Three Shades of Mentoring

Discovering a mentoring moment is not difficult to do, especially when you have cultivated an eye for it, through time and experience. For example, when we hired a talented young man for a field position, we knew he was bright, motivated, eager to learn and grow by applying his previous experience. At the beginning, I witnessed first-hand how he treated volunteers and got along with everyone. Together, we trained the new volunteers, eventually launching a successful campaign. One day, this young gentleman took my place to speak at a luncheon of which I could not attend due to another scheduling priority. It would be his first time he would be speaking in front of a group of people. However, it was not his scripted speech I was concerned about. Upon arriving at the office that day, he came in dressed in a worn dark suit, an unpressed shirt, and wore white socks, which vividly stood out with his dark suit and black shoes as he sat down. He was literally a fashion mess. At first, I asked myself, “Is this the right time to address his clothing presence?” Well, within a minutes to spare before he left to the luncheon, I just decided to hold back. It was too late! The reason for my decision was there was not enough time for him to go home to correct the issues that were so evident to me. And, I did not want to throw him off his game that day.

That day I decided not to say anything, until the following day, when no one else was in the office; just him and I. This lapse of time provided me some time to think through my approach and messaging. Approach has a lot to do with how we transition from one conversation to the right one to find that critical moment to introduce a sensitive subject into the conversation, without wounding a highly motivated employee. Messaging, on the other hand, has a lot to do with the words, tone and how someone will feel when they are being corrected on an issue.

When the right moment came, I applied these three strategic mentoring techniques to my mentoring encounter:


1. Survey

I define survey as a specific conversation to gather vital information. When I survey a mentoring situation, I tend to retrieve and receive information or feedback until clarity and understanding emerge from the conversation. So, I asked him about the luncheon and his speech. By doing this first, before engaging into my initial objective, I created a relaxed atmosphere, where we were laughing and enjoying the moment. I also provided some feedback concerning his speech, with a light touch of noteworthy tips so he could connect better with others to maximize his efforts on his next mission. After chatting a bit and breaking the “ice” per se, I transitioned into his professional attire.


2. Sensitivity

Knowing he was still in his early twenties, he did not have the time, money or perhaps the mentoring to acquire a distinct wardrobe line, to define his own style of dress or even build upon his personal knowledge of his overall professional appearance. So I had to ease my way in. So I said, “Hey, you looked good in the suit you wore yesterday! However, I believe I can help you improve on a few things. Would like to hear how?” His immediate response was, “Certainly!” I found the open door I was seeking. So, I started with the most obvious – his socks. I advised him to wear a pair of socks more in line with the color of his suit and shoes. I told him how important details were in a professional setting, such as shiny shoes, and updating his tattered shoe laces. Next, I mentioned that he could take his shirts to have them pressed at a small expense. In addition, I advised him details are critical in the public eye, especially among professionals. They will notice the “details” in a person’s appearance in public. “If you can get good at the details,” I said, “You will attract more people to you.”



Thirdly, and perhaps the most difficult part of this mentoring moment was asking him to upgrade his suit. In other words, I said, “When you get your first check, spend a little money to purchase a new suit or two.” I told him where he could find specials at several outlets by providing at least four locations. I advised him on the colors for suits for the different seasons and occasions; the type of ties and shoes to buy. Finally, and perhaps the most important, I extended my personal finances to help him, only if he took the two for one special. He was elated and grateful that I would offer my personal finances to bring him up to speed on his professional attire. I did this purposefully to show him that I had real “skin” in the game too.


The aftermath of this encounter was worth an awkward mentoring moment. Our team took a trip a few days later, and the particular event we were to attend required all of us to wear business-casual attire. Upon leaving the hotel, I was surprised to find this young man in a new suit, a pressed shirt and shoes with a mirror-like surface. When we encountered each other, I could see the self-confidence and pride in his demeanor, as if ‘look what I did – I took your advice.” His stride that night was much different as he stood among professionals, looking and acting very much like a professional himself.

As mentors, if we are building the proper awareness at all times among our team members, a mentoring moment will present itself on any given day throughout the week. Your standards will expose the lack of standards in others. A business leader or mentor should improve building their awareness by taking the time to observe, evaluate, so when the time comes to relate well in a mentoring opportunity, you will be way ahead of the game.

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