Is high risk-aversion to change and modernization ever warranted?

I feel like that argument is so overplayed: “Because we're so special, we can't modernize our software.” We need to stay because this is the way we've always done things. You need to make some bold choices to your business. And this risk/reward perspective isn't moving things forward, especially in healthcare and financial services. We've been stuck in the 1950s on both without embracing true digital transformation because of various risk factors.

I think you're right. Now in this particular case, I actually side with the airline because when you look at the numbers and you look at what would have been required, I actually don't think it would have been a good idea for them to do that. But I do agree with you. I think some people use it as the wet blanket to throw on top and say, "Well, this is the way we've always done things, so we're not going to modernize it." You have to look at the value equation, right? It's risk and value. What is the risk of doing it or not doing it? And what is truly the value of doing it or not doing it, right? When we talk about technical debt, just because I have old stuff running doesn't necessarily mean that's bad.

It kind of comes back to people's expectations. And what's your customer's expectation? And to kind of go back to financial services, if an ATM goes down, and there's another right nearby ATM, that's kind of acceptable. But if all their ATMs in a region go down, that's a huge risk and that's a huge impact to your business.

You get what you ask for, right? I've had conversations with executive recruiters that have clarified the same point. They're not asking for what they really need, but the problem is they've been conditioned on what that traditional CIO looks like for so long. They actually don't know what that proper CIO looks like or how to ask for that person, because they're conditioned that it is that back office organization, sadly.

You should not be pattern matching against the CIO candidate. You should look for the candidate with traits that map to what your strategic business initiatives are. And that candidate should be able to articulate how they will drive that forward. Both with strategy and tactics. And if that's not the case, they're not the right candidate.

Change is absolutely needed. Thinking about the branding, I think IT is perfectly okay. I mean, otherwise you're just changing the deck chairs. You change the titles and you hope things change accordingly. So, how do you start to turn that battleship in the bathtub? You have to start making those changes. First building the relationships, having the right context, setting the right culture, bringing the right organization into place. I mean, there are a series of traits that an IT leader must exhibit and execute on, straightforward and right away. It's not something where they can say, "Okay, I'm going to learn it, I'm going to incrementally improve upon it." No, it needs to be now.