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How to Ask Magical Questions

If you check into a Marriott hotel as a Platinum or higher member, you’re supposed to be given a nice room. There are various restrictions to this benefit, and of course it all depends on which rooms are actually available—but most of the time, if a suite is for sale, the hotel is supposed to assign it to elite members.

That’s what’s supposed to happen. In principle, many Marriott hotels ignore the promised benefit and simply leave the suites unsold.

If you have the right status level and you know how this works, you know to inquire about the room type at check-in. When the associate informs you that you’ve been “upgraded” to a smoking room with two beds overlooking the parking garage, you can respond by thanking them and politely asking, “By the way, are there any unsold suites tonight?”

I’ve had Platinum status with Marriott (previously Starwood, RIP) for more than ten years, and I’ve had similar interactions dozens of times. No kidding, about 50% of the time, a suite magically appears in the reservation system!

But of course, you have to know to ask. If you don’t ask, you don’t receive. (This isn’t like asking for an upgrade on a flight, by the way—except for the few times when it is.)

This example leads to a greater metaphor. All parts of life feature magical questions, which, upon being asked, can open up all sorts of fun rewards.

Many of these magical questions are like the hotel example: it’s a specific question you need to know. Others, though, are fairly general. They apply in lots of situations!

If you prefer, you can think of them as power questions. Learning to ask them gives you, in effect, a new superpower.

Here are three of them.

1. “Is there any other way to…?”

This is probably my all-time favorite question. You can phrase it lots of ways in many different situations. In effect, you are rejecting a proposed offer (rule/guideline/norm/etc) and looking for alternatives.

Notice that you aren’t necessarily suggesting a particular alternative at this point—you’re merely asking about options. In fact, you’re not even asking what those options might be. You just want to know: is there any other way?

Very often, of course, the answer is yes, there’s at least one other way to accomplish pretty much everything. Probably even several other ways at minimum. Once that point has been established, everything else tends to get easier.

2. “Can you help me with …?”

Another general question with many use cases, this question makes things personal by directly appealing for personal help.

Side note here: in all of these scenarios, it’s important to be respectful of another person’s time and energy. You want to ask for intervention when it genuinely matters, and when it doesn’t create an unfair burden for someone else.

Still, it’s generally true that most people like to be helpful. So don’t overuse it, but do give them an opportunity to be helpful!

3. “What would you suggest here…?”

A bit less personal than the previous one, this question invites the other person to brainstorm with you. Maybe they know something you don’t. Maybe they know the specific magical question that would change everything—but they’re not just going to volunteer it without being asked for input. So, ask.


As you go through life, pay attention. Most situations allows for magical questions that can open up entirely new pathways.

Ask and you shall receive—but first, think carefully about the right question to ask.


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