Here's a philosophical statement for you...buckle up.
Every relationship has a level of success directly proportionate to the effectiveness of the communication between the two parties. Mouthful—did you catch that?
Basically, the more effectively you communicate with another person, the more successful the relationship. The trick is, there is always a risk, or gap, between what you want to communicate and what will ultimately be communicated.
Good news—for those especially prone to fear, anxiety, or seriously limited resources, there is a way to mitigate that risk. Consider the following diagram:

This illustrates how one might better predict successful communication. Each of the circles above represents a bucket, or category of information you should master, relative to your tolerance for risk. The more informed and harmonious the circles, or the more the circles overlap, the less the risk. Basically:
- What is the context, situation or experience in which you're trying to communicate something?
- Who is the stakeholder, or what is the relationship you're trying to promote and what do you know about that stakeholder?
- What knowledge, skills, or experience do you have to help ensure that your effort hits the sweet spot?
Here's an example:
Prudence is about to celebrate her 30th birthday. Felix needs to deliver something extraordinary to make sure she knows of his love and devotion. Let's peek in on Felix as he follows the above model:
- First, he knows that big milestones are hugely important to Prudence and therefore must be hugely important to him.
- Second, he also knows that Prudence is sensitive about turning 30 and that acknowledging her age is treading on dangerous ground.
- Third, he knows that Prudence loves koala bears and original artwork.
- The birthday is less than a week away so Felix knows that he has limited time and resources to pull off something truly creative and wonderful.
- Finally, as a professional ice sculptor, Felix determines that he can create a magnificent koala sculpture to serve as the centerpiece of a romantic dinner for two. Best of all, he can do it in the time and budget available to him.
- Felix knows from past experience that her participation in the meal will mean success, while failure, well, will be immediately evident.
So here's the ultimate question: What are the odds that Felix's plan will result in communicating the requisite level of thoughtfulness and affection? Odds look pretty darn good. The circles overlap quite a bit. The risk, or gap, is probably very small. In fact, it might just be fail-proof. How often can you say that about a marketing tactic? Your challenge is to master the three circles of information when your stakeholder becomes hundreds, thousands, or millions of relationships, but the principle is the same.
Put another way, you're trying to make your sweet spot look like this:

Rather than this:

There you go. That should help your marketing, management, or love life be more than just a crapshoot. Go gett'em tiger!