For me, handling difficult people is about holding space for them to work out whatever is causing the difficult emotional experience. I think it's worth noting that multiple interviewers asked me this question multiple times- and certainly, it IS an important aspect of the position, but I also get the sense that Digital Ocean might have a greater-than-average number of "difficult people." Who knows. However, it's my belief that highly technical people (of which DO has many) have an even greater responsibility to NOT be "difficult" regarding technical matters, because they should know better. The IT department should NOT have to do a bunch of emotional labor to legitimize their work and convince paranoid staff to chill out.