Caroline L. Arnold: Part 1 of an interview by Bob Morris

ArnoldCaroline Arnold has been a technology leader on Wall Street for more than a decade, managing some of the financial world’s largest software development teams and leading some of the industry’s most visible and complex initiatives. A dynamic and engaging speaker, she has appeared before groups as large as 5,000 people. Caroline is a recipient of the Wall Street & Technology Award for Innovation for building the auction system for the Google IPO, and her name appears on technology patents pending. Caroline serves as a Managing Director at a leading Wall Street investment bank. Caroline graduated from the University of California at Berkeley with a degree in English Literature, and lives in New York City with her husband and daughter.

Her book, Small Move, Big Change: Using Microresolutions to Transform Your Life Permanently, was published by Viking Adult (January 2014) and is now available in a paperbound edition, published by Penguin Press December 2014).

* * *

Morris: Before discussing Small Move, Big Change, a few general questions. First, who has had the greatest influence on your personal growth? How so?

Arnold: I’ve been influenced by many people in important ways, but my daughter Helen has had the greatest influence on me. Watching another human being develop, and putting that person’s well being first, has been a great learning experience for me and has expanded my view of life and changed my personal values.

Morris: The greatest impact on your professional development? How so?

Arnold: My father, who always wanted me to be a writer, and Guy Chiarello, who by example and encouragement got me to take the long view of my career. While we were at Morgan Stanley, Guy trusted me with amazing opportunities.

Morris: Years ago, was there a turning point (if not an epiphany) that set you on the career course you continue to follow? Please explain.

Arnold: For a few years I was a programmer, working strictly on a consulting basis because I felt it gave me more freedom and at some level I felt unready to say, “this is it, this is what I am doing for the next five years.” Giving up consulting to work on Wall Street was a big decision, but I knew it was the right one when one day I realized how much I was looking forward to the next five years advancing my career in one place.

Morris: To what extent has your formal education been invaluable to what you have accomplished in life thus far?

Arnold: My education at the University of California at Berkeley gave me a great classical education, exposed me to great works and great thinkers, and taught me critical thinking skills that I apply today both in writing and in Technology. I majored in English Literature, but I also had concentrations in Economics, Philosophy, and Drama. These disciplines may seem far from computer programming, but logic, problem-solving, connecting disparate pieces of information, and creativity are all part of good technology solutions.

Morris: What do you know now about the business world that you wish you knew when you went to work full-time for the first time? Why?

Arnold: It took me awhile to discover that the greatest pleasure in work is accomplishing something as part of a team, rather than entirely on your own. My first years as a programmer I had my own consulting practice, and I designed and implemented solutions either on my own or with one partner. When I gave up my practice to work on Wall Street, my orientation was towards solving everything myself, being entirely accountable. Within the first year I was given a team to manage and I managed them as an extension of myself, rather than seeing my role as enabling and energizing the team. Once I realized that success lay in empowering the team and investing in each person’s growth, I began to grow not just as a technologist, but as a human being.

Morris: Of all the films that you have seen, which – in your opinion – best dramatizes important business principles? Please explain.

Arnold: Hmmn, I love movies but am having a hard time thinking about one with business principles that I endorse. I guess I could say that Broadcast News shows the power and limitations of pure professional passion to meet the challenges of a changing industry.

Morris: From which non-business book have you learned the most valuable lessons about business? Please explain.

Arnold: I learned a lot from reading Adam M. Grant’s Give and Take, which I found a refreshing read on how to thrive in competitive environments while enabling and empowering others–an intelligent take on how good guys can finish first. So much of what gets written and quoted is about winning the rat race while Prof. Grant’s book assess the broader stakes in professional behavior.

Morris: Here are several of my favorite quotations to which I ask you to respond. First, from Lao-tse’s Tao Te Ching:

“Learn from the people
Plan with the people
Begin with what they have
Build on what they know
Of the best leaders
When the task is accomplished
The people will remark
We have done it ourselves.”

Arnold: Love the quote and believe in the principle. The leader’s job is to inspire passion and performance in others, to work in service of the team’s success.

Morris: From Howard Aiken: “Don’t worry about people stealing your ideas. If your ideas are any good, you’ll have to ram them down people’s throats.”

Arnold: Well, while I think it’s true that the truly transforming idea may be one that is so alien that others don’t seize on it (i.e., steal it), plenty of good ideas are recognized immediately and promoted by others as their own. But I would still advise not worrying about those who will steal your ideas, because you need to share ideas in order to advance them.

Morris: From Richard Dawkins: “Yesterday’s dangerous idea is today’s orthodoxy and tomorrow’s cliché.”

Arnold: True, and the time required to go from dangerous idea to cliché is shrinking rapidly as technology renders iteration and adoption ever faster.

Morris: From Isaac Asimov: “The most exciting phrase to hear in science, the one that heralds the most discoveries, is not “Eureka!” (I found it!) but ‘That’s odd….’”

Arnold: Great discoveries and ideas are often born of observing what one perceives to be an anomaly.

Morris: From Thomas Edison: “Vision without execution is hallucination.”

Arnold: Yes, executing a vision is the entire ballgame. I have known many of vision who simply couldn’t get from whiteboard to implementation.

Morris: Finally, from Peter Drucker: “There is surely nothing quite so useless as doing with great efficiency what should not be done at all.”

Arnold: The wisdom and challenge of this is timeless, and I’m going to consciously think about it more often. How often do we refactor processes that we should just kill? How often do we feel productive doing something that is really marginal to productivity…like answering every email immediately?

Morris: In one of Tom Davenport’s recent books, Judgment Calls, he and co-author Brooke Manville offer “an antidote for the Great Man theory of decision making and organizational performance”: organizational judgment. That is, “the collective capacity to make good calls and wise moves when the need for them exceeds the scope of any single leader’s direct control.” What do you think?

Arnold: I don’t think this is either/or. A great leader making great decisions can change the fortunes of any initiative, as can the collective wisdom of a team. Ideally, you have both – a visionary leader and a smart team empowered to question the leader and advocate direction. I think the “great man” theory has a lot to do with the cult around Steve Jobs, but Steve Jobs was a singular person of fierce passion and conviction who was an business ascetic of sorts, unwilling to compromise, willing personally sacrifice. That he built a great company is undeniable, and if he left behind a great team, it will survive him. Jobs is so unusual, thought, I think that people get into trouble who try to emulate him. Leadership is personal, although lessons from others can, of course, be understood.

Morris: Here’s a brief excerpt from Paul Schoemaker’s latest book, Brilliant Mistakes: “The key question companies need to address is not ‘Should we make mistakes?’ but rather Which mistakes should we make in order to test our deeply held assumptions?'” Your response?

Arnold: I’m not sure I have enough context regarding Shoemaker’s argument, but I don’t see any value in seeking to make mistakes. That we will make mistakes is given; the question is, can we learn from those mistakes and can we spot the opportunities that might arise from such mistakes and embrace them?

Morris: You’ve just summarized the purpose of strategic mistakes. I think that is what he had in mind. Take risks where, if an experiment or test fails, the most valuable information will be generated. Some mistakes create much greater value than do others.

Here’s another question I have been eager to ask you. In your opinion, why do so many C-level executives seem to have such a difficult time delegating work to others?

Arnold: I don’t know that the stats on C-level executive delegation are worse that mid-level managers, but from personal experience I know that there are many reasons one can fail at delegation: a misplaced sense of control; waiting too long to delegate an important task so the only option is to follow through yourself; fear of giving up line job responsibilities in favor of new management responsibilities.

Morris: The greatest leaders throughout history (with rare exception) were great storytellers. What do you make of that?

Arnold: Leaders are responsible for advancing a compelling narrative for their enterprises. A good leader creates a narrative with meaning that inspires team with a sense of purpose and motivates top performance.

Morris: Most change initiatives either fail or fall far short of original (perhaps unrealistic) expectations. More often than not, resistance is cultural in nature, the result of what James O’Toole so aptly characterizes as “the ideology of comfort and the tyranny of custom.”

Here’s my question: How best to avoid or overcome such resistance?

Arnold: Relating this question to the one earlier about storytelling, you have to create excitement around change and a story that people can identify with and embrace. You need to counteract the fear and threat of change with the excitement and opportunities created by change. But people aren’t naive, they know that in any adaptation there will be winners and losers.

Morris: In recent years, there has been criticism, sometimes severe criticism of M.B.A. programs, even those offered by the most prestigious business schools. In your opinion, in which area is there the greatest need for immediate improvement? Any suggestions?

Arnold: I’ve known great leaders who came from business school and great leaders who came up through the ranks without an M.B.A., so the value of the degree depends on individual circumstances. I really don’t feel qualified to opine on the programs themselves. However, it makes sense to me to question what the essential academics of such a program should be, and what should be left to learn on the job.

Morris: Looking ahead (let’s say) 3-5 years, what do you think will be the greatest challenge that CEOs will face? Any advice?

Arnold: The same challenge they face today – leading change as the rate of change increases.

* * *

Caroline cordially invites you to check out the resources at these websites:

Her website link

Twitter link

Link to video of her presentation at Microsoft headquarters

Facebook link

Posted in

Leave a Comment