How to Ask Great Questions

by Ruth D Schwartz

Christie walked into her mastermind meeting complaining bitterly. Angela, Christie’s head bookkeeper, had messed up a spreadsheet for a client . . . yet again. How was she going to make money at her business? How was she going to release her Golden Handcuffs? How was she going to ever please this client if her head bookkeeper could not get it together?

We let her vent and rant for a while. Hey, we’ve all been there, right? And then finally I looked at her and asked her this question, “How can you turn these feelings that you’re having into great questions for Angela?” Oh, she had one right on the tip of her tongue. She turned to me and she said, “What’s your problem?” And then Mark, who was sitting next to her, said, “Yea, and then we’ll ask ‘Why the heck did you do that?'” And Steven turned around and said, “How could you possibly make such a big mess?” Okay you guys, alright, great, get it off your chest. This is the place to do that.

But now let’s talk about to how to ask really great questions. I want to give you a little trick. We’re not going to learn how to ask snarky questions that are going to put people on the defense and make them feel bad. What we want to do is create a new habit for ourselves so that in these one-on-one situations-and not just the bad, difficult performance situations, but the good performance situations, too-we create outcomes that serve us and our business and our leadership roles while helping make that person successful. Now, this is not a conversation about taking somebody who is a complete disaster in their job (for whatever reason), that’s a different conversation. This is somebody who is worthy who is making mistakes. And that was the case with Angela.

Here are a couple tricks that you can do to ask great questions:

Avoid questions that start with “why.”

When we ask a question that starts with why we are inviting people to tell us the story that they are telling themselves. The story that they want you to hear. There may be a time and a place for the story, but it is not when you are in your coaching leadership role. This is a practice that I want you to get good at, because when you are in your coaching leadership role, when you are shifting from being a manager into a leader, you put that coach hat on and you ask great questions.

Ask questions that start with “what” and “how.”

Asking questions that start with the words “what” and “how” is a simple tool to help you make form better questions. In the situation with the mastermind group, I turned everybody in the room and said, “Okay, now, coaching hats on, using your new trick of what and how questions, what can you come up with?” Here are some of the things that they decided:

• How does this problem happen?
• What outcomes would serve us better?
• What system can you create to get a better outcome for yourself?
• How does this affect you?
• What training skills or resources do you need?
• How can I support you in fixing this problem and getting greater success?

You see how we tried to turn it into a positive? When we take the burden off ourselves we are not managing the situation, we are helping our employee manage their own situation.

That is what we do when we are looking at the smaller picture. But asking questions works when we’re looking at the big picture, too. For example, if your leadership role includes that of the designer or the great visionary and you are trying to bring to your team an alternative future that’s going to inspire everybody to new heights but you simply don’t know what it is or don’t know what to do, you are absolved from knowing the answer-if you know how to ask the right questions. So in a group you can ask your team, “I want to envision a new future. How would you envision that future? What do you think we need to do? What do you think we have to put into place to start creating this new future, this envision of what we can become?” The minute that you use groups of people to ask big picture questions, the more powerful you are as a leader, and quite honestly, a lot easier it becomes for you.