5 Conversational Temptations Mentors and Parents Commonly Face

Conversation, though natural to us, is not something we naturally think to work on. Here are ideas to help you grow as a parent or mentor.

While our example remains the most powerful means of shaping our sons’ and students’ character, our words still matter. Whether a father counseling his son or a teacher offering advice to a student outside of class time, conversation is the main medium of mentoring.

Conversation, though natural to us, is not something we naturally think to work on. Whether you are a parent, a teacher, or a formal mentor, here are some ideas to help you improve your mentoring conversations. The reflection is structured around five conversational temptations we commonly face, along with positive advice for avoiding these pitfalls.

Temptation 1: Taking a Structured, Box-Checking Approach

Mentoring conversations, regardless of whether you are a parent or a formal mentor, should feel neither like a visit to the doctor’s office nor a legal deposition. Though you may have a formal structure in mind, the tone ought to remain informal and easy-going. To this end, the setting matters. Taking a walk, throwing a ball, or sharing a meal, for example, can create a relaxed environment.

Only when a boy feels at ease will he speak openly. If he does not feel comfortable, he will be more likely to say things that he thinks will make you like him.

Another way to keep the conversation from feeling overly structured is to involve the mentee in shaping the topics for discussion. You might begin with:

1. What’s on your mind?

2. What should we talk about from the last few weeks?

3. Is there anything that has been bothering you?

4. Is anything concerning you?

5. What’s made you happy recently?

6. What are you looking forward to or worried about?

Temptation 2: Thinking Meaningful Conversations Must Be Filled with Meaningful Content

It’s common to believe that mentoring means delivering all the right advice and instructions to shape the boy. But often, we are going to shape them through liking them more than by telling them what to do. A child is a young person who desperately wants to be liked, because to be liked is to be affirmed, and to be affirmed is to be seen as good, which is to be loved. Boys will become good because they know they are first loved. If they feel unloved, they may act out in a thousand ways as they seek to be seen.

Conversations that seem unproductive—talking about sports, hobbies, whatever is on the boy’s mind—can, at times, be even more helpful than an unnatural conversation about something serious. Conversations like these communicate to the boy that you enjoy spending time with him. They help foster the environment in which he will be more likely to want to bring up big topics when the time is right.

Rather than forcing a big topic to be brought up, it is better to keep a few ideas in the back of your mind and bring them up if a fitting moment presents itself. You should be ready to have many prepared conversations that never end up happening, or that don’t happen in any given conversation.

Temptation 3: Focusing on Solving Problems

It’s tempting to tell the boy exactly what he needs to do, especially when we see clearly how certain behaviors would benefit him. But just because we see what the right answer may be, and just because we tell him what he should do, does not mean that he will embrace it. Our goal isn’t to point out what’s wrong and prescribe a fix but to help him want to grow.

Instead of solving the problem for him, ask, “What do you think you could do about this? What goal seems attainable to you?” Even if his goal isn’t perfect, that’s okay; it is better for him to embrace an imperfectly good goal than to disregard the perfect goal you have set for him. Even beyond solving any single issue, you’re helping him take ownership of his life and learn to find solutions himself.

A particular way this attitude typically manifests in conversation is in our manner of listening. Consider two ways we can listen to a mentee:

1. Listening to find weaknesses and offer remedies.

2. Listening for opportunities for growth.

These two modes of listening may seem similar, but they are each informed by a vastly different way of seeing the boy. They lead to two different attitudes—and boys will sense these attitudes. The first approach makes the boy into a problem to be fixed. It subtly assumes a negative mindset. The boy becomes like a broken car and the mentor or parent a mechanic. Though you may offer objectively good advice, this mode is mechanical and somewhat disrespectful. The second approach, on the other hand, recognizes the fact that the boy is a person with free will, and it frames any challenges the boy may be facing in a positive light, as opportunities for growth.

Imagine the scenario in which a boy tells you that over the weekend all he did was watch YouTube, sleep-in, eat some food, and play some video games. One response could be to tell him straightforwardly: “Hey, next weekend, it would be a good idea for you to get up earlier and do homework right away. Trust me, you will feel better at the end of the weekend.” A more fruitful approach, however, would be to first seek to engage the boy’s innate desire for the good. You may ask a question like, “What kind of weekend would you say on Sunday evening, ‘That was awesome’? What might that look like?” Usually, an open-ended starting point like this leads to a more constructive conversation.

Temptation 4: Mistaking External Actions for the End Goal

Change often begins with new outward behaviors—but lasting transformation occurs when interior dispositions shift. The ultimate aim is that the boy internalizes the desire to do good, not just that he performs good tasks out of a rote sense of duty. The goal, for example, is not simply to get a boy to do acts of service, but to help him become a charitable person. Acts of service done freely—because the boy has embraced them—are a means to develop a stable disposition of charity. But doing acts of service just because “Mom said so” or to earn necessary service credits for graduation may not cultivate genuine virtue.

In conversations with mentees, then, it is important to help the boy understand the deeper ideals behind his actions. Two steps are necessary for this:

1. He discovers the kind of man he wants to become.

2. He finds repeatable ways he can practice being that man.

Questions that open horizons and help him to think big are helpful. I have mentioned the following tactic in a previous article, but the example bears repeating. Suggesting that he make a “business plan” for his life is one idea that illustrates the point.

Temptation 5: Wanting to Become Indispensable to a Mentee

For people who have a desire to help others, there often arises the temptation to become indispensable. This temptation can subtly turn our generous desire to help others into a self-seeking desire to feel helpful. We ought not help others for our emotional satisfaction but simply for love of the other.

The role of a mentor or parent is to accompany and guide, not to carry the boy. The true goal is for our mentorship to become obsolete. We want him to become a friend, not for us to remain his crutch.

A question you can ask yourself: What is the quickest way to become unneeded by this mentee?

Don’t Look to Have Transformational Conversations

Let me conclude with one final temptation that summarizes the rest: it is the temptation to try to make big changes in the lives of our mentees.

Most of the change that parents and mentors witness will be small and seemingly insignificant, yet these small shifts can have lasting effects. Transformational moments don’t always come with grand acknowledgments; our mentees may never explicitly thank us for changing their lives, which is probably a good thing, lest we become proud. Occasionally, we may be the instruments of profound, visibly life-changing transformations—typically with older mentees or children with whom we have developed a close relationship—but we should not make that the standard of our success.

We should not look to have a transformational conversation every time we meet with a mentee or chat with a child. These attempts tend to be dramatic and awkward—like bad actors overacting in a bad movie. Instead, simply look to have good conversations. If any of them become transformational, it is because God wants them to be.

Above all, we must pray. What will move a boy to want to live a better life is God’s grace. Sometimes He may choose to use our words.

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