1. Is the Pilot Licensed? - As of August 2016, the FAA requires that all drone pilots have a Part 107 drone/UAV license to operate legally as a commercial pilot. It is a good first step to ask if a pilot has this license. To be sure, you can ask them to show you their certificate. The FAA is handing out large fines for those operating without this license or for those hiring an uncertified pilot. Those who knowingly hire unlicensed pilots like Realtors or even real estate developers can face fines starting at $11,000 per occurrence.
2. Does the Pilot Have Insurance? - This is another good question to ask your potential hire. When selecting a drone operator, you will want to consider one who is insured. This can protect you and the operator in the event of an accident. Though insurance is not required by the FAA Part 107, it is important that the drone operator carries at least a liability policy.
3. Are They Educated About Airspace and Flight Restrictions? - It is essential to hire drone operators who are knowledgeable about the safe conditions for certain operations. In order to fly for commercial purposes inside certain types of airspace (specifically, Controlled Airspace), a drone operator will need to obtain certain waivers and authorizations to fly in that airspace. Other types of operations may require other specific waivers, such as night operations and flying over people.
4. How Much Experience Does the Drone Operator Have? - Do you want just some person with a drone? Although the FAA requires the 107 certificate to fly a drone commercially, it does not require a drone operator to pass any sort of skill test. Make sure you ask the operator you are thinking about hiring how long they have been flying drones and how kong they have been in business.
5. Does The Drone Operator Have Examples of Their Work or a Portfolio? - It is common practice in the photography and videography industry to ask to see a portfolio or examples of a photographers work before hiring them to do a job. You don't want just anyone with a drone to take photos or film for you. The drone operator should be able to produce previous examples to show the quality of work you are likely to get. Make sure that the person that you hire is a photographer who can fly a drone.
The bottom line is you are paying good money for a good product. Make sure you hire a professional. The five points above are marks of someone who has taken the time to be knowledgeable of their craft, they make sure their clients are protected, and they are putting forth the best product they can. Don't hire just some guy with a drone because it will end up costing you more in the long run.