What It's Like to Lead an Engineering Org: Thoughts on "CTO in the Loop"

I just read CTO In The Loop by Balki Kodarapu. It’s free on Kindle through July 20th, so if you want to give it a read, go do that now.

It’s a narrative arc following a developer, “Sam”, who starts as a software engineer at a startup, and ends up a fractional CTO after a career that includes engineering manager, director of engineering and VP of engineering at a company that IPOs. The book was a fun read, and does a good job describing what it’s like to build a company and a software business from the early days to a more mature organization.

The realities of Sam’s growth ring true: he starts out focused on features and clarity, and then moves up levels of abstraction. He loses touch with tasks and areas that used to matter, but gains higher level views and more ability to influence the organization. As a director, if you’re still reviewing PRs the way you used to, you’re basically breaking your organization

We also see the evolution of several other characters, including Priya the project manager, Mei the UX designer and Jack the senior developer. Some of these folks stay with Sam across companies, while others pop in and out, just like real world colleagues.

Some details felt a little forced; for example, locking down a GitHub repo and preventing merges to the main branch are treated as a major effort, when most software shops do that pretty early.

I especially liked the portrayal of the thorny moments of management that Sam encounters:

I also really enjoyed the emphasis on integrity, and how the protagonist was repeatedly challenged to hold onto it through different stages of business growth. I think integrity is an easy thing to write about and much harder to actually live. In the moment, you tell yourself that just this one tweak that you might feel uneasy about will move the business in a positive direction. But doing this repeatedly only works in the short term.

The benefit is immediate and the cost is deferred, and avoiding these kinds of decisions is a constant challenge as an organization grows.

The hard part is that it’s rarely obvious where the line is. Most people agree you shouldn’t commit fraud. But there are dark UX patterns that benefit the business. For example, you could make it much harder to unsubscribe from a service than it was to subscribe; every organizational incentive points that direction.

Another example is the integrity in making it easy for a customer to leave: making it easy for people to export their data and take it with them. That’s a frustrating tradeoff for whoever’s job it is to sell the product, but it’s a pretty clear-cut example of integrity. You want to earn people’s business, not hold their data hostage.

There are other places integrity shows up over the course of a career, but the author does a good job of showing how it is hard to maintain, especially when you are focused on the day to day of building a software business.

CTO In the Loop is a fun, easy read. I read it on the Kindle app in about 2 days while on a vacation. I’d highly recommend it to people early or mid-career in software who are curious what life looks like at a different level of the org chart. When I was younger, I assumed people at higher levels had a lot more control, agency, and power. That’s true, but they are also further from the customer, removed from knowledge of how technical systems actually work, and have a lot less clarity about the day to day. To say nothing of many competing demands that folks at the director or higher level have on them.

Writing code, or telling an AI how to write code, is one thing. Thinking about what the company looks like in one year or five, how to bring different teams together, how to manage investors and understand the market, and how to keep every department rowing in the same direction: that’s a tremendously difficult job. This book is an accessible narrative of those tensions, to which I don’t think new or even mid-career developers usually get exposure.

So go check it out. Did I mention it’s free on Kindle through July 20th?

Balki, thanks for writing this excellent, interesting fable of a software developer’s career.