Are You Risking Career Suicide When You Kiss the Ring?

Short answer, it’s never worth it

I doubt that anyone, as a child, said “When I grow up, I hope that I can be a sycophant!”

Yet, think about how many times you have observed sycophantic behavior during your career. I remember seeing it for the first time at one of my part time jobs during college. One of the employees would rush to greet the owners every day when they came in, asking how their days were going, and making small talk. I’m not sure how he thought that would help him, but he never missed a chance to ingratiate himself with them.

The industry game

During my past decades in Silicon Valley, I continued to witness my fair share of people “kissing the ring.” Within companies, there were always a few people who would kiss up to their manager and more senior leaders in the organization. To be clear, there is nothing wrong with being polite, respectful, and recognizing someone’s position within the company. But, I think we all recognize when someone crosses the line into obsequiousness.

As I left the corporate world and began spending more time with startup founders, angel investors, and VCs, I saw this behavior repeated even more frequently. At a number of events, several founders would encircle the resident investor, desperate to capture his attention and get their chance to pitch. They would laugh at every ridiculous joke, nod at every comment, and heap praise upon the…