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Is there going to be a mass exodus of tech workers out of cities like SF?

Top Answer : There's a mass exodus underway right now from San Francisco urban center to suburban areas. It's significant enough that rent has changed drastically. The house values in suburban areas are increasing. In some cases it's not just moving from the city to the suburb, it's moving to a different state or a different country. Countries are offering tech worker passports, where you can literally become a citizen of another country and still maintain your job somewhere else.

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Should CIOs get an MBA?

Top Answer : I think they should, because the CIO doesn't have to be the smartest technical person in the room anymore but you have to be able to explain technical things to business people in non-technical terms. Additionally, the qualities that CFOs are looking for in a CIO come down to trust and credibility. That's not just the technical credibility, it's also the financial credibility. It comes down to dollars and cents. If you haven't taken basic financial accounting and you don't know how to be financially or fiscally responsible or credible, you're doing yourself a disservice. So having that MBA, it just gives you a leg up in those regards. It's harder to play catch up without it. It's not impossible. Plenty of people have figured it out, but it gives you a solid foundation on which to build. I was taking some classes at Columbia before I made it out to UCLA, and there was a book that I read called Political Savvy by a Columbia professor named Joel DeLuca, and it really sort of highlighted the value of office relationships and identifying the different people along the way so that you can influence decision making. You may not be able to directly influence somebody, but you may have some pull with somebody who knows someone who knows someone, and then you'll be able to influence it in a transitive, as opposed to direct, way. So when I first got to UCLA I brought an IT vision and roadmap with me. At the top of that roadmap is "business strategy".  Right below business strategy is the business relationships. The key to success is the way in which you manage those business relationships. I spent the first 3–6 months on this job not talking about the technology, but just building those business partnerships, and I can't tell you how well that served me now during the pandemic. You have to build those bridges and you have to start those relationships. Our dean of career services said to me about 2 months in, "You know, I've never once had a CIO come over and talk to me in my office,” and that sounds so obvious, but nobody did. I'd been handed a big caseload on Salesforce when I walked in. I brought all of the senior leaders around the school who had skin in the Salesforce game around the table and said, "All right, what are we going to do here?” They replied, “Oh, this is great. We've never had one of these meetings before."  You just sit back and think how is this possible? This just doesn't sound logical. But you kind of have to be able to understand all the individual pieces, then put it together. Then once you do that you can actually start to move the needle and deliver on things. You've built the credibility, you've delivered something, and the business sees the value in it. It’s one-on-one building those relationships and then also building them upon each other so that you can get value for the whole organization. People are always going to think myopically, because they're always worried about their function first, but you've got to convince them at a macro level, for whatever it is your business is trying to do, that there's value there and you're helping to put all of the different pieces together. I tell my staff our goal is to facilitate business conversations, because it almost seems that the business doesn't talk to the business, and we can at least facilitate those conversations, and there's power in all of that.

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How should startups respond/pivot to the pandemic?

Top Answer : There's probably some startup opportunities in the area of education. We have great universities in the greater San Francisco Bay area, Boston and elsewhere, and these do effectively manifest as sorting hats. But what they really have is great teachers and networks. There is an opportunity to extend, not just these online classes, but be able to extend that community in a meaningful way into the middle of America, and build on top of this shift. Like all education startups, it's a long road. It would take a brave investor with commitment to the founders, but I do think that this is a trend that will happen.  I also think that the way we approach IT may change. If we look at what it means to onboard an employee who's never going to physically be in the office, there's lots of supply chain relationship management problems that actually exist. The HR startups, that are frankly just web form versions of the paper processes that companies were doing, those companies that are domain experts in doing these things online, they are still burdened with heavy paper processes. I think that there are startup opportunities in the area of how do you automate these core business processes. Another area that is particularly interesting is the way we use work laptops at Google. Let's say my work laptop were to die, I would drive to the closest Google office, I would walk in. And then there's just a stack of laptops there where I come in and I badge and I walk away with a laptop and they assume the one that was unplugged when I badged was the one I took. Then I log in, they cross reference it to that, and now that laptop is associated with me and my downtime is an hour round trip. I think that there will be somebody who's successful in this area to augment the IT desktop lifecycle. If you look at fully loaded costs of an employee, there's a lot of value to be extracted, if you can compress that into a more complete solution.

Would you accept a role at an organization if you knew that the org structure, culture, etc. would put you at a disadvantage?

Top Answer : I've been tapped on for a few CIO roles recently, and my first question is “what's my reporting line?” Because I've had situations where the reporting line is into a CTO who's under a CFO, who's reporting to the CEO. If that's the case, then structurally it's going to be just another battle that you have to deal with. I think more and more CIOs are very cautious about getting into companies which have a pre-existing structure in place that puts them at a disadvantage. I would say technology leaders, not just CIOs, but even CTOs and CPOs, are demanding from the get-go that they have that seat at the table if the companies are eager to pursue the digital transformation journey. And I think that's actually the right thing to do because in this day and age, I think every company just has to be incredibly digital and incredibly enabled from a technology point of view. It can't have these strategic conversations three or four years down the road. So I actually see there's a bit of a pivot where technology leaders are from the get-go demanding a certain setup, because even if you get that setup, there's a lot of challenges to deal with.  I've spoken to some recruiters on this, and what I found is that even recruiters recognize this. There's a lot of pre-filtering going on, on both ends, to understand the leveling of the setup. People have these conversations during interviews even before engaging in the company. All of us who've been at somewhat senior roles for a while, we know how difficult it is to change that setup. If it's not already addressed upfront, building up the network and creating these relationships is a lot harder to do, especially if you are coming in at a somewhat junior role and level compared to the rest of the business leaders. So recruiting firms are now starting to advise companies to make these structural changes before opening up the job if they want to get the top talent in tech. I think in some cases, the companies have even updated the requirements to make that position change.  Of course there are legacy companies with a different setup that don't have any intent to change. But then you know that you're going into a role that’s not looking for that. You're going into a role that’s just looking for an operations lead. There are some tech leaders who are happy to do an operations role and who don't want to maybe take that much responsibility in terms of business growth, but then there are others who are ambitious and they want to do that. Those are the ones who do look at these parameters in terms of what are the opportunities getting into the company to deliver on a growth path as well.

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Do CIOs ever purposefully hinder innovation in order to prevent risk of failure and protect their own career should things go awry?

Top Answer : I had a CIO say to me recently, when talking about a modernization project, "How can you guarantee me that I'm not going to end up in some trade journal as the next grand failure?" So they agree with the objectives of the project, but there's personal risk in not wanting to be the next magazine article about a huge failure. And the flip side of that, that I run into all the time: CIO comes in, they're there for two years, make some decisions, get a project started, and then they leave. And there isn't enough continuity of leadership in order to see this stuff through. Because it starts getting a little dicey and it's the squishy middle that nobody wants to hang around for.

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How long should an IT executive's resume be?

Top Answer :

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What's the biggest mistake marketing teams make when trying to sell to IT buyers?

Top Answer : I could go on FOREVER about how bad the marketing is to me. From email addressed to the wrong person, to coy 'I enable high performance' emails...  the list of bad marketing could go on forever. MOST OF ALL< STOP CALLING!!!