Chapter 1: Freedom with Fences—Robert Stephens Discusses CIO Leadership and IT
Founder and Chief Inspector of Geek Squad and Vice President for Best Buy, Robert Stephens is an
articulate information technology leader and innovator who feels most comfortable and direct
when sharing his insights and experiences by speaking rather than writing. This chapter
transcribes a dialogue based on several recorded sessions with the editor. Section headings were
subsequently assigned by the editor to indicate changes in the themes of the discussion.
THE CIO LEADERSHIP PARADOX
Joe Stenzel: As an innovative IT entrepreneur with experience in both the arts and
engineering sciences, you’re schooled to appreciate the vital balance between the creative
dimensions and professional disciplinary standards of CIO leadership expectations and
responsibilities. Describe how this apparent paradox plays out in the current information
Robert Stephens: The nature of the game has changed from the perspective of the CIO, especially in
the last five years. Some of the rules for IT architecture and design are partially less formal, moving
back in the direction of the mainframe, server client, and dumb terminal, but rapid prototyping is
the area where innovative playfulness will soon be codified. With the development of mobile
applications, smaller screens, and fewer buttons, it will be increasingly important for the CIO to
avoid becoming too formal. CIOs will increasingly promote a cultural layer of playfulness within the
enterprise and IT organization—a virtual sandbox if you will—as a part of the CIO’s arsenal, point
of view, and leadership attitude.
Balance is everything. We have freedom to innovate in play, but it has to be a freedom with fences.
There’s always a tendency to equate playfulness with the ignorant or the rule breakers. What about
HIPAA? What about Sarbanes‐Oxley? Critics will tell us that we can’t playfully innovate while
protecting our enterprises. They’re simply wrong. CIOs get paid to help innovate and stretch. IT has
become even more central to business success than ever, because the lines between an internal
enterprise IT system and a customer‐facing experience are diminishing all the time.
We need a balance between the formal discipline and playful innovation that characterizes the CIO,
and the metaphor is really the human brain. The more we learn about the brain through functional
MRI and PET scans, the more we learn that everybody is creative, everybody is methodical,
everybody has varying degrees and kinds of intelligence by which we express our unique gifts—
cognitive, emotional, social, ecological, artistic. Much of this is inherited, and the rest is fostered by
the environment. The CIO facilitates creation of an innovative environment within the IT
organization and the greater enterprise by setting the tone as a disciplined, but innovative, chief
Innovation is art. Balancing is an art. As an inherently playful activity, art shows us the way to
creativity and innovation. CIOs have to get things done, but business pressures place the CIO in a
position of constant paradox: innovate, but keep the enterprise safe and secure. Business is how we
live, and art is why we live. Back and forth, back and forth.
I’m only now coming up with the words to articulate this human intellectual dynamic. Art and
playfulness are essential in life, and strategically essential in business. Art is that abstract, shapeless
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playground from which new ideas spring, and that’s why it’s so relevant to business strategy:
processes very quickly become commoditized, copied, and stolen. As Picasso said, “Bad artists copy.
Good artists steal.” The CIO has to find a way to help enterprise employees find access to that
artistic space where they develop newer, brighter, faster, cheaper forms of products and services.
That’s why every art historian should take an engineering class and every engineer should have
that art history class—CIOs included.
This suggests that balanced leadership is characterized by highly personal frameworks for
understanding disciplined creativity.
I share the conclusions drawn in Richard Florida’s Rise of the Creative Class and Daniel Pink’s A
Whole New Mind about the importance of developing the right‐brain, but the message I want CIOs
to understand is that everybody has artistic capacity to some degree, especially our employees. I
learned two important things in my two short years of art school. Maggie Phillips was a member of
one of the first graduating classes from the Institute in the 1920s, a classmate of Georgia O’Keeffe,
and my 2‐D drawing instructor at the Art Institute of Chicago. She’d walk around us as we were
drawing—like a football coach on the sidelines—and she would train us by saying:
Don’t look at your hands. Don’t look at what you’re drawing on the paper, look at what you’re
drawing—the real object. Your mind will draw and express the object only as well as it has come to
know that object. There is no perfect line except the one you draw without editing, without that
parental frontal cortex telling you the “rules.” Ignore that voice.