Keith Webb has a fantastic website in the arena of coaching and many of these concepts can be directly applicable to mentoring! I encourage you to explore the many resources such as this on his website;

In coaching, why is important. Why the client wants to achieve that. Why they reacted the way they did. Understanding why helps the client to change. As important as why is, I rarely use the word “why” in a question. Why? I’ll tell you.

It’s said that if you ask “Why?” five times you’ll get to the root cause. In conversations, asking “Why?” five times usually irritates the client or causes defensiveness!

It’s easy to ask “Why?” But expect to hear a short, simplistic response, or “I don’t know.” In working in an area where a client is stuck, they often don’t know why, that’s why we’re coaching together. My job as a coach is to help them explore the whys of their situation.

Asking “Why?” often produces simplistic, single reason responses. To find out many reasons, ask this question… CLICK TO TWEET

Simplistic to Multiple Responses

Asking “Why” can easily generate simplistic, single reason responses that are top-of-mind.

Question: “Why did you join this organization?”

Answer: “To make a contribution.”

Surely, this person has multiple reasons for joining the organization, yet asking “Why?” didn’t draw out those reasons. Instead, rephrase “Why?” into a “What?” question to cause deeper reflection and generate multiple responses. To do this begin with “what” and ask for something with an “s” on it.

  • What factors did you consider in choosing this organization?
  • What outcomes do you hope to achieve by working here?
  • What options do you see in contributing to the team?

Each question will get to part of the “Why” but does it in a way that draws out multiple reasons and from several perspectives. You can then add, “What else?” to draw out even more reasons.

Missing Context to Focused Reflection

Asking “Why?” doesn’t give enough context. What are you asking about? Do you want the client to reflect on reasons, motivations, anticipated results, or what? Asking specifically about each area will generate a much richer response.

Get To Motivations

  • In what ways does this plan line up with your calling?
  • What would achieving that do for the organization?
  • What benefits would you hope to receive?

Analyze the Situation

  • How would you summarize the results of your time here?
  • What are the key decisions you’ve made that have gotten you this far?
  • What do you think are the causes of this problem?

Consider Alternatives

  • What are your reasons for doing it this way? What other ways might be possible?
  • How did your team adopt this policy? In what ways does this policy serve your team today?

Don’t ask “Why?” if you really want to know why. Instead, use this technique… CLICK TO TWEETForming questions that focus the context and elicit multiple responses will cause the client to reflect more deeply. It may take a series of questions, but those questions will be more reflective to the client and examine causes from multiple perspectives.

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