Get Open

Reading Time: 5 minutes

Nearly everyone I know had to take either the ACT or the SAT at the end of their high school career.

I took the ACT. I hated the ACT. I will fight the ACT.

Remember what it was like? If you were an over-achiever, you spent the prior weeks practicing, studying, preparing. If you were an under-achiever, you spent the prior weeks praying, slacking, cramming. Ask me how I know.

All of it was bad - the math and writing and science and whatever else was on it, all horrible. But my absolute least favorite part of this vicious hellscape of a test was the written response questions. At least with multiple choice questions, I had a decent mathematical chance to get the right answer. But open-ended questions were brutal. Open-ended questions required thought and demonstrable recall - it’s hard to fake your way through an open-ended question. I tried.

(Sidebar to my mom, who I know will read this eventually: I did study a little bit. I promise. And you’re the best.)

Have you ever been in a conversation with someone and all they give you in return to your questions are one-word answers? If I ask you a question that you can reply to with one word, I think that’s more my fault than yours. I need to ask better questions and create opportunities for you to engage. I can’t force you to be a good communicator, but I can press you for more than just a single syllable in return.

Many years ago, I remember going on a sales call with a potential customer that I had not met. We had exchanged some emails but I didn’t know what he looked like, what he cared about or what the potential was for him to become a real, buying customer.

When I walked into his office, he stayed seated behind a giant, oak desk (sidebar: if you want to be an intimidating figure, stay seated behind your desk when someone walks in. The bigger the desk, the more intimidating.). He welcomed me in and ask me to sit down. I desperately searched the room for something to talk about - luckily, he had all kinds of things hanging on the wall and on top of his desk to serve as conversation starters. He had lots of sports memorabilia hanging on the walls but for some odd reason, I focused on some golf riff-raff on his desk. I don’t know anything about golf - why I started there, I’ll never know.

I remember being nervous but somehow having the wherewithal to cobble together a question about his golf game. It wasn’t a good question.

“So, you like golf, huh?”

(I mean, come on. That’s the question I started with?!)


He didn’t have to say anything else because I didn’t give him any opportunity to say anything else. That’s a nothing question, a throwaway question. 

Luckily, I regained my composure and followed up with something about football (he had a framed jersey hanging on the wall), and football is something I do know. 

“And, judging by all the other stuff on your walls, you like all kinds of sports. Nice jersey - who is your favorite team?”

That’s better. Once I had him answering with more than just a monotone yes or no, we were off and running. 

One of my favorite things to ask someone is “what’s new?” I ask my friends, I ask my family and I ask my coworkers - “what’s new?”

That question seems simple enough but packed inside that phrase has been a wellspring of conversation starters for me. It forces the other person to think, gives them an opportunity to tell stories and has countless directions to go in once it’s thrown out in a conversation. You should try it.

If you are a manager of people, it’s easy to give direction by telling people what to do, or by telling them what your preference might be. It’s not easy to invite them into the fray and to challenge them to think for themselves. However, when you do the latter, you get better results and more well-rounded employees. Asking open-ended questions can help provide the invitation to participate in solving problems and being engaged.

I once had a guy working for me that I was trying to mentor and grow. He was very smart and worked hard, but didn’t have a lot of experience. I remember a project where I was asking a lot of him, and he was doing his best to solve problems in an area where he had never worked. When we first started the project, I was just telling him what to do. It was draining for me and probably frustrating for him. About midway through, I decided to start giving him more responsibility. I started asking for his opinion, and I was asking in a way that forced him to make decisions. 

One of the best ways to have engaged people is to ask them to make the decision. Don’t tell them to make it or influence their options - just invite them into the proverbial arena and ask them to battle WITH you. 

I began asking him “what do you think?” and “what would you do here?” and “what would you recommend?”

Those are open-ended questions that are inviting and challenging. It’s good to have both.

I encourage you to ask questions that invite people into a discussion with you. It’s an excellent skill that can unlock business opportunity, improve your leadership skill and help you engage your audience.

Do This:

  1. Start a meeting with a question. This doesn’t have to be a business meeting - it could be dinner with your family. But think ahead of a time this week where you’ll be meeting with others, then ask an open-ended question to start. For a business scenario, consider questions like “What’s the most interesting thing you saw this week?” or “What is the very best thing that happened to you since our last meeting?” If it’s a personal meeting, go with something like “What should we do tonight?” or “What was your favorite part of your day?” My family shares our daily ‘highs’ and ‘lows’ every night at dinner. I love it.
  2. Think of a time when you were getting one-word answers to a question. First dates are great for this. Then jot down three or four bulletproof conversation starters that you can start using this week. Shoot me a note and tell me what your best lines are - not pick up lines. Conversation starters. Weirdo.