Your “WHY” Matters

Fueling Resilience Through Motivation

Your “WHY” Matters
Rob Shepherd
January 6, 2026
Mentor

“When people ask me how I motivate my people, my answer is that I don’t. I don’t try to push or pull people. Instead, I try to inspire people and help them find their own motivations.”

~ John Maxwell

Mentoring relationships can help both partners cultivate resilience and benefit from it when things get tough. Let’s look at ways we can create the right environment for this to happen.

Know Your WHY

All the information-gathering questions (who, what, when, where, how, and why) will help guide the search for a mentor or protégé, but your reason for forming such a relationship will have a crucial impact on the quality of your affiliation. 

Discovering your mentoring WHY can be a straightforward process:

1. Consider why you’ve looked for mentors in the past. Perhaps you were climbing the corporate ladder and recognized the need for insights about your aspirational position, which you couldn’t obtain without inside help, and you found a mentor who was considering succession planning. You may be able to repay that gesture in kind and have a desire to do so now.

2.The mentor selection process can be awkward—who chooses who and to what end? A formal mentoring program can pair two people for a specific purpose, while more informal relationships might develop in response to the needs of one or both partners. The format might drive the behaviors within the relationship, guiding your purpose for engaging with the other.

Help Your Protégés Know WHY

While it’s important to understand your reasons for serving as a mentor, it’s only one factor. I experienced a mentoring failure, which I believe was caused by misaligned expectations, because I didn’t explore why he sought out a mentor. I could have built more trust—critical to a resilient relationship—by demonstrating my concern for his needs more clearly.

Here are some foundational steps to ensure you make the right connection with your protégés from the outset:

1. Make the protégé the center of attention. You should learn as much as you can about them as soon as possible, which requires active listening and patience. Resist the desire to share too much about yourself—there may be time for that later.

2. Ask thought-provoking questions to draw out the other party. One of the most common considers legacy, such as “What would your obituary say?” You could also use more near-term ones, like “What problems would you love to solve?” You can discern emotional issues as well by asking about when your protégé feels fulfilled and considering how that might stimulate other behavior.

3. Focus on empathy. Think of this as “perspective taking,” involving not just a cognitive understanding of your protégé, but also engaging in an affective connection. You want to appreciate his environment and desires.

4. Guide them toward clarity of expectations. Remember, you are trying to help your protégé discover her motivations rather than providing a checklist for success. She should anticipate more questions than answers.

Challenge Assumptions

We make assumptions about how we and others see the world in order to manage the thousands of decisions we must make every day. However, as Henry Winkler said, “Assumptions are the termites of relationships.” Even if the assumptions later prove to be correct, failure to examine them may leave our blind spots intact, leading us to unwisely trust our intuition and create a tenuous connection with our protégés.

This ties in with your protégé’s goals within the relationship. If he isn’t clear about the reasons for getting together, you may both wander into the wilderness. For instance, suppose you are trained as a counselor and your protégé is struggling to maintain emotional stability at work. You may sense an underlying mental concern and offer a therapeutic solution, while he is simply dealing with a difficult boss and seeking practical advice. Some open dialogue could avert this confusion.

1. Ask direct questions. Mentoring is not for the timid, and shared expectations may not readily appear. Look for implicit expectations that either of you might have and bring them into the light by openly addressing them. This can kill Winkler’s destructive termites.

2. Provide frequent check-in opportunities, asking questions such as, “What are we missing in our conversation?” or “Is this what you meant?” This can pave the way  for a deeper exploration of unspoken beliefs before they become deeply held expectations.

3. Listen. I can struggle with quietly listening after asking a thought-provoking question, which sometimes limits my ability to integrate the answer into the conversation. Listen for both content and emotion to help you chart the path forward.

4. Withhold judgment. Whether or not your assumptions are correct isn’t really the issue, so don’t focus on their accuracy. Rather, make sure you understand their implications. Using our example of a protégé’s difficult boss, your assessment of your partner’s need for therapy may be valid, but unrecognized on his part. Deal with his expectations first, and then perhaps the window will open for further conversation about your perception of his additional needs.

Remember Your WHY—Both of You!

Revisiting your reasons for mentoring—and asking the same of your protégé—can breathe life into your relationship.

1. Review your progress. “Are we heading in the right direction?” This powerful question is open-ended enough to give the protégé much latitude in describing the situation and signal your willingness to modify your approach.

2. Hold your plans loosely and don’t be afraid to change direction. We bring some agenda into our interactions with others, even when we’re trying to be other- centered. Add a healthy dose of humility to demonstrate your ability to follow your protégé’s lead in the relationship.

3. Allow for an organic termination. A keen understanding of WHY can help set the scope of the relationship. Your protégé may have made other professional contacts because of your guidance, in which case both of you might be best served by transferring your time and attention elsewhere.

Refine Your WHY

I grow along with my protégés, even when the going gets tough, but I’m still not the expert that I envision in my mind’s eye. Stephen Covey’s seventh habit, “Sharpen the saw,” gives us some guidance to move closer to mastery. We must take time to refine our motivations—our WHY—to be as resilient as possible for those who seek us out.

To summarize:

  1. Know why you’re a mentor
  2. Find out what your protégé needs
  3. Maintain a shared mental model
  4. Keep why at the forefront of the relationship

You can use these practices before you begin to mentor, while you’re actively engaged in a mentoring relationship, and while reflecting on past experiences to boost your readiness for the next encounter. The most important thing to do is to use them. Your WHY won’t protect you from setbacks, but it will carry you through them as a mentor worth emulating.

This post offers a glimpse into a chapter from Mentorship Mastery: A Holistic Guide for Virtuous Leaders. For a deeper dive into the ideas, stories, and tools behind this perspective, we encourage you to read the full chapter.

Rob Shepherd is a Baltimore-based Captain for Southwest Airlines, having retired from the Air Force after 25 years, mainly flying airlift aircraft and serving in three command positions. Rob holds degrees in Computer Science from the U.S. Naval Academy (B.S.) and the University of Idaho (M.S.). An SLG Mentor and former SLG Board member, he also leads the C.S. Lewis Institute Fellows Program in Annapolis as City Director. When he’s not traveling, Rob enjoys cruising the Chesapeake Bay with his wife, Mary Beth, on their Ranger Tug Kairos, reading, and running. They have two grown children and two granddaughters.

Your “WHY” Matters

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