“Successful people ask better questions, and as a result, they get better answers.”

― Anthony Robbins, Motivation Guru

This is one of those strategies you might question a bit why it’s important, no pun intended. In terms of applicability and importance, questions are probably the most important tool for problem solving.


What is the Power of Questions?

Asking simple questions is one of the most underutilized and powerful diagnostic tools. Think about going to an emergency room. They have a set of questions that allow them to diagnose your symptoms and narrow down potential ailments quickly. Strategic leaders have a similar purpose and should use questions more often to understand the context, root causes, and potential solutions to a situation.

When you talk there are only two ways to communicate; assert or ask a question. Asserting is stating your opinions or facts. Asking questions allows you to get more facts and opinions about a situation. Asking the right questions can open your mind and organization to new potential improvements, innovations, and often the next big product idea. Strategic leaders are magicians in quickly diagnosing a situation simply through the questions they formulate and ask.

The simplest and often most powerful strategy framework is also the oldest. Asking or answering the Who, What, Why, When, Where, and How can provide the context people need to better understand a situation. It is the go-to framework, whenever you are trying to better understand a new situation or explain a path forward.


business questions best practices


How do you ask the right questions?

As a strategic leader, the right questions are your best and most often used strategy tool. Questions serve as your guide on your journey to better understanding situations. Choosing your questions wisely often determines the fruitfulness of your journey. Here are some tips for asking the best questions:


Use Open-Ended Questions

Open-ended questions don’t have simple yes or no answers. Open-ended questions allow conversations and problem solving to build and grow, whereas yes or no questions can quickly shut down a conversation.


Shut Up and Listen

Always be aware and mindful of how much time you are talking versus asking questions and listening. We’ve all been through the “being talked at” disease that some people have, and it is such a turn-off. And, as you listen to someone’s answer to your question, process it, and think about other hypotheses you may have or any other questions you need to be answered.


Use the Five Ws and One H for just about anything

The Five Ws and One H are the Who, What, Why, When, Where, and How questions. You can use the Five Ws and One H in almost any situation, including:

Creating a company strategy
– Who is our target customer?
– What is our differentiated value proposition for our target customer?
– Why would target customers choose us versus the competition?
– Where should we expand geographically?
– What is our marketing, distribution, and pricing strategy to drive profitable growth?
– How can we drive the efficiency and effectiveness of the organization in developing and delivering the value proposition and journey?
– When should we execute and stage our different growth initiatives?

• Understanding a past situation
– What happened?
– Who did it affect?
– Why was it important?
– When did it happen?
– Where did it happen?
– How did it happen?

• Understanding a potential product
– What is the product?
– How will it be used?
– Who will use it?
– Why will they buy it?
– Where will they buy it?
– When will it be launched?
– Where will customers buy it?

• Communicating a new program or process
– What is the program?
– Who does it affect?
– Why is it important?
– How does the program work?
– Where do I learn more about the program?
– When does the program start?


Use the Inverse of the Five Ws and One H

Invert the Five Ws and One H, when you face a particularly tricky issue or are struggling to get everyone’s head around the problem. Ask who is involved, and also who is not involved. Ask what it is, and also ask what it is not. Ask where does the problem occur, and also ask where the problem does not occur. Ask when does the problem exist, and when does the problem not exist. This line of questioning will set boundaries around the Who, What, Where, and When. Once you have established these bounds, the next question(s) should be around what is different or has changed. This line of questioning will lead you to the How. Once, you have established the How, the Why will follow. And, the How and Why will then lead you to possible solutions.

Go back to the Basic Question

If you don’t get any worthwhile responses, ask “Why are we trying to solve this issue?” or “Why are we spending our time trying to solve this issue?” These questions can help focus the team and elevate the sense of urgency.




Exercise 1 – Build Your Awareness

How often do you or others ask questions? In your next conversation or meeting, tally up how many questions people ask and who is asking the questions. What types of questions are you asking; open-ended, rhetorical, prioritization, why, when, how, etc.? What do you notice when people ask different types of questions? Do you think you should ask more or fewer questions?


Exercise 2 – Create a Question Guide

Before your next important meeting, write down the questions you need to be answered, and then be sure to ask them during the meeting. Even more powerful, if you are one of the leaders of the meeting, prioritize and post the questions on the whiteboard and start the meeting by saying “These are the questions we need to answer during this meeting. Are there any others and are they in the right order?” Then structure the meeting around answering the questions.


Exercise 3 – Determine the Most Powerful Questions for You

As you incorporate more questions into your conversations and interactions with people, start playing around with different types of questions in different situations to see which ones are the most powerful. Open-ended questions are really useful when you want to understand the context. Forced prioritization questions (What are the top 3 most important…?) are great to help prioritize thinking. Wrap-up questions (What are the next steps?) help drive to the next steps and actions. The 5 Ws and 1 H are perfect when you are planning an initiative, working on an idea, or problem solving.


Exercise 4 – Read a Room

The world is made up of introverts and extroverts and most meetings or conversations are dominated by extroverts, often at the expense of the quality of interaction and insights. Next time you are in a meeting, read the room and see who is dominating the conversation, and then reroute the conversation by asking someone that has been fairly quiet, “What are your thoughts on the topic?”




 Learn more about Joe Newsum, the author of all this free content and a McKinsey Alum. I provide a suite of coaching and training services to realize the potential in you, your team, and your business. Learn more about me and my coaching philosophy.
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