Dropbox lies squarely in the "ruinous empathy" quadrant of business culture. Promotions are measured by the number of friends you make, not the results you achieve, which results in decision making by committee and projects that lag on for months at a time because nobody is willing to take ownership or say "no." At the same time, projects spanning 6+ months of research, design, and engineering can be derailed by the opinion of a single manager in the pursuit of "perfect" rather than "better".
Staff lack a clear vision for Dropbox. Milquetoast strategy updates and new opportunities receive endless bravado but when it comes to actual execution there's little follow-through. Meanwhile, the core Dropbox product continues to suffer from longstanding problems like convoluted sharing and horrendously slow performance.
We use Dropbox Paper, our own docs offering, for absolutely everything—from project management to calendaring to to-do lists to meeting notes. What results is total chaos. There is no sane way to organize docs, which get produced at an astounding rate: product managers regularly compose dozens of new Paper docs in any given week. There is no way we would organize ourselves this way if we weren't so committed to using and abusing our own tool.
Simple bugfixes languish in backlogs for months or years without resolution. Abysmal developer tools and nonexistent analytics slow the company to a crawl.
We talk a big talk about "designing a more enlightened way of working" (corporate thinkpieces go up on the blog every few weeks) but how can we hope to improve work for others when our own house is a mess?
All these issues aren't new, and they're well-known to anyone who has been in the organization for longer than a year. We will talk about them and collectively agree they need to be addressed, but for whatever reason, nothing ever seems to happen.
