Software pricing. The lion's share of enterprise IT budgets still goes to the big software companies, whose complex licensing schemes and software audits rake in billions upon billions. Yes, we're gradually moving to subscription models, but some seem to willfully emulate the complexity of licensing plans. No wonder more companies are adopting open source -- or building their own applications rather than buying.
Inaccessible data. Inside enterprises, access to data needs to be closely controlled, but all too often valuable data remains inaccessible to those who are actually authorized and could benefit enormously from it. Carefully enabling that access requires hard work. In the public sphere the problem is simpler: All public data should be accessible via well-formed APIs. Businesses should have easy access to useful data collected by federal agencies and state and local governments. Today, even policymakers need to dig for it. While we're at it, let's make the Web machine-readable.
This is obviously a partial list. I'm sure you have your own favorite sticking points to add, and you're invited to do so in the comments section.
I don't mean to minimize the advances we've seen -- and not just technological ones. For example, over the past decade technologists have become embedded in lines of business, to the point where even talking about the divide between "business and IT" seems passé. Technology literacy in general, propelled by everything from free MOOCs to clever mobile apps you can't stop using, keeps rising year over year.
But transformation? You can't just chant "the Internet of things" and expect wholesale change. I hold out hope that the increasing sophistication of users will help surface old problems that demand roll-up-your-sleeves commitment to solve, because without that we'll never make it to the next level.
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