Remarkable seasoned individuals have the capacity to become irrationally invested in the success of young ambitious people. That’s why I am a big fan of mentoring. So when The Indus Entrepreneur (TIE) offered mentoring-in-motion for its delegates in 2014, I signed up to be a mentee.

The idea was simple. Individuals send their profiles to TIE, which does the mentor-mentee matching. An event sponsor provides the cab. Mentor and mentee ride together to the event venue, and use travel time for mentoring discussion.

I couldn’t be happier with my mentor. He had retired as the top executive at one of the largest companies in India. SENSEX component company no less. He was on the board of multiple listed companies in India. Part of advisory board of a prestigious American university. Post retirement, he had started a social impact company. An industry stalwart in every manner. I was excited and nervous to meet. Here’s how it went.

Event had a 9am start. The cab picked me up at 7:15am. We drove to the house of my mentor. On the way, I was practicing questions I would ask to learn and impress. We reached at 7:50am. Our driver informed his watchman. He told us that sir is finishing his tea and would join soon. I started practicing an ‘opening pitch’ of my startup vision. 8:05am. I was comfortable with my pitch and ready to greet him. 8:15am. I requested the watchman to check again. He told me that sir will be out in a moment. 8:30am. I started getting a little antsy. I didn’t have his number. I also felt it would be inappropriate for me to ask the watchman again. I called up the TIE representative to get in touch with the mentor.

8:45am. My mentor rushed out of his house. He was shocked to see me waiting. He claimed there was some miscommunication. He wasn’t informed about the schedule of mentoring-in-motion initiative. He didn’t know that a participant was waiting for him. He felt bad. He apologized. I didn’t know how to react. I was overwhelmed because I felt that it was big of him to say sorry. Then something strange happened. He said had he known that I was waiting, he would’ve invited me in for tea. He was ready to move when the watchman first informed him, but since it was only a driver who was waiting, he decided to take it easy.

I felt perturbed by his statement. I felt he was debasing an individual. He was failing to see a personality behind a humble title. Isn’t empathy a core leadership attribute? Isn’t it a hallmark of great leaders to care for those who might not be valued? Was I guilty of idolizing him and then expecting that he meets my ideals on every aspect? But who am I to judge? He has definitely impacted far more lives than I can imagine. Needless to say, my mentoring conversation didn’t go well. I lost an opportunity to build a meaningful connect.