Fred Wilson recently published a post that I can wholeheartedly agree with him on. Regarding employees leaving your organization he gives the following advice:

The thing I caution against is the tendency to get upset at departures and departing employees. I’ve seen leaders take the mob boss approach of “your are dead to me now” with departing employees. The better approach, which I think is a hallmark of great companies, is the idea that departing employees who leave on great terms are roving ambassadors for your organization. After all, you never know when you are going to come across someone again in business. And it might be a situation where you need something from them.

I’ve hired, I’ve fired, and I’ve been the one that has gotten the news of the departure of a valued member of the team many, many times throughout my career. I’ve also been the one to do the departing.

Let me recount to you a few of these situations and what I learned from them.

First, I’ll start with my own very early career. For a few years I hopped from job to job in relatively short order trying to find the right fit. One such hop was to a healthcare group of companies where I was tasked with managing their IT infrastructure. I did some pretty fun things there (it was the first time I used fiber optics, wow) and learned a lot in only a few months but I was over my head a bit and I knew it. I saw an ad for a web programming job I jumped at the chance.

This is when I learned how to properly allow someone to quit their job. I walked into my then boss’ office, crying (I was 19 and knew the man personally since I was 9 or so). I really felt like I was letting him down by quitting only a few months after getting hired. He asked me why I was quitting. I don’t remember my exact words but I said that I really thought my career was going to be on the web and not in setting up networks or debugging terminals. I wanted to write code.

His response to me has stuck with me ever since and I believe it is why I’ve always allowed people to depart any organization I’ve been part of in the best possible way. He said: “Colin, you have to make the right decision for your family.” (I was newly married at this point.) He continued… “If you think this is the right decision you have to do it. And if our company could have been a stepping stone for you then that is great.”

As Wilson points out above, if he would have flown off the handle I would have never had a relationship with him again. Instead, whenever he needed me I was there for many years afterwards.

Second, fast forward to when an employee of a company that I was part of came to me first to break the news of their departure. They were trying to do damage control by telling me first. I wasn’t this person’s boss. But they knew their boss would lose it. They were right. I tried my best to act as humanely as my boss did from when I was 19. I wished them well. Then I did my best to settle down the boss prior to the news getting to them. It worked out in the end and that person is still a friend to everyone at that company to this day.

Third, fast forward again to when an employee and friend left the company that I owned. This is much different. Being part of a company and owning a company are two very different things. The loyalty you feel to your own company far outweighs any devotion you may feel to one that you do not (even though I consider myself a very loyal employee). When you own the company, and an early employee leaves, it stabs you directly to the heart. You believe these early people have your back through thick and thin. When you find out they don’t and they jump to whatever is next it hurts terribly. I learned a lot from this experience. Years later and I’m still reeling over this person’s departure.

Even though I was more upset than I had ever been in my life I believe I still handled myself in the same way that my boss when I was 19 did. I gave them no pushback, no hurtful words were shared, and I did my very best not to speak too poorly about them behind their backs to others within the company.

The lesson that I learned from this experience is that many people out there view a job as “just a job”. Others fit into several categories. Some small percentage are willing to ruin their lives in order to have the company make it. Some people look up to these individuals. I do not. I admire their accomplishments and their drive is incredible but I fit somewhere between “just a job” and “willing to die”.

I’m glad Wilson brought this up in his post and I’m very glad he’s mentoring the entrepreneurs he talks to about this topic.

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