1) Check the class of airspace
2) Check the weather
Look up the weather for the day of your operation. Nav Canada's Forecasts and Observations site can come in handy for that. The regulations don't specify the conditions for flying, but it needs to be safe. The regulations recommend flying in good weather and daylight for first-time flyers. In the end, the decision to run the operation is up to the pilot in command. It's also a good idea to plan a back-up date in case the weather changes.
3) Check for notams
Notice to Airmen (NOTAM) are any warnings or things to take note of in the area you are going to fly. Check the Nav Canada Flight Planning Site for any NOTAMs for the aerodrome you plan to fly in and take note.
4) Check the perimeter of your flight path
Look at the specific area on the map (such as on Google Earth) that you wish to fly in. There may be important geographical features to take note of, such as proximity to buildings, public spaces, etc.
5) Check the security
While checking the perimeter for your flight path, also ensure you take note of all entrances and exits to the area. Devise a plan for how to restrict access to this flight area until the operation is over.
6) Gather a team
The operation needs at least (2) people involved: the pilot in command and a visual observer. Additional team members to monitor the perimeter/secure the area may be required depending on your specific operational area.
7) Submit a request for authorization
8) Prepare/Maintain your equipment
Before you actually head out for your operation, make sure you check your drone equipment and prepare your crew. The lithium powered batteries should be equally charged for the drone and controller. Inspect the drone for damage to propellers or casing, ensure the camera is in working order, etc. (Make this a full list when I interview Pat and Ed)
9) establish a line of communication with the nearest ATC
Take note of your nearest Air Traffic Controller (ATC). In cases where you are flying in controlled airspace, you will have to establish a line of communication with the nearest ATC for your aerodrome upon arrival. In cases where you are flying in uncontrolled airspace, you will still need to communicate with the nearest aerodrome in cases of drone flyaways or loss of controls. This can be a simple phone call and does not require a two-way radio.