Blaine: You bet! That was quite a mouthful: all of your titles and companies. I almost didn’t make it through, but I managed to get to the end. So obviously, you’ve got a lot of great experience and we want to hear all about it.
Will: Thanks. I’m excited, Blaine. Thank you very much for having me.
Blaine: So the first thing I want to talk about is, at the top of your LinkedIn profile it says you are known for creating order from chaos. What does that mean? That must mean something to you. You must have seen a lot of chaos in your experience as a consulting CIO and in other roles.
Will: Definitely Blaine. No one ever calls me throughout my career coming up and tells me, “Man, I made 100 phone calls. I sent 30 e-mails yesterday. Everything worked without a hitch.” Everyone always calls me and things are down, all hell is breaking loose. “I lost out on a million-dollar deal. It was in my outbox. I couldn’t log in here. I couldn’t log in there.” It’s always been like that and it’s just magnified. You get people saying, “We’ve had a disaster. We need to recover. We’ve had so much of our intellectual property on there.”
So, bringing order to chaos means usually I’m called in. I’m calm, collected, and I’ve got to figure it out and get it fixed. At the end of the day, it becomes veni, vidi, vici. In my eyes, I love being able to come into that chaos, bring order to it, and then move on to the next fun challenge. I’m kind of weird in that sense where I love bringing order to the chaos, then I get bored really quickly and I’ve got to get to the next mess to fix up.
Blaine: Sounds good. So how did you get to where you are today? What’s your backstory?
Will: My backstory is I fell in love with computers at a young age. If not, I’d be a surgeon right now doing surgery. But, once my dad bought me a computer at age 11 or 12 years old, I fell in love with computers and I’ve just been doing technology ever since.
The great thing is I work in what I love, so it’s not really work. All day, every day, when I’m not doing something that is quote unquote “billable” or for an organization, I’m doing fun projects with my kids and kind of living vicariously through them with cool stem projects and stuff like that; having that love for technology and also just having the love for constant learning, lifelong learning.
I have numerous degrees, numerous certifications, but it’s all a byproduct of like a stamp on the knowledge and that journey of knowledge. That journey comes from just having the love for technology. That’s taken me progressively through my career where I’ve been able to be a subject matter expert and deal with all of the past technologies and a lot of the future technologies.
Blaine: Very interesting. Well, thank you.
Sort of related to that lifelong learning you were just talking about, you actually recently wrote or published an article on The Real-Time Enterprise blog talking about how CIOs need to transform or perish. What’s the core thesis you had in that article?
Will: That was a great one. It was just from the standpoint of seeing all too much where you keep the lights on CIOs and the “I” in CIO which is normally Chief Information Officer. You have some people say Chief Innovation Officer. You’ve got to become innovative. You’ve got to keep up with the Joneses, keep up with the trends and the technologies.
The reason I was saying “transform or parish” is you get people to stay in that mindset of keeping the lights on. What I said earlier was I’m a veni, vidi, vici kind of guy; order to chaos. I need to create order, but then I get bored. I’ve got to move on to the next challenge.
Sometimes what you get is CIOs and executives that want to stop and smell the roses and then time, technology, and the trends pass them by. You end up two, three years and wow! Now, you’ve got so much technical debt that it’s hard. It’s like quicksand. It’s hard to get out of it.
The thought process around it was that you’ve got to transform. You’ve got to transform the organization, the culture, and your mindset to be a mindset of digital, utilizing digital technology, being able to be innovative, but being able to have the core foundation in the culture and in the organization to adapt to change as it presents itself, even in real time, to be able to adapt to that change. Otherwise, time is going to pass you by. That can get into numerous examples.
I’m sure there’s infographics you will see all over Twitter and everything like that showing you Blockbuster, Yahoo, AOL, or Myspace on what happened and the lessons learned. Pets.com! For a long time, I used to have a running joke saying I bought my first goldfish from pets.com. People forgot about pets.com but then you have stories now that are success stories. It’s like, “Man that’s what pets.com did in 99-2000.”.
Then, chewy.com. Chewy. I’m like, “What’s the difference?” Chewy did it better. Chewy did it at a time that they were able to be more agile; at a time where they were successful and had a successful exit selling to PetSmart. That’s how I looked at it. You’ve got to transform or you’re going to die. You’re going to end up like one of those examples of a failed company.
Blaine: Absolutely. Well, I’ve got a surprise for you, actually! I’ve got an original pets.com sock puppet right here.
Will: That’s awesome, definitely!
Blaine: It’s one of my little holdovers from the first dotcom boom. I actually had it sitting right next to me on my table. When you brought up pets.com, I had to!
Will: That’s awesome. A lot of people don’t remember that. When you look at it, it’s ahead of its time when you see the success story behind Chewy that just exited for $3 billion or something like that to PetSmart.
Blaine: Well, you touched on a lot of topics for us to dive in deeper. But, fundamentally, a lot of what you talked about was digital transformation.
First thing I just have to ask, you’re a fellow at the Society for digital transformation. What does that mean?
Will: The Institute for Digital Transformation is an organization with like-minded experts like myself that have been through the trenches; that have done successful digital transformations and they can share that knowledge with others. We speak on certain topics like that: what are the challenges? What are the challenges with people going from a traditional to agile business?
The way I look at it is standing on the shoulders of others. I always love speaking to people and helping people when I attend events or when I’m mentoring people and having them live through my experiences: “This is the challenge. This is the pain point. This is what we experience”.
The institute really just helps people along that journey. Basically, it’s saying, “Hey, we’ve been there. We’ve done that. We’ve got the t-shirts or whatever like that.” [laughter] Were able to assist and help you with the mindset because there are different ways to skin the cat.
Also, I finished my MBA about 10 years ago. I got a PMP 10 years ago as well. There’s just things within both of those: my MBAs in project management, my PMP 10 years ago, neither one of those two did I learn agile or scrum. I had to learn it after the fact. I had to go get a certified scrum master certification and read on it.
Going back to what I said earlier: lifelong learning, it ends up being, “Wow! I got a degree ten years ago.” Imagine someone that got it 20 years ago or 30 years ago. You’ve got to keep up with that. If you can go to a repository where you can learn, where you can sit there and you can learn from other people and read articles. Now, all of a sudden, you can get that concentrated knowledge. And I think at the end, it’s about the betterment and to help better execute and deliver on transformation initiatives.
Blaine: So it sounds like the fundamental notion of the Society for Digital Transformation and a good concept generally is it’s not about reinventing the wheel. This is about building on the learning and experience of folks that have been doing these kind of transformational projects for years. We think of digital transformation as being mostly about the new thing or something highly innovative and it could be. But, that’s not to say there isn’t a lot of experience of other people who’ve done similar things or related things that you can build on top of.
Will: Exactly, Blaine! Yep.
Blaine: Interesting. Obviously, everybody’s talking about digital transformation these days. I think, to some degree, it’s an overused term. How do you think, in your experience, companies are doing on that path toward transformation? Is it still mostly about keeping the lights on and maybe doing infrastructure transformation moving to the cloud or are companies actually changing fundamentally how they operate? What are you seeing or what are you feeling out there?
Will: It’s a combination of what you mentioned as well as some of the other parts of the trees. It’s a combination. You’ve got some people that say, “Man, we want to move off of infrastructure, on premises infrastructure, and go to the cloud.”; Infrastructure as a service, platform as a service, microservices, software as a service, et cetera.
They think, “Okay that’s digital transformation.” And that’s one part of it. I worked at an organization that had a platform that was created to drive healthy habits to lower health care costs. What they didn’t know is that data is the new goal. All this data they had from this platform were now people were sitting there and getting their diabetes checked, losing weight. All this data that they had with demographics and everything, if they could just de-identify that data that’s in their data warehouse, that’s utilizing it’s purpose, now all of a sudden, this is another revenue stream.
Now you’re looking at digital technology. We just happen to be a company that saw rising costs in health care. We wanted to drive those cost down. Now all of a sudden, we have data that can help identify and not only bring down healthcare costs, but help companies that are doing research into seeing trends and seeing what’s working. There’s other examples of that. I think digital transformation also needs to take into account where the market’s going, what the trends are, and how that technology can help organizations evolve, even what their base product is and transform the company itself.
Blaine: As we’ve just been discussing, it’s as much about business model transformation as it is about a technology transformation. Who do you think should fundamentally own digital transformation initiatives in organizations? Obviously, your background as a CIO at multiple companies and a CIO for hire puts you on the IT side. But, a lot of people are saying, “Well, but fundamentally, DX needs to be driven on the operations side or the LOB side, line of business side.”
What do you think about this question about digital transformation: IT or OT?
Will: It’s a great question, Blaine. Normally, you would have someone that would come here and be completely biased. And I am to an extent. I believe every company is a technology company, stuff like that. But, when it comes to owning digital transformation, to me, the best qualified person/team to deliver the results successfully should own it.
I know CIOs and my mentor, he did not come from an IT background. I came up from an IT background. I fell in love with computers, everything. He came from the business and he is great. With all my education (I even have a master’s certificate) I feel that the best education I got is my one hour a month calls with my mentor, Frank Wander.
I would get the concentrated version. I would talk with him about a challenge and he’d be able to tell me, “Oh Will! That’s simple. It’s this, this, this. Here’s what you do.” I’d just sit there and my jaw would drop each time. I was like, “Wow! I went through all these use cases, business cases in business school and none of it has prepared me as much compared to what Frank’s telling me from real-world examples.”
To me, personally, it’s whoever has the capability of being a leader, being able to take it by the rein and lead that effort and can get the teams to believe in that vision. That should be the best person. Whether that person comes from IT or from the business, fine, because at the end, the intersection between business and IT, it blurs the line.
Again, if you go back to my first thing where every company is a technology company, then the IT is part of the business. It’s not just a servant to the business. It is part of the business. And in a lot of cases, you’re starting to see CIOs. I’ve got good buddies of mine that were CIOs that are now Chief Customer Officers, CEOs of companies that are not necessarily technology companies. They could be telecommunications companies and now they’re CEOs. That’s because technology is part of the business now and a fundamental part of it.
Blaine: Very interesting. Really interesting. You’ve talked a lot about agility a couple of minutes ago and you talked about agile scrum and some of the technical ways of literally becoming sort of a capital A agile company. Do you think that is the core to agility or is there more to it than that?
Will: I think with agility, I like saying “learn quickly”. Like I was saying earlier, “lifelong learning”. A lot of people say “fail quickly” or “have a short memory”. I like saying learn because I don’t think it’s ever failure. I’m one of those guys like, “Hey, he has a record of 32 wins, 32 W’s, 2 L’s.” The two L’s are lessons. I don’t say losses.
For companies to sit there and increase their agility, they have to be able to learn quickly. They have to be able to embrace and foster a culture of idea sharing and not be afraid to fail or learn quickly – not to be afraid of it. There are so many examples that you can go through. You see all the motivational infographics all over the web, “You miss every shot you don’t take.” Too many people are fearful.
Years ago, I was one of the testers for Google Glass. So, I had Google Glass and everything, and Google wasn’t afraid to come out with that, to challenge that. And then, to sit there and say, “Hey look, we’ve got to bring it back. We have to bring it back in house, do whatever, live to play another day, and re-evaluate it.” But again, they weren’t afraid to challenge, to come out with it. They could have taken off and there would have been millions of people as opposed to the initial eight thousand or whatever that had Google Glass, but they weren’t afraid to take that challenge.
Apple is another company that did the same thing. I remember the iPad and the iPad launch and everybody making fun of the name, alone. Think about it: iPad. Now, it’s like second nature to people. They all have iPads. Remember, they also came out with the Apple Newton years ago as well and that failed miserably.
Blaine: That’s absolutely right. Well, thank you. One of my favorite parts in these interviews is when I get to ask a guest about what part of conventional wisdom they would like to call bullshit on. Any particular area where most people are saying X and you’re saying Y?
Will: Yeah oh definitely! This is just a rant for me. Even recently, I tweeted about it a couple of days ago I think. It’s fresh in my mind.
It’s SME: Subject Matter Expertise or Subject Matter Experts. I’ve been in environments, I’ve attended events where somebody is a security expert or a cloud expert or a panel full of RPA experts. They’re speaking on things and it’s like, you’re speaking on a panel about RPA and you’re an executive recruiter. What do you possibly know about robotics, robotic process automation? What do you know about artificial intelligence?
I know people that are speculative in the bitcoin market and then they’ll turn around and they’ll talk about blockchain. What do you know about blockchain? What do you know about all this stuff except that you’re investing? So, you look into the research, you spend an hour a day. So now, all of a sudden, you’re a subject matter expert?
I’ve seen social media experts or SEO experts with 200 followers on Twitter. It’s like, “Well, if you’re an expert, then I must be a super duper expert or something like that.” That’s my pet peeve or rant where I call bullshit because who knighted these people as SMEs? Is it just them calling themselves experts?
I’ve always said and I always tell people I should be from Missouri. I’m originally from New Jersey. I should be from Missouri because you’ve got to show me. The only way I’m going to believe you is if you show me that you’re an expert. So, you say you’re a cloud expert. Show me how you’ve migrated workloads into the cloud.
Don’t just tell me that I should be migrating it. I’ve got to keep up with this. Don’t give me an infographic. Don’t give me percentages, everything like that because I can google that myself. I love reading. I could read articles myself.
So that’s the thing that’s always bothered me is who knights these people as SMEs? Are they just knighting themselves? Why should I trust them? I get that all the time, all day, every day at events, on Twitter, people pinging me about opportunities and stuff like that. It ends up being who made an SME?
Blaine: I absolutely agree with the core point. I think blockchain is absolutely the worst I’ve ever seen in that regard. As you say, cryptocurrency has sort of ruined blockchain. It moved the discussion out of being about a core technology which is quite interesting with a wide range of applicability. It is now all about a speculative investment environment. I think the general public can’t really separate the two. The whole domain is just full of these SMEs, as you say, who are all looking for big expensive consulting contracts to help companies figure out their “blockchain strategy”.
I’ve never seen anything like it, actually. You’re right. AI, some of the other technologies, cloud, they went through some of that, to a certain degree, but nothing to the extent of blockchain. I think it’s because it’s applied to the cryptocurrency and the whole investment and money side. It attracted the SMEs like flies to rancid meat. It’s just unbelievable. I think that’s a good observation.
I don’t know if that’s a contrary opinion. I think most people would agree with you on that point, but I think it’s a well-made point. To wrap it up, Will, any key takeaways or tips for business leaders, maybe in particular, who are trying to figure out how to drive transformation in their business?
Will: Oh definitely. Some key takeaways and tips for business leaders who are trying to drive digital transformation is to really have an understanding of their core business (the people, process, and technology) and what the impact of the digital transformation journey will be. Expect the unexpected. Plan, plan, plan.
One of the biggest clichés I always use, and my wife beats me up about it, is “measure twice cut once”. One of the biggest things, 90 days post implementation, gauges the impact of the digital transformation, the benefits realization. When you started a journey, what was it that you were trying to accomplish? 90 days post implementation, did you accomplish that?
And rinse and repeat because, depending on the time in your digital transformation, new technology may have come out or new threats, if you’re looking at it and doing a SWAT analysis to deal with it. So, kind of re-measuring it and reinvesting.
The great thing is, like we discussed earlier with the agility aspect, change is good. If you’ve got to change mid-flight, if you completed it. And all of a sudden, you say, “Oops! There’s this new technology. We’re going to go over here.” It’s OK to sit there and do it over. What is not OK is not to have this culture. Because eventually, if you just sit by, then obsolescence will kick in. You’re going to sit back and you’re going to be that Blockbuster, you’re going to be that Yahoo that made all the wrong choices along the way because you thought, “Hey there’s no threat.”.
One thing that Gary V says, “Wake up every day being scared of your competitors.” I think if people adopt that kind of mindset that there’s somebody out there that is hungrier. There is some company out there that is trying to eat your lunch, that’s trying to disrupt you. If you can adopt that kind of mindset and that culture, I think it will lead you to be able to be innovative, to not be afraid to fail, to not sit on your laurels and to really continue that.
Again, to me, digital transformation is not, “You want to go from A to B.” It’s a mindset. It’s changing. It’s being able to see the forest for the trees and being able to adapt and adopt a mindset of real-time business strategy, real-time execution and changing the strategy on the fly, if need be.
Blaine: Perfect. I think that’s a good bit of wisdom there: “Digital Transformation is not A to B.” I think a lot of companies think about it as A to B. It is a mindset. Right on. Very well said.
Well that wraps it, Will. Thanks so much for joining us today. It was a really insightful conversation.