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Supplemental Table of Contents

Preface
Who Should Read This Book?
The Modern Enterprise
The Role of the Modern CIO
Styles of Management
The Rise of Agile IT
Introducing Agility to the C-Suite
Measuring for Success
Fail Early, Fail Fast, and Reap the Benefits
Design for Delivery
Design for Operationalization
Design for Governance
Organizational Optimizations
Inspect and Adapt
Conclusion
About the Author
Appendices

",{"_138":139,"_43":44,"_47":48,"_45":46,"_65":66,"_140":141,"_153":136},"previewContent","

\n Supplemental Table of Contents\n
\n Preface\n
\n Who Should Read This Book?\n
\n 1. The Modern Enterprise\n
\n 2. The Role of the Modern CIO\n
- \n Workforce Culture\n
- \n Personal Technology\n
- \n Delivery Paradigms\n
- \n Information Security\n
- \n Redefining the CIO Role for Today’s Workplace\n
\n
\n About the Author\n

Supplemental Table of Contents

\n\n\n\n

Preface
Who Should Read This Book?
The Modern Enterprise
The Role of the Modern CIO
Styles of Management
The Rise of Agile IT
Introducing Agility to the C-Suite
Measuring for Success
Fail Early, Fail Fast, and Reap the Benefits
Design for Delivery
Design for Operationalization
Design for Governance
Organizational Optimizations
Inspect and Adapt
Conclusion
About the Author
Appendices

\n\n\n

Preface

\n\n

The journey of a thousand miles begins with a single step.

\n\n

– Lao Tzu

\n\n

In almost three decades of technical and strategic consulting, I have\nfound only one constant: change. Technology changes. Work culture\nchanges. Economic models and theories of management change. And business\ndrivers change to, as they race to keep up with all the other changes.

\n\n

In my career, I’ve seen information technology’s first tentative steps\ninto the business world, followed by its never-ending evolution into the\nengine that powers the modern information and consumer economies. As\nmore and more business functions came to rely on IT, a new executive\nrole emerged to tame this unstoppable hydra: the Chief Information\nOfficer (CIO).

\n\n

The role of Chief Information Officer began its rise to prominence in\nthe early 1980s, but it’s arguably in the past 20 years that the CIO has\nbecome an indispensable part of modern, post-startup organizations with\nresponsibilities well beyond the purchase and integration of key pieces\nof technology. Today, with information technology touching almost every\naspect of business, the CIO is often a full partner in a company’s\nexecutive committee and a driving force in shaping a company’s\norganizational strategy.

\n\n

As the scope of the CIO’s responsibility continues to expand and evolve,\nchanges in the marketplace and the workforce have created a paradigm\nshift. This shift requires a new management model to harness the power\nof the new paradigm, so that today’s CIO can power business innovation\nrather than attempt to hold back the tide. That model is agility.

\n\n

The values and principles of agility were formalized in 2001, in a\ndocument colloquially known as the Agile Manifesto. Originally rooted in\nthe domain of software development, the manifesto has gained increasing\nrelevance to the practice of IT management and strategic leadership, and\nthat trend is likely to accelerate in years to come.

\n\n

Because the manifesto originated with software development, it’s very\neasy to find books, blogs, training seminars, and other resources\nfocused on how to apply agile principles to programming or web\ndevelopment. There are also books on agile principles as applied to\nmanufacturing, project management, and (to a lesser extent) product or\nprogram management. There are even a few books on agile business\nstrategy, especially using the Lean methodology. However, there is\nalmost nothing in the marketplace focused on the pivotal role the modern\nCIO plays in an agile context.

\n\n

Having spent more and more time in recent years helping senior\nexecutives transform their organization to take advantage of this new\nparadigm, I realized that there was a deep need to educate the denizens\nof “Mahogany Row” on how to incorporate agility into their day-to-day\nroles within the organization, and to show the modern CIO the bright\nfuture that lies ahead by transforming from a traditional or modern CIO\ninto an agile CIO.

\n\n

The CIO is a critical strategic leader for many organizations, and is\nwoefully underserved by the amount of information that specifically\ntargets the CIO role. That is the problem I set out to solve, and this\nbook is my answer.

\n\n

Within these pages, you will find a condensed version of the advice I\nhave been providing to CIOs and other senior executives across the\ncountry and around the world. For the cost of a book, you can discover\nknowledge that other companies have paid millions of dollars in business\nprocess re-engineering and organizational transformation to learn.

\n\n

It’s my hope that this book helps you become the agile CIO your company\nneeds you to be today. Furthermore, I hope it enables you to forge the\nfuture of IT for yourself and others.

\n\n

As every journey requires a first step, I hope this book will serve as\nyours. I wish you every success!

\n\n

Todd A. Jacobs
\nBaltimore, MD - Spring 2017

\n\n\n

Who Should Read This Book?

\n\n

This book targets anyone responsible for IT executive management. Chief\nInformation Officers in companies that are looking to improve alignment\nand efficiencies within IT will likely benefit most from this book, but\nother governance and service delivery roles will benefit as well.\nWhether you’re a VP of Engineering looking to improve time to market, a\nVP of Infrastructure that needs to reduce your labor or capital costs,\nor a Chief Information Security Officer that needs to ensure that\nsecurity controls are implemented throughout the IT organization,\nthere’s valuable information here for you too!

\n\n

This book is also designed to assist business process consultants and\nagile evangelists in working with leadership to transform the\norganization through a practical application of the Agile Manifesto at\nthe executive level. Most of the available literature focuses on\nteam-based engineering and project management techniques, but this book\nmakes the same values and principles relevant to those entrusted with\nsteering the organization. A more agile “tone at the top” can help teams\nand senior leadership collaborate more effectively, and this book can\nhelp shape that collaboration.

\n\n

In short, anyone who values a more effective IT organization will\nbenefit from this book.

\n\n\n\n\n

\n1. The Modern Enterprise

\n\n

Remember those classic Oldsmobile commercials that said, “This is not\nyour father’s Oldsmobile?” While information technology (IT) today has\nthe same mission it has always had, the culture, ecosystem, and\norganizational needs that it serves have evolved drastically over the\npast 20-30 years.

\n\n

The sheer scope of enterprise technology has far outgrown historical\nmodels of management, and today’s Chief Information Officer (CIO) needs\nto stay ahead of the curve. Sometimes this means betting on a technology\nor service, but more often than not it means adjusting to the modern\nmarketplace where delivery cycles are often measured in weeks rather\nthan months or years.

\n\n

In my father’s time, IT was a “thing” that was replacing people or less\nefficient tools. His stenographer was replaced with a Dictaphone, and\nthen eventually by a do-it-yourself word processor. This was both\nempowering and frustrating, because it enabled greater levels of\nself-service to more people while removing organizational bottlenecks,\nbut it also required shifts in the way people thought about and\nperformed their jobs.

\n\n

Perhaps that shift in technology is hard to fathom today, when the\nsmartphone in your pocket has more functionality and raw processing\npower than an entire office had back in the early days of computing. But\nthat shift is still going on today, and continues to accelerate. Today\nwe’re replacing our Dictaphones with word processors by:

\n\n

Replacing on-premises servers and datacenter management with cloud\nservices.
Abstracting “things” like server racks into virtualized resources such\nas compute and storage nodes, containerized services, and even\n“serverless” computing (e.g. AWS Lambda).
Outsourcing commodity IT services like DNS, backups, hierarchical\nstorage, and web services.
Relying more and more on vendors, platform providers, service\nproviders, and open-source software to build and maintain things that\nwere once managed solely in-house.

\n\n

This is nowhere near to an exhaustive list, nor is it meant to be. It\nsimply highlights that the pace of change, and especially the\nintroduction of new paradigms in IT, continue to increase over time. New\n(and sometimes disruptive) technologies are also forcing new paradigms\non enterprise IT management, and the modern CIO no longer controls the\ntap through which new technology appears. Instead, the mission has\nbecome one of creating a healthy, dynamic framework through which the\norganization can sip from a technology firehose without drowning in the\ndeluge.

\n\n

This requires a shift in thinking from old models of centralized service\ndelivery to one of empowerment through self-service. The need for IT\ngovernance and strategic curation has not gone away; in fact, it has\nincreased dramatically! But the new paradigm to enable it is a tripod\nthat rests on three legs:

\n\n

automation,
self-service, and
team-based empowerment.

\n\n

Like DNA, the agile CIO can successfully combine and recombine these key\nelements in creative ways to build the right culture, infrastructure,\nand services to take an organization to the next level. But before a CIO\ncan be an effective agent of change within the organization, it may be\nuseful to examine the role of the modern CIO in more detail.

\n\n\n

\n2. The Role of the Modern CIO

\n\n

Times have changed, as has technology and its central relevance to the\nmodern enterprise. So, it seems appropriate to pause to look at how\nthose changes have impacted the role of CIO. To be successful, it’s\ncritical that everyone in the organization understands what the modern\nCIO has become, and how effective an agile CIO can be within this new\ncontext.

\n\n

In times past, the CIO was often responsible for choosing the computer\nand software systems available within the organization, and tasked with\nthe responsibility of managing IT assets and service delivery. While\nsome of this remains true, the role has broadened in the modern context.

\n\n

Some of these changes are driven by trends in enterprise technology, but\nothers are being driven by changes in workforce culture, commoditization\nof personal technology, new project and product management paradigms,\nand the rise of information security as a distinct role within the\norganization. Before we can talk about how these changes have affected\nthe role of the CIO, we should look at a few key examples to give us\ncontext.

\n\n\n

Workforce Culture

\n\n

Shifts in company culture are ongoing and evolving. Today’s workplace is\ndramatically different that it was when many of today’s senior CIOs\nentered the workforce.

\n\n

In many companies, hierarchies have flattened, and in today’s\nmarketplace respect is more often a function of a meritocracy rather\nthan one’s position in the organizational chart. Some companies have\ndone away with offices in favor of open-office plans, and “Mahogany Row”\nis more of a concept than an actual location now.

\n\n

In some companies, “office casual” has replaced suits and ties even at\nthe board level. Even sales people rarely dress formally, unless they’re\nvisiting a client with a very traditional culture. Especially in places\nlike Silicon Valley and technology startups, comfort and casualwear are\nthe order of the day.

\n\n

And when was the last time you called your boss, or even the CEO of the\ncompany, by anything other than first name? There are doubtless still\ncompanies where C-level executives are addressed as Mr. or Ms., but\nthey’re a vanishing breed. And even in those companies, the rest of the\norganization continues to become (at least in theory) more egalitarian\nand much less formal.

\n\n

Incentives and leadership have changed, too. Companies lost a great deal\nof top-down power when workplace culture shifted from long-term\nemployment rewarded by raises, canalized career paths, and funded\nretirements to an at-will, free-agency model. While this has created\nbenefits for both companies and employees, today’s competitive companies\nknow that they need modernize their incentive structure and leadership\nstyle to attract the best of today’s modern workforce.

\n\n

Companies can’t hold onto experienced Gen X people or upwardly mobile\nMillennials through promises of a gold watch and a retirement party the\nway they could in my father’s day. Instead, new workplace norms like\ntelecommuting, work-life balance, and employee empowerment are the tools\nthat agile CIOs can leverage to attract (and keep!) the best and\nbrightest.

\n\n

Your personal experience may be different from this view of the modern\nworkforce. There are always exceptions to any generalization. However,\nit’s important to acknowledge these shifts in the workforce and\nworkplace attitudes to understand the agile CIO’s role in the modern\nera.

\n\n\n

Personal Technology

\n\n

Time was that all technology within a company needed to be blessed by\nsenior management. Did you need a database? The CIO would negotiate for\none. Did you want a new tool for software development? The VP of\nEngineering would ask for funding to buy commercial licenses.

\n\n

Today, the monoculture of the past has been replaced by the complex\nintersection of:

\n\n

enterprise systems with employee-owned hardware like cell phones and\nWiFi-enabled devices; and
mashups of corporate-owned IT systems and user-installed software and\nexternal web applications.

\n\n

This can present a support or security challenge for a traditional CIO.\nRather than hand-selecting every piece of hardware and software for the\norganization, today’s modern CIO focuses more on curation, integration\nstrategies, and enabling self-service delivery to ensure corporate\ninterests are served while simultaneously preventing the IT organization\nitself from becoming a bottleneck.

\n\n

This culture shift isn’t only about technology, though. It’s also part\nof the workforce culture shift discussed previously. Today’s employees\nare often expected to be highly available, whether at home or at work,\nand so striking the correct balance between embracing personal\ntechnology and maintaining adequate governance is as much art as\nscience, but the agile CIO collaborates to ensure the right balance is\nfound for each organization.

\n\n\n

Delivery Paradigms

\n\n

In days gone by, software and service delivery had a slower cadence,\nwith a great deal of up-front design and specification for projects that\ncould span years. Today, a CIO would be hard-pressed to defend delivery\nof a strategic resource that exceeded 18 months. In fact, many agile IT\nshops currently target 30 days or less for a functional deliverable, and\na growing percentage are embracing paradigms such as Continuous Delivery\nand Continuous Deployment to reduce lead time to almost nothing.

\n\n

These changes don’t come without cost. The table stakes for this\nparadigm shift is an investment in automation, culture change, and\ncontinuous process improvement. However, the agile CIO has more\nvisibility into every level of the IT organization and its ongoing\ninitiatives than ever before, and is better able to pivot strategically\nto meet changing business needs or disruptive technologies.

\n\n\n

Information Security

\n\n

The scope and importance of information security has grown dramatically\nin the past several decades. Thanks in part to private sector\nregulations such as Sarbanes-Oxley (SOX) and the Payment Card Industry\nData Security Standard (PCI DSS), security compliance has become an\nintegral part of IT infrastructure and service delivery.

\n\n

Some companies have managed this growing need through the creation of\nChief Security Officer (CSO) or Chief Information Security Officer\n(CISO) as distinct roles within organizations, while others have\nexpanded the role of CIO to encompass the additional responsibilities.\nHowever, even with a dedicated CSO or CISO, responsibility for\nimplementing the organization’s security policies within enterprise\nsystems rests firmly with the CIO.

\n\n

Whether security and audit roles report into the CIO or not, the modern\nCIO must carefully balance the requirements of IT service delivery with\nsecurity compliance. This adds complexity to the CIO’s role, but modern\nagile practices can reduce that complexity to manageable levels once\nagain.

\n\n\n

Redefining the CIO Role for Today’s Workplace

\n\n

As the pace of technology continues to increase, and the complexity and\nubiquity of IT continues to grow, the modern workplace demands a\nredefinition of the CIO role. The modern context also requires a\nparadigm shift in the way that today’s CIO provides strategic\nleadership within the organization. Based on experience within a large\ncross-section of industries, the emerging trend towards agility at the\nexecutive level seems clear.

\n\n

This new paradigm requires the application of agile principles to\nstrategic planning and thought leadership at the C-level, and nowhere is\nthis more apparent than in the pivotal role of CIO. By adopting\niterative strategic plans, emergent design of enterprise-scale IT\nworkflows, and empowerment of business units through self-service\ntechnology, the agile CIO can align enterprise service delivery in ways\nthat were difficult to imagine even ten years ago.

\n\n

So how does one adapt to this new workplace reality and become an\nagile CIO? Subsequent sections of this book will unpack the concepts\nof the agile paradigm shift in greater detail, and lay out a roadmap for\nbecoming the agile CIO your company (and your career) need you to be.

\n\n\n\n\n\n\n\n

About the Author

\n\n\n

\n\n\n

Todd A. Jacobs is President and CIO of CodeGnome Consulting, LTD.\nCodeGnome is a boutique consulting firm that specializes in CIO advisory\nservices and DevOps transformations. He also currently serves as\nPresident of Maryland Mensa.

\n\n

His latest book, The Agile CIO, is currently available exclusively on\nLeanpub. Other IT-related publishing\ncredits include:

\n\n

“Managing Docker Instances with Puppet”, Linux Journal 274 (February 2017): 92-111.
“Provisioning Docker with Puppet”, Linux Journal 272 (Dececember 2016): 72-80.
“Secure Token-Based Authentication with YubiKey 4”, Linux Journal 265 (May 2016): 82-102.
“Configuring One-Time Password Authentication with OTPW”, Linux Journal 225 (January 2013): 76-88.
“Understanding NTP Reachability Statistics”, Linux Journal, January 2004. https://www.linuxjournal.com/article/6812.
“Improving SSH with Keychain”, Sys Admin Magazine 12, no. 1 (January 2003): 21-24.

\n\n

In addition to his deep expertise in IT and security management, Todd is\nalso passionate about technology and process. He loves working with\nLinux, Docker, and Puppet, and enjoys programming in Ruby. He’s also a\ntop contributor and community moderator on Project Management Stack\nExchange.

\n\n

He currently lives with his wife and son in the greater Baltimore area,\nbut travels frequently for business and public speaking engagements. In\nhis rare but treasured free time, he enjoys reading, writing, gaming,\nfine dining, and Netflix binging.

\n\n

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