How to Ask Great Questions

The humble question is, perhaps, one of the most underutilized tools in business and among leaders. Questions can spur innovation, help you identify unexpected weaknesses in a plan, and build trust. Unfortunately, asking great questions doesn’t come naturally to most people. It’s not a topic that gets a lot of coverage in business degree programs, so most leaders lack any specific training for it. That puts the onus on you to develop your question-asking skills independently. The good news is that there are some things you can do that will build on the conversational skills you have to empower your question-asking in the long term.

Ask More Questions

You can’t become good at asking great questions at a basic level unless you practice asking more questions. Practicing helps you hone things like your question timing. For example, is a lull in the conversation just the other person thinking or a natural break in the conversation that you should fill with a question? Asking more questions also helps you hone your question crafting. You’ll often struggle to formulate questions if you rarely ask questions. If you ask questions all the time, you develop a skill for crafting questions with nuance.

Understand the Type of Conversation

The kinds of questions you ask and how you approach them can vary significantly based on the type of conversation you’re having. In a conversation with someone you just met, such as a potential business partner, the odds are good that both people are feeling open-minded. This is what you might call a cooperative conversation. Both parties will likely provide detailed answers up to a point, and neither person is likely to shy away from answering questions provided they aren’t too sensitive.

The other kind of conversation you’re likely to have is a competitive conversation. These are conversations where one person wants information, potentially sensitive or professionally damaging information, and the other person probably wants to avoid providing it. In these conversations, you’re likely to find people deflecting questions with questions, providing short or uninformative answers, or providing answers to unasked questions. You can deploy several strategies to ask great questions in both scenarios.

Ask Follow-Up Questions

Few things have the power of follow-up questions. It’s a direct signal to the other person that you were listening when they spoke. These questions also signal that you are genuinely interested in the discussion topic. Take asking someone about their hobbies as a case in point. How often have you seen someone ask a question about other people’s hobbies and then immediately change the subject after getting an answer? It’s just short of shouting: “I’m not interested.” When someone asks a follow-up question about the other person’s hobby, it sparks an immediate, positive response.

Of course, in a competitive conversation, follow-up questions have a different purpose and a different kind of power. A follow-up question signals that you aren’t going to let a topic drop. It can serve as a subtle reminder to the other person who holds power in the situation. It can also signal that you noticed the other person avoiding the initial question. The upside of follow-up questions is that they generally require little from you in the way of creativity. Instead of generating a question from whole cloth, you’re just following a minor conversational fork in the road.

ask a question


You should consider the sequence in which you ask your questions. The nature of the conversation or your goals with the conversational partner can play a significant role in making that sequence decision.

You’ll typically start with softball questions if you’re meeting someone for the first time and want to get to know them. These questions keep the conversation moving and let you glean some information about the other person. You can use that information to ask follow-up questions that become more sensitive as the conversation evolves. In getting-to-know-you conversations, starting with non-sensitive questions makes the most sense because it helps you build rapport, get a feel for their style of answering questions, and provide the other person with opportunities to ask similar softball questions.

The opposite sequence is often the most effective when the conversation involves sensitive or problematic information. Open the conversation with the big, uncomfortable question and let the other person get their peak anxiety out of the way. Let’s say, for example, that someone blew it with a customer or client. They blew it so badly that the customer or client ended their relationship with your business. You will have lots of questions about this situation. Dancing around the big question — “So, you blew it there, did you?” — leaves the other person in a constant state of anxiety about when you’ll bring it up.

Starting with the big question can relieve some of the other person’s anxiety and, ironically, make them more willing to answer your uncomfortable follow-up questions. It’s not that those questions are substantially less sensitive or problematic. They feel less intrusive relative to the biggest uncomfortable question.


The tone is one of those things that too many leaders don’t think about enough. Leaders often use decisive, no-nonsense tones when asking questions. It’s not always the best approach. A decisive tone can generate a fast answer but not necessarily a thorough or well-thought-out answer. That kind of tone works best when the information you want is quantitative in nature and not subject to much debate. For example, “Where were our sales numbers on Widget X last year?” It’s a straightforward question that should prompt a swift and straightforward answer.

When you want information that isn’t quantitative, it’s often best to ask the question casually. Let’s say that you have concerns about an employee. Let’s say you start with a brusk question to their immediate supervisor: “Is Jeremy drowning here?” That question can make the supervisor hedge their answer if they don’t hate the employee. The supervisor may read your brusk tone as a prelude to firing someone and wanting to protect their subordinate.

Asking questions casually can help people open up about topics that don’t lend themselves to a strict yes-no dynamic or rely on easily found data. Take that employee that concerns you. You could ask the supervisor casually: “How’s Jeremy acclimating to work?” The question isn’t asking for substantively different information, but the casual tone and framing should elicit a more thoughtful response from the supervisor.


Great questions can vary from one context to another. Take a one-on-one conversation with someone you’re getting to know. Asking if that person has family in town or about their past experiences are perfectly normal questions. Since the conversation is primarily closed to everyone except the two participants, it’s psychologically and emotionally easier for the other person to answer those questions.

All of that changes when you move into a group setting. An innocuous question about family can look wildly intrusive in a business setting. Even in a casual work get-together, asking about someone’s past can put them immediately on the defensive. Many people don’t want to share any but the shallowest personal details with their coworkers. They may fear gossip or prefer to keep work relationships strictly professional.

You should also gauge the conversation around you. How personal or impersonal is the conversation in general? Is everyone talking about sports, the last book they read, or their favorite Food Network show? People in a group like that will likely shut down if you ask personal questions. Are people sharing pictures of their kids and discussing elder care strategies for their aging parents? You can ask much more personal or probing questions in a group like that because the group dynamic supports it.

Become the Great Questioner

Asking great questions isn’t something that happens overnight, but it is a fundamental skill that you can develop with time and effort. Start off simply by asking more questions. You’ll get at least some results if you ask good-faith questions with a non-confrontational tone. Remember what kind of conversation you’re having at any given moment since that can inform your question-asking approach. Leverage follow-up questions to gain more significant insights or redirect the conversation back to a necessary topic.

Sequence your questions from easy to more complex or vice versa where appropriate. Monitor your own tone. A question in a casual tone can often elicit more thoughtful and thorough answers than brusk questions. Always bear the context in mind. One-on-one conversations are different animals than group conversations. Read the conversational depth and gear your questions accordingly. Finally, keep asking questions. Practice won’t make you perfect, but it will make you better and more effective.


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Posted in SEO

Published on: 2022-10-31
Updated on: 2022-10-31

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Isaac Adams-Hands

Isaac Adams-Hands is the SEO Director at SEO North, a company that provides Search Engine Optimization services. As an SEO Professional, Isaac has considerable expertise in On-page SEO, Off-page SEO, and Technical SEO, which gives him a leg up against the competition.