Companies have adopted, improved, and innovated technologically to fit business needs for hundreds of years. Now, we are living in a moment that will be historic as CIOs move entire companies from on-prem to online.

In this episode, Tim Flower and Thomas McGrath of Nexthink speak with Martha Heller, CEO of Heller Search Associates, on episode 3 of the Digital Employee Experience podcast. After speaking with numerous CIOs before and during the pandemic, Martha shares what she has seen on the front lines of these executive roles and…

  • The CIO Paradox
  • Digital Transformation as a Team Sport
  • Re-Inventing Company Culture

For more information on CIOs and how decisions are driving organizations to be more technology enabled, Nexthink has an on-demand webinar for listeners of today’s show put on by Slater and Gordon’s IT team. For more information, head over to or LinkedIn to stay connected!

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Speaker 1 (00:01):
You’re listening to Digital Employee Experience, a show for IT change-makers. Let’s get into the show.

Tom McGrath (00:09):
Hello change-makers. I’m Tom McGrath, with me as ever is Tim Flower. Tim, how is it going? What’s keeping you busy this week?

Tim Flower (00:15):
Hey, Tom, I’m doing really well. Thanks for asking. Plenty keeping us all busy right now, right? But it’s all really good stuff. And I’m really looking forward to talking with our guest today.

Tom McGrath (00:23):
Well, before we do, let me admit to something. I have done something I think is known as LinkedIn stalking you. And I’ve seen with my own two eyes that you’ve got a very distinguished career, but I didn’t see the letters CIO there on your work history. Why is that Tim? Did that amount of power scare you? Is it still on the Tim Flower career bucket list? What’s the explanation?

Tim Flower (00:43):
No, it’s not on the bucket list. There are different ways to look at your technology career, right? One is to stay close to the action, stay close to both the employees, and staff, and the technology. You’ll be a leader in that way or climb the corporate ladder. I’m not the corporate ladder kind of guy right? I really like the frontline action.

Tom McGrath (01:06):
Fair enough, Tim, fair enough. Power obviously not for everyone then, but if you do aspire to sit on IT’s iron throne, already do so perhaps, today’s episode is a must hear. After all our guest, Martha Heller has written two hugely influential books on the Modern CIO, The CIO Paradox: Battling the Contradictions of IT Leadership, and Be the Business: CIOs in the New Era of IT. She is also, and not least, the founder and president of Heller Search Associates, a recruiting firm specializing in CIO and IT leadership roles. Martha Heller, welcome to the show.

Martha Heller (01:41):
Thanks, it’s great to be here.

Tom McGrath (01:42):
Martha, The CIO Paradox, could you begin please by telling us what it is, and comment as to whether 2020 has started to resolve the tensions and contradictions in the role or exacerbate them?

Martha Heller (01:56):
Absolutely. So, the CIO Paradox is really… the concept is just that the CIO role is being set by a series of contradictory forces. Those contradictory forces are always there, they don’t go away, but successful CEOs learn how to manage through them. Just as a couple of examples, security versus innovation. Absolutely nothing can go wrong from a risk management perspective. Everything we do has to be risk-free or be able to be managed from a risk perspective, you can’t leave any holes and it has to be highly secure. But you’re also accountable for trying new things, throwing things at the wall. Hey, if it fails, it fails. How can I be accountable for a function that can never fail and yet also build a culture of fast failure into my organization, smart failure? That’s a paradox. It exists, it’s important, but it never goes away.

Martha Heller (02:43):
Another I call the futurist archivist paradox. As CIO, I’m accountable for the future of the company, because what we invest in today is either going to be wonderful for us or restrictive for us in the future. And it’s my job to define our technology future, which is the future of our company. But I’ve also got to deal with decisions made about a legacy system, made probably 10 years before I even joined the company. So that’s an example of a paradox, but the one that is really my favorite because it speaks to the challenge of being a CIO is what I call the accountability versus ownership paradox.

Martha Heller (03:17):
So just a little story, I would get up in front of a crowd of CIOs, and I would mention an IT project and somebody would raise their hand and say, “Well, in my company, there are no IT projects. There are only business projects. That’s how we conceptualize all of our projects,” but I think, okay, those are pretty words. But then a week later when that CIO calls me and says, “Hey, I’ve been let go because our ERP project went south,” I think, huh? Why are you the one holding the bag? I thought that was just a business project? And so the paradox there is that CIOs are so often accountable for driving technology adoption, for a certain return on investment of technology decisions, when in fact they don’t own those teams that are actually going to adopt those technologies. That to me is the most pernicious of the paradoxes. But in terms of the latter part of your question, and has the pandemic exacerbated that, I would say absolutely it has. Because now we’re relying on technology even more.

Martha Heller (04:16):
So any of the challenges of the CIO role are going to become more acute. That being said, it has also given the CIO some relief regarding these paradoxes. Because of the pandemic CEOs who have been resistant to letting employees work remotely, CEOs who have been resistant to adding a stream of maybe digital products to their product line, they’re over the hump. Because for CEOs who say, “Oh, we can only sell our product with a handshake.” Well, there’s no handshakes happening right now, so those CEOs have to get over the hump. So I would say the pandemic has not resolved any of these paradoxes. They never will be resolved. But what the pandemic has done is it’s made CEOs see the value of technology investments in an area where they previously have not. And anytime you get a CEO who has an appetite for increased technology investment and for technology adoption within their companies, that’s good for the CIO.

Tim Flower (05:16):
When you look at the paradox, if you think of it as a pendulum, right, and we’ll take the one paradox of taking a greater risk versus playing it safe. How do you think that plays out in a business? Is it driven by the mindset of the CEO or of the business leaders that says, “Hey, we can’t play it safe. We’ve got to go down this more aggressive approach,” which kind of puts the CIO at risk. But they’re almost in a place now where they’ve got to not only take the risk, but taking that risk means they need to be more technically astute about what that path looks like. Do you think it’s driven by business and CEO, or how much of the CIO really have a say?

Martha Heller (05:48):
From my perspective, the CIO needs always to be pushing the boundaries, knowing what’s possible. If we did this, we did this. Let me explain to you how we can push the dial while at the same time investing in the security that’s going to allow us to reduce our risk. It is up to the CIO to align with other executives who agree with that perspective, and then to present in a very data informed way to the CEO. And then it’s about getting the board on board. So the CIO is not in a vacuum going to make a unilateral decision about risk-taking and investing in new technologies. But if the CIO is sitting around waiting for somebody else to stick their neck out and take that risk, then the business will not evolve and will likely fail. So it’s the CIO, who’s got to get it going. But if the CIO finds that he or she is the only one in support of an idea, it’ll never get executed.

Tim Flower (06:44):
And you’ve been at this research for a while now, do you think over the last 10 months, the pandemic, and when we say pandemic, we equate it to remote work, but do you think the pandemic accelerated this evolution of the CIO? Or is this something that was already underway because of technology evolution? What’s your thought of the last 10 to 12 months on the acceleration?

Martha Heller (07:02):
Sure. So this is what I think happened in the last 10 to 12 months, and you’re right. We think of the pandemic as remote, but it’s not, it’s also acceleration of a digital agenda, which is about customer interaction, which is about products and all of that. I think what happened was in March, the CIOs really stopped working on their high value digital agendas and just got everybody remote, which was obviously a tremendous effort. And I really did a whole listening tour of Fortune 500 CIOs for several months at the beginning of the pandemic, and it sounded like things went pretty well. There were a couple of disaster recovery plans that people wish they had that they didn’t have, but people got remote pretty easily.

Martha Heller (07:40):
And then CEOs looked at their CIO and said, wow, that was pretty impressive. I have a degree of trust in my CIO now. And I anoint him or her with leading the charge on our digital agenda, because I can’t meet with customers anymore. We better get that digital agenda off the ground. So I think the last couple of months have been very, very good for CIOs, in that they’ve had an opportunity to perform in a crisis mode and they, for the most part, from what I can tell delivered on that. And so now there’s been a lot of trust. But what I will also say is that, speaking personally, in March when all this came down, I thought, oh, what happens to an executive search firm during a pandemic? And during a likely recession that’s going to come from that? And I called my brother, who’s a bankruptcy lawyer, and I said, okay, this business has been great for 10 years. What’s going to happen now? Walk me through it.

Martha Heller (08:31):
And before he got a chance to advise me, we started signing searches left and right, to the point where we had a stronger year in 2020 than I even anticipated back in 2019. So what happened? What happened was, some CEOs were not so pleased with how their IT leadership team thought to manage the crisis, and those CEOs have been invited to pursue employment elsewhere. But I think what has also happened is CIOs have had a chance to see how their executive colleagues handle a crisis. And if this pandemic isn’t enough to get CEOs, and boards, and executive committees, to think things are different now, not just because of the pandemic, but because we’re no longer in an industrial economy. We’re in a digital economy. If we don’t change things dramatically, we won’t succeed regardless of when the pandemic subsides. So I think a lot of CIOs have said, huh, I may walk to another opportunity where that executive committee sees the future in the way that I do.

Tim Flower (09:30):
That’s a great point. The trust in the CIO and the reputation that the CIO has built is a double-edged sword, right? You’ve got that trust and confidence internally, but now it’s also a resume builder and you can go pitch that to someone who actually direly needs your expertise.

Martha Heller (09:45):
That’s exactly right. Trust takes a long time to build, but just a second to lose. So taking the trust that your company has in you and now parlaying that into a new role is a sound strategy. But I think what’s also happening is CIOs who decided to stick around in their roles are now able to move forward on some investments that they had met too much resistance prior.

Tim Flower (10:10):
So let’s talk a little bit about that. The CIO that had a significant project in front of him that he put on hold, he or she put on hold, addressed the remote work and the business continuity planning that they needed to put into place. Now it gets back to that digital transformation project that was put on hold. Are they looking at it any differently? Is there a different approach to now collaborating with the business, pulling off a big project in the new world versus the old world?

Martha Heller (10:35):
It’s so funny that you asked that. One of the questions that I asked on my listening tour is, what have you learned about your team, your organization, your capabilities? And I learned how much we can accomplish if we work together. I learned how having a life and death goal, which is what we literally had, right. Getting people home safely is a matter of life and death. I learned what a motivator that is. I’ve never seen my team move like this. I’ve never seen our 80,000 employee population adopt a new technology as fast as everybody adopted Zoom or Teams or whatever we’re using. So my question then to them is, okay, great. How do you keep all of that speed and collaboration and productivity when you don’t have the life or death burning platform? When the burning platform is simply growth, revenue, and customer acquisition, say, and not we’re in the middle of a real healthcare crisis. How do you keep that motivation going?

Martha Heller (11:36):
And every one of them said, good question. We’re working on that. So I’m very hopeful that the leadership lessons learned during the last several months can be applied to the future without that healthcare crisis. But to answer your question more directly, I don’t think that the way companies and CIOs approach digital transformation, digital investments, all of that, is going to change dramatically, as organizationally, structurally, as a result of the pandemic. But I do think that the collaborative nature of a culture has gotten a boost. I’ll say that in a better way. Digital transformation is a team sport. IT can’t lead it, the business can’t do it on their own. Everybody’s got to work together. That’s hard because we grew up in an industrial environment where it’s all about silos and specialization, and I do my thing, and you do your thing, and I know what I’m accountable for.

Martha Heller (12:33):
Well, all of a sudden in a digital or data economy, everything has to be collaborative. Everything has to be cross-functional. Everything has to be a team sport. That is a really, really hard culture to build if it hasn’t been your past. Well, during the pandemic, we all worked collaboratively. There were crisis management teams. There was no stopping and saying, wait a minute, what am I accountable for? What are you accountable for? So harnessing that, the culture of collaboration is alive and well in the pandemic. So I don’t think it’s a new approach to digital. I think it’s a stronger sense of collaboration, which is the right approach to digital.

Tim Flower (13:09):
Yeah. And I’ve seen that too. And IT collaborating with partners that we don’t normally collaborate with, like HR, when you’ve now gone from 10,000 people in one office to 10,000 offices, all with one person, you’ve got a different environment. And HR really needs to start thinking about employee wellness and wellbeing. Businesses is concerned about not only productivity of employees, but quality. And do you think that those things now are starting to… If the transformation projects in execution don’t change all that much, other than collaboration, do you see investment decisions on which transformation projects to actually pursue changing? In other words, is it all about revenue, profit, and risk mitigation, or does the employee experience, employee wellness, employee turnover, does that now start to also guide some investment decisions?

Martha Heller (13:58):
It’s a great question. I’m going to give you first my cynical response. The only reason employee happiness matters is for productivity and revenue and profit. The reason the board cares about the happiness of a plant worker is because they want that product out to the customers. But at the same time, I think that the… Let me say it this way. Corporate cultures, which are all about employees, are built over time, and companies tend to take those cultures very seriously. Right? It’s a very important thing to them. And I remember I was just in a blog interview with the CIO of Jet Blue, and he was sitting in some random office at Jet Blue. There was nobody in the building. It was just him, and behind him on the wall where their values, integrity, whatever those values are.

Martha Heller (14:43):
But the last one was fun, with an exclamation point. And I looked at him and I said, “How much fun are you having right now?” And he said, “Not a lot. I like to be with people.” So, if we are back to the office in let’s call it June, I think companies will just continue along with the cultures and the values that they’ve always had. And the employee engagement that they’ve always had. If we are permanently changed as a result of this, and I don’t know who knows the answer to this, but if we’re permanently changed and we’re really not coming back to the office in the same way, we’re going to have a much greater percentage of remote work. Companies need to reinvent their culture. You can’t just say, oh, it’s the same culture, except now we never see each other. What kind of culture is that?

Martha Heller (15:23):
So I think the pandemic, to go back to your question of, investments are so often around the customer and product and all of that, and efficiencies, what about investments and employee engagement? I do think we’re going to see more priority on employee engagement, because we’ve got to figure out how we’re one company when we’re not all together. So rather than thinking of it as investing in the employee, I think of it as investing in a newly digital culture, which takes some real technology.

Tom McGrath (15:51):
If it doesn’t the whole question of employee experience become absorbed to a large extent by digital employee experience, if everybody’s working remotely, and what are the implications of that on the CIO’s duties and oversight?

Martha Heller (16:05):
I mean, in some ways it makes the CIO’s role harder. It used to be just give them a laptop, give them the phone, a couple of systems, they’re fine. But now… Let me give you a great example that a colleague of mine just mentioned to me. So this was the CTO of a huge healthcare plan. They’ve got about 80,000 employees. It’s, I don’t know, a hundred billion dollar company, something like that. And he said everybody came to work. They had cubicles and all of that, and if somebody had an issue with some kind of system, somebody would pop their head out of the cubicle, look around and say, is anybody else having trouble logging into the yada yada? And everybody would say, yes. One call goes to the help desk. One call goes to service desk. We here in sector G are having issues.

Martha Heller (16:49):
Now, because everybody’s home. Everybody makes the call. Everybody calls the service desk. So internal, call center help desk tickets have spiked for companies, because you don’t have word of mouth anymore. And so it was earlier this week that I had that conversation and I thought, boy, that’s an unexpected implication.

Tim Flower (17:09):

Martha Heller (17:10):
So I think in some ways, look, when you have a culture that is hungry for the technology that you’re giving to them, your job is easier. But when you have a culture where everybody is relying on technology all of a sudden, in a way that they haven’t in the past, your job gets a little harder. The pandemic has been good for CIOs because the appetite for technology investment and adoption is higher. That I would say is the punchline. It doesn’t mean that there aren’t lots of little challenges and difficulties along the way, like call center volume spiking.

Tim Flower (17:45):
It feels also like the appetite for risk is also higher, right? There’s more tolerance for taking a risk and maybe stumbling along the way because we’re in such extreme times. Are you seeing that as well?

Martha Heller (17:58):
It’s interesting because I see both sides of it. So what we do here at Heller Search is executive search. So I write blogs. I interview CIOs all day long. I’ve been doing that for a very long time, but that doesn’t pay the bills, right? What pays the bills is executive search. So that’s where I spend a lot of my time, as does my team. And one of the things we’re noticing is a little trepidatiousness on the part of the CIO community. And we recruit at other levels, right? VPs of this, that, and the other, where there’s some risk of me leaving this role right now, because I know what I know.

Tim Flower (18:33):

Martha Heller (18:34):
I’ve seen my team, my leadership team, in action. I’ve seen the executive committee, I’ve seen the board and the way they work, and I don’t know about, if I go join your company, what am I going to find there? And also relocation, right now is real challenging. Because if I’ve got a kid in junior high school who makes friends through playing sports, how am I moving right now when that kid is not going to have that opportunity? So it’s interesting. The minute you saw, when you said the word risk, I thought I’m seeing actually lower risk tolerance out in the market. But I think that’s more about me and my personal career, and how much risk am I going to take right now. When it comes to taking risks, I think risk management is alive and well and companies don’t like to take risks. I don’t know if COVID has changed that. I will say, though, that CEOs who do not believe, have never believed, that a digital product will sell, now are taking a risk on that kind of thing.

Tim Flower (19:31):
Yeah, so I think what we might be able to say here then is whether there is risk or if the risk has been mitigated, CEO’s in today’s age still need to be adaptable. They need to adapt. And they also need to push their entire technology team and portfolio to adapt as well. If we put ourselves in the seat of a CIO that’s not necessarily successful in doing that, do you see other CXOs? And you mentioned that the CTO big player in large corporations, we’ve got a great customer at Liberty Mutual. They’ve got a chief experience officer, the CXO, you mentioned the digital officer. Do you see these new CXO roles starting to take a piece of the CIO’s pie? Or do you see them as just more collaboration partners?

Martha Heller (20:24):
I see them taking a piece of the CIO’s pie, and I see that as a good thing. So, I interviewed the chief digital officer and the chief information officer of Nationwide. I did a blog with both of them. And I thought, huh, this is going to be interesting. What is the CIO responsible for versus the chief digital officer? And it was very, very clear. The chief digital officer has the digital product roadmap. We need an Apple watch app. We need one login, as opposed to three. We need a way to sell our incredibly complicated insurance product to a younger generation with only three clicks. We need to price it this way, we need to deliver it to the market this way. But I got to tell you, CIO, I got no idea what the underlying technology is. I don’t know what the architecture is behind that thing. I don’t know how to get that up.

Martha Heller (21:13):
But still, the CIO can still be a visionary and say, microservices architecture, there’s the vision. We’re going to put in a data lake, and we’re going to put in a data integration layer, and we’re going to… There’s vision there, but it’s vision on what are the engines that allow that chief digital officer to get those products into that market fast. Now that’s how Nationwide, but I just talked to a CIO of a higher ed company, right? They’re switching from being a print company to being a digital company. She happens to have an engineering background, she’s old IT, and she’s the chief digital officer. She’s got a whole product development. So some of it depends on the business. Some of it depends on the actual players. They have a CIO who has an engineering background and can be a head of product development, great. It’s one goal.

Martha Heller (21:59):
But I do see CIO, CTOs, chief digital officers, chief product officers, chief data officers. I do see them taking some of the CIO’s responsibility. And I say good, because when the company becomes a technology company and you’re the head of technology, boy, that’s a lot of responsibility. I think of it as the democratization of IT. It can’t all belong to me anymore. The more my plant managers can do self-service RPA, the better. We’re doing a search right now for the same company, two roles. One is a VP of digital engagement. That role reports into IT, into the CIO. And the other is a VP of marketing technology. That role reports into marketing. One’s responsible for the marketing technology stack, and the other is responsible for customers’ digital engagement with the company. Boy, those two folks better work really, really closely together. Because you don’t want two different technology strategy. But when your company becomes technology, how can the CIO have all the accountability for all technology development, adoption, demand? It would become an impossible role.

Tom McGrath (23:08):
If you’d like to hear from a CIO that really has successfully balanced and negotiated many of the paradoxes thrust upon them in 2020, and implemented an incredible experience first digital workplace for their employees, check the show notes and listen to an exclusive CMSY interview with Slater and Gordon’s John Granger. Now you will not regret it. Take care.

Speaker 1 (23:33):
To make sure that you never miss an episode, subscribe to the show on Apple podcasts, Spotify, or your favorite podcast player. And if you’re listening on Apple podcasts, make sure to leave a rating of the show. Just tap the number of stars you think the podcast deserves. If you’d like to learn more about how Nexthink can help you improve your digital employee experience, head over to Thank you so much for listening. Until next time.