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Why CIOs and CTOs Suffer from the Raw Technology Persona

Written by Dan Woods | September 12, 2013 | 0 comments

This is a chapter excerpted from a book called Education of a CTO

Technology Magicians

The raw technology persona appeared early in my life. As a teenager, my first technical manuals were books on magic. From the moment I saw the diagrams showing how to make a fan of cards or deal from the bottom of the deck, the love of technique grabbed my soul.

Magic, especially sleight of hand magic, is a great metaphor for technology. In most magic books a trick is described first through an explanation of what the audience sees – the effect – and then a description of what the magician does to produce that effect – the technique.

Sleight of hand technique is an arcane world of subtle, invisible moves combined to create an illusion. Magicians can sit for hours showing each other techniques for manipulating cards and coins. This is a strange phenomenon to watch because the sleights are designed to look like normal actions, like turning over a card. An outsider sees magicians handing a deck of cards back and forth and doing simple things like straightening the deck or placing a card back in the center of the deck, all while murmuring comments and stroking their chins. The action is completely unseen by the uninitiated observer.

It is common to find a magician who can do fiendishly difficult card technique yet rarely performs a trick. Those of us who love technique for itself frequently fume when a less skilled magician gets a big reaction from an effect produced with a simple method. This is exactly why David Blaine, the dashing young performer who is featured on TV specials and gets lots of publicity, is unpopular with many magicians.

At the beginning of the dot com gold rush, Netscape was held in similar disdain by engineers at Silicon Graphics. In “The New New Thing,” Michael Lewis describes how in 1995 the Silicon Graphics engineers, who had just finished building an enormously complex interactive TV system, were miffed that a bunch of lesser engineers were awash in attention and money for performing a much simpler trick, creating a browser.

The essential flaw of the raw persona, in both magicians and technologists, is the triumph of technique over effect. For the magician, the fascination with sleight of hand leads away from performing entertaining tricks. For the technologist, the fascination with technology leads away from creating business value.

If the goal were to amuse oneself with complicated technique, nothing would be amiss. But for a magician who aims to entertain and a technologist who seeks to create business value, the effect is the most important element. In this chapter we take a detailed look at the different aspects of the raw persona that lead technologists astray.

What is the Raw Technology Persona?

A persona is a face, a façade presented to the world at large. The raw technology persona represents the role that technologists play with their natural tendencies in charge.

Habits of thinking, inclinations, weaknesses and strengths of character all make up the raw technology persona. The result is the familiar figure we know and love: The geek, the impractical, brilliant technologist who can perform amazing feats but is hard to talk to and borders on unmanageability.

As we will see in this chapter, the raw persona is an interlocking web of traits that misdirects the talent of the technologist from the optimally productive role in applying technology. We personify the raw persona as a mischievous little monkey who wants to play with his toys, make everyone happy, and spend most of his time thinking about the perfect world of technology in the abstract.

The raw persona explains a lot about what goes wrong in companies when they try to use technology. It also explains the frustrations of technologists. For example, why is it that:

  • Most technologists know they are regarded as extremely smart, yet wonder why they rarely are asked their opinion about important issues outside of their bailiwick.
  • Most technologists know they tend to underestimate the time and cost needed to accomplish technology projects yet, again and again, they over-promise.
  • Most technologists have instincts about business strategy, but cannot find a way to coherently make a case and guide the consensus.
  • Most technologists think that if they work hard and their department does well this will be automatically noticed, and they will be fairly rewarded.

The technologists who fall prey to these problems are not ignorant or terminally ineffective people. Rather, these observations ring true because they flow directly from the strong character and admirable traits we see in most technologists. The raw technology persona does its damage when these traits are taken to extremes, unguided by experience or practical limits of the business world.

As the technologist walks the halls of a company, attending meetings, interacting with customers and executives, the monkey is always with him, allowing the full effect of the raw persona of the technologist to burst forth with no editing.

The monkey sits on the shoulder of the technologist, whispering in his ear, encouraging him to do what comes naturally, regardless of the task at hand. It is as if the monkey hypnotizes the technologist into a trance that keeps him focused on technology and technology alone, that new information or evidence of problems cannot penetrate.

When a technologist faces the job of estimating the deadline for a difficult project, the monkey in his brain tells him: “No problem you can do it. It will only take a week,” without much thought about what could go wrong. The monkey is eager to please and fascinated with complexity for its own sake. The goal of this book is to help technologists recognize the thoughts than come from the raw persona, control them, and then use them to the best advantage.

The raw technology persona is one dominated by the following features:

  • Optimistic
  • Mathematical
  • Innocent
  • Accommodating
  • Creative
  • Focused

Working together these positive attributes hamstring a technologist. We will now examine these traits in detail and explain how they reinforce each other.


Optimism is a fundamental trait of technologists and also the largest threat to their success. Whistling a happy tune, technologists dig their own graves, one promise at a time. The inability to set appropriate expectations about technology projects is the largest problem in the industry today.

Deep in their hearts technologists believe that technology is a force for good and if properly applied will make for a better world. Technologists want to help their companies succeed. They want their perfect system in place so it will be admired and do its good work.

This service-minded optimism fuels ambition. When technologists set to the task of planning a project, they do so through rose-colored glasses. They overestimate their skills, underestimate likely problems, and reach for too grand a solution. The result is familiar disaster.

Optimism and an accommodating nature are at the root of this problem. Creativity, obsession with technology for its own sake, and a talent for mathematical, abstract thinking make it worse.

Optimism about Capacity

Technologists are supremely confident about their own capacity for work and for solving problems. They know they can get the job done. The harder the challenge they face, the better. They enjoy the thrill of trying something difficult.

In the high-octane culture of Silicon Valley, it is important to have suffered to make an accomplishment all the more significant. If a team was not pulling all-nighters, perhaps the leaders were timid about the goals. If you did not swing for the fences, you were just a wimp.

An experienced manager outside of the technology culture will brag about going home early the night before a big launch because everything was so well planned. The typical technologist’s attitude is more proud of the fact the team had to carry servers uphill through a driving snowstorm at the last minute. This sort of macho thinking gets technologists in trouble and leaves little room for error or for the unexpected.

Technologists regularly confuse the process of thinking something through, a mathematical process that happens quickly in the mind, with the process of actually doing something, which will take a long time in the real world. Difficult problems are partitioned, encapsulated, and categorized and then the technologists assume they will be quickly resolved, even though they have no basis for that assumption.

This hubris extends to blind faith in the intrinsic value of technology. When presented with a clever new system, the creative mind of the technologist spins webs of possibilities about what could be done. Sales executives love this dreamy look of excitement about technique for its own sake. The trance of potential keeps at bay any regard for the details of execution or the difficulty of changing the behavior of a large group of people.

Optimism about Difficulty

While technologists carry the torch of optimism forward and attempt daring projects, they are blinded to stones along their path that may trip them up.

The process of looking for problems involves shrinking the vision of what can be accomplished. When imagining all a system could do, a technologist is free to fly unimpeded in any direction. The process of looking for problems brings the technologist down to earth, which is such a bummer.

Technologists’ hostility to scrutiny leads them away from healthy skepticism. It is depressing to consider limitations and make a list of all the things that could go wrong. The list gets long so quickly. Taking every threat into account leads to a schedule that seems to stretch into infinity. Technologists incorrectly feel there is a trade-off between appropriate suspicion and a positive attitude.

This attitude creates resentment toward those who do attempt a systematic search for threats to a project. Technologists tend to think of people who look suspiciously on their rosy schedules as professional naysayers who do not “get it.”

When problems do crop up, the technologist’s optimism and confidence leads him to have faith that difficult problems can be worked out in a jiffy. It leads us to the situation in a famous cartoon in which one side of a black board of equations is linked to the other side with a circle containing the words “Then a miracle occurs.” In most projects, several such circles are present in the planning. Problems must grow into a crisis to force technologists to make a sober assessment. By then they have already burned much of their credibility with the rest of the company.

Optimism about Complexity

Technologists are frequently bored with what works. It is supremely dull to create business value with a simple, proven piece of technology that involves no risk or creativity. Where’s the challenge in that?

Part of this is a service ethic. Technologists want to solve the whole problem and make a system that accommodates every need of the users. Lost in the desire to serve is the risk of failure brought about by solving too much of a problem.

A less noble part is a fascination with complexity. Optimism coupled with an innate creativity and fascination with technology is a powerful elixir. It intoxicates the technologist with delightful visions of skyscrapers of technology that could be put to work solving problems. The raw persona delights in daring projects, the challenge of building such beautiful things.

Optimism drives technologists toward the idea of excellence, but also prevents them from achieving it. One result is a simple rule: The more a technologist is excited by a project, the higher the risk of failure.


What does a real programmer use to write a program? A pencil.

The idea behind this riddle is that the essential work of programming is constructing a mental model of a problem and cleverly connecting all the parts. After this fundamental work is done, a programming language may be use to render this construct into a system. I have chosen to use the adjective “mathematical” to refer to this fundamental analytical work of constructing a system in the abstract.

From the beginning of their education, technologists are taught to use mathematics and abstract thinking to solve problems. Equations, graphics, or records in a database are employed to represent the real world. Changes and transformations are modeled through computer programs that modify this symbolic universe. Training in computer languages, data structures, and databases provides provide a powerful mental toolkit with which a programmer can create systems of monstrous complexity.

The intricate world of technology is an alluring and attractive universe. With a language like Java or Lisp under your belt, the possibilities just don’t seem limitless: they are limitless. If a problem can be expressed as an algorithm, it can be modeled, and most probably solved.

The problem with mathematical thinking is that technologists are seduced by their talent for it. Imaginations boil over with ideas, which are honed into a perfect solution. Unfortunately, while the mind is a friendly home for such abstractions, the business world in which most solutions must operate is chaotic and imperfect and impervious to their mathematical allure. Technologists do not recognize this. Rather, they let the idea of the perfect system take them forward without suspicion.

The flash of inspiration during the creative process is compelling. It is a thrill to create or to see new kinds of connections and relationships or to discover another dimension that organizes the problem in a unique way. The technologist feels great because his mind has just expanded and he now sees over a hill or around a corner that he hadn’t realized was there.

To ensure success, however, the flush feeling of inspiration must be followed by scrutiny to see if the new idea fits well into the real world. Technologists frequently exempt their precious ideas from such scrutiny. They are not interested in discovering blemishes. The talent for mathematical thinking leads technologists to think far more about the beauty of the abstract system and not nearly enough about the threats to the success of the system.

Another common pitfall of mathematical, abstract thinking involves confusing the act of organizing and encapsulating a problem with the hard work of understanding the nature of each of the parts. It is this sort of thinking that is a major cause of technologists’ poor estimating skills. The technologist imagines that because he has partitioned a problem, he has somehow solved it.

In a business context, the presentation of a problem to a technologist frequently becomes the inspiration for construction of beautiful abstractions. Technologists trumpet capabilities and flexibilities that are impressive but may have little value to the people using the system. Technologists frequently think that the technology is sufficient because of its arcane beauty. This escape from reality reduces the value of technology to the rest of the company.

Technologists are too often advocates for technology, not for the business use of technology, which frequently leads business executives to wonder if the engineering staff is living in the “real world.” In fact, technologists most of the time are not. Technologists think of technology as a world unto itself and assume that others will see its beauty and be attracted to it.

If others will not join the technologist in his abstract world he resents it. It brings the technologist down. The technologist imagines that the doubters just don’t understand the perfection of this system. If they did they would stop being so negative.

The conundrum is that the technologist’s ability to create an abstract world allows technology solutions to be built, but the technologist’s desire to focus on that abstract world instead of the world in which the system will live works against the solutions being effective.


Most technologists are innocent and guileless and would be happiest in Mr. Rogers Neighborhood where everyone is a good neighbor. The corporate world is no such place but with a mixture of faith, trust, and naïveté most technologists prefer to ignore that fact.

Except at the highest level, technology departments are sealed off from the struggle for survival that is common in most businesses. Technologists like it this way. They get to focus on technology and leave the hunting, killing, and skinning to the rest of the company. While this childlike cocoon protects them from growing up, innocent faith also drives technologists toward ambitious goals and innovative solutions.

Trust is efficient. If employees do not have to watch their back, then all of the energy of an organization goes into moving it forward. A key element of success in any organization is the belief in each person that will do his or her job. But such faith should be justified. “Trust but verify” as the Russian saying made popular by Ronald Reagan goes.

Without much verification, technologists believe that the world is fair and merit will be recognized and rewarded. Technologists prefer the idyllic, hometown view of life in corporate America instead of contemplating the actions necessary in a world populated with self-interested sharp operators. In such a world, you have to watch your back, trumpet your accomplishments, make alliances, worry about your image, and promote yourself and your department. You have to be a politician.

Politics are inevitable because the contribution everyone makes in a corporation is not clear. If a product was a success, why was it a success? Was it marketing, programming, or sales? Almost always it was a combination of many factors, including blind luck. There is no omnipresent executive who can see what everyone did and how much impact it had.

Most office politics is about managing perceptions of yourself and others. Generally, in situations in which contributions can be measured objectively, rewards are passed out according to those objective measures. But in all other situations, most situations, rewards and credit accrue to those who are perceived to have contributed.

It is not corrupt to put the best face on your work, especially when you have done a good job. But technologists frequently put the worst face on their work out of the belief that they will get credit for their honesty. It did not work for Walter Mondale when he promised to raise taxes in the 1984 presidential election, and it does not work for technologists either.

Naïve faith also prevents technologists from asking important questions about how a business is going to succeed, why its strategy makes sense and how the company will make money. It is easier to have faith than to learn enough to have an informed opinion. Such faith can be a convenient way to avoid the conflict that may arise from skepticism.

In situations involving vendors and consultants, the faith of the technologist ends up with too much trusting and not enough verifying. It is sometimes difficult for a technologist to understand that statements made in marketing and sales are exaggerated to the point of falsity as a business practice. This works against efficient evaluation of vendor technology and also leads away from proper support of the marketing efforts of a technologist’s own company.

The strength of the innocent nature is that technologists maintain their childlike enthusiasm for their work. Staying in the playground of the world of technology protects technologists from becoming jaded but it prevents them from seeing the world as it is and making the proper decisions.


When the CEO asks the technologist a question the answer is almost always yes. Can you build it? Yes. Can you build it this fast? Yes? Can you build it for this price? Yes.

Most technologists are eager to please. They want to be of service and use technology to help others achieve their goals. This accommodating nature is a key trait of the best technologists. Obnoxious or uncommunicative programmers are rarely very good.

Technologists like fulfilling plans presented to them. It means they can focus completely on technique and leave the effect to others. Technologists revel in the power of their tools and are happy for the opportunity to show them off and build something real.

But accommodation goes too far and prevents legitimate questioning, most often through unchecked feature creep. Business users ask for feature after feature and technologists just say yes without considering the consequences. The door on new features often never closes.

Worse yet, technologists agree to wildly optimistic schedules or to do a job with a much smaller team than is actually necessary. Technologists think that this accommodating attitude is helping, when it actually hurts when the impossible cannot be achieved. If technologists were less accommodating and pushed back against faulty assumptions difficult questions would arise early and more projects would succeed.

The other side of accommodation is fear of conflict. When conflicts do appear, the technologists seek to avoid them, out of rhetorical ineptitude more than cowardice. Technologists are frequently incapable of waging a campaign of persuasion and they use this inability as a get-out-of-conflict-free pass. When they do have the appetite for a skirmish, technologists lack the knowledge of the business to make their objections stick. Purely technical arguments may not make sense to decision makers.

As a result, technologists almost never attempt to forecast which battles are likely to occur, prepare their case beforehand, and market their views throughout the organization. Technologists’ collegiality makes them think that battles should not need to be fought, that the company should accept the merits of their case without persuasion. They also frequently decide not to join the battle but rather wait for more information, letting the opportunity to join the decision-making fray slip by.


There is a phenomenon called the “Programmer’s National Anthem” that Dick Vile, a programmer that I knew at Fame Software, once pointed out to me. If you sit in a room with developers long enough, eventually you will hear an extended “ooohhhwww”, as in “Oh, now I get it.” This anthem bursts forth at the crystallizing moment after hours of creative thinking spent solving a hard problem or tracking down a difficult bug.

Technologists are sometimes accused of lacking in imagination, of being as dry as dirt. The truth is that as you walk by programmers staring intently at pages of code on a computer screen, their brains are seething with creative thoughts. They are shuffling through alternatives and creating new ones. This is hidden because most people do not understand the medium in which the creativity is expressed. As one recipient of an award from the Whitney Museum put it “Perl is my medium.” That’s great, but how many people know that Perl is a programming language and can judge the quality of the art?

The truth is that technologists are frequently afflicted with too much creativity. When a problem is presented, it becomes the springboard for a vision of a system that could do hundreds of things to help the users. [The trance of possibility] Brainstorming sessions are an opportunity to sail off into the unknown world of what is possible. In an instant, engineers get worked into a froth in front of a whiteboard, filling it up with odd shaped lines and boxes and circles as their imaginations run wild. In this excitement the vision of the system becomes too complex, too fancy, and too general. The business value that the system is supposed to create, the realistic ability of the users to adopt the functionality of the system, and the risks that complex features may pose are all forgotten in the face of the beautiful abstract construct.

The absence of practical guidance shows up with the engineers, after having figured out some interesting approach, go grab the VPs of marketing and sales out of their offices and show them the whiteboard. The engineers play the role of eager children seeking approval for their latest drawing. The VPs look at the board and haven’t a clue about what is being presented. They ask questions, get the idea, and then ask “So what?” The engineers point out the raw power of what they have thought up and the VPs point out the hurdle that the beautiful construct must overcome: making users happy and increasing sales.

At this point the engineers become frustrated. They don’t understand how the VPs do not understand the beauty of what they have created. The VPs point out that the technical beauty must be delivering value to the customer. Despair generally follows, as the engineers realize they are not going to get approval to build their fancy idea and that they do not know enough about the customer to bridge the gap.

At the best companies, this struggle continues until a way to create value is discovered, but frequently despair and frustration end the conversation. Such conversations also die because the VPs, who are in the habit of hearing impractical ideas from technologists, do not really listen.

Creativity is needed to construct a system. But the scope of the creativity should include not only the technology of the system, but also the business processes that will support it. Technologists excel at the technology part of this equation but don’t generally have the knowledge to apply their creativity the business issues.


Technologists are hyper focused. They latch onto problems like a bulldog, struggling to find a solution for the innate thrill of it and ignoring everything else. There are those who are distracted by novelty, but primarily technologists are afflicted by too much focus rather than too little.

The pathology of too much focus expresses itself many ways. The worst is when we become technology-obsessed. This sort of hyper-focus leads us to think only of the technology instead of developing a more complete understanding of the customer and creating business value.

The focus on technology alone or technology for its own sake also results from technologists’ abilities and knowledge base. They know technology rather well and can make great progress. They don’t generally know the business issues equally as well and it is harder for them to make a contribution. People in general like to stick with what they know, with what is comfortable and familiar. So do technologists.

Most technologists, who have risen to leadership positions, really do know their subjects thoroughly. They not only know the systems they are in charge of from top to bottom, they also are in love with their detailed knowledge.

Technologists are not like other people when it comes to detailed knowledge. They don’t want the short version. They want the long and complex story with all the subtleties and tricks. This generally makes technologists good at what they do because they can keep very complex, intricate models in their heads. It leads to the trance of complexity, a state in which the technologist gets lost in creating a Byzantine solution that is fascinating in itself, and excludes consideration of the goal of the system.

Technologists are frequently fooled by this love of detail into thinking that other people care about it as well. They don’t. Most people technologists speak with want the headlines, and simple short headlines at that. Technologists somehow think that no, if they really understood the beauty and detail of the technology, you would really see things differently.

The intoxication with detail prevents communication at an appropriate level with many of the technologists’ colleagues and customers. Opportunities to communicate with colleagues are lost because a technologist tells them how to build a watch instead of what time it is. How often does a VP ask a technologist a question only to regret it and to quickly find a way to stop the technologist from talking? The technologist, faced with the question, enters the trance of complexity and just starts shooting out his thoughts on the matter, explaining all the nooks and crannies. Frequently, the VP has to interrupt and ask the question again. The technologist, puzzled, thought he just answered it. After the second or third such attempt to communicate, technologists are written off as a useful source of information.

The problem with the focused mind of the technologist is that it prevents the simplification required to make decisions when running a business. In most business problems there is a fog of detail and significant conflicting information. Technologists are paralyzed is such situations because the can construct and equally valid argument for a number of positions. They blanch at the idea of an oversimplified model of the problem that obscures the complexity of the situation. They are nervous about advocating for the position with the least flaws because it is not perfect. The focus on all the details prevents the technologist from picking one argument, simplifying it, and then explaining its essence.

So, like all the other traits, focus enables technologists to effectively perform their job, but also throws up a barrier. It prevents them from communicating and addressing issues outside the world of technology.

Summary of the Raw Persona

What do we have when we look at these traits as a whole? On the positive side we have an admirable collection of features that are vital in a successful executive. Technologists are optimistic, visionary, trusting, accommodating, creative, and focused. This is a powerful set of tools for making a valuable contribution to the enterprise. Without the features of the raw persona, it is hard to imagine a talented, effective technologist.

But the full value of these traits muzzled in most technologists. Too often, the excesses more than cancel out the value of the positive aspects. The optimism, vision, and confidence that inspire a technologist to tackle significant problems become overwhelmed by unrealistic schedules, bloated requirements, and insufficient attention to managing risks. So it is with each of the traits described above.

One way to look at the raw persona is as a condition similar to a high-function autism. Technologists are quite capable in sharply defined domains, but have limiting blinders that stop them from seeing outside of their areas of expertise, even when it is vital to do so to solve the problem at hand.

In fact, the raw persona may actually be a mild form of autism. An article in Wired Magazine’s December 2001 issue reported on the outbreak of Asperger’s syndrome, a malady with similarities to autism, in the children of Silicon Valley. The article argues that there may be a genetic determinant to the syndrome and that the condition is exploding because so many engineers are reproducing with similar partners. Hans Asperger, the discoverer of the syndrome, made this observation. “It seems that for success in science and art, a dash of autism is essential.”

Another way to view the technologist is like a fabulous writer with nothing to write about. Technologists can do anything with their technology, but until they are set in a context that gives them a goal, they have nothing to do. Technologists lose themselves in the world of what they could say and don’t bother to worry about what they should say.

A less charitable way to look at the raw persona is as an affliction of permanent youth, retarded development, a reluctance to become an adult and address all the attendant problems and difficulties that are implied. People afflicted by the raw persona need to grow up, look around, see that they are falling short and take responsibility for making the changes that will improve their performance. It is easier to live in the smaller world of the raw persona, but the role of technologists has become too important for this to be acceptable. The fastest way out is for technologists to realize their shortcomings as a class, address them, and then play a far more productive role in our organizations.

A heroic urge lies deep within most technologists. Whether you imagine Hephaestus, the Greek God of technology, or Mr. Spock, the Vulcan – the roman name for Hephaestus – playing the role of creating a vision and then leading the way to bring that vision to life is a thrilling prospect. But as technologists pursue their mission, the raw persona, the devious little monkey, uses the technologists’ fundamental character to induce a narcotic state of delusion. The various trances are compelling and difficult to escape.

The largest tragedy of the raw persona is that all of its aspects lead technologists away from asking basic questions about the business strategy and developing a sophisticated understanding of the businesses we are attempting to aid with technology. If technologists are to become the heroes that they know they can be, they must step out of the cocoon of technique and embrace the world of effect, of business value.

The goal of this book is to bring an awareness of how the raw persona seduces the technologist in various situations and to suggest methods for breaking out of the trance and growing into an evolved technologist who achieves brilliant effects.

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