Transformational CIO Agenda: Strategy 2021

The Chief Information Officer role is central to business process transformation and corporate innovation. In this episode of CXOTalk (#676), we talk with two prominent CIOs about the CIO role in 2021.


Oct 30, 2020

The Chief Information Officer role is central to business process transformation and corporate innovation. In this episode of CXOTalk (#676), we talk with two prominent CIOs about the CIO role in 2021. The conversation goes beyond cloud computing strategy and digital transformation into the CIO agenda and the most important CIO priorities for information technology today.

Tim Crawford is ranked as one of the Top 100 Most Influential Chief Information Technology Officers (#4), Top 100 Most Social CIOs (#7), Top 20 People Most Retweeted by IT Leaders (#5) and Top 100 Cloud Experts and Influencers. Tim has served as CIO and other senior IT roles with global organizations such as Konica Minolta/ All Covered, Stanford University, Knight-Ridder, Philips Electronics, and National Semiconductor.

Isaac Sacolick is a successful CIO and author who has led digital transformation, product development, innovation, agile management, and data science programs in multiple organizations. He was most recently the Global CIO and a Managing Director at Greenwich Associates, a leading provider of global market intelligence and advisory services to the financial services industry. Previously, he held CIO roles at McGraw Hill Construction and BusinessWeek and was a founding CTO at media and social networking startups.


This transcript was lightly edited.


Michael Krigsman: We're discussing CIO strategy and priorities with two top experts.

Isaac Sacolick: I do a lot of work helping organizations with their transformation programs. We do a lot of work around Agile and DevOps product management and data analytics and AI. We have a StarCIO Agile Planning Program that helps organizations develop their Agile culture, and I do a ton of writing on my blog,, InfoWorld, and other sources.

Michael Krigsman: Our second expert today is Tim Crawford.

Tim Crawford: Thanks, Michael, for having me. It's great to be here again on CXOTalk, and especially with both you and Isaac, talking about this really important subject.

I'm Tim Crawford. I'm CIO and Strategic Advisor with AVOA. The nature of the work I do is really more of a CIO at large, so a lot of assessments, executive coaching, helping folks through their transformation journey.

Like Isaac, I do a fair amount of writing and speaking and just working with really smart folks. I'm hoping to learn as much as I'm hoping to share what I've learned through the process.

Michael Krigsman: Now a quick thank you to Productiv, a SaaS management platform that unlocks the power hidden in your SaaS applications to bring you higher ROI, better team collaboration, and lower license costs.

What is a transformational CIO?

Tim, we're talking about this idea of a transformational CIO. We've spoken about it in the past. Give us a quick rundown. What do we mean by that? You're the first person to have used that term, that I'm aware of.

Tim Crawford: The transformational CIO has changed and it hasn't changed. Fundamentally, the difference between the traditional CIO and the transformational CIO is that the traditional CIO is more focused on back-office, technology focus, and they've centered their organization in that way.

The transformational CIO, on the other hand, is far more business-focused. What that means is that they have stronger relationships with the rest of the C-suite, including the CEO. The CEO is probably one of the closest relationships that they have. If not, their direct report.

It's also understanding how technology fits into the mix to achieve those business objectives. That's a really important distinction here is that integration between business and technology. It's not just technology and being reactive but, rather, being proactive as part of that C-suite.

Isaac Sacolick: I would say, having that digital mindset is really about growth and understanding where the industry is going, where markets, and where customers are going. The transformational CIO is talking to customers, is learning about prospects. They're really outgoing and learning about what's happening in other industries. They bring a lot of agile capabilities into their organization, not just in IT but bringing it to other parts of the organization so they're collaborative.

In terms of technology, they're really looking at the scope of the business through a digital lens. What that means is technology is changing so rapidly. We're getting new capabilities from application development to edge to analytics and AI. Getting a sense of what needs to change when is a really important part of the transformational CIO.

Michael Krigsman: Why are we even having this conversation? If we were talking about any other position, any other leadership position in business, it would be fairly obvious that the person needs to understand in-depth, in detail, the business. Why are we giving the CIO kind of a pass to even think about not doing that?

Tim Crawford: The first thing is, you have to look at the anthropology of IT. When you do that, when you look at the history of IT, it really kind of speaks to an organization that was taking a really complicated problem, business problem, and solving it.

As you've gone through the decades since the start of IT, through the evolution of IT, we never really came back and reconnected with the business in the ways that we really needed to. That demand has been growing over time. It's not that it went away. It's just that we could get away with not having a really strong connection between the two.

Now, fast-forward to today, and that connection absolutely must be there. It's been growing even before the pandemic hit us. I know we'll talk a little bit about that but, even before the pandemic, the demand to connect technology and business together in a meaningful way has been increasing. The CIO absolutely has to lead that charge.

That's been one of the problems is that we've been able to wiggle our way through this and make it work for some period of time. The pandemic has really brought a spotlight to the need to make that connection a solid line rather than a few steps removed.

Isaac Sacolick: I think part of this that also is different is that the CEO and the board and, really, the CIO's colleagues want the CIO's input. I don't know if that was always the case five to seven years ago, but they want the CIO to really explain the art of the possible in language that they can understand and they want them to do it in a way that is executable. Right?

Tim Crawford: Yeah.

Isaac Sacolick: We don't want to hear about some far future, cognitive AI if it's not relevant and if it's not executable by the group. That CIO is there to explain it, to sell it at times, to get buy-in, to think through what parts of the organization need to transform first and sooner, where there are disruptive factors that might impact business, where there are some opportunities.

It really has become a two-way street. It's not just the CIO really stepping up. It's really the CEO and the board and their colleagues, the SLTs to come back and say, "Look. We need the CIO to own parts of this transformation program."

Tim Crawford: You're absolutely right, Isaac. I will take it a step further and say that the rest of the organization outside of IT has been increasing in terms of their needs and reliance on technology. To some degree, they've tried to do it themselves, but they've quickly realized the complexity of doing that. It really takes them afield and out of their wheelhouse.

It's really been adding pressure to that of the role of the CIO. We talk about the CIO but, realistically, for those listening, it could be any role that is the senior-most person in IT. It doesn't necessarily have to be someone that holds that CIO title.

The importance that I would amplify there that Isaac just said is, it's become a two-way street. The executive team knows that they can't just keep IT in a box and it's far removed. It has to be part of your core program to survive today and moving forward.

Practical implications of the transformational CIO role

Michael Krigsman: What are the practical implications of this for the CIO role and for CIOs that are thinking forward into the next year?

Isaac Sacolick: Continual evolution of the digital operating model within IT is really important. How do you build collaborative practices that bring ops and dev together, that bring data technologists and data scientists with the dev teams together that really educate the business on how to be an active stakeholder or an active product manager or product owner? There's an entire collaboration that needs to happen for the CIO to be successful.

Also, thinking about the skills and the leadership qualities of their staff, of the organization itself. The CIO doesn't do this work by themselves. Most of my interactions tend to be with secondary reports and sometimes even tertiary reports to a CIO that their roles are expanding. Right?

Tim Crawford: Mm-hmm.

Isaac Sacolick: They're expected to have business acumen. They're expected to negotiate with stakeholders around scope or to take on a transformational program.

How does the CIO work with their staff on communications? You're going to start with a whole new set of programs, a whole new set of initiatives. How do you educate the organization around what the strategy is, what the roadmap is?

You listen to what I'm saying. I'm talking about communications. I'm talking about marketing, selling, collaborative. This is not sitting and coding. It's not looking at service desk tickets. This is really being a part of the business and saying how to make technology work together.

Tim Crawford: You have to understand the business operations at its core. You have to understand how the company makes money and how it spends money. I know that I've said that before I know that sounds super simplistic, but it's actually not.

It's really getting into the bowels of how your company engages with its customers, which then leads to how you drive customer engagement, how you're engaging with your customers, how that's changing. Remember, all of this is evolving and changing over time.

A business is a living organism. It's not a structure that you build once, you're done, and you just keep multiplying it as part of scale. Rather, this is an organization that has to evolve and change over time.

The CIO needs to think about how they can play a role in that whether it's organization, culture, process, technology. All of these pieces have to come into play, whether you're talking about the customer engagement end of it or the business operations. Both of those are incredibly critical, especially today.

Michael Krigsman: Arsalan Khan takes some issue with a couple of things being said here. He's on Twitter and he points out; he says, "Okay, so we want the CIO to be transformational but still the majority of companies don't even include CIOs in their annual reports as a key executive." In a way, are you guys talking about a theory of an ideal world?

Tim Crawford: This is where I've talked about this in the concept of the three-legged race. There are three components that have to move forward as part of this evolution. We're focused on the CIO may be as part of this conversation but the rest of the IT organization also needs to come along in this transformation journey.

There's a third piece to this in this three-legged race and that's the rest of the company and how it perceives the role of the CIO and the role of the IT organization. This fundamentally comes back to the relationships that the IT leader has with the rest of the C-suite and the value that they're executing on in terms of providing that direct business value to achieve those business objectives.

If there's a disconnect between those, you're absolutely right. As a CIO, you're not going to get invited to that table. You're not going to be seen as another C-suite executive.

However, if you are delivering on those objectives and you are focused at the business level and you do have those strong relationships, not only will you be working at the C-suite level like the rest of your peers and the title that you hold, but you'll also be engaging more regularly with your board of directors. That's another piece to this that has to be understood.

You don't just get a seat at the board table either. This is where relationships are where it starts. If you do not have a good relationship with your CEO, for example, you will not get invited to the board meeting. That is your doorway to the board.

Again, kind of back to what Isaac was saying earlier. This is less about technology and more about everything else in the soft skills. We have to think about where our focus is.

Michael Krigsman: Isaac, what are the practical implications, again, for a CIO strategy?

Isaac Sacolick: There's a bit of a continuum right now in terms of how different businesses and different industries view the strategic needs around technology and how they view the CIO and how they view IT. It doesn't come overnight. It comes through a crisis. It comes through opportunities.

The one thing the CIO can do to help themselves is when you develop business acumen and you can ask questions from a business perspective, when you can challenge people's thinking, when you can bring solutions and then express what the problem is and what impact it's going to have on the organization. When you can do that continuously without getting under people's skin in a way that gets people to think differently and do it in a way that gets the CEO thinking differently, then the CEO is going to slowly start saying, "I want to understand what this person is saying."

Now, this is not about shipping jobs to the ones that really want CIOs that are transformational. We're all in our roles to make our roles successful, and so part of that is using that acumen to ask questions, challenge the status quo, bring solutions in, and I think that's a big role for CIOs today.

Tim Crawford: The one thing that I'll add to what Isaac said, everything he said plus in business terms. When you have that conversation, you must have that conversation in business terms.

Do not bring up technology terms. Do not bring up the jargon. Bring up business terms. How are you going to engage at a business level? That is the start. The language, the relationships, the way you approach it, what you prioritize, and why you prioritize it, all of those factors come into play and that helps you derive your strategy which, in turn, helps you decide how your organization should be structured, how your processes should evolve.

Let's face it. If you fast-forward to today, take all of this, and put it into today's language, the reality is what you were doing a year ago is up for grabs. It's totally different today. That's something that I think we have to take a really hard look at is, how has it evolved? Again, it comes back to starting with the business, starting with understanding what your business is, how your customers are evolving, and then going from there.

Business impact of transformational CIO strategy

Michael Krigsman: We have a very, very fundamental question from Wayne Anderson on Twitter. Wayne, I'm paraphrasing here but, basically, what he's saying is, does being a transformational CIO have some sort of major business impact? To put it another way, why should we care about this?

Isaac Sacolick: If you're going to the board and you're going to the CEO and you're coming to them with opportunities to reduce risk, to make things more efficient, or bring technology in to automate processes, quite frankly, they're table stakes. They're things that are just expected of CIOs. They're what CIOs have traditionally done.

When you get that chance to voice things, you need to be talking about growth. You need to be talking about customer experience around where market opportunities exist. You really need to talk about where data and analytics can become a strategic advantage.

It's not just to bring ideas to the table. It's where you are willing to put your name against something that's in an area that the CEO cares about. The CEO expects you to do some of these other things.

Tim Crawford: The key here is, if you boil it down, companies that compete with one another will ultimately be decided on how they use data and how they use technology. That sounds pretty dramatic, but I think that we actually will start to see that as we go forward.

Two competing companies, the way that they define success versus failure is who is able to use data and technology in a more meaningful way to do three things. Those three things, again, I have these little tools that I use. I call it the Ternion Concept.

It's three focus areas. To Isaac's point, these are the focus areas of the executive team, of the CEO, which is business growth or revenue growth. The second is customer engagement. The third is operational efficiency.

If you are focused on those three, this is actually one of the differentiators between a traditional CIO and transformational CIO, a traditional CIO being focused on operational efficiency, transformational CIO also being focused on customer engagement and revenue growth. It's a huge differentiator. It changes the game and it also helps you see the path that is going to differentiate your company from your competition. That is really important, especially in this day and age.

Isaac Sacolick: Yeah, and if I were to add a fourth wheel in here, it's about just pure business and technology agility. The things that are different about the CIO role is the rules of the game tend to change, sometimes slowly, sometimes there are market forces.

You look at what's happening in different industries. It hit media over a period of about a decade from 1990 to about 2000 in terms of the impact of the Web. But now, it's happening in financial services.

You think about the impact of technology that happened in waves of three to five years. That changes the role of the CIO. It changes the rules that we can play with.

Then you have some really harsh impacts like a pandemic where everybody overnight is working from home and everybody is looking at you and saying, "How are you getting our work done more efficiently?" That's a big part of the CIO role is just having the entire organization in a form of agility that when something is abrupt like a pandemic or something is happening gradually that you have the tools, the processes, the leadership, the collaboration, the principles in place that people can react to it and sometimes be proactive about the things that are coming down for that particular company.

Michael Krigsman: We have a very interesting question from Twitter, a very important one. Shahid Masood said, "CIOs are overseeing multiple projects in high-pressure environments. How do they deliver projects on time when there are competing priorities, especially in this pandemic situation, and how does a CIO balance keeping their time between keeping the lights on and strategy and innovation?"

Isaac Sacolick: I've written about this a few times. I don't know of a single organization that expects technology and expects data and analytics and does a terrific job of prioritization. There's always higher demand from IT and from data scientists than what these companies can provide.

This really starts with the dialog the CIO is having with their board, with their organization. Then also, when they start talking about their direct reports, thinking through what are really the most important strategic initiatives to drive transformation and having a real conversation around that. Then getting tactical, using Agile processes to negotiate around scope but also being very good at executing on time.

I always tell people if you hit your timeline and if you hit your quality but I have to negotiate on scope with you, then that's a two-way conversation that we should be able to have. We want to be able to get things to market faster. We want to be able to get feedback because so much of what we're doing today is both impacting employees, it's impacting customers.

Instead of trying to get the scope 100% right, let's get it out to market a little bit faster. Make sure it's good enough quality. Then being able to get feedback for us to get a better set of priorities going forward.

Tim Crawford: It's a tough role and serving as a CIO is both a privilege and an honor but, at the same time, it's an incredibly tough place to be. You have to get into that mode of understanding what the table stakes are. You have to execute on those, first and foremost.

If you don't do that right, the rest won't matter. Nobody will be focusing on anything above that. You have to get those fundamental pieces right. End of story. Full stop.

Once you get past that, once you get those fundamental pieces, to Isaac's point, this is a team sport. This is not an individual sport.

You have an organization for a reason. You need to bring that organization along. You need to help them be as successful as you want to be successful because if they're not, you won't be.

It's important to get those table stakes underfoot. Once you do that, then start looking at the opportunities to engage from a business perspective.

The first thing I would do is just ask yourself, where can I provide the greatest value the quickest? Speed comes into play, value, business value. Forget about technology value. Just saying that you can do something faster or you can become more flexible in doing it, that's not going to cut it anymore.

You have to have some tangible outcome in the work you do and there has to be a very clear line of sight in doing it. Start there. Show that you can execute on that, that your team can execute on that, and it will grow from there.

From experience, you'll end up with more resources than you know what to do with. That's a great place to be but you have to do it in a meaningful way, and you have to be mindful of what the rest of the organization is doing.

If you're not in tune with the rest of the organization, you could be thinking, "Okay, I'm aligned in a certain way but now I'm way off in the distance and the company went over this way." Especially in this day and age where we're changing on a dime multiple times every week, it's incredibly important to stay in tune with that.

Role of the CIO in marketing strategy

Michael Krigsman: Wayne Anderson says, "How does a transformational CIO adjust to a defensive market like we're in today? What changes in the role, in the thinking, when the market is struggling?"

Tim Crawford: It comes back to your perspective, your lens that you're looking through. I would look at it as, sure, there are aspects that are defensive, but I think this is greatest opportunity for CIOs and businesses to employ technology.

Being able to bring data into the mix, we haven't been able to do that in a meaningful way in the past. We should have but, now more than ever, let's do that.

The second thing is, you can actually start taking risks today that you couldn't take a year ago. Now, with our business down, now is the time to take these big bets.

If something goes sideways, number one, people are giving out hall passes. They're going, "You know what? We're all dealing with the pandemic. It's okay. Just get things together, learn from it, and move on."

If that same kind of going sideways event were to happen a year ago or a year from now or two years from now when things have started to recover, you're not going to get that luxury. You're not going to have that ability. Now is the time to kind of double down on accelerating those innovations and finding ways to put yourself in an offensive position as opposed to a defensive position.

I think there are opportunities across the industries to do this, whether it's education, oil and gas, healthcare, financial services, high-tech. All of them have opportunities to do this and the transformational CIO is the lynchpin to be able to move that forward.

Isaac Sacolick: I think you are looking for places to be offensive, particularly in down markets. Think about yourself and your needs have changed dramatically from a year ago. Even in a B2B world, their needs have changed dramatically.

It's almost like a big record scratch. Everything that was our source of belief in terms of what was important changed back in March, and that creates opportunity. It's not just a defensive matter. It's an offensive matter.

Also, the rules of operating have changed. If we talked a year ago about this time, we would have never guessed this shift to remote working. The organizations that are figuring that out faster, they're figuring out how to use collaboration tools, how to be innovative during this period of time, they're going to get some edges over everybody else.

Tim Crawford: Yep.

Isaac Sacolick: The perfect time to really stretch what you're doing. You have to do it in an empathetic way. People are going through different situations.

There was a question earlier about portfolio and demands. You really have to be smart about how many different things you're assigning to teams and people and be very selective about the projects you go after. But you can really get an advantage when people can work remotely and have fewer distractions that they were having in their offices.

CIO transformation beyond cloud migration strategy

Michael Krigsman: Ben Haines, who we all know is a CIO and he's been on this show several times, is saying, "When you talk about a transformational CIO, it seems like a simplistic term because there is no implication of being forward-thinking and business-driven. Transformation simply means changed. Oh, I've moved from on-prem to the cloud. Let me pat myself on the back. What about that dimension?"

Tim Crawford: It's not. It's not. We only have so much time to talk about what it is and what it isn't, but the reality is the transformational CIO is an incredibly complicated being and it's a being, a culture, and a person that's evolving over time.

It's not where you go from A to B and you're done. It's A to B to C to C prime to D to D prime to E to F to Z to R to S to M.

Isaac Sacolick: [Laughter]

Tim Crawford: You're having to jump around, just like our business changes.

I go back to what I was saying earlier about the organization needs to be organic. It needs to evolve. So does your thinking as an IT leader.

The transformational CIO understands that but understands that, like we talk about the new normal, there won't be any one new normal. There will be a collection of them and they will evolve over time and evolve again and again and again.

It's really a changing of the mindset. Yes, we boil it down to try and communicate it. But the reality is, all of the traits, if you were to map out each of the different traits, it's an incredibly long list. I know Ben knows that but, for those that are listening, it is a complicated conversation to have.

Isaac Sacolick: Ben is one of the top CIOs I know out there and he's right. Look. If you look at anything that you're trying to do as a CIO and it's taking something you do today and targeting to make it work better, that's probably not transformational.

Tim Crawford: No.

Isaac Sacolick: That's just the transition from one efficiency to another efficiency, one set of problems probably to a new set of problems. That transformational CIO, when Tim and I are talking about growth and customers and data, it's because you're changing the rules by which the organization is behaving and what you're going after.

Tim Crawford: Yep.

Isaac Sacolick: It's hard to explain it in words, but if you're just shifting to e-commerce and you're a brick and mortar, okay, so you have a new sales channel and you have a new way to market it. You're engaging with customers in a completely different way and you're offering a different set of services. You're selling services instead of products. You're doing subscription models against those products.

Now you have a whole customer service and retention angle against that. You have to sell that very differently. You have to be able to measure the engagement level of your customers through a subscription model. Those are game-changers.

You might be a brick and mortar company and now part of your model includes offering technology or selling some of your data back to them in anonymous ways. Those are game-changers. That's what we're talking about when we're thinking transformation.

When you're thinking a few years down the road, part of that role of the CIO is any label in technology is going to have tens, hundreds, or thousands of choices. Do you build something on a public cloud or you do it in the private cloud? Do you do it with a partner? Do you do it with cultivating the skillset internally to use a low-code platform?

Picking those choices in a way that becomes sustainable platforms that you can continue to do agile and oriented improvements, these are the things that the CIO has to do some of the prediction through and say, "This is where the market is going. That's where I'm putting my bet here."

Tim Crawford: One quick thing on that and then, Michael, I'll turn it back to you. The one quick thing on that is it's not just that the CIO is doing that. It's that they have developed an organization around them that can also do that. That is just as important as them being able to do it.

Balancing innovation and maintenance in information technology

Michael Krigsman: Lisbeth Shaw has a great question. She says, "How does a transformational CIO define the right kind of innovative strategy given the constraints that most companies are dealing with?" I think that this is important because it gets right to the heart of how do you manage the day-to-day realities of the grind of IT and still be transformational and still invest in innovation.

Isaac Sacolick: Constraints are really important. I think that's what drives innovation and I think that's what drives competitiveness within the group. If you have an open checkbook, you're buying lots of things and probably not getting value out of it.

Part of innovation, when you're under constraints is, how do you extend the walls of IT outside of IT? When we talk about self-service data capabilities or citizen development programs, a lot of that is saying it's really about the impact that technology makes and how the IT group enables that but doesn't necessarily mean all the solutions and the innovation have to be built and managed in IT.

Tim Crawford: I think constraint is good. I had the opportunity to work for an organization. Unlike most IT orgs where you are constrained by budget, this particular organization I was not constrained by budget. I had more money than I knew what to do with. I will say that that is actually a worse problem to have than the constraint because it causes you and your organization to stop thinking and making decisions in smart and clever ways.

I think, especially right now where companies are trying to preserve cash, they're trying to cut spend as much as possible. We have to think about more clever ways to manage It but it's also forcing us to get more innovative where we place our bets.

We have to think more clearly on what is that direct connection. How can we make every dollar count or every euro count or whatever currency that you work in? How can you make every piece of work that you do really count the most? That causes you to focus and make decisions in a very different way.

Cybersecurity and the CIO role

Michael Krigsman: Shelly Lucas tosses up two separate issues. Let's take them in turn. Number one, the role of cybersecurity in the transformational CIO's offensive agenda in a defensive market.

Tim Crawford: Cybersecurity is so complicated and it's on the minds of every board member now more than ever. Risk is something that has to be managed. You have to take the offensive on it. You absolutely do, especially as we push people to work from home, running on networks that we don't manage, running on equipment that don't have standard configurations.

There is a reckoning day coming for us and we all know it. Those of us that are in the trenches, we know it. We have to get aggressive with it and we have to be smart about where we spend the dollars to do it.

If you were to just bring in a whole bunch of tools and cobble them together, that's not going to solve it. If anything, it'll cause you to head for bankruptcy. I think you do have to take an offensive measure and there are a lot of strategies, a lot of thinking around how to take those strategies and apply them.

Customer experience and the CIO role

Michael Krigsman: Isaac, Shelly Lucas also raises the issue of customer experience, which is a topic that you and Tim spoke about a few minutes ago, the role of customer experience in the transformational CIO.

Isaac Sacolick: It starts with developing who your customer is, your segments, and your personas and partnering with parts of the business that have a vested interest in this. Usually, it's a product group or a marketing group.

I think a key area for the CIO is around measurement and being able to illustrate where customers are experiencing product. I think projects like Customer 360 projects are really important around that. Ultimately, it's around providing a mechanism for capturing feedback, doing an experiment, finding out what the impact is with the customer, and then readjusting your strategy around it.

Culture change and the transformational CIO

Michael Krigsman: Shahid Masood asks, "Organizational transformation or digital transformation involves culture change. Besides managing the technology change, how can we manage this cultural change effectively to help staff embrace new technologies and processes?"

Tim Crawford: Legacy is one piece you have to think about. First and foremost, start with business transformation. Never start with digital transformation.

If you're starting with digital transformation, that's a fool's errand. You have to think about how your business is evolving and use that as your North Star.

From there, you start to understand, as I said earlier, how you can align the decisions you make and the strategies you put in place for IT and your organization can align with that business transformation. Now you can start to determine how processes, how organizations, how the culture needs to change, how the people need to change.

Some of those folks are along for the ride. Some of those folks will come with you. They will evolve, but you have to be realistic and understand that there are some folks in your organization that they will not come for the ride. That's a tough conversation to have but it's a reality that we all have faced as leaders.

You have to do that parsing exercise to find the right alignment and the right organization to carry you into the future. But it starts with having a vision that is clear, aligns with your business, aligns with where the customer is headed, and that people really understand it in their terms.

Michael Krigsman: Arsalan Khan says, "So, the nature of a CIO's work has shifted from traditional CIO to transformational/consultative. Is the next phase to be CEO since most companies are trying to call themselves tech companies now?" Isaac, thoughts on that?

Isaac Sacolick: It takes a very special set of skills to go from a leadership position in IT to being a CIO. The same thing is true going from a CIO to a CEO. If you have that growth mindset, if you understand your industry very well, you understand what customers are looking for, and you develop that board relationship, that is where that potential can come from. It comes from really understanding growth and customers.

Advice for Chief Information Officers

Michael Krigsman: What advice do you have for CIOs today, moving into early next year, dealing with all the stuff that we're dealing with, how to maintain and be a transformational CIO in the face of all of these obstacles, and what are the opportunities?

Isaac Sacolick: It's about focus right now and focusing on fewer things but executing them well. We're not trying to spin up innovation labs for the sake of innovation. We're not trying to take a 2,000-person IT group and spread them across 200 initiatives.

Pick the ones that are truly going to drive growth, customer experience, and data and analytics and execute them well. I think that's one big part of it.

Then also, to follow up to an earlier question, to really get more people in the organization changing behavior and changing their practices, focus on learning. The job people are doing today is going to evolve dramatically over the next few years. If you're an IT stuck on a technology or if you're in business and stuck on a certain business process, learning and pushing learning is a great way for people to expand and look at different ways from a different lens.

Tim Crawford: Let's get really pragmatic about this. Number one, understand your customer. Number two, understand your business. How is your business evolving to be able to meet that customer today and how that customer is evolving. Then number three is, what pieces of data and technology are going to help that process and that business transformation take place? Focus there.

The rest of it, quite frankly, can slide by the wayside at this stage because you're not going to be able to do it all. But if you focus on those pieces and, as Isaac said, you do it well, that will then give you the air cover to be able to do other things.

For right now, in this pandemic, in this economic downturn, we have to focus on what matters most. What matters most is the customer, it's our stakeholders, it's our business, and being able to do that in a meaningful way at a reduced spend level. That's where innovation comes into play, strategic innovation comes into play, using data, artificial intelligence, machine learning, and automation in smart ways, not just applying it like peanut butter, but be very smart about how you use technology.

Michael Krigsman: Another comment from Twitter, and this is from Paige Francis. She points out: "Keep the focus more on business outcomes and less on the need for ego-stroking. The foundation must be strong. Own it. A low bar is the best bar to start with."

Tim Crawford: I'll call it out. I had the opportunity to present at a Women in Technology conference a year or so ago. One of the things I said on stage was, "IT is an old boys' club. It is what it is."

One of the things that that tends to spawn off is this egocentric culture. We have to get beyond that. We have to bring diversity into the mix. Diversity is a strength, not a weakness. We have to change the way we think about our teams, our people, and our staff and the value that we deliver to the organization.

I really welcome. I've interacted with Paige a number of times. I really love her thinking, and so I would welcome more of that.

Isaac Sacolick: The entire industry needs a little bit of humility and humbleness. That's part of learning and part of helping your staff learn about how the business is operating.

That means that you can ask questions and that means that when you put people on teams and you create agile structures, there's collaboration, and there's diversity built into that thinking. We know the statistics that diverse teams perform better.

Michael Krigsman: Shahid Masood says, "What is required for him to upgrade himself from an IT director role to a transformational CIO role?"

Tim Crawford: The gap between CIO and one level below CIO is the biggest and hardest gap to cross in the IT organization – full stop. It's always been that way.

The best thing you can do is go back to the fundamentals that Isaac and I have both talked about. Educate yourself on the business. Educate yourself on what your organization does, what it should do, what it shouldn't do.

Understand what are sacred cows in your organization, too. Understand things that you're doing that you've always been doing it and you're continuing to do it but maybe you shouldn't do it.

I think, again, that North Star is your customer and your business. When you start evolving and changing the way A) you talk, so the language you use, B) how you execute and what you execute on, people will start to notice pretty quickly.

There is a wanted thirst across the organization for someone who can bring technology and data to the forefront, so don't think that people don't want it. People are desperate for it. They just don't know how to ask for it. If you can start to demonstrate that you can deliver on those principles that we've talked about in the last 45 minutes or so, you will start to get noticed and magical things will start to happen.

Michael Krigsman: Another question from Ben Haynes, "What skills should a CIO be recruiting for in his or her leadership team now?" Isaac?

Isaac Sacolick: Leaders need to be highly versatile in the different areas that you're assigning them. I'm going to try to put the two questions together.

You need people on your team who are willing to get out of their comfort zones. I'm going to hire a head of app dev. I'm going to hire a chief data officer. I'm going to hire maybe a head of product. Then there are going to be a lot of things that fall into the gap.

The first is, if you want to be positioning yourself as somebody who has CIO potential, in addition to the things that we've talked about, get out of your comfort zone. If you've been a head of enterprise architect for 15 years, you're not CIO material because you haven't gotten out of your comfort zone.

It's building up three or four different skilled areas, working in different areas of the business. That's going to show that diversity of thought, skill, and practices that a CIO needs. That's essentially what the CIO needs as well.

If you hire a head of security, for example – a very important role – if that head of security isn't interfacing with the business and figuring out how to make sure that you can impact the business but also maintain risk, it's not going to work very well.

CIOs have to look at those skills that are versatile but also look at skills that complement what they do well. If I'm not good at managing cloud or I'm not good at managing quality, look for people who are going to complement your skillsets.

Tim Crawford: Look for someone like an Isaac or a Tim. Maybe Isaac has a background in applications and Tim has a background in infrastructure. Okay, but can I take Tim and put him in charge of applications and how well would he do? The same thing for Isaac. You need to have people that can pick up these other areas, do them well, and lead those teams.

Again, I think it's more soft skills than hard skills, but look at the networks that they bring around them. Who follows them? It's not just CIOs here. Even lieutenants and people further in, who is looking to them for advice and leadership? Those are the folks that I would really look for.

Michael Krigsman: We have one more question coming in from Brian Lilly. He says, "How to lead IT, the leadership qualities, the best practices in a globally distributed organization that is probably not coming back to the office any time soon." The leadership in a distributed environment, how do you do it? What advice do you have? What are your thoughts?

Isaac Sacolick: I think it's about setting principles so that people in your organization can make decisions and work collaboratively together. You think about the world a year ago. You could get on planes 12 times a year and visit different offices, get in front of customers, or go to a tradeshow and learn something. All that is much more difficult today.

You could have a meeting for eight hours to get to a consensus around something. It might have been inefficient, but you got to an answer around something. That's very difficult to do today.

I look at how are you empowering your teams to understand what's important, what are their guardrails, how they should make decisions, how they're collaborating, and where they're making some wrong turns that they can course correct. As a leader, you have to set those principles and what's important and give your teams the room to actually execute after that.

Tim Crawford: The other piece to that, and I'll go to a mutual friend that Brian and I both have. He's a fellow CIO as well. He couldn't get on a plane and go to Asia to meet with his staff, but he could get on Zoom or video conferencing and start to understand what they're going through.

Not everything is about business. It's about the people too. Let's face it. Isaac and I meet in New York City and we might talk about business, but we're also going to talk about, "Hey, how are the kids? How are things going for you?"

You have to find ways to learn more about the people and what makes them tick as well. That connection, that personal connection, is something that is much harder to do at a distance but it's something that we as leaders have to do. We have to find ways to create that connective tissue with our leadership teams and with our staff.

They have to be part of that equation and they have to understand the reasons why. When you start to head down that path, it really creates a completely different dynamic and a different relationship you have with those folks. Again, it comes back to soft skills more so than hard skills.

Michael Krigsman: All right. I think our show for today is done. We'll have to do it again. We've been speaking with Isaac Sacolick and Tim Crawford. Gentlemen, thank you so much for taking your time and doing this today with us.

Isaac Sacolick: Great being on the show with you, Tim. It's always an honor being with you.

Tim Crawford: It's always a pleasure. I look forward to the next time.

Michael Krigsman: Everybody, thank you so much for watching. Thank you particularly to the people who joined in and asked questions. Check out We have great shows coming up. Be sure to subscribe to our YouTube channel and subscribe to our newsletter. Do it.

Thanks so much, everybody. I hope you have a great day, and we'll see you again next time. Bye-bye.

Published Date: Oct 30, 2020

Author: Michael Krigsman

Episode ID: 676