Ingratiation and ulterior motives underlying friendly behavior are most easily detected when the ingratiator in some way is dependent upon the target. This can occur, for instance, when the ingratiator is a single man out to find a date, and the target is beautiful woman; or when the target is the ingratiator’s teacher in school or supervisor at work, or is generally a powerful person in a company or in politics. Because such asymmetry in power makes it more likely that friendly behavior by the low-status person is seen as ingratiating, this presents the ingratiator with a dilemma: 
When it matters most, that is, when you depend very strongly on someone, ingratiation is most likely to backfire because people will easily see through your hidden agenda, and you lose your credibility.
Conversely, it is relatively easy for powerful people to ingratiate lower-status persons without being suspected of insincere motives. However, the incentives for doing so are also smaller, because high-status persons usually do not need favors from those with less power This dependence is probably underestimated by lower-status persons. Because ingratiation is less easily noticed in these cases, ingratiation by powerful people may actually go on a lot more than we think.
Ingratiators in low-status positions use several strategies to resolve the ingratiator’s dilemma, that is, to make their efforts more credible when flattering someone they depend on. These have been described by Edward Jones in his seminal book on ingratiation, which appeared in 1964, and it seems the world has hardly changed since then. The first strategy is to build a power bank, by starting the flattery long before you need a favor from someone. By ingratiating yourself for a longer period, you build up credit, which you can later withdraw. Obviously, this is a lot more effective than walking up to your boss and saying, “Wow, you are such a great supervisor, and by the way, can I have the day off tomorrow?”
A second strategy around the ingratiator’s dilemma is to find a setting where the power imbalance is less salient. For instance, people take their boss out to the pub or invite them to their house for dinner, thus creating a setting where it is not that obvious who is in charge and who is not.
Third, people sometimes obscure their behavior, for instance, by disagreeing with their supervisor on trivial matters. This way, they won’t look as though they blindly follow and support their supervisor, and they convey the impression that they are independent.
Finally, it is a good idea to flatter someone via somebody else. For instance, it could be very strategic to tell the boss’ secretary that you have never had a better supervisor than this one, and that you are happy to work very hard for this boss because he or she is inspiring the best of you. With a little luck, the secretary will tell your boss you said this, and your flattery will have a great deal of impact because you are not suspected of ulterior motives at all.
References:
- Jones, E. (1964). Ingratiation, a social psychological analysis. New York: Appleton-Century-Crofts.
- Vonk, R. (2002). Self-serving interpretations of flattery: Why ingratiation works. Journal of Personality and Social Psychology, 82, 515-526.