The Best Types of Questions to Ask to Improve Your Outcomes
As a leader, the questions you ask shape your decisions and the culture you build. Great questions unlock better thinking, drive meaningful conversations, and create real progress. A well-placed question can uncover hidden challenges or spark innovation. On the other hand, the wrong question, or even the right question asked the wrong way, can shut down discussion and create defensiveness. Knowing how to ask the right question at the right time makes all the difference.
"The wise man doesn’t give the right answers, he poses the right questions." — Claude Levi-Strauss
In Are You Asking the Wrong Questions?, we explored how curiosity, empathy, and courage create a foundation for better leadership. But having the right mindset is not enough. The way a question is structured determines how helpful the answer will be. This article focuses on five key types of questions: What Do We Know? What If…?, What Should We Do?, Why Does This Matter?, and What Is Really Going On? Each one plays a role in gaining deeper insights, making improved decisions, and guiding a team toward better outcomes. Let’s look at these and see how they can work for you.
Types of Questions
What Do We Know? When facing a problem or opportunity, good decision-makers start by figuring out what they already know and what they need to learn to make the best choice. These may also be thought of as investigative questions. You are trying to flush out facts and details about what is already known and further identify what might be missing. Curiosity and active listening drive the value of this type of question more than most.
What If? These questions help you think in new ways, look at the problem from different angles, and come up with creative solutions. What if questions can be a place to have some fun but also push others to think outside the normal constraints. Asking what if allows for you to suspend current norms or restrictions and say, “But, what if we did…”? These allow for some speculation to happen as well. It creates the potential for introducing different scenarios and situations without saying those will be the case. These types of questions can help to generate many new ideas.
What Should We Do? These questions help you decide what resources, people, and time you need to take action and get results. The what should we do series of questions begins to formulate the foundation of what is necessary. They get to the operational and productivity aspects of uncovering the information you need. This also allows you to transfer the thinking back to the other person and ensure you are not missing anything. I would also classify this as a way to test close your questions. You are asking if we are ready to make a decision here to see what else may come up. If the person you are speaking with is unsure of what to do, you can reestablish the line of questions. When they provide ideas for what should be done, you can then determine if more information is needed or if the person sees a path forward with what you’ve already discussed. This is a powerful question for learning and developing others.
Why Does This Matter? This helps you dig deeper, look beyond the obvious, and understand the bigger picture of a problem or idea. People like to know the reason behind what they are doing. It is an important part of any change management curve. But asking the question about why it matters is a little more than just ‘why.’ This connects it to the purpose. This should connect to a larger vision for where you’re going as a team and company, or even their personal development or success. Again, this is a great place to check for understanding. Are they able to see those connections, or are they just trying to get through this line of questions? You can measure how they are interpreting the conversion and where it is going versus this being a back-and-forth questions and answers session.
What’s Really Going On? Sometimes, people don’t say what they are really thinking. This may be the trickiest type of question, and depending on how things have progressed prior to this point, this question may not be necessary. These questions help uncover feelings, concerns, and unspoken issues that could affect the decision. So, ensuring you have a good sense of where the other person or people who are taking part in the discussion is critical. Remember, What’s Really Going On is the type of question, not the question to ask. This type of question is far more subjective. You are looking for their thoughts and opinions more than facts or specific information. In many cases, questions like these might be the first question to ask. It can allow people to be heard. The change management curve opens up dramatically when people feel they have been heard and understood first before you try to explain why the change is good.
Using The Types Of Questions
The types of questions above are independent of each other. You do not need to use them all the time or in any type of order. Some will naturally fit in at the beginning, and others may play a more important role once you have been in an established conversation longer. But there are no specific rules as to how you would use these. This merely categorizes the types of effective questions you can ask that will lead to the most productive outcomes and results. As with most other frameworks, with practice, you will make these yours, and you will know what questions to ask in which situations. Below are some examples of questions that fall into the categories above. They show how the different types of questions guide conversations and decisions in distinct ways.
Types of Questions - Wrap Up
Asking questions is such a valuable tool in many ways. You can learn, teach, and gather information that will lead to better, more collaborative outcomes when using good questions. Asked the right way, questions empower all parties involved to participate fully and be a part of the success. We’ve all experienced someone asking questions the wrong way and how those can make you feel. Take time to practice and work through how you ask questions, the questions you use to begin conversations, and how others react as you are asking questions. In fact, select just one of the question types above and use it during our next team meeting to see how everyone responds to it. Then, ask for feedback (yes, even more questions) to help you hone the skill set of being an effective question-asker.
How do you see using the different types of questions helping you learn and lead more effectively?
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