Southwest ran the same strategy from 1967 to 2025 and then abandoned it. Gerardo A. Dada's explanation in OutPosition is that management got bored. He has the paperwork. A September 2024 investor presentation called free checked bags the company's top differentiator, named by 82 percent of customers, and priced the switch at $1.5 billion in new fees against $1.8 billion in lost market share. Five months later, bag fees were listed as significant new revenue initiatives.

Southwest’s sudden change is the type of example that leads OutPosition. Dada writes that strategy gets lost because it’s confusing and difficult, but more importantly, because it’s easier to explain the past than to predict the future. This is why the author feels that most executives do not have a strategy at all. Ask them for one, he writes, and you get revenue targets, product roadmaps, and cultural statements. A real strategy names what the company will not do and holds that line for years.

He has held senior leadership roles at Microsoft, Rackspace, and SolarWinds, among others, and his best material comes from his own stories. He heads the Rackspace section "A Personal Story," and it reads like one. He watched a new slogan go up on the building after the company had already moved on to the next one. Readers will appreciate how practical Dada’s advice is. He doesn’t promise an answer, just clarity and a method.

His aim is to treat strategy, positioning, and differentiation as one discipline instead of three. He separates strategy from positioning, brand, and tagline, and gives each one a job. It is the best explanation I have read of why a company can sound different and still lose. His Differentiation Quality Scorecard runs twenty-seven tests against a claim before you build on it.

Chapter seven is the strongest. Dada sorts the ways good strategies die in execution into six gaps, and the first comes with a test you can run this week. Ask five managers from different teams what the company's strategy is, who its ideal customer is, and who its real competitors are. He expects partial answers and polite improvisation. The obvious issue is that few within any given company are on the same page.

The executives who need this most are the ones who suspect their own company has a list of goals where a strategy should be. This book would be incredibly useful for a small business owner who oversees many roles, including strategy. Dada provides a genuinely helpful method, and his years of experience back it up.