Surely there are people more expert than me, but I'll tell you what I do (having read some information about it), obviously the most important thing: maximum priority to the sponsor's objectives. Then:
1) Clear all pre-set goals (I love this part )
2) Don't set too many goals (depending on the cyclist 2 max 3 per season)
3) Set the target for tour riders and some of their wingmen (no need for 8 in peak)
4) Set the goal for classic hill racing cyclists
5) Set the goal for cobble racing cyclists
6) Set secondary goals for smaller riders
Unfortunately there is no quick way to do it, let's say that in a certain sense it is also the fun and study part of your team, it generally takes me 15\20 minutes.
Something that has worked for me in the past is to group riders into "mini-teams" of ~4 riders each, and then plan for those mini-teams. For example, in a WT team, you can have 3 stage race teams, a cobbles team, a puncheur team and one or two sprint teams. And then you combine the teams for stretches of the season to cover every race.
For example, you make a team for your main stage racer that includes three good mountain helpers. And then you set the calendar for that team, maybe PN+Catalunya -> Tour -> Vuelta. For PN+Catalunya, they're joined by a second stage race mini-team. For the Tour, they're joined by a sprint team. And for the Vuelta, maybe they're joined by the third stage race team that also did the Giro. And maybe those other two stage race teams don't have three climbing helpers, but only two and then also a sprinter, so sprint stages in the stage races are covered.
The cobbles team can join stage race team three during TA to prepare for cobbles, during the cobbles they're joined by the hills team who prepare for the Ardennes, and the hills team is then joined by stage race team two who prepare for the Giro and so on and so on. And then maybe the cobbles team re-joins with the hills team in the second half of the year to do Bretagne, Canada etc.
You will have some inefficiencies, some riders riding races that aren't 100% optimal, and of course you can't enter 8 riders into every race (but this way you can cover for injuries or manage fatigue). You will also have to include CT races to make sure your riders get enough race days. But generally, with only a little bit of "puzzle work", you will have every race covered with just 8 different schedules. Plus, once you have figured out the schedules for the mini-teams, you can basically use the same schedule every year, and just move a rider from one team to another, or add new signings to a certain mini-team etc.
It may take some time to think this through, but I've found this approach useful in the past.
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