Digital Transformation is an “all hands on deck” exercise – Interview with Former Federal CIO, Tony Scott

 -Tony Scott Interview Digital Enterprise & Transformational CISO Assemblies

Tony Scott, Retired Federal CIO – U.S. Government, Former CIO VMware, Microsoft and Walt Disney joined us as Keynote Speaker at the Digital Enterprise Transformation Assembly and Transformational CISO Assembly back in June.

Digital Diary spoke to him just after his keynote presentation to find out a little more about how the role of the CIO has evolved.

The role of the CIO is changing rapidly as businesses look to digital technology to transform. Over your 40-year career, how have you seen the role evolve?

TS: I think the biggest change has come in terms of the relevance of the CIO job to the core mission of the organization. The challenges associated with rapidly changing business models and digitization of business processes place the CIO and his/her team right at the center of the action, and this is a pretty exciting place to be in most cases.

What are the biggest challenges facing CIO’s & CTO’s today?

TS: Certainly, cyber security has become one of the biggest challenges, both from a technology perspective, but also from an overall risk perspective, and obviously also from a human resources perspective.

Second, I’d say that right up there on my list is the challenge that many established organizations have with migrating from whatever legacy application and infrastructure architecture they may have to a more modern continuous upgrade model. IT in many new organizations have a flexibility advantage because they are starting from a different place, and have no legacy to deal with.

You had held the position of CIO both in government and industry. Can you tell us a little bit about the similarities and differences between working in the public and private sectors that you experienced?

TS: Many of the challenges are exactly the same. But, in the government world, the biggest difference I noticed (especially at the Federal level) is that the funding model for IT is all messed up. There is no such thing as a “business case” model or review for modernizing or improving things because the government goal is not to make a profit. In too many cases, it takes a crisis to get the money to fix something. Second, there are many rules and laws that need to be modernized to match todays realities. That said, I consider working in public service one of the best things I’ve been lucky enough to do, and I think we need a lot more people to do this, even if it’s just for a few years.

Cybersecurity is a huge topic of conversation, with the instances of hacks or ransomware increasing, most recently WannaCry. What can businesses learn from this situation to protect themselves in the future?

TS: My view on this is quite simple. Start with the basics. Make sure people are trained (end users and IT staff), and make sure that basic hygiene factors (patching, two-factor authentication, good architectural reviews) are followed. Make sure good incident management and recovery practices are observed, practiced, and continuously improved. When it’s time to exercise the drill for real in response to an incident, it’s best to have it well rehearsed and debugged.

You have overseen strategies driving modernization and efficiency, changing the way we think about modern data management and open-source advancements. How do you stay abreast of the latest technology and innovations?

TS: I stay current mostly by reading and by constant interaction with a variety of tech people, including the VC community, tech companies, entrepreneurs, fellow CIO’s, and by watching carefully what people are doing. I also get involved professionally when I’m asked to help solve some really hard problem, and I have a set of friends and former colleagues that I can draw on to get perspective.

In any company, the culture and leadership can often make or break digital transformation. What advice would you give to CIOs and CISOs leading the digital mindset change in their business?

TS: First, this is an “all hands on deck” exercise. I’ve seen way too many failures occur because of what is called the “cool kids” syndrome. Anytime a cultural divide is created in an organization where some people are made to feel “special” and everyone else is just along for the journey, I think it’s just the starting point for failure. In one way or another, everyone has to be on board, and the strategy and the operationalization of the strategy ensure all are pulling their weight and in support of the strategy.

What do you see as the future of digital enterprise?

TS: Simply said, it is the future. With maybe a few exceptions, survival as an institution will depend upon that institutions ability to adapt and change at digital speeds and engage with customers and its broader ecosystem through a wide variety of mechanisms – almost all of which will have been invented in the last ten or fifteen years, and many of which have not been invented yet.  That said, there is also likely to be a shortening half-life of many things as well. We may very well see a much faster meteoric rise and fall of certain technologies.

Last month, you joined us at Digital Enterprise & Transformational CISO Assembly as our keynote speaker. What were your key takeaways from the event?

TS: Great energy in the room, and in the hallways, as well as very engaged dialogue on current trends and issues. I always learn a ton and was happy to hear many conversations about the journey that many organizations are on, as well as hear about solutions that are being offered in the marketplace. Our challenges are great, but it’s through these kinds of events we can improve our “game” for the next set of challenges we face.

During your Keynote at the Digital Enterprise & Transformational CISO Assembly, you talked about how the Federal Government is the biggest enterprise in the world, what is your best advice for IT executives managing large scale enterprises?

TS: Build a great team. This is something that as a leader you have to be almost maniacal about in some sense. It’s a lesson I’ve had to learn over and over again. In so many cases, an organizations performance can be dramatically impacted by the caliber of the players, as well as how they work together, with the latter being the more important of the two. Figuring this out isn’t always easy, but as a leader, I find myself constantly coming back to the question of what I can do to help the team perform better.

What do you see as the benefits for C-Level executives attending an intimate event like ours?

TS: First, great networking. Second, insight into current issues and trends as well as the opportunity to discuss with peers and other leaders various approaches to addressing these issues. Third, it’s a great way to benchmark your own capabilities, performance, strategies, and results.

You speak at multiple events, what stood out to you about the Digital Enterprise & Transformational CISO Assembly and encouraged you to attend as the Keynote Speaker?

TS: I love the topic and thought the approach, format, and venue would lend itself to a high-quality conversation. Turned out to be exactly that!


Tony ScottTony Scott served in the Obama administration as the 3rd Federal Chief Information Officer (Federal CIO) for the U.S. Government and was appointed to that role by President Obama in February 2015. The Federal CIO has oversight, budget and management responsibilities for the more than $85 billion that the Federal Government annually spends on IT. In that capacity, he created the government-wide response plan after the OPM cyber security hacking incident, including the Cybersecurity Sprint and Implementation Plan (CSIP), which dramatically improved the information systems security posture of the Federal Government. His numerous appearances before Congress, and many other forums – providing CXO level public and private sector insight on matters such as digital workplace transformation, cyber security, governance, open data, and workforce diversity have been widely recognized.

Immediately before joining the Obama administration, Tony was the Chief Information Officer at Vmware. Prior roles include the Chief Information Officer at Microsoft Corporation, Chief Information Officer at the Walt Disney Company, and Chief Technology Officer at General Motors Information Systems & Services.

Tony holds a Bachelor of Science Degree from the University of San Francisco in Information Systems Management, and a Juris Doctorate (law) degree from Santa Clara University. He was inducted into CIO magazine’s “CIO Hall of Fame” in 2009 and has been a frequent keynote speaker, panelist, and advisor to numerous industry and government events. Tony is also a licensed pilot and enjoys flying his own plane whenever possible.


Digital Enterprise Transformation AssemblyWe are thrilled to announce the participation of Robin Bienfait CEO, Emnovate as Keynote Speaker at the November edition of Digital Enterprise Transformation Assembly.

Robin Bienfait is a global senior executive and board member with 30 years of leadership experience in enterprise technology, mobility, and security. Leveraging her C-level success driving transformation for AT&T, BlackBerry, and Samsung. Robin is presently the Chief Executive Officer and Founder of Emnovate, Chairman of Global Aviation and Partner with Valor Ventures. Emnovate is an advisory firm that delivers enterprise class services to help businesses embrace innovation. Robin has been selected to multiple public and private boards due to her collaborative, entrepreneurial approach to strategy creation, consensus building, corporate governance, and shareholder relations. Robin is a past member of the Hewlett Packard Advisory Board and the Cisco Strategic Advisory Board. Robin is also a member of the Georgia Institute of Technology Advisory Board and a Tiffany Circle Member of the American Red Cross.

Join Robin at the Digital Enterprise Assembly this November, simply by filling in our inquiry form >

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