Oh, does it ever encourage fluff! Plenty of long form stories posted to HN fit into this category. They begin with a meandering anecdote, build to a surprising or paradoxical end, and only then does the actual story start.
I get bored with this approach when I can't see a connection between the anecdote and the title. A non-fiction title is a promise to the reader. Renege on that promise and the reader is gone like Enron. Long form starts to break the promise when the anecdote gets so shaggy that you forget the title and therefore the reason you're reading the article.
The linked goes on to take apart the syntax Gladwell uses, which is useful to know. But the most important thing Gladwell does AFAICT is to closely align his anecdotes with his controlling idea. That means:
1. Choosing only those anecdotes that optimally align with the controlling idea (theme).
2. For each anecdote, culling stray details that don't align with the controlling idea. This is a painful process for writers, which explains why there are so many shaggy tales told in Big Idea nonfiction.