While I've had some weird technical problems (I've worn a number of hats across Network/System Admin, to both front and back end web Development) the hardest is always the non-technical issues.
A few years ago I was contracting for a company that had a Native American Casino as a client. They wanted to build a gamified app/site to engage their customers more.
The single hardest problem was trying to look at the situation from the players point of view. Gambling like this (slot machines) is inherently an illogical thing to do - they know they're never going to make back the money they put in, but they walk away with a smile night after night.
Trying to rationalise (so we could understand their goals and what they might want out of an app/site targeted at them as players) proved impossible for basically everyone on the team.
A few years ago I was contracting for a company that had a Native American Casino as a client. They wanted to build a gamified app/site to engage their customers more.
The single hardest problem was trying to look at the situation from the players point of view. Gambling like this (slot machines) is inherently an illogical thing to do - they know they're never going to make back the money they put in, but they walk away with a smile night after night.
Trying to rationalise (so we could understand their goals and what they might want out of an app/site targeted at them as players) proved impossible for basically everyone on the team.