The 50th Law (with 50 Cent)

4. Allay their insecurities. Everyone has particular insecurities
—about their looks, their creative powers, their masculinity, their
power status, their uniqueness, their popularity, et cetera. Your task is
to get a bead on these insecurities through the various conversations
you draw them into.
Once you’ve identified them, you must first be extra careful not to
trigger them. People have grown sensitive antennae for any words or
body language that might cast doubt on their physical appearance or
their popularity, or whatever their insecurity may be. Be aware of this
and be on guard. Second, the best strategy is to praise and flatter those
qualities that people are most insecure about. We all crave this, even if
we somehow see through the person who is praising us. That is
because we live in a tough world in which we are continually judged,
and yesterday’s triumph is easily followed by tomorrow’s failure. We
never really feel secure. If the flattery is done right, we feel that the
flatterer likes us, and we tend to like people who like us.
The key to successful flattery is to make it strategic. If I know that I
am particularly awful at basketball, praising me for my basketball skills
in any way will ring false. But if I am uncertain about my skills, if I
imagine I am perhaps not really so bad, then any flattery on that score
can work wonders. Look for those qualities people are uncertain about
and offer reassurance. Lord Chesterfield advised his son in his letters
(later published in 1774), “Cardinal Richelieu who was undoubtedly the
ablest statesman of his time . . . had the idle vanity of being thought the
best poet too: he envied the great Corneille his reputation. Those,
therefore, who flattered skillfully, said little to him of abilities in state
affairs, or at least but en passant, and as it might naturally occur. But
the incense which they gave him, the smoke of which they knew would
turn his head in their favour, was as a . . . poet.”
If your targets are powerful and quite Machiavellian, they might feel
somewhat insecure about their moral qualities. Flattering them about
their clever manipulations might backfire, but obvious praise of their
goodness would be too transparent, because they know themselves too
well. Instead, some strategic flattery about how you have benefited
from their advice and how their criticisms helped improve your
performance will appeal to their self-opinion of being tough yet fair,
with a good heart underneath the gruff exterior.

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It is always better to praise people for their effort, not their talent.
When you extol people for their talent, there is a slight deprecation
implied, as if they were simply lucky for being born with natural skill.
Instead, everyone likes to feel that they earned their good fortune
through hard work, and that is where you must aim your praise.
With people who are your equals, you have more room to flatter.
With those who are your superiors, it is best to simply agree with their
opinions and validate their wisdom. Flattering your boss is too
transparent.
Never follow up your praise with a request for help, or whatever it is
you are after. Your flattery is a setup and requires the passage of some
time. Do not appear too ingratiating in the first encounter or two.
Better to show even a little coldness, which will give you room to warm
up. After a few days you have grown to like this person, and then a few
flattering words aimed at their insecurities will begin to melt their
resistance. If possible, get third parties to pass along your
compliments, as if they had simply overheard them. Never be too
lavish in your praise or use absolutes.
A clever way to cover your tracks is to mix in some small criticisms
of the person or their work, nothing that will trigger insecurities but
enough to give your praise a more realistic hue: “I loved your
screenplay, although I feel act two might need a little work.” Do not
say, “Your latest book is so much better than the last one.” Be very
careful when people ask you for their opinion about their work or
something related to their character or their looks. They do not want
the truth; they want support and confirmation given as realistically as
possible. Be happy to supply this for them.
You must seem as sincere as possible. It would be best to choose
qualities to praise that you actually admire, if at all possible. In any
event, what gives people away is the nonverbal cues—praise along with
stiff body language or a fake smile or eyes glancing elsewhere. Try to
feel some of the good emotions you are expressing so any exaggeration
will seem less obvious. Keep in mind that your target must have a
relatively high self-opinion. If it is low, the flattery will not jibe with
how they feel about themselves and will ring hollow, whereas for those
of high self-opinion it will seem only natural.