Sooner or later, as a business owner, you'll have to fire someone. Sometimes it's easy: When you catch someone trying to force a company copy machine into the trunk of his car, it's really easy to say, "You're fired!" Most of the other times,  it's not that easy. In fact, it's really hard.

And sometimes the people you fire are your friends, or friends of people in your office. I received this email from the human resources manager of a small business. She wrote:

I am the HR person--as well head of all things admin--at a small nonprofit. We have a new executive director, and he plans to fire a colleague who I've socialized with quite often. I agree that he is justified in firing her: she is certainly not a stellar employee, and has been warned before; and as a manager, I've fired people like her. He has never fired anyone before, and I am going to give him some advice. One piece of advice I would normally give is to have a second person in the room--but in this case, I am the only obvious second person, and I am concerned that my presence will hurt more than it will help. What do you advise? For anyone conducting a firing meeting alone, what is your advice for lawsuit avoidance?

In a big company, of course, you can bring in the HR person who isn't friends with the target. (And on a side note, this is one of the many reasons I discourage HR people from becoming friends with people at the office. Friendly, yes. Friends, no.)

So, how do you conduct this particular termination, or any one where the boss or HR is a friend?

First, give yourself a pat on the back for dealing with performance issues. In some cases, the person being fired (and remember, firing is different than laying someone off--we're talking about firing here) is just not capable of doing the job. She's trying and working hard, but just not cutting it. In most cases, though, it's a matter of refusing to listen to feedback, not trying, or pushing the limits of company flexibility.

But, at the end of the day, the person needs to go. The three major rules for firing someone are exactly the same for a person you like and a person you don't like. These rules are:

1. The person that says, "Your last day is today" is always the direct manager. Always. If that person is in a coma, you can delegate it up, but not down. It is also not the HR manager. It is the direct manager. If you don't have the guts to fire someone, you need to get out of management. Period. It's hard. It may make you cry. It will probably disturb your sleep for many nights. It is still part of the job.

2. There is always a witness. No exceptions to this. Terminations are often heated and the employee can become defensive. People hear things that weren't said. You need a witness. This witness should be one of the following people: The HR manager, a peer of the direct manager, or the direct manager's supervisor. Under no circumstances should it be a peer of the person being fired.

3. The reason for the termination never changes. You can have 14 reasons for terminating someone, but they all need to be written on any performance improvement plan and/or termination paperwork. You may not say, "Jane, we're terminating you for being late," and then when Jane sues because she says you fired her for being pregnant, change your mind and say, "Well, we really terminated you for gossiping, never getting your expense reports done and sleeping in the break room." Courts don't like that. It makes it look like you don't think your original termination reason was a good one, and therefore the reason you didn't state the "real" reason was because the "real" reason  must be an illegal one.

So, be careful before you speak, because it's a one-shot deal. (Exception: If, after you terminate someone, you find out that they were doing something terrible, you can include that in their file, but any defense of termination is the original reason. Consult your attorney if you're nervous.)

Okay, so all that stays the same. What changes when it's someone you like? Well, for one, the HR manager is right in her letter--it's not a great idea to have her be the witness. But, in the absence of someone else who can do it, it falls back on her. If it's the manager's friend, then the  manager still has to do it. If it's just someone everyone merely likes, the HR manager is an excellent choice for a witness.

But, you don't have to be mean. (You should, in fact, never be mean.) You can offer whatever help you truly intend to offer. In the case where someone is failing because they just lack the skills, you can say, "I'd be happy to act as a reference for your skills as a dragon trainer, but if someone asks about your project management skills, I'll have to be honest. I recommend you pursue positions which will use those dragon-training skills." But, do not say you'd be a reference when you really don't intend to. That's not nice. That's actually mean.

You need to be extra careful to stick to your script. In fact, I recommend writing down what you want to say, and checking each thing off when you say it. Why? Because it's hard to say "you're fired," especially to a friend. So, make sure you say it all as you intended.

It's super important to be willing to fire your friends, if you're going to ever fire anyone at all. Why? Because, while it's perfectly legal to treat your best friend differently than other employees, it may not look so great to a court when your best friend takes two hour lunches every day and then you fire someone who is a different race/gender/religion/sexual orientation (in some states) for coming in late three times. That person may argue it's their immutable characteristic that put them out of a job, not their tardiness. Regardless of the truth of it, you don't want to be in the position where you have to defend yourself against that.

Overall, firing someone you like isn't that much different from firing someone you don't like. It's just more painful.