For starters, which city you recruit your diplomat in plays a crucial role. Here you are more focused on avoiding traits then picking up certain ones. The main negative trait, and most common from what I have seen, is Dogmatic Beliefs (IIRC). This comes from having a certain level of church in that city. Maybe begins at Abbey, but def with Cathedral. The real problem with this trait is that it becomes worse with time. Dogmatic Beliefs is only -1 but eventually becomes Would-Be-Inquisitor, a -3. So avoid that.
To counter this, cities with advanced civic improvements in the city hall line increase the chance of having positive traits added at recruitment. However, I have found that the negative religious traits have appeared a lot more than the positive civic based ones.
A bit of luck comes into play as the new diplomat could have no natural skill or could have up to +2 with traits such as Natural Mediator. That is simply chance but usually new diplomats have some kind of base trait that adds skill.
As for training them, getting them the first two levels of experience (Promising Diplomat/Good Diplomat IIRC) is fairly easy. Within two or three successful negotiations, they have usually reached this point. This can be done by sending them out to do the basic trade rights/alliance/map info exchange, almost always a guarantee at the beginning of the game. Keep using that same diplomat and pretty soon he will reach that third level (forget what it is called) and have +3 experience. The flipside to this is that any negative aka rejected negotiation has the chance of adding the negative versions of these traits, like Poor Diplomat (-1). Again, a string of these and the negative points start adding up. Pay attention to the balance indicator at the bottom (demanding, generous, etc.) and help get good results to build experience.
At this point, the diplomat is probably far from home and will start picking up a few extra traits. The key is to get that first one because like the religious trait, this expands with time. Bilingual is fairly common (+1) and will eventually become Multi-Lingual (+2) and Translator (+3). The key to this is keep him moving all around the map. Also, certain ancillaries will start appearing for the same reason. Foreign Dignitary is the most common (+1). I can’t recall the others off the top of my head but they come from travel and time. Not much you can do but hope.
Another tact is bribing. If you have a little extra cash, seek out small stacks (1-3 units) of rebels or factions you can suffer to have relations worsen with. Note: Don’t try this until you have reached around 4/5 experience. I’ve never seen this work without a decent diplomat and you don’t want to risk picking up negative traits due to failed negotiations. Make sure the stack is not a family member, unless the loyalty is extremely low and/or they have a trait that makes them extremely easy to bribe. Even then, I avoid doing this because then he becomes a member of my family and a liability. The point of all this is two-fold. First, successful bribes increase your diplomats ability to do just that. The trait line (Switches/Changes/Breaks IIRC) loyalties increases 10/20/30% chance of successful bribe. IMO, it’s really good to have at least one diplomat that is good at this to either get you out of a tight spot or intervene in a foreign situation and influence the outcome to your benefit. (Think bribing off a Milanese Army that is going to attack Venice when Venice is your ally, etc. No open war but you still stopped their army and their borders from expanding.) As for your diplomat, successful bribes can lead to gaining the Discreet (+1) and then Secretive (+2) trait. I’ve never seen the (+3) trait but I suspect it exists as the corresponding Bribe traits got up to three levels.
That should get you a 10+ experience diplomat in time. I usually get to 7 no problem and 10 about half the time. On a side note, I had long thought that diplomats should be able to achieve Master Diplomat (+5) just like spies (Master Spy) etc and other agents. I was never able to until recently and it was only through constantly opening negotiations, as trivial as they were. I honestly would have my diplomat speaking to someone every turn, even just to exchange or sell map info. So getting to +4 level (Excellent Diplomat maybe?) is fairly easy. However, that last level seems almost impossible to reach consistently. CA seems to have balanced this out however by all the other ways to gain skill.
Hope that helped. Diplomacy isn’t this games strongest part, but still good. However, I have found with a one or two powerful diplomats in key regions (Iberia, N. Italy, Constantinople) you can really influence the world at large and shift the power balance as you need it.
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