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Are you sympathetic to startups? Why or why not?

Top Answer: Over the years I have definitely found a lot of interesting ideas among startups. I may not have engaged with all of them or given them business, but I did show them which direction to take in terms of what they could be doing differently. I gave them informal mentorship rather than getting into a formal engagement with them. During my time as a CIO and even now, a lot of them return with feedback on what worked and what didn't, as well as whether the conversation was worth it or not. That's a good place to be. I have been sympathetic to startups because they're struggling to do something new. We should hear them out. I’ve realized that within the ecosystem, not everyone is amenable to spending time on startups.

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What was the primary driver for your business to consider working with an outsourcing partner?

Top Answer: It was cost savings. Then we squeezed the service providers so hard for more savings that in the past 5 years we started insourcing more for “better service and value”. And they are willing ultimately to spend more than with outsourcing but so far not more than what we had 10 years ago. The turn over of leaders is so great few were here 10 years ago so they don’t know the history. I guess it’s just the natural cycle. Cut costs until you cut too far then try to build back to what you must have to run the business

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How are startups being evaluated?

Top Answer: We’re evaluated based on the actual problem that we were solving and the market need. In my first startup, we decided to create a product but the problem was not there. That's where we began a spiral of failures. In the second startup, we had a problem, but first we explored whether it was a market need or not. Once we found out that it was a market need for a lot of people, that was a proven concept. I do invest in startups as an angel investor here, and the first thing that I look for is whether there is a market need. The need may not be there right now, it could be in five years’ time. But in that case, I also look at whether the team is capable enough to handle the four or five years of struggle that they will have to go through.

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What's it like to be a consulting CIO?

Top Answer: I never aspired to be a consultant or advisor, I just fell into running a small consulting business. I used to think it would be very frustrating to give advice and not be able to put my ideas into action, but I've actually found the opposite to be true. I have the fortune to work with companies that really seem to value the guidance that I'm giving them, and most of the time they try to do something with it.

IT leaders are struggling to become business partners because they are being held back by focusing on a process-driven operating model instead of a service-optimizing operating model.

Top Answer: They will struggle as long as IT is only viewed as a cost to be reduced in their business. If you want to work in a company where IT Business Partner role is empowered, ensure they don’t have double digit cost reduction as a goal every year. The lowest cost option is rarely the best solution for the business but it does help IT reach cost reduction targets

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CISOs, what's the secret ingredient to a healthy and productive relationship with your cybersecurity vendors?

Top Answer: Plenty of coffee dates. :) But on a more serious note you as a CISO need to know what you need and vendors need to have patience and understanding that not all technologies are relevant or needed for a particular organization. Pitching all the products your company offers doesn't make a lot of sense most of the time because there might be overlapping technologies in use and worst case scenario you end up looking desperate as a vendor if you pitch too many things. 

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What’s the most effective approach to outsourcing: the partner model, or the direct model?

Top Answer: When I was building out my applications team in India, it took a long time for me to find a leader, but it was such a critical hire.  You need someone with the right level of maturity, who you can communicate with, and feel like you see things the same way. They are going to be on the ground during your night and you have to be able to trust them. Eventually I found someone good and now, in turn, he can start hiring a team there. A good portion of our company is in India, so I want to take full advantage of the talent out there. I’m thinking about a model in which you have a business analyst who is closer to some of the business folks here in the US, and has a counterpart in India who is more of a techno-functional person. They can work together and either one of them can cover for the other. This is the first time I've ever direct hired. But the more I learn about it, the less it intimidates me. You need to hire ahead of your need, because you need to have some slack in the system. In the past, I've always worked with a partner and now I really appreciate how much they were doing for me behind the scenes. When you are the person who has to deal with replacing someone who's leaving, it can be very painful. If I had a choice, I would continue doing what I did before, which is call my partner and say, "I need a person." And they would have a bench to choose from. I don't want to oversell the partner model, but I've had good experiences. The key is to be very engaged: I wasn't hands-off and I interviewed everybody who joined the team. If you’re doing it yourself, there's just some extra work that you have to be ready for.

Could it hurt a startup’s chances at investment if the projections are too conservative?

Top Answer: Everybody looks for ambition, persuasion and lofty goals. But you don’t want to say, "Here's our $10B market and we will be worth $500M in the first two years." That’s not going to happen unless you have a track record of building. There are always people who bring in different thought leaders and executives for their advisory board or board of directors, and that increases their chance of success. Then you can make some bigger claims because you can say, “I'm getting this person from Andresen and Horowitz to advise me on the healthcare sector,” or, “I'm getting one of the co-founders of Sequoia Capital on my board.” That obviously opens a door for you, but 99.9% of startups won't have such influential people on the board, so how do you set realistic expectations? It doesn't mean that you won’t have lofty goals, but don't go for 100X when realistically 1X is what you're going to gain — go for 10X. It’s about finding that balance because it's an art, not a science. You learn as you go that if you over promise, they're going to ignore you. If you under promise, they think you're too conservative.

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What discourages an investor from funding a startup?

Top Answer: Some of the smaller startups that I have worked with got checks from folks who steered them in the wrong direction because of something they've seen, or they're chasing whatever other venture capitalists are doing. And I'd say, "Whatever you're doing over there, I can't pitch it internally to Flex, or to my friends and peers. You can chase it, but I don't know that area, so I’m not going to sign a statement of work (SOW) or invest." For us, we either invest in you and grow you through, or we sign an SOW and you do the work. Those are the two methods, and the relationship does matter.

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What should startup founders consider when looking for suitable investors?

Top Answer: It is a dating exercise in the end, so do you really want to hang out with them? I look at my capital table today and  2% to 5% of my investors are active in the company. My lead investor is in it every week — we're meeting multiple times, and not about status updates. The conversation is: how can I help? What are you thinking? How can we adjust this partnership? I can call him and we can just get through whatever we need to figure out. That's such a big difference from traditional arrangements, where you hand in your recorded report and tell them your metrics, etc., rather than discussing how you're going to disrupt the market. That is a big deal. Those people are also the ones that will say, "Okay, then I'm willing to write another check." But it also comes down to what stage you’ve reached.

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