A former colleague makes it an interview question. He asks the recruiter what the procedure is if he wants to buy a product or use a service under $100/year. If the bureaucracy is overwhelming, it's a major red flag.

When I was working at Cisco, the general rule was to get manager approval and just go for it. Of course, these days, there are security concerns but for most cases, it's not a problem.

In a different company, it was sooo hard to get anything that they refused to buy JetBrains IntelliJ and forced us to use Eclipse. Most of us ended up buying it ourselves.