Manager Therapy

Like most software engineers who transition into people management, I did most of my learning by trial and error. “Engineering Management 101” doesn’t appear anywhere on my college transcripts and to the best of my knowledge, is not a course that is offered as part of any major Computer Science curriculum. I happened to start my management career at a big company with an established employee education program, including some courses on the tactical skills of management. So, I got a little formal training on giving feedback and having career conversations. But nothing at all that told me what my new job’s day-to-day should look like. What should I be doing with my time? How much code should I be writing? How should I measure my own success, now that my success is the success of my team?

Stumbling across Kate Matsudaira’s wonderful essay Becoming A Manager was a revelation. She seemed to share all of my questions. She described exactly what I had been feeling. This difficult transition that I was experiencing was normal. I wasn’t alone. I discovered an entire ecosystem of software engineering management essays and blog posts. Our whole industry seemed to be realizing that none of us have been taught how to do this job. New and experienced managers were writing what they discovered as they went along, both the good and the bad. Reading what these other managers had to say was a better education in management than any skills training or course that I attended.

By the time I joined Flatiron, I had already managed people for a few years. But the first group of managers that stepped up after me began like I did, with no formal training in engineering management but with a willingness to learn and a desire to make their teams succeed. I started a monthly engineering management reading group for two reasons: to help these new managers understand exactly what their new job was asking of them, and to help them avoid the loneliness and uncertainty that I had felt as a first-time manager.

All you need to start a successful manager reading group is a scheduled time and a commitment from participants to do the reading. We meet over lunch on Fridays, a time that feels relatively unscheduled for most people. An optimally-sized group for encouraging discussion and debate seems to be about 8 people, although we’ve fluctuated both larger and smaller.

Diversity in your choice of readings is essential to maintaining the interest of your reading group members. Try to balance a mix of short essays and longer books, and tactical skills-based how-to’s with more philosophical works. Some of our favorites from over the last year and a half that we’ve been meeting include:

  • High Output Management
    If I was going to teach a course on engineering management, I would use Andy Grove’s classic, High Output Management, as my textbook. Super tactical and meaty, it has enough content that you can easily spend more than one reading group session discussing it. We devoted two sessions to this book: the first one as a free-form discussion, and the second deep-diving into the chapters on meetings and “task-relevant maturity”. Cate Huston has a more detailed review on her blog.

  • Management Time: Who’s Got the Monkey
    This essay, from a 1974 issue of the Harvard Business Review, feels a little dated in its language, but still prompted a great discussion on why and how to delegate. It takes aim at one common new-manager bad habit: taking on your reports’ problems as your own. A great counterpoint to this article is Marco Roger’s outstanding Engineering Management and Diversity, which addresses the opposite bad habit: managers who view their role as controlling or commanding a team, rather than serving it.

  • Three Signs of a Miserable Job
    Like Patrick Lencioni’s other works, Three Signs is a quick and entertaining read, written in the form of a management fable. Although it’s more philosophy than tactics, our manager reading group has found itself referring back to this book over and over. The “three signs” are remarkably simple, almost obvious, but knowing what they are and being alert for them within your teams can help you avert problems before they become serious.

  • On the more tactical side, Michael Lopp’s humorous blog post, The Update, The Vent, and The Disaster, teaches new managers to recognize some common patterns for 1:1s. Kate Heddleston’s blog is an embarrassment of riches. I’ve found her post, Criticism and Ineffective Feedback especially valuable.

  • On Being a Senior Engineer
    Finally, I couldn’t make a recommended reading list without including this essay by John Allspaw. Yes, it’s not really about management. Nonetheless, it’s my favorite essay on engineering, hands-down. I make a point of re-reading it every 6 months. You should too. It will make you better at life.

In practice, our discussions at manager reading group, or “manager therapy” as we’ve sometimes joked, rarely stick strictly to the books or articles we read. Participants are encouraged to treat the group as a safe space where they can bring up and discuss real-life management challenges that they encounter. By recognizing that other people share our experiences, we are able to share tips and advice, becoming both more confident and more skilled in this strange new role that we’ve all taken on.