The right questions to ask
If you’ve ever hit a baseball with a bat or hit a tennis ball with a racquet, there’s a sweet spot that makes the ball go faster and with more power and accuracy. From the moment at the point of contact, you just know it feels right. Similar to figuring out the right question to ask to get the best answer possible.
When you learn the right questions to ask, it not only unlocks new perspectives, knowledge, and insight for yourself, but it allows the other person to think about the best answer to give you. Everyone always talks about win-win situations and providing good questions is one of them.
The right questions to the right person with the right timing is a tough equation to get correct every time. But it’s magic whenever you do. You’ll most likely be rewarded for it as well, and it’s something you’ll spend your whole life developing.
Different levels of questions
I believe questions differ in levels based on the person, context, and timing. We’re taught that “how” and “why” questions are best because they require more explanation. More explanation doesn’t mean it’s better. A lengthier response isn’t needed when you’re short on time or if the other person isn’t in the mood to think about it.
But that doesn’t mean we should ignore the “what” and “where” questions. As you’re in the beginning stages of learning, understanding the linear relationships are important. You’ll ask what does this do or where does this go? Linear questions give you an easy solution that lays a foundation. If I do this, abc happens every time, then the next time I do this, I should expect abc. We need to understand the basics before we can move on to more complex things.
The how and why questions can also be asked in conjunction or as a follow-up to understand causal relationships — why and how things happen.
This gives us further information on a topic and broadens our horizons. One of my favorite soccer players to watch is Lionel Messi. I would notice that he would walk around the field a lot. You would probably see him sprinting for a limited amount of time. This was the complete opposite of what I was taught growing up and playing club soccer. It wasn’t until it was explained to me that when he’s walking, he’s scanning the field and reserving his energy for decisive moments that can impact the game. If you just run around all game, you’ll be tunnel vision and won’t have the energy to make an important decision that can help your team.
You can get more when you start to combine both types of questions. In this state, you’re in curious mode — think about an 8-year-old child asking their parents questions every few minutes. The key is to do that but not be as annoying.
We have to be cognizant of the other person’s time while maximizing learning. Busy people won’t give you the luxury of spending hours answering questions, especially people who are experts in their field. So the question becomes what are the best questions to ask?
If you have time, do some research to get an adequate amount of knowledge, and ask a thoughtful or insightful question that will evoke a great answer. If you get a chance to make them think before their answer, it’s probably going to end up being a great question.
Bill Belichick, head coach of the New England Patriots football team, is notorious for his stoic, one-word answers. It’s no secret that he doesn’t like the media because they would ask him rhetorical questions. You have one of the greatest minds in NFL history and you’re going to ask how he feels after a loss?
In the clip below, a good question is handsomely rewarded with a very detailed response about a certain position and its history. Everybody wins in this scenario. It might take a lot of research and questions but if you can get that one question right, you can unlock new insights and appreciation from the person answering it.
The wrong question
There aren’t stupid questions, but there are wrong questions to ask. Whether you’ve asked the wrong person, at the wrong time, or using the wrong question, you ultimately get nothing or it’ll negatively affect you if you do it incorrectly.
I used to work for a hot-headed manager who would call people out on disagreements in front of everybody in meetings. To say that it was a complete waste of time and a power flex was an understatement. Any time someone would disagree with a point he made, it soon turned into a shouting match. We had a co-worker named Chad who played it well, where he would wait until after the meeting, and meet with the manager alone in his office. Chad would butter him up for a bit and then subtly ask we are doing this and explain the ramifications.
I would ask Chad if it was exhausting having to do that every time, and he would say it was, but it was necessary or else the manager would blindly steer us into bankruptcy.
It didn’t make sense to me back then, but when dealing with someone with lots of ego, a direct confrontation wasn’t the answer. You probably wouldn’t ask someone for a favor after they’ve received bad news right?
Just as asking the right question is important, so is selecting the right time and the right person to ask.
The right person will unlock new opportunities and grant you passage to people who will give you better answers. One of the most important things I’ve learned in life is how to fight overdraft charges for banks. Sure it’s only $30–40 dollars but it’s messed up how if you go under a penny, you get slammed with this charge. I tried to call and get it overturned. It was denied a few times, but once I got a hold of a different person, they were able to help me.
The blockage might be the wrong person you’re asking. That’s the gatekeeper, and you’ll have to wait until a new person comes along to ask it.
Not asking the right question or asking questions that waste time are other forms of wrong questions. I understand that you’ll need to ask obvious questions to confirm, and it’s important in situations, but asking questions that add nothing to the conversation may negatively affect you.
You’ll see this most with reporters who try to bait athletes or politicians so they can get a “gotcha” moment. It’s to sell papers and get headlines, but it’s probably more worthwhile to ask a question and see how the person processes things and their thinking. This will give not only you a better understanding, but everyone else in the room.
Questions that are loaded to invoke a negative or explosive reaction aren’t worth asking. Particularly if we are trying to build a relationship or to learn. That’ll just guarantee to establish a negative reputation as the person who does such a thing. You won’t ever get taken seriously nor will you get the best answers.
The ever-lasting chase
Just as we strive to improve in various aspects, we should also make asking good questions another area to master.
Asking good questions requires work and effort, which are appreciated by those who have put in thousands of hours in their craft. In a way, it’s the art of humbling yourself and working to find the right words to understand someone or something. If you think you’re smarter or better than others, you won’t ever put the time in to ask questions.
The humility of knowing we can always learn more makes it a worthwhile chase.
Recently, the “best question” method I’ve been asking is being specific. Everyone can ask a general question and the person being asked can choose whatever direction they want to go. Most of our questions will be in this form. But, being specific requires understanding of the topic and forces the person to think a bit more about their answer.
They won’t give you the cookie-cutter answer to a general question. For example, if you ask any rich person what you should invest in, they’ll tell you to put it in an index fund and let it compound. That’s a good answer, but specificity will provide you with more insight.
You can tell them based on the research you’ve done, options A and B provide adequate returns, but option C can give you more returns with slightly more risks. This will show them you’ve done some leg work.
A better question might be asking them about specific skills that are important or required to enter a field. Maybe that’ll connect you with someone who has more experience than them.
If you can ask a question that can’t be answered with a 5-second Google search, you have something good going.
Keep chasing the art of asking better questions. Everyone has valuable knowledge to share and it’s up to us to figure out the right words to say.
*Check out my last article on a culture of excellence*
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