🎂 Fireside Chat: Challenges IT Leaders Face Today

Hello and welcome to our executive fireside chat here on our last day of Birthday Week 2022.

My name is Rebecca Weekly and I am the VP of Hardware Systems Engineering here at Cloudflare.

And I'm so excited to be here with Roger Eisen, who is actually going to talk with us a little bit about being the CIO of a publicly traded company, some of the challenges of that domain and so many other factors.

So with no further hesitation, maybe I would you like to introduce yourself for the audience?

Very good pronunciation with the name Rebecca.

We've been practicing right now.

So first of all, first of all, thanks for having me here.

I'm very excited to be talking to all of you guys.

Yeah.

So just a little bit of myself. Maybe I'll start a little light.

So I did get into it by pure accident.

It was not part of the plan.

I studied engineering and I achieved to consistently fail all my programing classes just one after the other.

That thing did make no sense to me, only to then end up spending most of my career doing programing and software development and spending a career in it so totally don't give up.

So I spend most of the career at a company called National Instruments or and I test and measurement and software and hardware company based in Austin always in the first part of my career was primarily on the back office functions.

So helping the company scale become global supply chain, financials, all that fun stuff, always a lot of strong partnership then with business operations.

So that bridge between business and it is an area that I really enjoy.

So I spent a few years doing that.

Then I started focusing more on more the front office of customer facing capability, sales, marketing services, digital, etc.

Also through my career being the one strange person in IT that can bridge between infrastructure and business applications.

So speaking both languages and that's something that set me up really to become the CIO of an AI in 2017 and then as a CIO, maybe just areas of focus now.

So what does a CIO do or what did I do?

There was wasn't leadership so new CEO, new leadership team, completely new strategy.

So the focus is, okay, do we have the right capabilities to enable and fulfill that strategy?

So that was priority number one, making sure that all our platforms, our business capabilities were set up to enable the new company strategies, drive growth, drive and play experience, drive profitability.

Priority number two then was the internal workings of it now, so modernizing the IT organization, changing the way we operate it to increase the pace of delivery, to increase the value that we deliver to the company.

And their priority number three is employee engagement.

So that was an organization of 500 people.

How do you drive engagement through the entire organization?

We went through all of COVID.

So now whether you have 500 people distributed all around the globe, keeping them engaged, etc..

So that's something that I spent a lot of time on.

And then I left.

Oh, that was.

Oh, that was yeah, that was challenging. Well, we'll definitely dig into that.

Yeah, we'll talk about that.

And then I left earlier this year, just I needed some time off and had some personal time.

Time for myself and for my family. And then one of the things that we were talking with Rebecca before was one of the things that I started doing this summer is I'm part of a of a national CIO group.

So as part of that, there's a leadership development program.

So they're looking for mentors.

So I have started mentoring some summit leaders kind of saying, okay, what are the struggle, the struggles they're facing, the challenges they have, and how can I share some of my experiences with them and how do I learn from them, too?

So that's something that's that's a lot of fun.

And it's such a gift, right?

There's you can find a coach to help you be your best self, but it's very hard to find someone who's done the same job when you're in a senior CIO level position, senior leadership position.

How do you find that unless you have some sort of a separate mentorship circle and to have one that is so specific in domain is really it's very interesting.

It's not.

Yeah, enough, enough.

And you're there in the middle, you're facing a challenge.

You think you're the only one that's in that situation.

And reality is the things that come up are very, very common.

It doesn't mean that they're easy to address, but they're very common.

Yeah, the design pattern, which then can make you that much more successful at thinking through other ways.

So maybe let's go back to sort of the first phase of that leadership.

So you mentioned three different areas that sort of mapping the service layers that are needed for your organization, for your leadership, making sure your team is ready and prepared to deliver that, and then making sure that you have your employees engaged.

I think we're going to dig into each and every one of those and mentorship.

But just starting in that zone of the challenges you've heard, being a mentor and with other people that you've mentored, you know, what situations have you heard leaders finding most difficult?

There's two that are extremely common, and so I guess I'll I'll enumerate them first and then we can go deeper into each of them.

The first one is establishing relationships now, and the more senior the person is, then you get into relationships with executives, relations with C-suite that don't care about it, or that's the perception.

So how do you establish that report?

How do you make sure you don't go above your boss, for example, know and or how do you handle that?

You don't want to bombard a person with two different or three different people trying to tackle the same problem.

So that's one.

And then the second one is and I guess that's probably relevant to you too as well in your job now is how do you define a strategy and propose investments and secure investments for to realize that strategy for things that are not very business facing or customer facing Now, the two areas that people struggle the most data investments and infrastructure investments.

I think that's something that people struggle a lot with.

So I so resonate with that latter one.

Again, when you're in infrastructure, you have that moment of.

Really?

People should only call you if things are broken, but you constantly have to look at ways to optimize and improve.

And sometimes that takes real action.

So maybe just speaking your advice in that domain when you've been working through areas of investment in infrastructure, particularly optimization, or how have you worked to get stakeholder alignment, get business folks to say, Yeah, that makes sense, or even other engineering teams that are trying to choose between new features and new products and innovating in that domain versus just making things run better.

Yeah, I mean, I think a mistake technical people, we make very and I put myself in that same boat we make it very often is we're really focused on the technology and we don't focus enough on what is the business value, how do we translate that?

And that is really difficult.

It sounds very easy and it looks very obvious when you see somebody doing it well now, but it's not that simple.

So finding that language that you can translate something, for example, that I have, I try to help infrastructure through that was we used to be organized around technology teams and technology pillars.

So you had done a lot of a lot of technical people just managing a specific level.

Can you hear me? Yeah.

Yeah. Okay.

So you had a lot of very technical people just going very deep in the technology, but how that got applied or how a service got delivered that went across for technology pillars that was lost.

Now you also get into technology, duplication, etc..

So we, we actually change the entire infrastructure team and looked at end user services so that we could map then what's the value that we're providing to the employer, to the end user, and try to change the conversation.

Interesting, of course, makes perfect, but.

That's one thing with it.

I think there's another find a business partner.

That is struggling with the problem you're trying to address.

And that may not be very obvious in core infrastructure challenges, but in the world of data, for example, that's also very I mean, we struggle.

On justifying investments there.

I've only been able to see it work when there's been strong business partnership.

Now.

And there's times where it just seems obvious. It's like, okay, we have to do that.

But if that partner is not there.

It's just not going to work now.

And we're better off saying, you know what?

It may be the right idea.

It may be a necessary idea, but the time is not right.

We need to wait.

And we do not just be pitching ideas until we find that partner. Because again, right now, because they are the ones that will speak that business language.

They are the ones that can translate that investment into the business results and the business outcomes.

Absolutely.

Otherwise, if it's perceived as an IT problem, we're just not going to be successful.

No, it has to be for the core business and services business.

And I think that's.

Just there's another thing that where I, I see a struggle and I see us making mistakes often is.

To try to strive for perfection.

Now.

And in a world that's fast again, data to me is the perfect world for that. Because it's fuzzy, it's difficult to explain.

Now.

And we tend to want to get to that perfect state as opposed to saying, yeah, we want to get there eventually.

But how are we going to prove the value?

How are we going to prove that the things that we're wanting to improve upon are delivering the results that we believe we're going to get?

So start with a small investment.

Look at what are we trying to learn from that?

And then use that to justify additional investment.

That one is an interesting one because I've seen people talk about these moonshot concepts, Right?

We've got to get to the moon.

If you actually break down how the moonshot program in the sixties went, it took a decade of systematic, small tests to choose to get to the moon.

One step at a time.

And every single phase was a huge amount of work and a huge investment.

Maybe not, maybe more in time than in dollars, and certainly in compute capacity relative to what we can do in a cell phone today.

But really, this, I think, is such an often misused term, like it's going to be perfect, it's going to be a moonshot, it's going to be this even moonshot.

We're just steps along a path with a good, strong vision of what the test needed to be to get to that end state and alignment with stakeholders.

But I mean, so I'm talking about how do we get investment from the company?

But I have I myself have been in positions internally within it where I've had to say no to what seemed very good ideas because they were only presented in terms of that moonshot goal.

And if the person can't articulate how to get there in steps as opposed to these are all the problems we're having today, this is what's going to solve all these problems.

And it's this investment of this so many millions of dollars and so many people and so much time.

It's like I can't stand up and explain that.

And I'm a relatively technical person.

If I can't explain why we're doing these and why this is necessary, then that's a problem.

Yeah.

Yeah. Transitioning in that.

Because I totally see the stepwise function.

But other areas where the culture can get into the way of that process would be.

I'd love to hear your thoughts on that because different companies think differently about how to share data, where to share data.

If a business case matters, If this is really pure technology, what in your experience has been a common theme of how culture helps in those decision making processes?

Yeah, I mean.

So I don't know that I'm going to answer your question because maybe let me go around a little bit of a circle.

So I think where the culture of organizations also has a has an impact is you think of a team like marketing, they usually have a ton of money.

They've got a lot of vendors just knocking at their door and they just want something.

Three months ago now it's like, Hey, I've got a vendor. They can implement this thing in two weeks.

I don't need you, by the way, I've got the money for all of this.

No.

And. And that's fine.

That's the way a marketing person works now. So I think that the discussion is not so much about, Hey, no, you cannot do that.

It's understanding when is it okay to go ahead and do that?

Versus saying, Hey.

Yeah.

You want to do this thing, you want to capture this information. But by the way, your sales team.

He's also looking for the same information in their opportunity management system.

They need that, too. How are we going to get it there?

And is this what we need to do right now or.

Yep, go ahead.

But let's also work on some connection that then later on we can surface that information somewhere else.

Yeah.

Not forget about that.

Correct.

But otherwise we tend to say just no, because we see all the problems. We're so much into the weeds of all the things that can go wrong two years later that we become naysayers and that goes back into that relationship building now is, hey, how do we focus more on.

On the positives rather than the negatives.

One of my pet peeves with my team that I always use is don't say no, but say yes.

If it's such a simple transition in your head to say, Yes, we could do this.

If it is truly that urgent for this conference you're about to start.

It would be good to think about how it fits into our sales opportunity lead gen process and if we can get the data in a separate CSV at least so we can import it into that system over time, whatever whatever the process might be.

But just to just give yourself a little bit of a check before you go into the conversation and try and be a partner and advisor and enabler of what the company wants to do versus a gatekeeper because of all the ways it could go wrong.

And then on the opposite extreme, you've got the supply chain guys that have done 4000 analyzes of all the productivity that are going to gain if they can take one second away from each from build process and they've got everything already thought through and, and the impact to their internal operations is also mapped out.

So you've got all extremes and that's that's where it's not company culture only.

It's the mental organizational culture. Absolutely.

That has and getting it to stitch together and maybe changing directions to slightly.

You mentioned a little bit COVID and leading through COVID.

I'm just curious, since you've been in this role for ten, 15 years, what kind of challenges are you seeing today and how does it differ from that sort of earlier era of a decade and a half ago?

Yeah.

I mean, I think the challenge is I think there's technical challenges and then there's people challenges now.

And if we start on the technical side, it's really been the, the, the democratization of it now where let's say the marketing team can just go and swipe a credit card and in, in two days they've got something up and running now to target a specific segment of their audience now.

So it's very easy to spin up software, to spin up technology, to spin up platforms.

And also the fact that in our phones we've got beautiful pieces of software through all these applications with very rich user experiences.

That's the expectation now.

And anything that it has to deliver know that it's going to have the same richness of an experience without a lot of the manpower to do it now.

So that's that's one of the challenges.

But on the technical side, I think on the people side with COVID, it's I'm not going to lie.

It's been tough. Now, I think on our end and I we already had like I said, we had about 500 people in the organization and 65 to 70% were outside of the US.

So it was a very global team to start with now.

But the lack of face to face driving change management virtually was brutal.

Now we did a lot of organizational changes during COVID and that's in hindsight.

That was a mistake because our change management process of just going through our main hubs, sitting down with people, having a lot of discussion on why we're doing what we're doing, what it means to them, just answering questions, No, just to make sure that it sinks in.

Doing that through just a little screen when everybody is at home and they've been there for 8 hours already with a kids screaming in the back and everything.

It's just.

It's super, super challenging. So.

But then you also have to find different ways of reaching out now. So that means more videos, more proactive communication to get your message across.

And then looking at ways also of just communications not being unidirectional.

Just how do you how do you have that dialog? And that is to always yeah, that's that's tough.

I used to travel a lot to every hop and just have just open like ten people in a room, talk about anything you want know, and just talk.

And, and I lost track of that.

No, because it's.

It's kind of.

Yeah.

What's tough? So and chat rooms.

I mean, there are tools that I know lots of lots of different I.T.

teams brought in through sort of a digital transformation to try and get to less email, more interactive spaces.

In the domain of virtual world.

And for global companies, this is not a bad investment.

Probably it was a five year plan and it became a six month pull in for a lot of I.T.

environments. But it also creates security issues.

It creates retention issues.

It creates.

Did you find from that lens of technical challenges, not just the people challenges, but the others as well?

Yeah.

So from like having the tools ready for day one, I think it was March 13 of 2020, I still remember it.

We were actually ready.

So we had been for the previous year on a path to really sunset of the legacy collaboration systems and standardize at an I was a microsoft shop for that.

So those teams we had been taking a more proactive ownership of the whole internal digital transformation and standardize standardizing everything on SharePoint and teams.

So we actually had we were migrating the last business unit.

On the first well, the weekend before lockdown.

Now, the...

So that is very lucky.

We were not common.

Diana We were ready.

And that change that I talked about, about having the infrastructure teams aligned by service was also paramount on sunsetting legacy VPN solutions that we had.

And just so we were very fortunate from that perspective, we were totally ready.

So the company transitioned without a hitch from that perspective. And then we had also invested on what role that we ended up calling digital ambassadors, which were people whose job really was to evangelize and support all these tools for the company.

So how do we work virtually?

So that's an investment that we made in the budgeting cycle in closing 2019.

So again, these people were ready on day one.

So everything from the perspective we were lucky.

Had it happened one year earlier, we would have been we would have struggled now.

But then on the second part of your question, like security, I mean, that was a challenge because reality for the last X number of years, everything we had been working in cybersecurity was to protect the perimeter with employees in the office.

And now all of a sudden you've got employees that are at home and then you've got also a lot of applications that have been moving to cloud.

And a lot of the assets that used to be in the perimeter are no longer and will no longer be in the perimeter.

So it's okay.

Oops, Now we need to change.

So, well, you adapt.

And again, it goes back into what are the baby steps?

Now, it's not about, hey, I need $10 million to put a zero trust infrastructure there.

It's like, okay, this is what we're going to do first, then we're going to move to that, etc..

Now, and you talk to leadership is the right pace, etc. and you do it this way.

But and this is in journeys that customers have with us in the zero trust space, it's absolutely like that.

You start with how do you eat an elephant one bite at a time. You don't even start with the first project to make the perimeter more secure.

A different view of perimeter, a SAS model and then email and then whatever they're doing that we like.

But that was yeah, especially the, the, the employees not being in the office that, that was, that was challenging because we had a lot of hardware engineers now and so they don't even have a laptop.

No.

And yeah.

So any and remote access into a experienced network appliance. And this is also where company culture comes in.

So and I was a company where I mean the founder was all about sharing everything, share all the information, share everything.

So everything is very open now, which was great.

But then when everybody starts working at home, well, you need to I mean, and even before that, it already had started to change a lot of, okay, we need to change our policies because it's a little too open.

There needs to be a little bit more rigor now and who needs to have more information.

But that changing that culture was also very interesting. Fascinating.

And let me kind of transition a little bit more to that last section about humans, although obviously we've we've been talking about employees and employee engagement throughout the throughout our conversation here.

And you have led, you know, Fortune 500 Company.

As a CIO, how did you create a culture of trust within that organization?

I think it's I have four things now.

One is overcommunicate.

Know and follow through.

So explain your plan.

Explain why and then follow through if the plan changes, explained why.

No, but do what you say you will do.

That's point number one.

The second one is transparency.

Doesn't matter if it's good news or bad news.

I have always said I can task the team to agree with every decision.

But I need the team to understand why decisions are made, and then they can make their choice as to whether they agree with them or not.

But understanding why a decision is made is critical.

So again, be very transparent.

People are smart, but they are going to figure out and sugarcoat things and sugarcoat things.

Now, be honest. The third one.

I think it's important because I struggled also to my career is, hey, how how do I contribute to the goals of the company now?

Is my job different here than if I was working at, I don't know, General Motors or any other company now.

So I spent a lot of time trying to explain the strategy of the company, the goals of the company, how it strategy and its goals align to that.

And then how every individual's job.

Up to that.

Now, whether it was somebody on the service desk, a network engineer, a Salesforce developer, it doesn't matter.

And infrastructure, people struggle with that often.

But for example, we had organizational goals.

Those were my personal goals for the year.

And we had every employee in the organization had to have their own goals aligned to those.

Except for their personal development goals.

No, but I'm calling out examples whenever we're going through company performance discussions, things like that.

How does our work contribute to that?

Just showcasing examples over and over.

I think that's that's impactful.

No.

It's impactful for the organization to be valued in the rest of the company.

It's also impactful for individuals, research shows, right?

If you don't, the people who are most engaged in their work.

To your last point about employee engagement are people who understand their purpose.

And the purpose may be to keep the facility safe, right? I mean, a security guard has no less purpose than an engineer to the outcome of success of the company.

But if you don't take the time to frame it that way, they may not think about it.

They may just be dialing it in every day.

And then you're not going to retain that talent for the company and love that.

And then there's one, one last one, which is I mean, be humble, but have fun.

Now, I have an accent.

As you can see, I'm from Spain and English is my third language.

So I use expressions that I sometimes translate directly from Spanish or I say them wrong.

Don't hide from that. Make fun of it now.

And there was a list going around the company of what was called Roger is a reasons.

Like I was in a discussion one day about something about scapegoat, something of a scapegoat now, and I called it a space code.

So they made me a T-shirt with a space.

So things like that.

I just I mean, we're going to be working hard.

We might as well have fun.

Absolutely.

Absolutely. Especially not losing that as we work more remotely.

So maybe because I know we're at less than a minute and I know people.

Do you just have any advice for any of the folks listening about your career, what you would.

To them to inspire them.

I mean, I my advice will be find somebody who you trust or who you admire.

To run ideas by.

To help mentor you, to give you the hard truth.

And that can hurt sometimes, but have somebody you trust to.

To talk to him on a regular basis.

It doesn't have to be your boss.

It doesn't have to be somebody in your group.

Just.

A person, your corner.

Thank you so much, Roger.

It was just a pleasure speaking with you. Thank you.

Thanks for having me.