This oreilly.com article about balancing quality and product features (from the perspective of a CTO/CIO) is a good read. The editor’s note states, “This is part of a series exploring the trials and tribulations of first-time managers. Camille Fournier, former CTO at Rent the Runway, is often asked for advice on how to make the transition from an individual contributor to a manager.”
I'm not sure why Apple has suddenly decided to make the future support of Mac Java uncertain (see "Mac Java deprecated; Did Apple just kill Mac Java?", and "Mac Java is deprecated: What it means"), but if I'm a CIO or CTO working at a company that has invested any money at all in Java development, Apple just sent a very clear message:
Don't buy any more Mac computers in the enterprise.