Advanced questioning


July 27, 2022

Questioning situations correctly is a secret weapon to solving difficult problems. 

The key to unlocking this secret weapon is mastering the art of asking the right questions. We can avoid bias and defensive thinking by asking probing or exploratory questions in the right situations. But most importantly, it's easier to find the core issue of a problem and solve it. 

Asking the right questions also relies on using the best communication style for the situation. Some problems require statements to clarify issues, while others need questions and synthesis to align stakeholders and resolve a problem. 

In this piece, you'll learn how to master advanced questioning using frameworks and real-life expert advice. 

Table of contents: 

Coming Soon.

D.A.R.E to ask questions

The right questions allow teams to work together, find higher ground, and solve hard problems. The best questions for these situations fall into four buckets: drilling, adjoining, rising, and exploratory. 

Let's break each one down. 


Drilling questions are the most common questions used to dive deeper into a topic.

These are the perfect questions to test assumptions so leaders can analyze a situation better. Examples of typical drilling questions are things like:

  • Explain step three of your analysis? 
  • What happens when your assumption is changed?

When to ask Drilling Questions
Although drilling questions are commonly used, they can sometimes feel accusatory. Use them wisely and, if you can, balance them with other questions or caveat them with a softer approach. We recommend asking questions like: "I'm trying to understand this point better. Can you please explain step three of the analysis?" to keep the discussion flowing. 


During a discussion, teams can speak past each other and zone out. 

Adjoining questions help bring stakeholders back together. They're also perfect if you feel like you can guess where a discussion is going, as these questions help you clarify what the rest of the team is saying.

An example of an adjoining question might be: Please, tell me more. Why do you think so? 

These questions help involve stakeholders in your discussions and make them feel heard. 

When to ask Adjoining Questions
Adjoining questions are some of the most underappreciated forms of advanced questions. People often don't ask these questions because they tend to make assumptions and complete any missing parts themselves. Adjoining questions eliminate assumptions and help bring your team together. 


Sometimes we feel the problem-solving has missed the bigger point and gone into the proverbial rat hole. 

Rising questions help you take a step back and see the bigger picture of a problem or situation. These are often questions like: 

  • What is the higher order takeaway? 
  • What would be our one line synthesis? 
  • How does this analysis connect with the core question?

These rising questions allow you to zoom out and realign the questions you're asking to ensure they're appropriate for solving your problem. 

When to ask Rising Questions
Rising questions are great to ask before certain situations, like a senior executive review. These questions take you to a higher playing field and keep you focused on the situation. 


The final D.A.R.E questions you can ask are exploratory. 

These are used when teams get stuck in group think during discussions. For example, a situation where everyone agrees with what the other is saying will not be beneficial for problem-solving as you'll get similar answers to every question. 

Exploratory questions help you overcome this. They help explore different aspects of a problem that might be ignored in a discussion. Here are some examples: 

  • What if we drop that assumption? 
  • How will different customers use this technology?

When to ask Exploratory Questions
In our mission to get things done, we risk missing out on excellent advice and ideas. Exploratory questions help us see a problem from every angle and spark fruitful discussions within our teams. 

Three steps to mastering D.A.R.E questions

  • 🤔 Assess. What are we getting stuck on? 
  • 🔎 Identify needs. How can we expand our thinking? 
  • ❓ Ask the right D.A.R.E.question. Don't be afraid to search until you find the right question—it helps you explore every angle of a problem.

💡 Prezent Pro Tip: A good problem solver knows the importance of asking questions, but a great problem solver uses different questions.

The three arrows of communication

Overusing one tool for multiple problems can lead to a myopic view of the world. Think of it as putting blinkers on a horse—you'll only ever see a portion of a problem with one communication style. 

Thankfully, there's a solution. When tackling business communication, we all have three arrows in our quiver: statements, questions, and synthesis.

Let's take a better look at how each arrow works.  

Image source

🏹 Arrow 1: Statements

The most overused arrow in the bunch—more than 75% of all business communication—is statements.

Statements put a stake in the ground and are mainly used to emphasize or address questions. While they're helpful if you want to be assertive and firm during a discussion, there can be downsides.  

Using too many statements during questioning closes our minds to competing or new viewpoints by being too firm. Once a statement is firmly made, it becomes harder to change course and can add bias to our thinking. 

That's where questions come in handy. 

🏹 Arrow 2: Questions

As adults, we ask a lot of questions—15 to 25% of what we say ends up being questions.

Your question arrow is best used to drill deeper and understand someone else's point of view. This arrow can also be used to rise higher and see the bigger picture of a situation. 

There are many opportunities to add multiple different questions to your arrow. Instead of sticking to common questions (like why? and what?), add probing questions like what if? and why not? to make discussions more interactive. 

🏹 Arrow 3: Synthesis

Synthesis is used to recap what others have said and summarize a succinct viewpoint.

However, it's the most unused arrow of the three. We use synthesis in less than 5% of all communication, but it's the arrow that makes people feel heard. It's also helpful to align stakeholders with a goal and uncover any blind spots in your problem-solving process. 

In a fast-moving business environment, leaders who synthesize efficiently bring teams together and get more done.

How to pick the right question arrow

  • Understand what each arrow does. In the early stages of problem-solving, take time to understand which arrow will be useful to start with. Explore using different arrows to get comfortable in different situations. 
  • Recognize when you need to change arrows. As you start solving the problem and aligning stakeholders, switching to synthesis is a powerful way to bring your team together. 
  • Use statements last. When the problem is nearly solved, and you need to emphasize the major point, using more statements can be extremely helpful. It also helps close the conversation and refocus your team on certain goals or next steps. 

💡 Prezent Pro Tip: The best problem solvers know that using all three arrows thoughtfully enhances problem-solving. 

Expert Corner: How Jennifer Lowry cultivates a culture of asking questions at Microsoft

Jennifer Lowry is a Senior Director for CX Product Management at Microsoft. In her role, she's mastered the art of asking questions and understanding just how powerful they are at giving customers a better experience.

She emphasizes over and over again that customers will notice when you start asking them questions because it shows compassion and care for them. "The thing about asking questions is, it requires curiosity, and they can surprise you," she says

Here's why questions are so important in Lowry's role at Microsoft. ⬇️

Not asking questions will cost you in the long run

Teams can resist getting curious with their customers without questions. 

Lowry says if leaders aren't asking questions like, "Hey, why did that interaction not go well?" or "Why didn't you choose our products?" they risk missing out on crucial information. 

"In a way, people can be afraid to ask these questions, but the worst thing is not asking," she says. "Every time I've asked a hard question or I don't know how an interaction will go going into it—we've got to a better place with customers." 

How to create a culture where people ask questions

Leaders should build an environment where they demonstrate humility if they want to answer questions, not just ask them. Lowry says she's cultivated this environment at Microsoft through her leadership style that relies on being humble around her team. 

"I also do it by being honest if I don't know the answer," she says. 

Part of the problem, according to Lowry, is that leaders are always expected to know the answer to a question.  Her solution? 

"Be open, and don't be afraid to say, "Hey, I don't know the answer, but I'll go find out or let's figure out the answer together!" she says.

Asking the right questions starts with frameworks

We all ask a lot of questions, but asking the right questions can help us solve problems faster. 

The advanced question frameworks we've discussed can help leaders align stakeholders, see the bigger picture of a problem and remove bias from decision-making. Once you master the art of asking the right questions and adapting your communication style to certain situations, you can effectively get to the bottom of a problem and solve it quickly.

Want to learn more about solving problems? Check out our detailed guide on the power of questions here