How to Ask Good Questions

Someone I know got a 44% raise at their last job because they were good at asking questions. 

I’ve seen non-profits raise six, seven, and eight-figure gifts from notoriously difficult donors because they worked hard at asking questions. 

If I could teach one class to every non-profit, student, or business professional in the country, it would be how to ask. 

That’s because we exist in a world of questions, and most people assume they know how to ask. It’s a reasonable assumption; they’ve been doing it their entire lives. But it’s a faulty assumption. 

Let’s unpack one of the worst offenders.

Have you heard someone say, “It’d mean a lot to me if you’d help out with this”?

Here are the reasons why it’s a red-letter superstar offender in the Worst Question Hall of Fame. 

Questions without a Question Mark

It’d mean a lot to me if you’d help out with this. 

Let’s start from the beginning. Questions have question marks, and this is very clearly not a question. By using phrases like “how,” “where,” and “would you consider,” we leave the tonal room at the end of the sentence for the other person to complete it. If you’re a music nerd, the question is a G7 chord that hasn’t yet resolved back to C. Questions open dialogue, and they put the power of answering on the other person.

But don’t all questions end in question marks? Start paying attention, and you’ll hear a lot of people who are doing this wrong.

“I need a ride, my car broke down” is not a question. 

“We should be paying less for this” is not a question.

“It’d mean a lot to me if you’d help out with this” is not a question. 

Questions are a dance, and a good question shifts the balance to the other person. But most importantly, actually asking (with the right punctuation in your voice) means a significantly higher chance that they’ll give you an answer. 

It’s easy to avoid answering questions phrased as statements. And if you feel embarrassed or awkward about asking at all, it probably took you some time to get up the nerve to spit out that idea. Why not save yourself the trouble? Ask for what you want -- directly, and with the proper punctuation.

What’s in it for me?

If you start your sentence, “it’d mean a lot to me,” I have bad news for you -- I don’t really care that much. I mean, I care a bit, but probably I’m more interested in the soccer ball that my kid just kicked into the gutter or the lousy health news my cousin just received.

“_______ will help us make our November goal!” That sounds nice, but why should I care about your November goal?

“We need your help” Yes, but what are you doing for me?

Here’s a good question I just got: “The battle to restore the soul of our nation won’t be easy -- Noah, will you stand with (a political candidate) because our country is worth the fight?”

I care about the soul of our nation. That’s what’s in it for me. And (theoretically) I can solve this problem by donating to this political campaign. 

Account for time.

So often, we make an ask, and we neglect to note the time period in which it should happen.

“Would you consider investing $1M into our company” is not as powerful as “Would you consider investing $1M into our company in Q3?”

My mom used to say, “Noah, clean your room.” I’d say “Ok, mom!” and keep playing on the computer. In her head, she meant “now.” But in my head, I was thinking, “when I get around to it.” 

Time is the only resource we can’t get back. It’s critical to include timing in almost every question you ask. 

Intentionally Pause.

Although it doesn’t relate to our topic sentence, there’s one more critical element of question asking: silence.

Get comfortable with discomfort, especially if you’re asking for something important. Our instinct is to fill awkward silences, but some of the best reporters know to ask questions and then choose to pause. 

I used to hold a stop sign in front of nervous candidates on phone calls to remind them to stop filling the air. Some people train candidates to ask, and then take a drink of water. Whatever your system, the best conversations happen when you let the silence hang.

The quieter you are, the more the other party will fill in the spaces. You’ll get more information by holding an awkward silence than you will by nervously filling a quiet gap with your voice. 

Asking is fundamental. It’s at the core of all of our lives. Asking for a raise, asking for a favor, asking for a sale, asking for an increase in your allowance. And as a society, we ought to take the craft far more seriously.


Thanks for reading! I write about fundraising for politicians and non-profits. Click here to check out our work.

Many thanks to Tom White, David Vargas, Fadeke Adegbuyi, Robbie Crabtree, Ayomide Ofulue, and Sara Campbell for their editorial contributions to this piece.