This guide focuses on providing an overview of interviews: what to prepare, expect, and follow up. We gathered real questions from real oneonone meetings, from real people.Fuel your next meeting with one of these 121 questions. I like to ask what keeps them up at night? What do they see as the biggest challenges facing the organization or the industry? No matter where your direct reports stand, it is worth bringing up career development in your to ensure you get the best out of your team. Asking the right questions in each oneonone meeting is important, so we've compiled 24 questions to get you started. Sample Questions to Ask on an Interview ; The Company. What do you see ahead for your company in the next 5 years? Ask general questions that reflect your enthusiasm in the work.