Becoming A Technical Leader

August 23, 2017
leadership book

title Becoming a Technical Leader

subtitle An Organic Problem-Solving Approach

link Amazon


Why did I read this book?

As part of attempting to build my own company and the leadership positions I’ve had at companies like Docker and Dropbox, I have a vested interest in being a better leader. This book was suggested to me as a good book on the topic.

Why should you read this book?

Anyone who wants to (or does) work with teams of people and wants to increase leverage for those they work with.

What did I get out of it

The book ended up solidifying and expanding ideas that I’ve already had and put into practice. In this way it was useful to read a more concrete exposition of those ideas. It was fairly interesting to map the concepts presented in this book to my own life.

Also an amazon list for further reading.


Modeling the world: Linear vs Organic

The book starts by exploring the definition of leadership in the context of different kinds of modeling. There is some light talk about psychology and the chapter comes to focus on Organic modeling vs Linear modeling.

Organic models can be contrasted with linear models on several dimensions: the way events are explained, the way a person is defined, the way a relationship is defined, and the attitude towards change.

I found the description of organic modeling that occurred throughout the book to be useful and interesting.

Leadership is the process of creating an environment in which people become empowered.

Organizing Life

The author tells stories about pinball players as a way to describe what it takes to achieve effects that require nontrivial effort. Desire is not enough to drive real improvement.

Their lives just weren’t sufficiently organized to learn anything that required a nontrivial effort.

This leads to the MOI model of leadership: Motivation, Organization, and Ideas or Innovation. I found this to be a useful model when reflecting on the problems I’ve seen and heard about at startups in the Bay Area (where I do most of my work).

Organizing Innovation

All of the most consistently successful technical leaders empower people by the value they place on innovation, on doing things in a better way.

The author goes on to describe the three main areas that characterize the problem-solving leadership style as well as show examples of M, O, and I based approaches.

On Improving

The next section of the book went through what it takes to get to the next level of skill. The author describes a series of cliffs and plateaus which are progressed through by trying new strategies. It is important to note that by trying these new strategies, one might move backward temporarily before hitting the next plateau.

I’ve experienced this myself with Volleyball, and other aspects of my life, Where learning to serve a ball with a different contact style might cause a higher percentage of misses before becoming a significantly better serve.

When you begin to feel you’re really getting good, start looking for some conceptual breakthrough

On Systems

This section goes into some detail about how leadership and management are not the same in the organic approach (as opposed to the linear approach). Especially with the recent rise of microservices and emphasis on design systems, delving into a systems based approach should feel familiar to many working engineers/designers/etc.

Because it’s an operating system, inefficiency under load is likely to stem from interactions between modules, not from individual modules behaving inefficiently

The above quote reminds me of a style of manager whose actions pin the failures of a team on individual ICs rather than the environment and interactions that occurred. Teams can be motivated and have useful ideas and innovations but if the organization of the team itself and the relationship to the rest of the organization is poorly handled, it will destroy most of the value that could be created and you will lose the team to better opportunities.

Obstacles to Innovation

The author next describes three great obstacles to innovation in an effort to move from theory to practice. The obstacles are personal in that one should evaluate themselves to find out if they are blocking their own progress.

  1. self-blindness, concealing your own behavior, so you have no chance of changing
  2. No-Problem Syndrome, convincing you that you already know the answer to all problems
  3. belief in the central dogma of academic psychology, blinding you to alternative solutions, even ones you could generate without help from anyone else

Developing Idea Power

Any real problem has one more solution, which nobody has found–yet.

The idea of this chapter is that binding yourself to there being a “right” answer is debilitating when approaching problem-solving. Even if there is truly only one answer, it is useful to approach a problem with a specific mentality for potential solutions.


How success can lead to failure (or how what got you here won’t get you there). The solution that solved the problem yesterday isn’t something you should hang on to when the time comes to develop new approaches. Developing personal vision is useful to a problem-solving leader for a number of reasons. Quality, as referenced earlier in the book, is defined as something that a leader with vision has the required obsession over. I liked this framing of quality because I felt that earlier in the book quality was given a very subjective definition (or rather, not given a definition at all).

Obstacles to Motivation

One idea that really resonated with me in this chapter was the idea that sacrificing people’s future possibilities to achieve something now is often the wrong move, especially for complex technical and creative matters. I appreciated the acknowledgment that there are two sides to this:

If you put the people ahead of the work, you may hurt your chances of succeeding with your project; but the people will be around long after the project has been forgotten, doing other projects and affecting the lives of other people.

I also appreciated the following conclusion, which is that a people first approach is the best move in the end.

In a complex environment, even the most task-oriented leader is forced to put people first, or the task won’t get done.

I heavily agree with the people-first approach, especially when considering how tight knit the industry is (especially in the Bay Area). One quote really stuck with me:

If you can’t do the task without exploiting people, perhaps you shouldn’t do it at all

Power Conversion

The chapter on gaining organizational power is interesting in that it describes power conversion vs point accumulation. Whenever someone says you are “earning points” or “paying dues” it is unlikely to pay off. Instead, take stock of what power you have (technical competence, positional power, etc) and find out how to use that to get where you want to go. The author goes on to describe how realizing this experience can be translated from gaining power for yourself to gaining power for the use of others. Gaining power for the use of others is far more interesting because there is a compounding effect on such use.

Some new team leaders merely continue to use their tactics to obtain what they need, not what their team members need … most don’t understand the leader’s role, to create an environment in which everyone is empowered.

Making Time

The book continues on and eventually comes to the topic of “making time” in a day.

to which two are added


The bibliography is large, consisting of at least 22 authors and their books. It does, however, have nice summaries of why you would want to read each book. This makes prioritizing any choice much easier.

I’ve compiled an amazon list of all of the books in the bibliography with the exception of one, for which I chose the updated and expanded version.