A past post discussed the power of why, suggesting that a well-placed “why?” can surface a wealth of information from the people who disagree with us—toddlers and workmates alike. Like almost everything in life, however, the power of why has limits. Why? To find out, let’s consider an age group somewhere between toddlers and colleagues—teenagers.

If teenagers do anything consistently, it’s to ask their parents for money. And since they want the money more than they want to explain the reason, these requests can often raise hackles. In such situations, a well-placed why can make life negotiable, whereas an ill-timed why can make life miserable.

To see what I mean, imagine that your independently-minded teenager Buck approaches you on a Saturday afternoon. Hopeful that he plans to acknowledge your existence, you smile at him cheerfully and say, “Hey Buck, how are you?”, to which he curtly replies: “Can I have some money?”

You need to know where he’s coming from. Good time to ask why? Yes. When you’re trying to understand a person’s basic motivations, whys are essential for doing so. So feel free to why-away. “To go to the movies,” Buck answers, adding that, “I need 35 bucks.”

Now, even boatload of sweets would not bring the total to $35, so you know this number is inflated. You need to bring it down. Good time to ask why? Probably not. Think about what would happen if you did. Would he stammer and offer the complete lack of an explanation? Or would he be prepared to offer a convoluted and esoteric chain of reasoning that somehow justified his outrageous request? Probably the latter. And think about what would happen then. Having anchored you on his unreasonable request, then explained it in a way that drives the anchor deeper into your sand, would he now reduce his number? No, you’d be giving him something much closer to $35 than whatever it really costs.

“But don’t I need to need to understand his calculations?” you’re thinking. “And don’t I have to ask ‘why’ to do that?” Well, yes, but not yet. Assuming you’re also interested in parting with a reasonable amount of money, I’d suggest taking this opportunity to make an aggressive counteroffer yourself. “How much does a movie cost these days, Buck? Like $10 with the popcorn, right?” Now, what is Buck likely to do? Thrown off by your gambit, he’s likely to make some concessions. First, he might ask for $30, then (when offered $10 again), $25.

But suppose he got stuck at $25—was completely unwilling to budge. You’re now staring at a huge gap between your $10 and his rigid $25. Good time to ask why? Yes. When your counterpart has already conceded and is now stuck, it’s a good idea to ask why again—now to understand the source of the rigidity. So suppose you asked “Why 25?” Maybe you asked it again, and asked it a couple different ways. “Because I have a date.” he finally muttered, embarrassed.

Voila! It all makes sense. You now know where he’s going (from why #1) and with whom (why #3); any parent of any teenager knows how essential this information can be. But you’re also giving him a realistic amount to do so (by avoiding why #2). And seeing your Buck in the early stages of young love, you’re more than happy to do so.

Bottom line: It’s good to ask why at the beginning, if you’re trying to understand their motivations. It’s good to ask why at the end, if you’re trying avert an impasse. It’s not so good to ask why in the middle, right after you receive a first offer that obviously needs to come down.

How have your whys helped or hurt in the past?