As someone in the technology sector, on a fairly constant basis I get asked the grown-up equivalent of “what do you want to be when you grow up.” This is, of course, “where do you see yourself in N years.”

Now, most of the time, this is a question with all the gravity of “nice day, isn’t it?” Sometime, however, the inquiry is sincere. And my answer is provided with the same weight as the question.

And, for reference, my answer hasn’t changed all that much since I was about seven. Happily, the way that I answer has become a bit more sophisticated. My end game position is that of CTO (Chief Technology Officer).

Many of my contemporaries have gone the route of management. This is cool with me. You shouldn’t be doing engineering and science if you don’t have it in you. By in you, I intend the sense given by The Oracle in The Matrix when she told Neo that you know that you’re the one when you feel it “balls to bones.” Seriously. There are far easier ways to make a decent living than the constant demands and uncertainty that comes along with the endeavor of technological advancement. Hell, forget advancement, just using technology is a hard slog.

For me, working with technology and constantly expanding the reach of my understanding within that sphere is one of my core drives.

So like anything else I’ve ever set as a goal, I researched this thing I’ve set my sights on.

Let’s unwrap what I understand today.

It’s relative new

As C-suite positions go, the CTO is really young. Only the CISO (Chief Information Security Officer) position is newer. As you’d imagine it’s not like there weren’t technology companies before CTO roamed the Earth. Prior to recognizing that the technology landscape was changing so quickly and on such a continual basis that a board-level position focusing exclusively on the implications of such change, technology was the domain of either the CIO (Chief Information Officer) or CEO (Chief Executive Officer).

There was a realization that technology falls into two broad categories: present and future. You can think of these as tactical (product development) and strategic (futures research). Investopedia says that a CTO “examines the short and long term needs of an organization, and utilizes capital to make investments designed to help the organization reach its objectives … [the CTO] is the highest technology executive position within a company and leads the technology or engineering department.”

This division of labor is not unlike the was that Computer Science became an independent discipline. It too is dual-rooted. There were schools where the computer (singular) was managed by the Math department and those managed by the Electrical Engineering department. You can tell the difference in the focus in curriculum. It will be either theoretical (math) or applied (engineering) in nature.

It’s not only one

The position of CTO is in no way one-size-fits-all. Presently, it’s possible to identify four distinct sub-species of CTO. This diversity reflects the nature of the companies and how technology fits into their culture and mission.

We can identify these four by where the fall on the spectrum described by amount of business change and percentage of products and services based on information.


CTO quadrants

As can be seen, these are four very different animals. This is why you would expect the CTO from a relatively stable business in the manufacturing sector like GE (big thinker) to be very different from one at a business experiencing near constant change and highly-dependent on information in its products like Facebook (visionary). Neither of those would look anything like the stable business, high-dependency Apple (external-facing) or high change, low-dependency AT&T (information manager).

The Infrastructure Manager

CTO quadrant - infrastructure manager


Typically seen in companies with low dependency on information-related technologies, but with business models experiencing large amount of change (technology change impacting how the business is run), the Infrastructure Manager CTO reports to the CIO and is responsible for addressing how to build out and leverage technology to reduce cost and encourage technology adoption across business units in order to gain efficiencies.

The Big Thinker


CTO quadrants - big thinker

The Big Thinker CTO is the response to never-ending growth of things utilizing information technology. We see this type in companies with stable business models and a relatively low dependence on information as a part of their products. We see their focus on strategic initiatives such as:

  • Advanced technology
  • Competitive analysis
  • Technology assessment
  • Prototyping
  • Planning
  • Setting architectural standards
  • These CTO answer to the CEO and peer the CIO. Here we have a division of the IT and engineering departments. They act as change agents, typically having a relatively small elite staff. They are influencers rather than controllers.

The Visionary and Operations Manager


CTO quadrant - visionary

In companies in the throws of business change (increased technology complexity) and highly dependent upon information in their products and services, the CTO will be the Visionary and Operations Manager type. Answering to the CEO, this is the prime mover of the company. Their responsibilities are all encompassing. They drive business strategies and exploit new technologies and then implement those same technologies throughout the business and product groups. We see the CIO reporting to the CTO in this view of the world.

The External-facing Technologist


CTO quadrant - external technologist

Information-driven companies with stable business models will tend to have the External-facing Technologist CTO. As with the Big Thinker type, this CTO peers the CIO with both answering to the CEO. Here the focus in on the identifying new technologies, exploiting them, and evangelizing them both in and outside the organization.

Areas of Impact

If we visualize the areas of impact for the four type, we can see the natural focus areas for each.

infrastructure managerbig thinkervisionaryexternal technologist


Greg Brockman, Stripe’s CTO, said that other CTO’s “viewed themselves as the facilitators of the technology organization. Sometimes this was about connecting senior engineers. Sometimes it was mentoring. … I realized the most important thing to do was to empower our engineers to make big changes and improvements.”

“It’s not a simple job to understand all the technology out there,” says Unisys Corp’s global CTO Fred Dillman. “Today the pace of change is so much faster, and businesses are becoming more and more dependent on technology. So the CTO is being asked to be the real expert in technology and understanding what technologies will affect the business in the future and help determine when and where to invest.”

My fit

So, where do I see myself in all this? Tricky question.

Honestly, it varies. As the Version Control Systems Architect at Metrowerks, I was evangelizing source code control. At The Altamira Group, I rocked the visionary thing. Most of my CTO-esque activities have fallen into the Big Thinker bucket. Researching futures and educating engineers and management is where I spend the bulk of my time.

Roger Smith noted that “[t]he significant role of technology in strategic business decisions has created the need for executives who understand technology and recognize profitable applications to products, services and processes. many companies have addressed this need through the appointment of a chief technology officer (CTO) whose responsibilities include:

  • monitoring new technologies and assessing their potential to become new products and services
  • overseeing the selection of research projects to ensure that they have the potential to add value to the company
  • providing reliable technical assessments of potential mergers and acquisitions
  • explaining company products and future plans to the trade media
  • participating in government, academic and industry groups where there are opportunities to promote the company’s reputation and to capture valuable data

Integrating these technology-based activities into the corporate strategy requires that the CTO nurture effective relationships with key people throughout the company. These include the CEO, members of the executive committee, chief scientists, research laboratory directors, and marketing leaders.”

Regardless of the specific needs of the organization, I’ll continue to strive to provide the best information in a timely fashion to those who need it.




I always find myself impressed at how nation-states and their leaders exhibit repeating patterns of behavior. This is expertly explored through space, time and scale in John Lewis Gaddis‘ latest book On Grand Strategy.

Dovetailing beautifully into my previous post’s assertion that I am an experiential gestaltist, Gaddis’ work takes us from Persia to Greece, China, Spain, England, France, Russia and the Americas. The book deconstructs battles and their attendant strategies, the motivations of their commanders, and the moods of the peoples involved.

From the outset, Gaddis presents us with the metaphor he will return to time and again. That of the fox and the hedgehog. These represent the approaches of alert outward-directed probing with stealth and of unwavering belief and inward-directed defense of that belief.

He shows that time and again battles are lost because leaders lack the ability to see changes in the situation before them. This may manifest in populations simply abandoning territory as was the case in both Xercesattack of Athens and Napoleon‘s of Moscow. Forcing your attacker to extend their supply lines should give pause to any commander, and yet, time after time we see overconfidence leading to defeat.

We see how Elizabeth skillfully balances force and guile to turn a seemingly weak position with respect to the attacking forces of Spain’s (God will make it work out) Philip. Like Xerces, Philip believes that his forces cannot fail. Less so because of their intrinsic numerical advantage and more because of his steadfast belief in his divine mission. His confidence extended to failing to provide adequate direction to his various forces and ignoring losses due to bad weather. Elizabeth, on the other hand patiently and judiciously used her limited resources.

The British colonies in North America are examined and we see the interplay between the colonials and the empire. As the United States are forming, the choice to kick the can of addressing slavery down the proverbial road of history is in full display as they draft their Declaration of Independence and Constitution. We jump to the American Civil War where leaders are struggling with the consequences of being at once a nation based on democratic ideals and yet built on slavery. They were very well aware that the monarchies of Europe still looked on them as an untenable aberration. A hypocritical one at that.

And we see into the churn that formed the backdrops of both World Wars. Also, how England worked to engage the United States and how others tried to prevent its engagement.

Throughout it all, we are presented profiles of leaders who are either able or unable to navigate the ambiguities of the realities before them. There are those without a compass, unable to achieve goals because there are none. There are those whose compass is trusted to the exclusion of the terrain. They find themselves, like those today blinding following navigation apps, ending up going off cliffs and ending up in lakes. Knowing where you are going is important, but if you fail to allow for the terrain and weather conditions, you will not do well.

On the whole, the book provides us a valuable mirror. It is amazingly timely given that we are in a period where our leaders seem again poised to engage in actions demonstrating that they have failed to either study of learn from the teaching of Sun Tzu, Thucydides, Augustine and Machiavelli. Their message could be described as success is found in following the middle way, embracing both certainty of mission, preparation and proper respect for the fluid nature of engagement.

I’ve just completed Robert Wright‘s latest book, Why Buddhism Is True. For me, the attraction was the subtitle: The Science and Philosophy of Meditation and Enlightenment.

Reviewing a book on philosophy is like trying to explain your existential motivations to a dolphin. You know that they’re really smart, but you’re never really sure that they get anything out of the discourse. That being said, I present my attempt. Hopefully, it will be minimally head-tilt inducing.

By way of background, I count myself among the Buddhist community. This to me provides about as much information as if I’d said that I work with computers. Yup, me and a hundred of million others work with computers. It tells you nothing about the form, function, depth of involvement, etc. Hence my choice of the word community. There is no single locus within Buddhism. Even whether it is a religion, a philosophy, or both is a point of discussion. On this, I point back to the sub-title’s attraction to me.

The reason I can even attempt a review is that the book takes a practical (as in practice) view of the topic. As an engineer, I appreciate the quantifiable. On this point, the book does not disappoint.

If I had to re-title the book I would name it Meditation: What’s in it for Me? Why? Because in a world where people barely make it past headlines, it pretty much covers the core of the discussion. The problem with this title is that it leaves out all the interesting bits that get you from introduction to summary. Sort of like renaming Bill and Ted’s Excellent Adventure to “be excellent to each other.”

The author is journalist, professor of Philosophy, and is of the Theravāda (specifically Vipassanā) school of Buddhism. I follow the Mahayana (specifically Zen) school. For the requisite pun, you could say that the distinction between the two is all or nothing.

Let me say up front that I am not a Buddhist scholar. I can’t read Sanskrit, Pali, or even Kanji to save my life. As such, many of the names and terms-of-art within the Buddhist world make my brain hurt. I can’t pronounce them. I can’t remember them. But I’ve gotten to the point where I recognize them in context. As an experiential gestaltist, I strive to integrate everything. In the process, the source wrapper is often discarded. This book accomplishes that unwrapping and, although it does use the terms from the source languages (mercifully translated), presented in approachable language.

Using this approach of going from the known to the unknown, Wright covers the methodological process of meditation and its effects as he has experienced them. He also relates the Buddhist underpinnings of the whys and wherefores of meditation as seen by various schools.

Next, he explores the various working models of consciousness used within the psychological community. From there he harmonizes the two.

In the final chapters, he brings us back to the big question areas of universality and enlightenment. He finishes by answering the question as to the tangible worth of meditation and will being at one leads to a grey existence.

I won’t spoil the ending for those of you who like to see endings for themselves. If you have an interest in the interplay between meditation, psychology and Buddhist thought, you will find this to be an interesting read.

Sometimes you can spend years trying to find a book that you can recommend to someone who’s asked you a question. My latest read, The Software Craftsman: Professionalism, Pragmatism, Pride is one such book. A recent volume in the Robert C. Martin book series, this volume by Sandro Mancuso is not what it appears to be. And that, is a good thing.

When you look at the other books in the Martin series (Working Effectively with Legacy Code, Agile Estimating and Planning, Clean Code, The Clean Coder, Clean Architecture, …) you see topics decomposed and methodologies expressed by which the title’s subject is achieved. That’s not what you get with The Software Craftsman. In my case, that was a very fortunate turn of events.

This is not to say that the journey of the software craftsman is not discussed. It is and in a reasonable amount of detail. But an equal amount of time is given to the ecosystem within which the craftsman practices. These parts of the book are not for the consumption of the craftsman or aspirant, but for the owners of the firms who employ (or should employ) them.

The book does well in describing the trials and tribulations of a member of the craft; from the point where they realized that they aspired to more than the dichotomy of coder / architect; to the creation of the volume itself. It lays bare this false dichotomy within the broader context of the entire point of software development. That being to produce value to the customer and income to the creator. Within that context, there is the easy path of whatever works and the hard path of building a thing that no only does what it is supposed to, but does it in a way which is both high quality and highly maintainable.

At it’s core, this is book about philosophy. In a landscape of Google and go; and compile it, link it, ship it, debug it; this is a thoughtful volume. It makes the point that I’ve never seen in print, that the individual software developer is responsible for their own career development. Not their manager, not their company, but they themselves are responsible. Heady stuff this.

As to the remainder of the book’s material, it’s more a wake up call to upper management. There you’ll find discussion of recruiting, hiring, retaining, shaping change and showing ROI. I know of very few who could look at this volume and come away unmoved.

It might be the separation of authority and responsibility, the hire for what we needed yesterday, the CYA so we get our bonus, or the factory worker mentality encouraged by so many firms today. If you can read this book and not get something out of it, you’re part of the problem.

Truly quality software is designed, built, and tested by passionate individuals working together toward the creation of something which will well serve the customer. Everything else is just code. Any 10 year-old can be taught to write code. I know, I’ve done it. Do you want your life’s critical systems to be build by 10 year-olds? Of course not, that’s a ridiculous question. How about people who are just doing it because they make a better than average day’s wage?

I hope you’re intrigued. At the very least, I hope you’ll reflect on your own views of the responsibilities of a software developer. At fewer than 250 pages, you can read this book in one or two sittings, but reading the book is only the starting point.


The book, The Character of a Leader: A Handbook for the Young Leader, is an odd beast. There aren’t many non-fiction books I’ve read where the author uses a nom de plume. According to the Amazon description the author Donald Alexander is an executive officer within the United States intelligence community. Presuming this to be true, they’re desire is to provide a foundation for aspiring leaders and not their own aggrandizement. I say aspiring here because a leader isn’t a title or rank, but rather a state or behavioral characteristic. Leaders can at the same time be led. They are also in a constant state of self-education.

The author argues that a leader is grounded in a set of core characteristics and beliefs about themselves and others. This position is opposed to those who believe that one can be an effective leader and hold that there are no absolutes with regard to attitudes and actions (moral relativism).

Given the books short length (about 120 pages of main text), it struck me as unusual that the introduction was about 15 pages in length. Why not simply incorporate it into the body of the work? My view is that this device allows the author to create the questions that the main text then answers. In a way, it is as though a student approaches a teacher and in asking questions inspires the teacher to assemble a lesson for all their students. I look at it this way because that’s what I have done in similar circumstances. It’s not usually the case that people coming to me with questions realize that their questions are of import to others, but it is the obligation of those of us who people approach with such questions to “spread the wealth.” Noblesse oblige, if you will.

The book is divided into sections defining a working definition of leadership, leadership and character, leadership traits, expectations, becoming a leader, and the fundamental obstacle  to leading (tribalism). It concluded with a call for leading with integrity.

No one who has been in a position of leadership will be surprised at either the structure of brevity of this book. You could put the totality of the facts conveyed onto a business card (I’d’ve said index card, but no one knows what an index card is anymore). But just like a PowerPoint, you don’t need to write every word you’ll speak on the slides (they’re not really slides anymore either). This book is a touchstone. For those newly recognized leaders, this book is a cross between a travelogue and a cautionary tale. For the former, the inclusion of additional material would simply be superfluous. For the later, it might convey the idea that the actions of a leader are paint-by-number, whereas in reality the are very much free-hand.

There are numerous quotes by and about leaders from various periods in history. These both build the case for the author’s assertion that character is essential to being a leader and provide jumping off points for further exploration of specific aspects of leadership.

I am impressed at the tightness of the narrative and the compelling argument made by the author. They strike me as one of those individuals that I would very much enjoy learning from and working along side.



I spend much of my time these days doing long-term strategic research and planning. Part of that time is spent identifying areas where technology training is warranted. The ways and means I use to create and present training materials have been developed through years of trial and error. In the midst of one particular line of research into a non-training-related area, I found Building an Innovative Learning Organization by Russell Sarder.

The book is relatively short, about 220 pages, but in many ways, you really don’t need more than that to cover the concepts of training. While it’s true that it would take far more to cover all aspect of training, from organization by-in, to facilities, to choice of materials, to length of courses, etc., those are details. And the details are as pointless as ornaments without a tree if you don’t have the fundamentals in place. That’s where this book shines.

Yes, there are all the requisite elements of a business-oriented book (voices from industry, outcomes of research, anecdotes, and the like). Not to mention the mound of acronyms tossed in for good measure. But, I expect those. This book asserts that learning should be a systemic attribute of any thriving company. As such, learning must be part of the culture of the company for it to be successful. You cannot slap training on the side and expect that you will have any serious ROI to the company. It would be like thinking that buying Girl Scout cookies or Boy Scout popcorn has a substantive impact on the members of either organization. Yes, it does provide financial support for programs, but it’s not “the program.”

Training needs leaders, resources, people interested in learning, and a purpose (lest we forget why we do training in the first place).

Training has a structure and that structure is not one-size-fits-all. People have varying modalities of learning. Even the best material won’t work well for everyone. This is were that whole (materials, time, place, etc.) details thing comes into play. But, again the focus of the book is to lay out the challenges and considerations, not specifics.

Finally, you need to see that training produces results. This can be fiendishly difficult to measure, so it’s vitally important to set expectations before doing the training. Being happy is not considered a valid measure of ROI for the company.

As mentioned earlier, the book is replete with references and for those who create training material or even those who want to create an environment within their company where can be effective. It is a good starting point. For those who have been involved in training for some time, the book can serve as a reference that can be used to educate management in the scope, cost and investment (they’re different) necessary to create a learning environment that will have long-term benefits.

Overall, a decent read. I found the interviews with CLOs (chief learning officers) incisive. As with all organization-level things, there are no easy answers. And you do get what you pay for. You’ll dispatch this book in a few hours and then find yourself going back over it later.


The latest trend seems to be reading what the rich and powerful read. I regularly peruse these lists of recommendations and occasionally an interesting title catches my eye. The Sixth Extinction by Elizabeth Kolbert is one of those books.

For a while now this book has been in my ‘highly parallel reading queue.’ This is to say that my usual method of reading consists of a bookshelf of a hundred or so books that I’m somewhere in the midst of reading. From this bookshelf, a subset of about 20 find their way to a smaller bookshelf. These will be read randomly a chapter or so at a time until I’ve worked my way through them and have to reload from the primary bookshelf. Occasionally, as with my last reviewed book, I’ll do a cover-to-cover in a burst, but that is the exception. I’ve got some books that I’ve been reading for the better part of 30 years (75% footnote material).

Needless to say, by the time I’ve finished a book there has been a fair amount of reflection and integration that’s taken place. The material in The Sixth Extinction is fairly heavy stuff. It’s not that the science is particularly difficult or that the writing requires you to keep a tablet handy for side exploration (I love side exploration). The thing is that if you have a decent understanding of the history of the planet (so far as we have come to understand it) and appreciate the impact that man can and does have on the biosphere, then by the time you finish the book, you’ll come away with a sense of profound sadness.

I’m a fan of John Brunner‘s work. He had a way of making the large scale personal. He also had a habit of killing off all his main characters within the first ten pages of his books (yes, this is a bit of hyperbole). In many of his works there is a sense that things aren’t going to work out, but you keep pulling for the hero anyway.

The Sixth Extinction is a methodical tour of the effects of the age of man (Anthropocene epoch). It takes us around the world, unblinkingly moving from one die-off in progress to the next. It puts a face and a context to each creature we’re introduced to. If the books thirteen chapters were made into a season of television, it would be the most stunningly depressing series ever. Whereas Carl Sagan‘s Cosmos appealed to our better nature and James Burke‘s Connections left us asking if we were any more than cogs, The Sixth Extinction ends with rats inheriting the Earth.

This may all sound like a bit of a downer, but it’s one of those mirror books that is a distinct departure from all the wishing that we lived back in 1950’s America or how can we become millionaires by eating the same breakfast as Warren Buffet or Mark Zuckerberg. We need to read books that show us the big picture. Otherwise, what’s the point of it all?

Many books on bad situations leave us with a call to action. Realistically though, the damage has been done. The question is one of how long it will take for all the dominoes to fall. For the vast majority of people, asking them to look further than their tribe is near unto impossible. Asking people to consider the planet, therefore, represents an intractable problem.

Read the book, if for no other reason than to come away with a greater appreciation of the impact of man on the planet.

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