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 investor for his infinite wisdom, brilliant timing, and wonderful generosity.
This was sad to observe in and of itself, but even more disturbing was how clearly the investor reinforced this behavior. He would say things like, “Do this for me, and I’ll let you pitch me for 60 seconds” or “Give me a ride to the hotel, and I might let you pitch me until we get there.”
Ugh. This type of scene was repeated often enough at startup events that I decided to tap out.
But, what’s the harm?

We’ve all witnessed the danger of kissing the ring of our new President. Those who rushed to please him, and secure a seat of power, soon began to regret their decision as they learned of some of the stranger job requirements. The smart ones, who knew exactly what was coming, politely declined roles with the administration.
Therein lies the danger of hitching your wagon to the wrong horse. You may not recognize that you’ve made a mistake until it’s too late. The events of the past few weeks in the Tech industry have hopefully been a wake up call for many people. Be careful who you get into bed with.
I’m surprised by the number of people who seem to be missing even an ounce of spidey sense. As the reports began rolling in, they rushed to support and defend their favorite horse. After all, some of them had spent years kissing the ring and were still banking on receiving some benefit in the future.
But, as it all came tumbling down, they discovered that this was career suicide. People began noting names, screencapping tweets, and creating lists of all of those who were on the wrong side of history. The smart ones stepped back, apologized, or silently withdrew support. The less clever ones decided to double down and dig themselves in deeper (I won’t even honor that with an example link).
Yes, this is an extreme example from an extreme situation. But it can, and does, happen frequently. Over the years, I’ve witnessed a number of people go down with the ship when they attached their career success to the wrong leader. When you do this, their brand becomes your brand. You can continue to hope that you are insightful and make wise choices about the people you allow to pull your brand underneath their umbrella. But, wouldn’t it be wiser to avoid this vulnerability in the first place?
Be smarter about your career
I suppose you could view ring kissing as a career hack, but you know how I feel about hacks. It may work in the short term and help you get ahead. It may even help you secure funding for your struggling startup. But, it’s like playing with fire. If you rely on this to get ahead, sooner or later you will get burned.
Put aside the potential career suicide risk for a moment. Do you really want to be that person? Is that the reputation you want? The industry is small and we all talk about the people we’ve observed playing this game, over and over again. You may think you’re fooling a leader with your behavior, but we aren’t stupid. We know what you are doing, and we don’t respect it.
Finally, do you really like the feeling inside when you behave that way? Who enjoys feeling so deeply indebted to another person that they are vulnerable to that person’s whims each and every day? No thanks.
The path may be longer and harder, but the reward is that much sweeter when you earn it yourself. Let the others kiss the ring if they want. You can rise above that.






