The Power of Asking “Why?”


A boss sits down to have a meeting with his employees. They’ve fallen short of a goal, and so the boss asks: “What happened? What approach did you use? How did you attempt to meet your goal?” One by one, the employees give him a litany of reasons, all of them centered on situations, experiences, and the steps they took in attempting to reach the goal.

They’ve failed to make the mark, no doubt, but even after this discussion, the reason for their shortfall is still unclear. That’s because despite all the questioning, the boss hasn’t gotten to the real issue. He’s failed to ask the most important question: “Why didn’t you achieve the goal?”

This scenario plays out all the time in companies, fostering a never-ending cycle where people are stuck in a place of great misunderstanding. Asking situation-type questions prevents the boss from understanding the real issue. It also keeps employees from doing the necessary brainwork required to uncover it. The results are answers that amount to fluff. Problems aren’t identified, and the proper corrective actions are not developed.

Leaders should focus on “why” people do what they do versus “what” they do. Asking the powerful question “why” forces people to think deeply. They can then peel back the layers of excuses and get to the root cause of the problem. For example, if employees have failed to meet a goal and are asked “why” questions rather than “what” or “how” questions,


When you face a recurring problem, ask “why” multiple times until you uncover a possible fundamental cause (this is an adaptation of a Japanese quality technique).

they might give responses like, “I didn’t prioritize my time.” So the boss must then go farther and ask, “Why didn’t you prioritize your time?” When the employees say they have too much on their plate, the boss, once again, must ask “Why?” The final answer: These employees are given many tasks from their boss and cannot distinguish between what is and what isn’t a priority. With the real problem revealed, the boss can now take appropriate action, perhaps setting up time to help them prioritize their many tasks.

The Challenge Behind Asking “Why?”

Asking “why” seems easy enough. It’s just a little word, after all. So “why” don’t company leaders ask this powerful question more often? Probing deep can be scary for a boss. It smells of confrontation and hints of accusation. Yet asking “why” doesn’t have to be confrontational or insinuate blame, depending on how the question is asked, the tone of voice used, the way it’s introduced, and so on.

Many bosses are also accustomed to being the go-to person for answers. They’re used to giving direction and opinion. It makes them feel valued and important, and reinforces their position of authority. Also, some bosses prefer to deliver the answers because they think it will save precious time. Unfortunately, when bosses routinely dish out the answers, they become enablers of that dysfunctional cycle, which is actually a huge time-waster. Employees regularly seek out the boss for the solution rather than being problem-solvers. This prevents the ability to develop real solutions, stifles employee growth, and ultimately limits company productivity.

The best bosses and company leaders are those who understand that asking “why” is a highly productive teaching method. And teaching—rather than preaching—and challenging people to think is what stimulates discovery, solutions, and growth. So the goal of any leader is to become a great teacher and develop the necessary skills. This includes not only asking “why” but then also giving employees an appropriate amount of time to determine the real answer. That could be as simple as waiting a few minutes for a response in a meeting, or perhaps sending everyone off to think about the issue, research the reason for the problem, and return at a later time with an answer.

Great bosses also teach by holding their employees accountable for not just the problem’s answer but also its solution. When the employees are used to going to the boss for answers and direction, they actually transfer the ownership of the problem from themselves to the boss. Consequently, they can then blame the boss for the goal’s shortcomings and failure. It’s no longer their fault because they didn’t provide the solution—the boss did. Assigning employees with the task of uncovering the reason for their missed goal or creating a viable solution to a problem or challenge puts the responsibility back where it ultimately belongs.

Think back to your favorite teacher, someone who really made a difference in your life. Did he or she give you all the answers? (No!) Did he or she make you look for the answers? (Yes!) Did this teacher hold you accountable? (Absolutely!) These are the ways great leaders help people learn, cultivate the potential of those around them, and enable growth.

Becoming the Great Teacher

So when it comes to teaching, how do bosses start? They must ask more questions in general. To get people to open up, it’s O. K. to lead with a few situational questions, such as, “What was the biggest challenge?” But don’t spend a lot of time here; quickly move on to the meatier “why” questions and get to the root of the problem. Once the issue is clear, employees commonly ask bosses for the solution, and this is the opportunity for leaders to push back and pose that same question to the ones who are asking it. It’s the employees who need to find the solution, articulate how it will be done, spell out why it’s the remedy of choice, and list the appropriate new goals that must be set to reach it.

Finally, great bosses realize that quick reactions and easy answers typically don’t produce the right solution. That’s where digging deep, allotting appropriate time for understanding, and empowering employees to think hard come into play. The teaching process is a challenging one if it’s going to be effective. But for great bosses and leaders, every day provides an opportunity to create the lesson plan that will develop employees. Their ownership in mining the solutions to challenges is what ultimately leads to growth and success.


  • Deal with “elephants in the room.”
  • Limit situation-based questions (i.e., what, when, how …?).
  • Ask more “why” questions.
  • Ask open-ended questions and keep yes/no questions to a minimum.
  • Wait for the answer once you ask the question.
  • Don’t give the answer to the question in your question.
  • Realize that “pregnant” pauses are part of the process.
  • Drill down on broad, general statements or “modifier” statements.
  • Listen for “modifier” words (i.e., working on, in process, considering, and thinking about) because you might not be getting the real answer.
  • Don’t assume the first answer given is the right answer.
Lee Froschheiser, president and CEO of Management Actions Programs (MAP), works with many premiere business leaders and companies nationwide. He is also co-author of Vital Factors: The Secret to Transforming Your Business—And Your Life. His consulting firm, MAP, specializes in creating goal alignment and uses accountability to drive company results. MAP clients include WebEx Communications, CORT Furniture, Border States Electric, Hawthorne Machinery, and the United Way. For more information call 1-888-834-3040 or visit www.

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