I usually ask something like, “Where do you want to be in five years?” This gives me a clear idea of whether I can help them achieve what they want with my current business. If they’re after a certain title, does their potential role have upward mobility? If they’re after a certain pay scale, what would it take to get them there? If they have other aspirational dreams, like living in a certain location or spending time with family, will this role help or hurt those dreams?

