Crafting Engineering Strategy

Chapter 23. Is This Strategy Any Good?

You’ve read a lot of strategy at this point in the book. You can judge a strategy’s format and its construction: both are useful things. However, format is a predictor of quality, not quality itself. So how should you assess whether a particular strategy is any good?

Uber’s service migration strategy (Document 16-1) unblocked the entire organization, allowing it to make rapid progress. It also led to a sprawling architecture problem down the line. Was it a great strategy or a terrible one? Reasonable people will disagree, but it’s worthwhile to develop a point of view on why you should prefer one interpretation or the other.

This chapter will focus on:

• Common techniques for evaluating strategies

• A rubric for evaluating strategies in phases

• Why ending a strategy is often a sign of a good strategist

• The problem with evaluating other companies’ strategies

• Why you can learn just as much from bad strategies as from good ones

Time to refine your judgment about strategy quality.

How Are Strategies Evaluated Across the Industry?

Before suggesting my own rubric, I want to explore some of the software industry’s methods for evaluating strategies in practice. I don’t particularly agree with these approaches—I think each misses at least one important nuance—but understanding their flaws is a foundation to build on.

Grading strategy on its outputs is by far the most prevalent approach, and it does make sense that a strategy’s results are ...