A Complicated Measurement
This one was incredibly difficult for me to find a rating for. This book contains a few gold nuggets of information that are worth five stars, but it also includes a lot of over explanatory and bloated pages.
How to Measure Anything would more accurately be titled "How to Reduce Uncertainty in Business Decisions". Hubbard outlines his process for reducing uncertainty in decisions by measuring what is critical for the decision. Often measurements that seem impossible really come down to accurately defining the definition. Once you have a definition of nebulous goals like "better culture" or "more secure IT" then you start to realize there is usually more information available than previously recognized. What he ultimately finds throughout his research is that well-calibrated estimators can do almost as well as the copious math functions that he provides.
Sounds helpful and interesting, right? Well, as mentioned earlier, there are some golden nuggets of information. Understanding the framework that Hubbard lays out for defining what to measure is priceless. The questions that he uses to calibrate estimates are now my default way to estimate anything from "How early do I need to leave to arrive on time?" to "How many hours of work will this project take?"
Unfortunately, it took a lot of digging to get to those golden nuggets. The first third of the book could have easily been skipped. It was overloaded with unnecessary self-justification. The book is full of redundant arguments on why to read the book with an open mind and not-so-cleverly disguised sales pitches for Hubbard's workshops to train teams.
This is what makes it so difficult to offer a blanket rating for. There are some five-star bits of content. Are you willing to dig for them? If so, this might be more than a two-star book to you. If not, I suggest LessWrong's post on the book. It's incredibly thorough review of the key concepts. This Is Important also has a good write up which is a bit shorter.
Overall, this was just okay to me. There are key concepts that will stay with me, but the book is need of some serious editing before it becomes one of my top shelf choices.