How to Ask Better Questions and Have Valuable Conversations

I’ve been thinking a lot lately on the power of questions. Asking the right questions can be the difference between a productive, engaging conversation, and a frustratingly one-sided one. So much of what we do in marketing requires us to ask questions of ourselves, our audiences, our data, and our results. 

Most of us don’t ask enough questions in our day-to-day lives. It’s something that Harvard Business Review cites as a huge missed opportunity. Asking powerful questions not only helps you learn valuable information, but also brings people closer together. 

I’ve been exploring new ways to ask better questions in my conversations lately and here's what I've found so far.

Start by Crafting the Right Questions

The Question Formulation Technique (created by the Right Question Institute), is a method for question generation that essentially boils down to the following:

• Choose a focus area for your questions. This might be a visual image, a theme, a phrase or anything that helps with the question creation process. The focus area should align with what you hope to learn by asking these questions.
• List as many questions as you can think of. Don’t stop along the way to think about the questions, just write down as many as you possibly can within a set time period. 
• Evaluate and prioritize your questions. Once you have your list of questions, sort through and prioritize them. Try to change any closed-ended questions into open-ended ones, categorize them, and improve upon them. 

Sometimes the right question is the catalyst for generating a game-changing idea. It can also be the difference between closing a deal and having one fall through. In your conversations with others, it's great to have a list of questions in mind you can pull from to keep the conversation going. Keep in mind though that there's a balance between having enough high-quality, thought-provoking questions and leaving space for conversation to develop organically.

Tips for Improving Your Questioning Technique

Keep your Questions Open-Ended

Try to avoid asking yes or no questions or queries that can be answered in one word. Questions like “How are you doing” are too easy to answer with a “Fine, thanks” and don't usually lead to valuable conversation. Push yourself to ask questions that will lead to a story. This could be as simple as “Where are you from?” or “What led you to the role you’re in now?”

Master the Follow-Up

Ask follow-up questions. Even if you feel like your question has been answered satisfactorily, don’t be afraid to press further and ask related questions to uncover more detail. You’ll often get valuable background information you didn’t even know you wanted. 

Get Comfortable with Silence

I recently read To Sell Is Human by Daniel H. Pink to learn more about successful sales techniques. In the book, Daniel mentions an improv technique that requires you to count 15 full seconds before commenting in a conversation. This gives you time to process what has just been said but also gives space for the person you’re speaking with to add to their thought and provide even more valuable information. This will also prevent you from interrupting someone in the middle of their story.

So often in conversations, we get excited when we can contribute that we interrupt and forget to keep listening. I'm often guilty of this one. It can be hard to sit and wait through a long pause, but you'll be surprised how much more you'll get out of a conversation when you let the speaker keep going.

Consider Recording Yourself

Record interviews you conduct with people and play them back to yourself to evaluate how you're doing. I personally HATE listening to recordings of my voice, but this is a really valuable technique for flagging your mannerisms and identifying areas you can improve upon.

Practice

Start by practicing these techniques with close friends and see what happens. From there, incorporate better questions and active listening techniques in conversations with people you don't know very well and watch how quickly your discussions will start leading to valuable, insightful information and relationships.

Connecting with others is often best done by asking the right questions, at the right time and in the right setting. You can’t earn a sale without asking the right questions. You can’t develop a successful marketing strategy if you haven’t asked the right questions. And you can’t build a successful business if you don’t know how to start with the right questions. The most innovative ideas start by questioning the status quo and exploring what-ifs.

And so, I’ll leave you today with this question: What can you do right now to start asking better questions for your business?