The Art of Asking Good Questions


Blue questionThere’s an old sales adage: the person who asks the questions controls the agenda

How well do you ask questions? Even though salespeople are very deliberate and strategic in their question-asking, most managers and leaders don’t think about this issue. After all, you don’t usually find “the ability to ask good questions” on any list of managerial competencies, but asking questions effectively is a major underlying part of a manager’s job, which suggests that it might be worth giving this skill a little more focus.

Dan Black, in On Leadership , states that “Having and maintaining relationships is essential when it comes to leadership. One essential aspect to learning about, connecting with, and relating to the people in your life comes through the art of asking good questions.” This is an essential ingredient to becoming a relational leader.  

Two basic question-asking principles can be valuable tools for a leader: open-ended questions and clarifying questions.

1. Open-ended questions can lead to a better discussion and a deeper level of conversation. This is because they require more than a yes or no response. One example is: “What is your most pressing business challenge in taking on this project?” This question type keeps a conversation alive and flowing.

2. Clarifying questions show engagement and bring clarification to what the other person is saying. Some examples: “Can you be more specific?” or “Can you share an example?” An interesting consequence to asking a clarification question is that it spawns successive questions.

Socrates observed that you can tell how clever a person is by their answers, but you can tell how wise a person is by their questions. Most of us never think about how to frame our questions, but doing so not only improves a one’s inquiry skills, it can, as our sales adage reminds, help us gain something strategically. 

There once were two monks who lived an uncomplicated life of peace and devotion at the monastery. Both were exemplary individuals, but each also had one vice, that of cigarette-smoking. Smoking was a privilege rarely granted by the Monsignor, and permission had to be granted.

One day, both monks had an insatiable desire to smoke, so they each separately approached the monsignor to ask permission to smoke. One monk returned shortly with an anger he could barely control, saying the monsignor had denied him the opportunity to light up. The other monk returned to their dorm and immediately lit a cigarette.

The denied monk was furious. “How did you get to smoke and I didn’t?” he queried. “I asked if I could smoke while I prayed in the chapel–I was flatly denied; what in providence did you ask?” The other monk smugly answered, “I merely asked the Monsignor if it would be all right if I continued to pray while I smoked!”

The art of asking good questions is essential in learning about, connecting with, and relating to the people in your life where relationships matter.