Ask HN: What challenges do your technical teams face?

There are a lot of components that go into building a great IT organization (big or small) and different solutions work at different levels of growth. I'm a bit curious to understand what challenges different teams face, and a bit about what their environment is specific to them. Failing that, if you know of some case studies and perhaps solutions to them please send them my way. As an example, I've worked with technical teams where the throughput was a slow trickle of features every 3 months which was a large constraint on the business. The team was about 50 people in size ranging from the interns up to the CTO. We identified one of the key factors preventing delivery was a (well earned) fear of things breaking in prod when deploy day comes every 3 months. Lots of solutions to this problem exist, and lots of them will make improvements to the throughput, but they must address the central issue of service disruption. So we started getting the team to improve test coverage and over a few months we went from zero tests to a culture that would laugh if the very notion of not testing was suggested. I'd like to hear a bit about the challenges you've had, been part of, or perhaps just seen from the side. Thanks!