Question) How would you go about evaluating a development manager? New developers?
Answer) You are a great judge of character, this you must rely on. Attitude is everything. BUT experience is a necessity... With that said, test and measure. Then test and measure, then test and measure. If you are looking for a manager test him with technical and people problems. Make sure you give him enough problems to make sure he knows what he knows. Same thing with developers, make them struggle. I had one interview where I had to answer the same question with multiple right answers, and after answering the question right 3 or 4 times the hiring manager told me one more way I could have answered... Tough but he knew what he was getting (of course I got the job, and respected him for what he did). At my auto repair shop we take our time with meeting them and getting to know them. The interviews are typically longer than an hour. We want to make sure they play well with the others in the shop. But tech is a different world of course, in a typical short interview it is hard to get to know how someone really is. I am a big believer in empowering others. At SWA I built several engineers by giving them tasks leaving them alone and then seeing how quickly they either did or didn't provide a solution. Those that did I built, those that didn't I got rid of. Bottom line test and measure.
Question) How would I go about instilling great development culture? How would I go about facilitating great development collaboration and discipline?
Answer) The culture starts with you. William Wallace (from the movie Braveheart) bled with his men, he took time to understand his men, and he died for his passion... He was easy to follow because he made you believe, but he believed. Don't ask something of your men you aren't willing to do yourself. Also get to know them. Take them to lunch on one on ones. Yes they are going to tell you all the negative things you don't want to hear but the will tell you everything you need to hear. Something I learned from one of the previous CTO's I worked for was he wasn't afraid to get down and dirty with everyone. What CTO does that... Very few. Don't force fun and don't make them salute the company flag, they will tell you how the want to be treated, you just have to listen.