I became a manager at a very young age. Back in 1991, I was working at a startup that provided ambulance dispatching as a service. I was the IT / product manager guy, keeping the software running and letting the developers know how it could be improved. Then, one of our offices shut down and my counterpart (a guy by the name of David Cohen) took over my role and I took over managing the call center.

Suddenly, in my mid-20's, I was managing 50 people, some of whom had been doing the same job for longer than I'd been alive. It was very intimidating. While it felt like trial by fire, bit by bit I improved. Twenty-five years later, I think I'm pretty good at it; I've figured out how to be a leader and not a boss. And while I pride myself on being good at having direct conversations, one of the most difficult parts of my job will always be making the hard decision to let people go.

Over the years, I've hired and fired hundreds of people and dealt with all kinds of situations. But after a lot of trial and error, I've come to the following conclusion: The best way to think about firing someone is to put your company hat on when you're making the decision, but replace it with your human hat when you deliver the news.

So, what does that mean?

Wear the company hat

Most of the companies I work with and mentor in my role at Techstars are small -- they're made up of hungry, passionate people that dedicate much of their lives to achieving a common goal. Part of that means early mornings, late nights, frequent travel in search of funding or customers, and often times sharing a lot more about our personal lives than may be the norm at corporations with thousands of employees.

In other words, the people we work with are also people we consider to be our friends; people we respect deeply and spend large percentages of our time with. So, it's no surprise that making the decision to let them go can sometimes feel impossible as you consider all of the personal factors that come with firing someone -- they're really nice, it will devastate them, they have a family to support, we spend time together socially, etcetera. But, as a leader you have to force yourself to avoid the temptation to prioritize personal factors when it's just not good for the long-term health of the organization to keep that ineffective person around.

That's why it helps to "put the company hat on." Although it's hard, try to be dispassionate about the person and consider factors like work performance, effect of the person on overall morale, and even what kind of precedent allowing an unproductive team member to stick around sets within your organization.

Show compassion

Once you've made the decision to let someone go, it's time to put the human hat back on. Starting with how you deliver the news. First and foremost, be sensitive. While this is a business decision for you, getting fired is a monumental event for the person on the other side of the table, sometimes with severe repercussions.

Be direct and concise, let them know that you have bad news, tell them that you're letting them go, and try to briefly explain why. Then be quiet and let them react. This last part is important; in our nervousness, we tend to babble on to fill the awkward silence. You've had time to think about how to deal with this conversation but, for some people, this is unexpected and it may take them more time to process the news.

Remember that each person reacts differently, so it's best to let them react in their own way, at their own pace. Some will want to talk you out of it, some will get mad and just want to leave, others will be sad and want to talk about how it will impact them personally. Try to be sensitive, don't offer blame, raise your voice or get into an argument. Listen, and respond accordingly for a reasonable amount of time, giving them the opportunity to voice their feelings and feel heard.

Have an exit strategy

That being said, always be sure to think through your exit strategy ahead of time, in the event the conversation drags on and you need to bring it to a close. You can try, "Well, you can pick up your final paycheck on Tuesday..." Find something that lets them know that the conversation is over and that the decision is final.

Follow through

Let me reiterate, firing someone is never easy, in fact it is so difficult that some people avoid it entirely. But the most important advice I can give to anyone about firing someone is to follow through. There is nothing worse you can do for your organization than continue to let a poorly performing team member linger, continuing the cycle of either bad behavior or poor performance, and signaling to the rest of your organization that it's acceptable.

Letting someone go can be unpredictable, potentially volatile and incredibly stressful, and there are no guarantees that it will end on a positive note without any negative consequences. But as the leader of your organization, or a manger within in, it's your responsibility to make the decisions that will put the team and organization in the best position to succeed. But remember your two hats and you'll put yourself in a position to do just that.