What’s the sound of one hand clapping?  Where’s Waldo? If the no. 2 pencil is the most popular type of pencil, then why is it still considered number two?

These are all questions that have mystified people for generations — and if you’ve been looking for a new job lately, there’s another question you’d probably agree should be added to the above list. It’s the question of how job candidates should handle the “Salary History” and “Salary Requirements” boxes you’ll find on virtually every online job application system today.

You’re damned if you do, damned if you don’t, right? If you enter a number that’s too high, you could price yourself right out of the job. And yet, if you insert a number too low, you could seem underqualified and/or leave a bunch of money potentially sitting on the table. And for those people who think you can just skip this question or put something vague like “negotiable” or “will discuss” I’ve got news for you — the programmers these days have gotten smarter and now usually set these systems up to force you to enter an actual numerical entry, as opposed to a text response.

So what’s a job hunter to do? Should a person simply follow the rules and enter the exact wage from their current or most recent job, despite the consequences?

Having reviewed a number of other articles on the subject — such as the ones you can find here, here, and here — it seems like the consensus by most experts is that there are four possible strategies you can consider:

1) Fill out the form with the full, unvarnished truth and enter your historical salary figures
2) Skip these boxes entirely or put a word like “negotiable” in there (if the system will let you)
3) Be rebellious and enter a nonsense answer in like $1 or $1 million in there to skirt the issue
4) Instead of your actual salary history, just put the number or range you’re looking to make next

Of all these possibilities, which are certainly subject to debate and might depend in part on a job hunter’s exact circumstances, I’ll admit that the first answer and the fourth are my favorites. In other words, if your research shows that your current or most recent salary is actually pretty much in line with the prevailing wage of the field you’re targeting, I can’t see any reason not to be truthful and handle things in literal fashion. By way of example, let’s say you’re an accountant making $60K and suspect that a new job you’re targeting pays right around that same range.  If so, just put $60K and call it good. There’s no need to get tricky if your current compensation isn’t dramatically out-of-whack with the anticipated range of the target opportunity.

As for those cases where you suspect you’re making significantly more or less than what an advertised job would pay — either because you’re willing to take a step back in salary, if needed, or perhaps have been under-compensated due to working for a start-up or non-profit organization — that’s when I’d run with option #4 above and just put your “best guess” of what a reasonable rate would be for the job in question. Sure, that may violate the exact letter of the law in terms of the application instructions, but given that they’ve designed these systems to have zero flexibility, I personally wouldn’t feel bad about handling things in the manner. If pressed later, in the interview process, you can always explain that you modified the number to reflect the current range you’re seeking, which you felt would be most useful to the employer in evaluating the potential fit.

Sure, once in a blue moon an employer could grumble about this approach, but hey, it gets you to the interview process and if you just stick to your guns and calmly explain your rationale for how you handled things, I can’t see many hiring managers kicking you out over this issue alone.  In their heart of hearts, I suspect most of them know these application processes are unfairly intrusive and rigid.  If you’re really worried about not following directions, however, perhaps you could follow the advice in the article here by Liz Ryan that suggests you simply stick a disclaimer in somewhere about how you handled things — explaining your response strategy in any “open comment” field you can find on the application form.

No question about it, salary requests are a frustrating part of the modern, technology-driven hiring process.  Rather than agonize over the issue, however, I’d recommend you simply embrace the realities of it, recognize that there are only so many choices you have for how to approach this issue, and pick the above strategy that you feel works best for you and your situation (I’ve shared my own preference) and don’t look back!