Adding Value as CIO in a Digital Native World with Paul Chapman


This week I’m joined by Paul Chapman. Paul is the Chief Information Officer at Box and former CIO of HP Software. Paul also serves on the advisory boards for a number of companies.

The role of the CIO is constantly evolving, and a CIO must reinvent themself to stay relevant. How does the CIO add value by creating frictionless experiences while facing a new style of IT? And how does a transformation roadmap play a role in charting the future CIO success? Our conversation covers all of this and much more.


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Podcast Episode

Episode Transcript

Tim Crawford:               Hello and welcome to the CIO In The Know, podcast where I take a provocative but pragmatic look at the intersection of business and technology. I’m your host, Tim Crawford, the CIO, analyst and strategic advisor at Avoa. This week I’m joined by Paul Chapman. Paul is the chief information officer at Box and former CIO of HP software. Paul also serves on the advisory boards for a number of companies. The role of the CIO is constantly evolving and a CIO must reinvent themself to stay relevant, value by creating frictionless experiences while facing a new style of IT. And how does a transformation roadmap play a role in charting the future CIO’s success? Our conversation covers all of this and much more. Paul, thanks so much for taking the time today to join the podcast.

Paul Chapman:              You Bet, Tim, great to be here.

Tim Crawford:               Paul, you’re the CIO at Box and advisory board member for a number of companies and the former CIO for HP software. That’s quite a background from a number of different perspectives. I’m glad that you had the time to join us today.

Paul Chapman:              Happy to.

Tim Crawford:               All right. So let’s just kind of dive right in and kind of poke the bear a little bit here. You know, we often talk about the CIO role and you I have had a number of conversations about this over the years. What’s different today and how do you see it evolving?

Paul Chapman:              You know, you and I have I had this conversation like you said a few times in the past, and one of the things I often do from a reflective standpoint is look back and say, okay, how did I sort of end up here today? And I think part of that was really driven by the fact that in technology, which is forever evolving, you have to reinvent yourself in order to stay relevant. And I think that, you know, that’s where they all say the pain of change is mandatory, it’s the suffering that’s optional. And I think I just heard someone say recently, the slowest rate of change we’ll ever experience is the one we’re experiencing now.

Paul Chapman:              And I feel like, so when you ask about the CIO role today and how it’s different, I think it’s forever evolving and constantly reshaping into, you know, riding the waves of technology that take us in different directions. And you know, like I say, the way I used to think about technology when I was at VM Ware versus how I think about technology and adding value when I was at HP versus at Box is very different. So I think the key thing there is as IT professionals and technology leaders, we have to be constantly reinventing ourselves to stay relevant. And I think that’s the same for the future. We need to continue to reinvent ourselves and stay relevant and figure out new ways to add value to our organizations.

Tim Crawford:               Do you think if I’ve grown up within the CIO profession or grown up within the IT profession rather, and have been a CIO for a number of years, do you think that that fits me well to be able to serve as a CIO today and moving forward? Or do you think there are things that really need to change in terms of skills or discipline or perspective?

Paul Chapman:              Familiarity breeds comfort, and I do think that often, you know, the conundrum that CIO’s ended up getting into is spending a disproportionate amount of their time, more and more of their time that is, goes towards budget as well as time on sort of yesterday’s investments. So it’s managing and caring and feeding for the tech debt and the operational responsibilities that go with that, which over time consume more and more of your time and reduce the time that you spend on what I would think is more forward thinking and innovative investment of time.

Paul Chapman:              And so I do think that is something that if you aren’t sort of willing to give up or not, sorry, willing to give up, it’s often how do you add value as the CIO and if you feel that how you add value as being disruptive, or disrupted I should say. And you are not sure what the meaningful outcome on the other side of the disruption is, I think it can turn into resistance. And I think at that point that’s where CIO’s can start to go backwards in terms of the value they add to the organization until the point of where potentially they’re asked to leave or you know, they are no longer adding value.

Tim Crawford:               Diving into the organization itself, there’s been this shift of the digital native workforce as well. And I know you’ve done some real interesting things at Box, which I wish we had more time to talk about. Maybe that’s a future podcast item, but how does the digital native workforce change this perspective and how does that start to impact you in a tech centric company like Box?

Paul Chapman:              Very much so. I often talk about the new style of employee new style of worker, one that has grown up digital, one that is much more used to consumer experiences in their personal lives and digital experiences and how they interact with technology and having been educated by the Amazons and the Googles and the Apples of the world entering the workforce now probably there’s more millennials in the workplace then, probably not. But if you think about digital natives and digital transients and so on, you know, the workplace today has become much more open, social, collaborative, much more digital. The workplace is much more digital than it ever was or should be. I think your ability to attract and retain talent is going to be tied into the workplace environment that you provide. And yesterday’s workplace won’t work today. I mean it’s not like one is wrong and one is right necessarily. It’s just they were born at different times. I’m sure when you entered the workforce, the desktop of yesteryear looks very, very different than the desktop of today.

Paul Chapman:              You know, work used to be a place you went to and now it’s much more of a state of mind, and you know, you have to rethink through the workplace, you know, how do you take the work out of work? How do you create frictionless experiences so your employees can be their most productive. And that’s certainly a shift I’ve seen is that there is, in a company like Box, we spend a disproportionate amount of time compared to what I’ve done in previous roles on workplace productivity. And that all goes into speed and agility and everything else that goes into that and we can talk about that in a little bit more detail, but definitely new style of employee, new style of workplace, new style of IT is certainly something we spend a lot of time, here at Box, in fact, we created a council last year, a future of work council with a couple of other silicon valley companies where we have a number of our customers are shared.

Paul Chapman:              And we invited them to provide input on how they’re thinking about the future of work and a lot of it is driven by these new campus experiences, these new technology experiences, and in fact I did just write a blog on, I made the title up, it was called the VP of Workplace Productivity, but it really goes to this merging of culture and the facilities and workplace and technology all working together and coming together to create the right workplace for the digital native workforce.

Tim Crawford:               That’s quite a bit more than what we’ve had to do when I first started in the workforce. And you’re right, the desktop system or I guess the computer, I wouldn’t necessarily say desktop, but the computer I started working on looks very different than how it does today. When you think about technology kind of fitting in with culture, with the workforce, especially when you talk about newer technologies, and I know you’ve spoken and written quite a bit about this, specifically about going digital and the importance of AI and cloud, you know, I don’t necessarily want to rehash the narrative that exists out there of motherhood and apple pie or you know, the path of roses, but what’s missing? What are people not getting when they start thinking about going digital, when they start thinking about things like AI and cloud, what’s missing in that overall narrative?

Paul Chapman:              It depends on how you think about what’s missing. The way I think about this is that you have to start somewhere and there is no big bang when it comes to AI and ML and so on digital even. It’s about incrementally removing or adding value to business processes or the way work gets done in a very incremental way. And it’s all about what I like to refer to as adding either digital labor or digital assistance. So it’s adding automated assistance or automated Labor to your business processes and how you get work done. And that could be at the personal level, so personal productivity, so an assistant that is out there helping me to be more productive and be more efficient. We can touch on what that looks like, and or digital labor or ultimated labor where you’re starting to see machine learning start to interconnect along say, a value chain for how a business process or workflow is executed on.

Paul Chapman:              And it sounds a little bit wordy or it’s really enabled. And this actually goes to sort of the last question a little bit, and that is when you are in a born in the cloud grown up digital company, you have a reference architecture that you run your business on and you provide productivity tools to your employees. That modern interoperable architecture that we’re built on allows us to do that in a much more seamless incremental way than say, would previous architectures in previous lives, you know, the architectures that we were working on were the best at the time and we evolved them in a step wise, incremental way. We can no longer in a step wise, incremental way create the modern reference architecture. We have to rebuild or rethink from the ground up. And so to your point, I don’t know if it’s about what’s missing per se in the narrative.

Paul Chapman:              What I do think though is that it is enabled through a modern reference architecture that was built for interoperability, that was built for agility and speed was built to allow these new types of capabilities, whether you call them AI or ML or automation to integrate into your architecture. And I think maybe what’s missing from the narrative is that right? If you weren’t already born in the cloud with a modern architecture, then you need to have a transformation roadmap that gets you there so that you can then take advantage of these new and emerging capabilities that are starting to emerge. And when I say starting to emerge, you know, I still think we’re just dipping our toes in the water here and there’s just a long way to go.

Tim Crawford:               And that’s really important. I completely agree that we are in the very, very early days, but if I were to take away, what’s your talking about, it sounds more like the incremental way of thinking doesn’t get you there. You have to completely change your traditional way of thinking as a means to provide the path or start to develop the path. And that path may change over time. But at least to get things off the ground, you have to change your way of thinking.

Paul Chapman:              Yeah, sort of the, you know, I like to use analogies because I think are great for, well one that can get you in trouble if they’re cheesy. But the one I just picked up on was, you know, electricity was not invented with incremental improvements to candles. And so it’s sort of similar. You know, if we evolve in a stepwise linear way, incremental improvements to our existing technology, legacy architecture, it won’t suddenly become a modern platform enabled API driven architecture. And anything that’s new today is being built for that architecture and the ability that we’re seeing. And to your point, even though you know, we’re just at the tip of the iceberg, so to speak, in terms of the maturity and so on capabilities, I am seeing it accelerate at a pretty hefty pace and that’s driven by the fact that we can actually turn on and contribute to the machine learning algorithms and so on. And it’s not taking six months or a year and a lot investment. It’s happening very quickly.

Tim Crawford:               But you put a lot of the foundation in place to make that a reality, didn’t you?

Paul Chapman:              We did. As I said before, we had the advantage of being a born in the cloud, grown up digital company being born this side of the century. So the thing is that we don’t have the anchors that hold back other companies, because at the end of the day you don’t just get to start with a clean sheet and an unconstrained view and rebuild from the ground up. You still have to take orders and ship product and recognize revenue and so on and so forth on your existing business model. But I do think that culture and business model and operating model enabled with technology, that’s really what’s creating the speed of disruption today. It’s a confluence of those things that’s happening.

Tim Crawford:               So I want to kind of riff off that a little bit. You know, as you think about how you align your role and where you are and your team is, how do you start to align that and build those relationships with the rest of the C suite and the board? It seems like there’s a pretty significant gap that exists today between the CIO and the rest of the organization. If I looked at it on the whole, not your org, but look at it on the whole, what I’m curious about is how do you ensure that you don’t have that gap? How do you close that gap?

Paul Chapman:              Yeah, it’s a great point. You know, I think that having perspective, right? So you mentioned earlier, you know, previously CIO of HP software and you know, their perspective is that companies are very successful and they grow and they get bigger and larger and more complex. And unfortunately internally things slow down because you spend more time running and caring and feeding and so on. And I think over time the barometer for how you measure adding value to the organization goes to the left and not to the right. And the reason I say that is, is that that complexity is what you run your business on and there is no forgiveness if it’s not available or it’s not functioning or what have you. And I think that that’s where the relationship with C suite to starts to become more, I say more distant or more fragile in that you’re not adding as much value anymore directly.

Paul Chapman:              You’re not enabling more things to be done, more revenue to be captured or go to market faster, whatever it might be, and so when we talk about the relationship with C suite, I think it depends on where you are in the evolution of the organization. I was talking to a CIO friend just recently and you know one of the other questions that comes up Tim, is often what is your engagement model with the business or what is your engagement model with the C suite? And one of the CEO’s I was talking to from one of the companies that I think actually was being successful in its transformation and change and really kind of breaking the company into evolving into a new company. When I asked that question, he said to me, actually he really was struggling with the engagement until the CEO said to each of the heads of lines of business, it’s no longer incumbent on IT to tell you what the partnership model is between it and the business. It’s yours as business leaders if we are going to evolve, transform and change. It is what is your partnership model with IT?

Paul Chapman:              And he said it completely changed the narrative. It completely changed the engagement model because IT is a great partner and a great enabler, but it’s always a lot harder when IT is trying to drive change or enable change across the business without sort of, the accountable part of the relationship for the outcome.

Tim Crawford:               True. If I were to push back on that a little bit, Paul, wouldn’t you also say that in addition to having support from above, having that air cover, if you will, from the CEO, doesn’t it also require the right CIO with the right chops to be able to not just build or establish those relationships but nurture them and grow those relationships as well?

Paul Chapman:              Absolutely. I think that’s why the combination has to be there. It can’t be one sided either way. If you have a CIO that has those attributes, which I think by the way are key to being successful in today’s enterprise, but you don’t have the engagement model the other way, then I think it’s a problem and I’m vice a versa. If you have an organization that is wired for change, is looking to drive change, is looking to enable transformation, and then you have a CIO who is very comfortable, caring and feeding for yesterday’s investments, then that won’t work either. You do have to have that right combination of partnership to make this work.

Tim Crawford:               That’s a great way to think about it too. So as we kinda wrap on this episode, last question for you. So what excites you most, as you start to think about both the CIO role, but where technology fits in and where do we go from here and the opportunity, what’s exciting you most? What’s getting the up and really kind of firing up?

Paul Chapman:              I think that today the ability to add value as a CIO is greater than it’s ever been. We’re now in a position, especially as we start to see more of our footprint move to cloud based delivery. We have this freedom from infrastructure today or a much more significant portion of our environment has a freedom from infrastructure. We’re federating out more things into cloud based services including what I think is one of the most interesting things and that is as I talked about architecture earlier, we are constantly, you know, with this best of breed eco system that’s available to us, which is service providers are maniacally focused on being the most innovative in the space that they’re providing a service on. We’re getting to bring all of that innovation that’s going on in that ecosystem into our organizations and at a very rapid pace. So the speed of enablement, the agility we and speed we have with which to do that is unlike anything I’ve ever seen before.

Paul Chapman:              And that’s allowing us to add more and more value at a very, very fast pace incrementally, to our organization. So that’s one thing. I think the second thing is, is certainly what we’re starting to see emerge now in and around a lot of the machine learning capabilities and some of this digital labor I was talking about that we’re able to introduce into our business processes and workflows. I’m really excited about what’s happening there, and like I said, it’s still in sort of some embryonic phase, but I can see the promise there and see where that’s going.

Paul Chapman:              And I think the opportunity to get closer to the customer, and get closer to where revenue comes from and as organizations around the world are thinking through their digital journey and transformation and so on, you know, we’re in a great position to be able to, and as you know that the CIO community is, I’m a big believer in wisdom of the community and I think the CIO community is one that is very eager to share and collaborate and maybe commiserate. So we have those moments. But you know what I’m saying, right? There’s a tremendous body of knowledge and wisdom that’s growing across our organizations today and that’s really what excites me most about the role. I think it’s moving further and further away from keeping the lights on and operational management and much more into the front office, partnering with sales, partnering with go to market, outside in IT, not inside out IT, and leveraging a lot of the innovation that’s occurring around us is the thing that excites me the most.

Tim Crawford:               That’s great. We’re going to have to wrap right here, but Paul, thank you so much for joining the program and hopefully you’ll come back and maybe we can unpack some of these other aspects.

Paul Chapman:              I’d love to. Thanks Tim. Appreciate it.

Tim Crawford:               Great. Paul Chapman, thank you.

Tim Crawford:               For more information on the CIO In The Know podcast series, visit us online at, or you can find us on SoundCloud, iTunes, Google play, and Stitcher. Don’t forget to subscribe and thank you for listening.

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