1. Do you own, operate, or manage the aircraft I will be flying on?
2. What level of liability insurance is maintained on the aircraft I will be flying on? For maintaining the insurance coverage? How much insurance do you maintain? In the event of an incident, do I come back directly to you?
3. Can you guarantee aircraft availability and in how many hours from making my reservation?
4. If unscheduled maintenance is required, how long will it take to find a replacement aircraft and will that aircraft be of the same type and quality as my original aircraft?
5. How old on average are the aircraft I’ll be flying on?
6. Can I specify the aircraft I want to fly on by aircraft type? Or just a general category?
7. Is there ample seating, headroom, and baggage space on my aircraft?
8. Who maintains the aircraft and how often is it serviced? Is the maintenance conducted by factory-authorized service centers or not?
9. How much experience do the pilots flying me on this particular aircraft have? In this aircraft type? In general? By whom are the pilots employed? What’s the average flying hours of the pilots and do they fly multiple types of aircraft or just one?
10. What level of training do the pilots you use receive, who trains them, and how often? Are both pilots type-rated ATPs and do they receive biannual full motion-based simulator training or do they have just an annual recurrency check?
11. Will I be billed for hours I’m not actually flying, such as daily hourly minimums, taxi time, and ferrying, cancellation, and late fees? Have I been told about all possible additional charges?
12. Are catering, telephone, fax, and other in-flight services included? Is there Wi-Fi on board?
This list is by no means complete
You should also ask any number of other questions that are important to you and the people with whom you fly. It is, however, a good place to start.