Ah, the life of an entrepreneur! The freedom, the sense of accomplishment, the potential financial rewards. There are a lot of reasons to wax poetic about business ownership. The occasional need to fire people really isn't one of them.

In fact, letting an employee go is often one of the most dreaded moments of new entrepreneurs. Is there anything that can improve the situation for both you and your soon to be ex-employee? 500 Startups recently spoke to a handful of their most experienced founders and investors to round up their wisdom.

Sorry, this is going to suck.

The first thing that stands out when you read through the post, is that nothing you can do will make this easy. Firing people stinks whether you're on your first business or your fourth. Feeling bad about the situation is unpleasant but also a good sign for your leadership, according to 500 Startup's Christine Tsai (who was previously in product marketing at Google and YouTube).

"Maybe people who are really ruthless about it just don't care," she says, "but hopefully, we never become that type of company where we just don't give a s*** about people."

But it can suck a little less.

Still, there are things you can do to improve the experience for everyone involved. First off, just bite the bullet. Letting someone linger when it's clear they won't work out, isn't a kindness to them, you, or the other members of your team. "It's better just to power through these tough decisions so you can get back to working on what really matters: building your business," advises 500 Startups partner Sean Percival.

Second, if the conversation comes as a bolt out of the blue to your employee, you did something wrong. "Be transparent about why the termination is happening. If you did things right, it shouldn't be a surprise to the person," says Tsai

Finally, prepare for the conversation in advance. "I thought of the key talking points that I wanted to make and wrote it out," Ethan Appleby, founder and CEO of Vango, explains of his first experience firing someone. "I actually went home and was by myself for an hour thinking about what I was going to say, trying to be as clear and concise as possible."

Got your thoughts in order? Good, then "keep it really short," he recommends. "Don't talk too much, just get right to the point." Let them ask questions, but keep emotions out of it. And don't do it on Friday, he adds, "so you can see if the morale of the team is ok and people can get their questions answered."

When to pull the plug

500 Startups isn't the only VC firm to address the issue of letting employees go recently. Union Square Ventures' Fred Wilson, mused on the question of how quickly you should pull the plug on problematic employees on his blog as well.

"I don't do a lot of hiring and firing personally, only at the highest levels. But I do observe executives in our portfolio companies struggling with these decisions," he writes. "I tend to like action, decisiveness, and a willingness to make a mistake over inaction, pondering, and a desire to get everything right. And so I generally coach executives to make a call and move on when they have concerns."

Still, he continues, recent conversations have made him question whether he's been too quick to advocate terminating a struggling employee, shortchanging coaching and talent development. You can check out the complete post for his full musings, but there's one definite takeaway from his comments -- everyone, even some of the country's most experienced investors, struggles with when to fire. So if you're confused and troubled yourself, don't beat yourself up.

What's your best advice for a fellow entrepreneur struggling with their first firing?

Published on: May 31, 2016