When you’re facing a confusing or ambiguous software problem, how do you get clarity?

It may seem obvious, but “keep asking questions” is generally the way. Keep asking different people, from different places until you gather enough to get some consensus. Don’t be afraid to ask people who you would think wouldn’t have input. You’ll be surprised what people know. 

I lead the Quality Engineering and Site Reliability Engineering departments for Duo Security, a Cisco company. We regularly handle 1-2 billion customer authentications a month and we have a complex distributed system built up over the years, that helps us handle this. Quite often I have to make decisions in areas that are confusing or ambiguous. My approach is to learn as much as possible about the problem, by talking to the experts within the org and outside (like our partners from AWS). Once you've gotten the right group of people together, layout the problem in front of us and listen to their advice with an open mind, any decision you make will be better than on that you might have made on your own.