Leadership Magic Trick: Genuine Open-Ended Questions
When it comes to the subject of asking effective questions as a leader, I see two major places where people go astray:
The first is trying to ask the “right questions.” I often hear the phrase “asking the RIGHT questions” as something one ought to strive to do. This concept tends to give the impression that to ask the right questions you need to be super smart, know a lot about the topic you’re asking about, and/or have a surgeon-like precision. When you try to ask the right questions, you’re focused on being right instead of learning and instead of gaining all available information to find the best outcome.
The second is asking questions to “lead someone to the answer.” How that manifests in practice is that you’re trying to lead someone to the answer you already had in mind. Like a kind of mental jiu-jitsu of getting someone to do what you wanted all along. Or the inception of an idea into someone so the other person thinks they came up with it themselves.
Asking the “right” questions and leading someone to “the” answer can be useful in some circumstances, but in the vast majority of cases when working with high performing or high potential adults it's much more useful to ask effective questions. Asking effective questions increases the amount of information to make decisions with and builds rapport along the way.
Instead of trying to ask the “right” questions or lead someone to “the” answer, this article will focus on asking effective questions. To ask effective questions you don’t need to be the smartest person in the room, you don’t need to know the most about the topic at hand, and you don’t need to be super precise in the questions you ask. The most important thing you can do to ask effective questions is simply to: only ask genuine, open-ended questions.
Below I will explain five concepts behind why open-endedness and genuineness in questions is so effective.
Genuine open-ended questions:
Engage other people’s thinking
Open up possibilities and creativity
Increase clarity and reduce speculation
Get you information you actually want
Build rapport
I will follow that with a magic trick and how you can put all this into practice.
1. Open-ended Questions Engage Other People’s Thinking
Asking an open-ended question offloads a large portion of the thinking from you to the person you’re asking the question to. This is particularly relevant when you are communicating with your direct reports. When managers think of delegating they often think of delegating tasks or areas, but not the delegating of thinking. If you’re doing the thinking, then your direct report isn’t.
Closed-ended (i.e. “yes/no”) questions require very little thinking from the person answering them. When only one person is doing the thinking in a conversation, you’re missing out on half the brainpower and knowledge.
There’s a game you may have played before called 20 Questions. In 20 Questions, Player 1 starts with something in mind such as a particular animal. Player 2 then asks yes/no questions to try to figure out the animal in 20 questions or less. Player 2 asks questions like “does the animal have hooves?” and eventually gets to questions like “is it a cheetah?” It takes a lot longer for Player 2 to form their questions than it does for Player 1 to answer them.
20 Questions can be a fun game because of the artificial constraints on the questions and the very narrowly scoped problem space of guessing something that can be expressed in one word. However, think of how much more efficient it would be to just ask “What is the animal you’re thinking of?” Boom. One question. Done. If it takes 20 yes/no questions to guess an animal, how many yes/no would it take to solve a complex business or relationship problem?
I coached a highly successful VP who nearly always asked yes/no questions. He knew the business inside-and-out, so while he could get by on just yes/no questions, he was having trouble delegating larger, more complex areas. Once he started asking open-ended questions he could see the wheels turning in his direct reports heads as he began to delegate the thinking to his team by asking open-ended questions.
2. Opened-ended Questions Open up Possibilities and Creativity
Yes/no questions constrain possibilities and options. Yes/no questions force the person asking the question and the person answering it to think in black-and-white / this-or-that. This stifles creativity and rules out legitimate options.
Open-ended questions open up possibilities and creativity. Asking an open-ended question creates a space where you can learn about a possibility you hadn’t even conceived of. When you ask a yes/no question, you’ve already conceived of both the possibilities of the answer (“yes” or “no”) and your question only gives you information as to which of the two possibilities it is.
Also, since the person answering an open-ended question is having to think about the answer, they will usually learn something too. Open-ended questions add rich information to a shared pool of information from which to work with.
3. Genuine Questions Increase Clarity and Reduce Speculation
Have you ever been in a situation where someone is asking a bunch of questions when it seems like they already know the answer? Or they are trying to get at something with their questions and you just wish they would “come out and say it?” It’s typically quite annoying to be asked questions in this way.
If you want to state something, state it. Turning a statement into a question is disingenuous and leaves the person being asked having to speculate what’s behind the question and what’s really going on in your head. This builds a wall between you and shuts down collaboration.
I had a conversation with a highly technical CEO I am coaching about not turning a statement into a question. The next week the CEO had a conversation with members of his team about the design of an engineering system. When discussing the design, he found himself concerned about the reliability of the system that was being proposed by the team. He started with his default behavior of asking questions related to his concern, which would allow him to only obliquely gain insight and hopefully lead his team to consider the reliability of the system being designed. This method ended up leaving his team confused as to what he was trying to get at. Remembering what he and I had talked about, he changed course and stated, “I am concerned about the reliability of this design.” He and his team breathed a collective sigh of relief that they could now actually talk about the CEOs concern directly.
4. Genuine Questions Get You Information You Actually Want
When you ask a genuine question, it means you really want to know the answer. How wonderful! Why ask questions you don’t want to know the answer to when you could be asking ones that you do?
5. Genuine Questions Build Rapport
When you’re not genuine, people can usually tell. When your question is actually genuine, it comes across as genuine. No one wants to answer questions to someone who doesn’t care about the answer. Answering questions that someone wants to know the answer to builds rapport.
The Magic Trick: What/How Questions 🎩
The easiest way to ask open-ended questions is to start your question with either “what” or “how.”
“What” and “how” are by far the most commonly useful ways to start open-ended questions.
Using “why” invites rationalization and puts people on the defensive. I don’t know exactly what makes that true, but it is. Anytime you are about to ask a “why” question, convert it to a “what” or “how” question and get more real and open information (even if it makes your question sound a little clunky to you).
There are some instances where yes/no questions and “why” questions are valuable, but in most collaborations that is a rare exception.
The reason that “what/how” questions are magical is because the simple technique of changing yes/no questions to what/how questions completely changes conversations for the better. And—if you’re someone whose questions are usually yes/no questions—it will rewire your brain for more expansive thinking and collaboration. It’s rare to come across something so simple that changes so much.
Because this is magic, you won’t believe it until you put it into practice 🪄
Putting This Into Practice 🤸
Everyone asks a different mix of types of questions. Some people almost never ask a non-genuine question, but nearly all of their questions are “yes/no” questions. Some people don’t like to make statements, and opt to ask non-genuine questions instead. Some people usually ask genuine open-ended questions, but have specific situations where they don’t. Some people ask a lot of open-ended questions that start with “why.”
No matter where you are, you can benefit by making your questions more genuine and/or making more of them open-ended by starting with “what” or “how.”
A few of the smartest, highly successful people I know used to only ask yes/no questions. And when they started asking what/how questions, it took their leadership, delegation ability, and team’s effectiveness to the next level. If you find that your questions typically start with “do” or “is” and you have a hard time even formulating a question that starts with “what” or “how,” I recommend setting a goal to ask one what/how question per day. Bonus points if you log the question you asked and the result it had in a spreadsheet or on a piece of paper. You can also put a coin, small stone, or other token in one pocket and once you ask your what/how question for the day, move it to the other pocket. Once you’re consistently asking genuine, open-ended questions, you’ll be thinking and collaborating in a powerful new way.
Some other ways to put this into practice:
Catch yourself when you’re about to ask a question where you’re not interested in the answer. Then ask a question you do want to know the answer to.
When you are about to ask a yes/no question (often one that starts with “do” or “is”), change it to a question that starts with “what” or “how.”
Ask yourself: “Where might I benefit most from being more genuine or open-ended with my questions?” Then set an intention to take action in a specific type of conversation or with a specific person.
Think of an area of collaboration where you are stuck. Ask yourself, “How can I be more genuine in this collaboration? What is a truth I am not speaking?” Then speak that truth.
Notice what happens when you switch a closed-ended question to an open-ended one or a non-genuine question to a genuine one.
My hope for you is to take what’s in this article and use it to increase your effectiveness by having a higher percentage of your questions be genuine and open-ended.
P.S. I help founders and technical leaders thrive while scaling their companies and teams through hypergrowth. I also coach successful individuals in their late 30’s and early 40’s who have reached a plateau and want to feel more alive again in work and life. If one of those sounds like you, send me an email at kevin@kevinricecoaching.com.
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