How to Ask Better Questions

how to ask better questionsEver find that you’ve been asked a question that’s not really “dumb”…but you don’t know where to begin answering it?

Granted, the world is filled with people asking dumb questions daily (and yeah — to hell with the “there are no dumb questions, only dumb answers” sing-sing crap). Sometimes though, our inability to answer a question has everything to do with it not being a good question. We lack context and other information that’s going to help us get the person in front of us from where they are to F&#K YEAH.

Me? I’m interested in not wasting time and getting people to F&#K YEAH.

But what if you knew how to ask better questions — ones that actually got you answers that you could do something with?

As a huge fan of getting shit done, I’m all about the better question. I’ve spent 24 years in pursuit of asking the better question, since the day I took my first commissioned sales gig at age 16. Learning how to ask the better question has made all the difference in my happiness as a human and a business owner.

Let’s get to it — and use my 24 years of mistakes to prevent you having to spend one more day making the same ones. After all, aren’t we all just trying to do the best possible business we can each day?

To show the evolution of the Better Question, I’m going to start with a vague-as-hell question and show the refinement process.

“What strategies would you recommend for growing my business?”

Understand Your Audience

Who are you asking to answer your question? This is the first consideration. Do they know you, your business, and the details surrounding your situation clearly enough to be able to offer an informed answer that will escalate your F&#K YEAH?

If the answer is no, you’d best get to ‘splainin, Lucy. And by ‘splainin, I mean super respectful of this person’s time, value, and expertise. Asking the better  question is about understanding the person in front of you, the expertise their experiences could offer you, and being respectful of their value and not trying to weasel free consulting out of them in under 2 minutes.

With this in mind, let’s look at the next evolution of the question:

Person Asking Question: I own a consultancy that works primarily with consumer-facing brands. The person in front of me just spoke at Ad:Tech, a conference specializing in digital advertising technologies. They created a successful customer loyalty campaign that increased sales 18% in one month.

The Better Question:

“I enjoyed your successes with your customer loyalty program and have customers interested in growing their brands through loyalty programs. Where did your company come up with the idea to create a loyalty program?”

Ask ONE Question

In all honesty, it was everything I could do not add to the end of that question, “…and what was the execution timeline from decision to implement until the launch of the campaign you presented?”

Because I wants all of the informations NOWS, pleeze!

Ask ONE question. Keep the “ands” out of your Better Questions. This gives you the better chance of getting an answer you can use to ONE THING that is pissing you off in your business (or life). Wouldn’t you rather get one kickass answer than two half-baked ones?

Cool things happen when you ask ONE question. You let the person standing in front of you who can help you give you ONE answer. You also give them the option to offer you multiple answers, if the question warrants. Don’t demand all of the informations nows, pleeze. Create an answer environment where you can continue the conversation.

Which is also the reason that Better Questions are never ones that can be answered with simply yes or no.

Offer Context – Quickly

I’m always able to offer better answers when the person doing the asking fills me in — and quickly — on a few deets that can hone my response. But dear god, people can go on and on, can’t they? No one needs to hear your life story in order to answer your question. Keep that stuff on lockdown for your therapist (mine also likes to tell me when I’m going off on tangents and asks, “What does this have to do with ______?” God, I love her appreciate her candor.) The person you’re asking to help you shouldn’t have to play the role of thought wrangler in order to help you.

Let’s see how this question evolves with this tidbit of advice, becoming the person asking the question above:

“I own a marketing consultancy that works with brands like yours. Ideally, I’d like to attract more clients like you to start conversations with us. Could you share a few of the most valuable things your agency brought to the table when they presented the customer loyalty program as a solution for your sales growth goals?”

Context? Delivered quickly. What the question asker hopes to achieve? Explained. Open-ended question asking ONE THING (how did the agency add value?)? Delivered. And I even timed it — delivered in 15 seconds.

Be Respectful

In every business context, a question you ask should do one thing: get you closer to the strategy or solution that will help you create kickass. You can’t get there, however, unless you’re respectful of both the answers you need and the person you’re asking to provide them. Especially in conference, panel, or event-type situations, a well-crafted question can maximize the price you paid for admission more than anyone else’s in the room. A crappy and poorly-focused question can do a few things:

  • Haaaaaaates you, Preccccciousssss. Events aren’t your own private opportunity to have all your business questions and woes resolved. Don’t hog the mic or assume that speakers and panelists want to solve only your problems. This is a sure-fire way to make yourself persona non grata with everyone else in the room, including the people you need answers from.
  • Waste your time and cash. Ever walk away from a conference, panel, or event and feel like you got jack shit out of the experience, even though you tried? Putting some focus behind your questions can give you answers that put you one step closer to kickass. Odds are, if you got diddly out of an event even though you tried, your question asking skills need some fine tuning. Why waste hundreds or thousands of dollars asking questions that have the potential, with a bit of work, to create changes in your business worth multiples of hundreds and thousands?

Don’t be a person or mic hog. Respect that there are others seeking advice. Make yourself shine with a clearly targeted question. ONE clearly targeted question. If you want to continue the conversation beyond this initial interaction, ask the person answering your question the best way to reach out for additional insight. Oh — and expect to pay.


And that’s it. You’ve got tools to ask better questions and get your business one step closer to kickass. If you have tips to share, by all means — let’s hear them. We could all do with a little work on our question asking skills!






One thing I would add is know why you are asking the question in the first place. I have worked with many sales people who just ask questions to fill space or because they were trained to without really know why. It drives a lot of customers nuts and makes them feel like you are really trying to steer them into a predefined answer. If you know why you asking the question in the first place you come across as sincere and you build trust allowing your client to open up more. Then you really start to learn something!

Those are my two cents.


addendum: yesterdays statement of fact has become today's engagement via question ie want more Facebook comments on your fan page? ask a question. Our weekly email news letter subject lines have all morphed into a question someone in our audience asked or would be interested in seeing the answer. 


As a professional fixer of stupid m-f 10-5 CST even "dumb" questions can provide valuable (website/email/blog) content. The flip side is having spent 25 years in outside sales, I learned to use questions as a tool to guide the conversation