What Does Good Engineering Leadership Look Like?

This is the first of a twelve-part series covering the sessions from Calibrate, an engineering leadership conference held September, 2015 in San Francisco. Content will be posted at a regular cadence throughout the month of November.

  1. Welcome
  2. Leadership. By The Numbers.
  3. The Engineer-to-Manager Transition: Surviving Your First 90 Days
  4. Agile Management
  5. Growing Your Career When Everything You’ve Ever Learned Before No Longer Works
  6. Up To Speed: The Importance of Proper Onboarding
  7. Crunch Time: The Death of Creativity
  8. Building and Maintaining Your Feedback Muscle
  9. Life After Diversity Goals
  10. Paying Down Cultural Debt
  11. On Management and Leadership
  12. Three Best Practices to Grow your Happiness as a Manager

In the welcome above, I focus on my own personal relationship to the content of Calibrate. What I’d like to do in this post is contextualize this experience within some broader trends over the last fifteen years of software engineering.

Does Process Define Effective Leadership?

When I began my career in engineering in the late 1990s, waterfall development – overseen by command-and-control management – was the standard. As such, the responsibility of management reflected the needs of waterfall: overseeing efficient execution of the “development” phase. The measure of a manager was how well they delivered to specification, which meant shielding engineering from interruption (and as a byproduct, crucial business context) and they became de facto project managers, assigning and monitoring projects to be executed as specified.

Fifteen years later, teams self-organize, cycle times are shorter, and we bristle at the mention of the word “waterfall”. Iterative models and their accompanying philosophies on team composition, communication and collaboration urge us to reconsider what it means to manage teams. Traditional management training, with its focus on topics like “resource planning and allocation,” has largely failed to keep pace with the concerns of modern engineering leaders.

What does a manager do if not dole out parcels of work and serve as an information conduit?

If we value the output of diverse, creative, highly collaborative teams, how can we support and amplify their efforts? We focus on things like mentorship and coaching within and across teams, with the requirement that we excel at skills like providing individual effective feedback and the facilitation of healthy group dynamics.


In 2010, with technology jobs thriving and Agile gaining significant traction, the Lean Startup team put on its first conference. Short cycle times and concepts like “minimum viable product” quickly became the norm. It’s now 2015 and:

  • The demand for all forms of product engineering teams (design, product, engineering, etc.) has continued unabated.
  • We’ve seen a corresponding growth in the number of engineering managers.
  • We strive to promote leaders from within for all of the attendant benefits it provides and the risks it mitigates.
  • The folks being promoted are primarily engineers.

…and one would therefore expect a large body of content around what it means to make this transition. Engineering leadership’s specific set of challenges with respect to the intersection of people, technology and process have not been met with either reference material or a developmental community surrounding it. Our primary means of learning is as-you-go.

We conceived of Calibrate as a way to bring together accomplished engineering veterans in addressing address the needs of newly-minted engineering leaders. We hope Calibrate – and the conversations it started – bring recognition to this important topic, and help foster a community of learning focused on leadership in engineering. As we share the Calibrate sessions with you throughout November, let us know how we did.