How (Not) to Ask for a Raise or a Date
Notably, both can critically depend on the first thing that comes out of your mouth.
Of course, timing is crucial: The move should be neither too soon nor too late, too cocky nor too wimpy, and most definitely not when the one being asked is least receptive or really busy with something really urgent.
The request has got to be credible; have just the right tone and degree of [in]directness; exude the perfect level of confidence, shyness, eagerness or hesitation—depending on the circumstances and the mindset of the one being asked; have a clearly defined emotional goal, e.g., to elicit positive interest or compassionate pity; and—if manipulation is required—staged with craftsmanship, cunning and impeccable timing.
And, of course, never ask when you aren’t looking and smelling your best.
Now, of all these variables, apart from attire and hygiene, which one is the most crucial and the most clearly and entirely within your control—and controllable in advance of the move?
It’s what you choose to say first—which must at least be recognized as crucial, if not decisive.
Why? In the psychology of presentation, what is called and confirmed as the “primacy effect”—the power and impact of a first impression, first stimulus, first number in a series, first scene in a movie, indeed, almost the first anything is virtually unmatched by anything else in a sequence of comparable elements, except by the “recency effect”—the impact of the final element.
However, if the primacy effect is negative enough, there may be no recency effect, e.g., if your target stops listening and cuts you off.
A third critical effect, the well-demonstrated “Von Restorff” effect, is harder to engineer in real-time interactions, but may be worth a try. Read the following list of words, but only once, without glancing at them again—no cheating! Then, immediately close your eyes and try to remember as many as you can, perhaps writing them down as you recall them: 
If, unsurprisingly, the first word you recalled was “evil”, you experienced the primary Von Restorff effect: Any item in a sequence that stands out is far likelier to be remembered or otherwise “register”.
[Although the primary Von Restorff research data are commonly word lists, it seems reasonable to expect a Von Restorff effect with sequences of other things, such as pure colors, shapes, movie scenes and conversations ranging from those about raisins and dates to those about raises or dates.]
If, in addition, you also easily recalled “quick” and “silent”, or words adjacent to them, you experienced a secondary Von Restorff effect: “heat” by proximity. Otherwise, if you recalled “dropped” or “round” more easily than others, the primacy and recency effects kicked in.
Most probably, “evil” stood out as the hottest term—and for many reasons: the color contrast, the underlining, italics, boldface, the emotive charge and the distinct category, viz., moral, in contrast to all the other emotionally and morally neutral terms. The secondary effect is the easier recall of whatever is adjacent or near to the primary hot item.
Capitalizing on the Von Restorff Effect
The relevance of the Von Restorff effect to asking for a raise or a date is that if your “pitch” is going to have a standout moment, you must, of course, make it work for you, rather than against you. But, in addition, you should consider what you say or do immediately before or after that moment, so that those will also be more likely to be remembered and to share in the “positive charge”.
For example, suppose your pay-hike pitch has as its Von Restorff sizzling centerpiece your mentioning that, through your initiative, you’ve snagged Nike as a client for your ad firm. It seems logical that you’d be in a great position to ask for that overdue raise at some point in the conversation.
But it may be even better psychology to ask immediately after you’ve mentioned the Nike haul, rather than before, to combine a Von Restorff effect with a “relative primacy effect”—viz., make the Von Restorff point in the conversation also come first in the one-two punch combination.
Whether it’s the primacy, recency or Von Restorff effect you want to capitalize on, it must be remembered that their power and impact can be emotional and/or cognitive. This means their having the strongest emotional impact or being what is most vividly recalled and durably remembered.
Taking a closer, detailed look at the primacy effect and assuming that the first thing you say is likely to have a vividly remembered impact, we can evaluate some popular or tempting ice-breaking openers:
1. “If…..”: At the starting gate, this one is a gamble. On the one hand, because it is purely conditional, the request or question can seem less threatening than a more direct approach. On the other hand, it can come across as “counter-factual”, the way “if pigs could fly” does and therefore mere unengaging speculation.
Examples: “If I were to ask you for a raise/date.…..”; “If you are open to the idea of a…”; “If you feel, as I do, that…” [Note: Hereafter “raise/date” will be designated as an “R?D”]
More generally, “if” conditionality can be a very effective “sales” tool: Instead of saying, “After you’ve bought this encyclopedia, you’ll see your son’s grades skyrocket”, you say, “If you buy this encyclopedia, you’ll see your son’s grades skyrocket”. On the one hand, this may seem less pushy, less threatening, less “hard-sell”, and can be very effective.
It also—and this is critical—can subliminally affirm that the “target”, the one being solicited, is firmly in control, because you are subtly inducing a deliberative state of mind in the target—a state of mind that involves an obvious presumption, if not exercise, of free will, which in turn reassures the target that [s]he is in control.
But on the other hand, the conditionality of “if” may inhibit NLP [neurolinguistic programming] induced visualization of actually having bought the encyclopedia and enjoying its benefits. “After you’ve bought the encyclopedia….” can accomplish that.
Recommendation: If the target is very independently minded and doesn’t like to be led or pushed, “if” can work. On the other hand, if the target is susceptible to NLP-based suggestion, it may be better to shoot for a fait accompli opener: “After you marry me…”, rather than “If you marry me…” or “After I get a salary adjustment…”, rather than “If I get a salary adjustment…”
2.“I hope you don’t mind….”: Too ominous in suggesting an imminent imposition. Example: “I hope you don’t mind, but may I ask you for an R?D?”
Recommendation:This could work with someone who appreciates your considerate hope more than the warning that there is something on your mind that [s]he may mind. In effect, this is a question of “Gestalt” psychology—namely, whether your thoughtful “hope” is “figure”—at the forefront of attention, or “ground”—i.e., relegated to the less significant background.
3. “I think…..”:Too presumptuous. Who cares what you think and want to pontificate about? Example: “I think that this is the right time to suggest a R?D.”
Recommendation: Unless your target is likely to be impressed by “I think, therefore I am”, this will probably not get you much traction. Sure, it may suggest you are insightful, farsighted, observant and confident—but most probably with and unappreciated by someone who isn’t.
4. “I have been….”: Sounds like a history lesson. Example: “As you know, I have been working here for six months now/I have always found you very attractive….”
Recommendation: This could work with the likes of Dickens fans—“It was a dark and stormy night”—who enjoy or at least can put up with a lengthy historical narrative.
5. “I was/have been wondering….”: This sounds too detached and timid. Example: “Recently, I was wondering whether this might be the right time to ask you for a R?D.”
Recommendation: Use it with someone you expect to be very guarded and defensive. Don’t use it with someone who is busy and/or impatient.
6. “I may be out of line here, but…”: Too defensive, negative, circumspect, self-invalidating, off-putting and seemingly disingenuous. The expected benefits of the “aw, shucks” carpet-pawing, averted-gaze humility and naïve candor will not materialize if this approach is taken negatively.
Recommendation: It may be safe to use this with someone who is not cynical or who is more attentive to what comes after the “but” than before it.
7. “I can appreciate that…”: This carries the same risks as any other opener that features “but”, since “I appreciate that….” always segues to “but”.
Recommendation: Same advice as given in #6.
8. “Even though…”: Ditto #6 and #7.
9. “This may seem strange, but…”: See #6-#8 above. Same analysis.
10. “Do you believe in Fate?…”: This will work if two conditions are met
—One of you really believes that Fate favors your request.
—Fate doesn’t disagree.