What are the key questions I should ask that could improve the chances of hiring a good assistant?

My Response:

Hiring the right staff is one of the most important, yet difficult things to do as a small business person. Some candidates interview well, but perform poorly. Others are slower starters.

The philosophy behind matching the right person with the position, based on their personality, skill set, age and the value they place on their own health is too ambitious for this forum. However, here are some questions you may find helpful:

"Describe the best boss you've ever had."
"Describe the worst job you've ever had."
"What's been the most satisfying part of the best job you've had?"
"What do you think would the best part of working here?"
"What are some of the things you do to advance your health?"

Ultimately, you want to uncover the candidate's values within the scope of the law. Shared values tend to increase the longevity of relationships. Skills can be trained. But values, personalities and world view rarely do.

Bill