is,

“How do you take care of the insecurity that arises from digital transformation?”

[00:09:33] And building on that, Alice's question is from a communication to staff perspective.

“Is it an issue if we don't know yet what the future will bring, for example, in the AI space? I know it will be beneficial for us, but I don't yet know exactly how. Should we be open that we don't yet have the concrete description of future AI solutions, but we're keen to investigate and would appreciate input from staff?”

[00:10:00] David Rogers: I love these two questions. The big picture framing by Kamal and then some of this nuance and specifics, given by Alice about, how do we communicate with staff? What do we say to them about, our thinking on AI and our particular organization, et cetera. Let's start with the big picture.

[00:10:21] So how do we deal with the insecurity, as Kamal put it, or I would say the uncertainty, of digital transformation. You're dealing with a tremendous amount of change. You're dealing with, in some cases, technologies like the latest wave of AI, large language models and, transformer based, visual, that are, moving very quickly right now.

[00:10:45] Many factors you may be facing that add tremendous uncertainty to really what's going to work, what's your path forward, et cetera. And. You need to go in with that fully in mind. I've written in one of the newsletter articles about what I call The Perils of Planning, and the point here is what you don't want to do is to go in with a long planning process upfront where you have this false distinction of your plan and then you execute.

[00:11:17] This is one of the biggest reasons why I always push back against the framing of strategy and execution as like a dichotomy or a sequence. there's strategy, but then can you execute? Those have to be linked. Everyone, the only way you execute is by constantly working on the strategy. And so, planning can't be this thing that gets done as a stage and then you go out and do the transformation that incredibly amplifies the risks of digital transformation. That puts you at huge risk of the insecurity and the uncertainty creating very costly mistakes. In fact, it's practically guaranteed. So instead we need to assume that there are tremendous uncertainties and take a very different approach to moving forward and taking an iterative and experiment driven approach as I advocate trying to create tools and processes to do this So to Alice's question, first of all, what about talking to the staff?

[00:12:20] Should we be honest and tell them, yeah, we actually don't know. We've got a good feeling that AI for our particular business model and our business industry, whether we're talking about, predictive models or whether we're talking about these new generative models, that we think one or more of these is, going to have a real positive impact, but we really don't know how or what it's going to look like.

[00:12:41] Yes. Absolutely be open, be honest. This is a really important leadership trait that is undervalued. One of the leaders I always think about this is Dean Baquet, who helped lead the New York Times through the really critical years of their digital transformation. He was leading on the editorial side of the business and while they were trying all sorts of things,

[00:13:07] he would talk about, frankly, this is a quote. We do not know what the future of journalism is going to be. We just try stuff. We throw things at the wall, so to speak. We try things. We make mistakes. We take risks. We screw up, but we find out what works. I didn't know that podcasting was going to become such a huge part of their business and how they engage their broader, particularly their non-subscriber top of funnel for their subscription model, but non-subscriber audience that brings them in.

[00:13:38] They didn't know, they just tried some stuff and some of it worked and some of it didn't. It's really important if you want to encourage people to take a smart experiment-driven approach where you're very metrics-driven and you're thoughtful and you define hypotheses and you test you keep learning and you don't waste resources.

[00:13:57] One of the most important mindset things is you have to model humility and say, look, I'm the CEO. I'm the top wherever I am. I'm in a leadership position. I don't know the future, right? That's not the point here. I was talking with a brilliant, a coach of startups in Silicon Valley yesterday about product management.

[00:14:15] And she said, yeah, big enterprises think that their job is to find the right answer. In the thinking of product management, that's not the point. You're not trying to find the right answer. You're trying to find something better than what you're doing now that you can measurably, measurably, test and say, oh, yeah, that's improving a business outcome, right?

[00:14:35] It's a very different framing and it's less ambitious and hubristic. understand that planning, your vision, your strategy, these are all in process. It's fine to have a plan. As long as you know that it is contingent, it is. Has it's marked by uncertainty and that you're going to keep changing it to evolve as you go.

[00:15:01] And the more that you are trying things, maybe if you are Alice using some of the newest, again, there are some very powerful AI machine learning models that are now several years old and have a lot of practice, maybe in a different industry than yours. And there's a lot of evidence of how to best apply them, some use cases.

[00:15:20] And then of course, there's these new tools that are good at some things and terrible at others but are moving incredibly fast. So, the more you have, the more technical uncertainty, maybe more market uncertainty. Perhaps you're trying something to serve a new customer you’ve never served before. You really don't know them very well.

[00:15:37] The more uncertainty there is, the more you want to manage this as an experiment. And that's what I talk about in particular in the book. On the subject of generative AI, I wrote an article at the end of last year called chat GPT is not a strategy. that's the headline, but the, heart of the articles are actually talking about a process for how do you take when something is very in uncertain early stages and you really understand the main thing here is we want to experiment and test and find what's A useful solution or a useful application of this new technology to our particular business taking very much not only is an experiment driven approach, but exact exactly.

[00:16:18] She said, tell the staff you would appreciate their input. You want to create a mechanism, which is all about, here's some business goals very broadly, but even at this stage, you say, look, we're not maybe trying to make a big business. lift on a KPI in the next 6 months, we want to figure out the most effective.

[00:16:36] Or the biggest opportunities to introduce into certain workflows or certain parts of our business, these new technologies, we want you to experiment, give people a process to propose an experiment, not just go run wild and do your thing, sign up, submit a problem to solve. We'll give you some guidelines.

[00:16:55] a bit of oversight, a little bit of resources. You're going to experiment for a bit on a defined problem with a defined metric of success, and you're going to report back what you learned. And we're going to have a lot of people doing this. You really want to engage the staff. You want to engage people at different parts of the organization.

[00:17:13] That's going to really accelerate how quickly you can move forward in this, highly uncertain, but exciting new space.

[00:17:22] Clark Boyd: Yeah, and you mentioned something that I think is a huge shift and a very difficult one actually for a lot of people is that shift from the pressure perhaps self-imposed to know where things are headed and how things are going to go. And I think when in a leadership position, all the studies would say that certainty is persuasive. If you need to bring people with you, if you're certain about where things are going, that could be very compelling to people. It's just not so compelling if you turn out to be wrong, of course.

[00:17:54] So you've got to balance.

[00:17:56] David Rogers: It can be an easy crutch, right? And I think really effective leaders express uncertainty about everything. But they are clear about picking a few things that they say here. The things we really know. Two examples, Baquet and the Times, they were very clear on the mission.

[00:18:16] They said, we're very clear. We've learned enough in the early years of the internet that the economics of content are changed forever. And we're not going back to the 20th century model of an advertising-led business model. So, it's like they were very clear of the business model challenge that was known, at Amazon, they always said, the fundamentals our customers will always want.

[00:18:41] a, a better price and more, selection and quicker deli and quicker, more convenient delivery. I think it was like two or three things they said, we know that's not gonna change. That's not like a tech trend. so that's, so know what are the things that you and as a leader communicate that and say, this is really clear what we're trying to do.

[00:19:01] And then you can be honest about saying, how are we using chat GPT or, what's the right geographic expansion strategy for our financial services firm or something and say, that's what we're going to be testing this year and exploring and learning. I think you're right. It's got to be a balance in terms of communication.

[00:19:23] Clark Boyd: Yeah, I don't think that's what we're trying to achieve is the certainty and the how we're going to get there is well, we live in an uncertain world. We're going to experiment and. We'll figure that out, but at least we know where we're going. That's the persuasive thing for people. Our next one is a question from Ben Childers and it's about human centered design in digital transformation.

[00:19:45]

“What are your thoughts on using the principles of human centered design? So, root cause analysis and systems thinking, iteration, and end user focus—as a foundation for successful digital transformations.”

[00:19:59] David Rogers: Great. Thank you, Ben. So great question. So I, over the years, have learned a lot from some amazing thinkers and writers in business, both in the academic and the purely practitioner world.

[00:20:16] And for the streams of thought that I kept coming back to that seemed very relevant to, I think, the challenges businesses face today are, agile software development, it's commonly called design thinking, and also frequently called human centered design, that would be maybe the second more common name for the same area, lean startup, and product management, these four all have important lessons.

[00:20:44] They all come from a particular area of work. Design thinking came out of design studios. Agile came out of software development practice. Lean Startup came out of small startups in Silicon Valley. Product management really came out of bigger digital native companies, Google and Amazon and others.

[00:21:04] I call these, but they all have a lot of, basically they have many. Similar principles at their age, have their own artifacts and traditions. And I think of them even as rituals, which is why I come. I group them together and refer to them as the 4 religions of basically the 4 religions of iterative innovation is what I call it.

[00:21:24] Because all of them are in their own way talking about how do we build new things? How do we solve problems? How do we innovate? But how do we do it? So, in a more iterative way, Approach rather than a sequential waterfall planning, heavy top-down approach. So, design thinking in particular.

[00:21:45] Yeah, so absolutely. I think these are all incredibly helpful in informing how we think about an effective digital transformation. So that's my short answer specifically. Does the design thinking, which is like some of these, it's not so much defined, there's not a set of texts you can read that are the collective wisdom of human-centered design.

[00:22:09] It's a grab bag, if you will, of tools and ideas. Things like root cause analysis also comes from engineering, dealing with machines and no people at all systems thinking is also not just about human systems. So, these things have been fields of research and study many of them for decades, but there's this approach these days of how do we pull these together and what we do in human-centered design.

[00:22:32] I think it's really helpful. I'll shout out a couple of things, strikes in particular, that approach tends to bring a real strong focus on problem definition, which is really helpful. very easily overlooked or undertreated in organizations. So really being clear, defining and clarifying and validating, what problem are we trying to solve, before we start building something incredibly important.

[00:22:55] Second, like all of the four religions, it's premised on building iteratively. Build something quick, cheap, doesn't even have to work. In the early stages, it's meant to illustrate something, but build quickly, cheaply, iteratively, and also tends to be focused very much on working in small and multifunctional teams, which is another great principle.

[00:23:19] Those are some of the strikes. The reason why I think it's useful to look across these and bring them together and additional thinking is, they each come from a particular background design thinking. I would say. can have the limits if you're not thoughtful about it.

[00:23:37] it tends to focus, in some cases, in many cases, on the current business, meaning I see a lot of it applied to using tools like user journeys, where you're analyzing the current customer's experience, right? Which is great for taking your current process and improving it. Sometimes organizations will grab onto that. Say, okay, we need to, the whole point of our transformation is to do customer journey mapping, and they just do a lot of mapping and analysis of what's currently going on in their customers’ experience, but that draws your attention away from thinking about what are things you could do, new problems you could solve, customers you could serve, looking beyond your current board.

[00:24:19] Another limitation when you look at the whole process of what I call the Four Stages of Validation. How do you take something from an idea, a possible innovation or improvement all the way to actually deliver at scale? Human-centered design tends to focus more on the early stages, problem definition, testing and validating the hypothetical solution, even then getting the early working versions in the hands of customers, seeing what doesn't work in context, but sometimes can be less attentive to the financials, The business model validation things that come in stage 4.

[00:24:55] I just know organizations who have complained to me. They said, yeah, our design thinking team will spend 12 months just talking to customers and doing ethnographic research and getting deep insights on unmet needs and it's very expensive and we didn't get anything for our return.

[00:25:09] So that's an unbalanced question. and then lastly, and this is true also, to a degree, of lean startup. Those two, because they come out of a background of individual teams, there's less thinking there about organizational scale, whereas like an agile, there's been a whole, it's a hard problem, but there's been a whole stream of thought of like, how do we scale what works really well as a small agile team into, many teams across organizations, product management is all about that scalability.

[00:25:40] So looking at, again, it's not just systems thinking about the end user, but the system's thinking of what's our organization? How do we solve multiple problems in parallel? And how do we allocate resources between them? And how do we not spend 12 months going down a rabbit hole here when there's another urgent problem that we should be thinking about?

[00:26:02] So anyway, just to say, give a little context, but yes, I think design thinking is incredibly helpful. And one of the things you should be, educating yourself about as you're thinking about effective digital transformation.

[00:26:15] Clark Boyd: Fantastic. And with that in mind, let's jump into our first “Lightning round,” a new innovation. So quick questions before we get into our second half question from Deneb Milano, who's with us. Hello!

“Will you have a course on this new book?”

[00:26:35] David Rogers: Yes. So quick answer. Yes. The new book again being The Digital Transformation Roadmap. I do already have a class; it is called Leading Digital Transformation, and this is an on-campus program at Columbia Business School. It is a four-day program.

[00:26:51] It's extremely application-based, people working in small teams. You are starting to actually develop your own roadmap for your own organization, and its next stage of change, during the course of the program. So yeah, so I highly encourage folks to check that out. We're going to be running it next in October. Again, if you just Google Columbia Business School Executive Education, Leading Digital Transformation, you'll find information on it. That is in-person on campus. We do not have an online program based on the book, yet. If one goes into development, I'll let you know, but that's not currently in the works.

[00:27:33] So far, the market has been somewhat senior level, it really benefits from being very interactive and in the room. I think there could be an online program, but we don't have one yet.

[00:27:45] Clark Boyd: Fantastic. Number two:

“Would you recommend adopting an overall vision statement and communicating it to the whole body of staff?”

And that question is from Alice.

[00:27:56] David Rogers: Yes, absolutely. In fact, that is step one of The Digital Transformation Roadmap to the framework, is defining that shared vision. Although the truth is, many organizations have already some kind of a vision statement, and most of them are not very helpful and not doing much for you.

[00:28:17] So that's why I've tried to spell out in the book, what really makes an effective shared vision. It really does align people, and I talked about these four elements, that was also one of the recent articles, from, Dave Rogers on digital is about the four elements of an effective, shared vision.

[00:28:35] So I encourage you to check that out.

[00:28:39] Clark Boyd: Fantastic. And our third and final one for this lightning round is from Sergio.

“What are the common pitfalls in digital transformation?”

[00:28:49] David Rogers: So, this is the classic, it's really the opening research that led to my writing of the book was trying to figure out why You know, we have these widely reported surveys showing that roughly 70 percent of digital transformation efforts are failing.

[00:29:08] Companies are actually putting people and time and resources into these efforts. And then they themselves are reporting that they're not seeing the business results, the impact that they hope for. So that was my big research question a few years ago, was to try to figure out why. and, in the five biggest root causes, since this is, again, a human centered design or, root cause analysis, my thought was, you see a lot of, I met a lot of companies talking about a million things going wrong in their digital transformation, but I wanted to see what were the underlying causes.

[00:29:40] And what I found were five things. almost every company that's struggling is. One, one or more of these is the problem. They're trying to transform, but they do not have that shared vision. They haven't really defined strategic growth priorities, they might just be chasing technologies or just looking for cost cutting measures.

[00:30:00] Third, there's no experimentation. They're still trying that planning process we've been talking about. Fourth, they lack flexibility in their governance and their management. So, they're trying to do new innovative things, but they're applying the same BAU business as usual, rules and procedures that were developed for the core.

[00:30:21] And lastly, I see companies failing because they are trying to transform, but they're not investing long term in the technology and data in the people and talent. And. Most importantly in the culture that they are going to need for a digital future. So those are the five most common pitfalls. The good news is that they are all soluble.

[00:30:44] They're difficult problems, but they can be solved. They have been solved by different companies. So that's my goal is to show what we can learn from those who have gotten past these barriers. 


Stay tuned…

…for Part 2 of this “Ask Me Anything” edition, in a few weeks!


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