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Stupid Guess.
Based on what I recollect reading spies are sent automatically as long as you are funding your spy operations. You can also prioritize a specific target country by increasing and decreasing the number scroller next to the target country selection from between 1 to 10. By the same token as I understand it you can also pre-select a specific mission and they will also go off automatically as long as you keep everything funded.
The developer AAR also suggested that a small amount of over funding can help increase the odds, but I cannot confirm this.
Based on what I recollect reading spies are sent automatically as long as you are funding your spy operations. You can also prioritize a specific target country by increasing and decreasing the number scroller next to the target country selection from between 1 to 10. By the same token as I understand it you can also pre-select a specific mission and they will also go off automatically as long as you keep everything funded.
The developer AAR also suggested that a small amount of over funding can help increase the odds, but I cannot confirm this.
The guess may have felt stupid, but it was correct 
I would also add to look at the screens in the "Intelligence" tab; just under the "Observation priority" line is a line for "Espionage budget" that has two numbers separated by a slash; the first is how much you are spending on the currently selected country with your currently selected espionage budget and country priority, that after the slash is the "par" upkeek costs of the spy network you currently have in that country. If the first number is lower than the second your network will tend to shrink and/or be ineffective; if the first number is higher then your network should tend to grow/succeed slightly more often.
Note that the priorities work on a pro-rata system, so increasing one country's priority will effectively reduce that of all others a little. To increase spending in one area you will need to both increase its priority and increase the overall budget.
I would also add to look at the screens in the "Intelligence" tab; just under the "Observation priority" line is a line for "Espionage budget" that has two numbers separated by a slash; the first is how much you are spending on the currently selected country with your currently selected espionage budget and country priority, that after the slash is the "par" upkeek costs of the spy network you currently have in that country. If the first number is lower than the second your network will tend to shrink and/or be ineffective; if the first number is higher then your network should tend to grow/succeed slightly more often.
Note that the priorities work on a pro-rata system, so increasing one country's priority will effectively reduce that of all others a little. To increase spending in one area you will need to both increase its priority and increase the overall budget.