Handling the tough cases

The tough cases for bosses are the people who are on the margin. Entire books have been written on the subject, but what follows is a few tips based on my own experience and from helping others.
Here are three tough cases:
-- The charming longtime employee who has evaded all attempts to get him to adapt to new technology. For a small organization to compete, every person has to contribute. You can't afford to have someone who is marginally productive.
-- The above-average performer who treats other people badly and won't contribute to the team effort. In other words, this is a self-centered person who meets individual performance goals, and no more.
-- The average performer who makes derogatory comments about others behind their back, rolls her eyes when asked to do anything she considers outside her own narrow definition of her job and generally oozes negativity. The negativity is infecting others.

You can't wait
As a boss, you have to take action as soon as you see that this person's performance is affecting the performance of others and the organization. You can't wait for this person to provide you with the perfect excuse to take action. The biggest mistake we all make is waiting too long.

Set a time for a private meeting. Make it clear that this is important and the person must attend. Ask a lot of questions during the meeting. What does the person think his job is? What problems is that person having in the job? What does the person want more of and less of in his job? Find out what's going on. Probe for information.

Set expectations and draw boundaries
Once you have some understanding of that person's perspective, you can take the opportunity to set expectations and draw boundaries. If the person's idea of job responsibilities is not in synch with yours, this is the time to make that clear.
Here are some examples of language you might use:
-- "Starting today, you need to change the tone you use when you speak to your fellow employees. Dismissive comments like "whatever" are not acceptable. One-word answers to your supervisor's questions are not acceptable. That has to change, starting right now."
-- "You have to become conversant with this new software package we use in accounting. Starting this week, you will begin a program of training so that you can fill out the online forms required to process orders, invoices and customer requests. You will be performing at X level by such-and-such a date. But the effort begins now."
-- "Starting today, your goal will be for everyone to say that you are a pleasure to work with. Making derogatory comments about the company or others is not acceptable and must stop immediately. If you are unhappy here, you need to keep that to yourself. You might consider what kind of work or company will make you happy. What do you think that might be?"

Consequences
Ultimately, there have to be consequences for failure to perform. It could be loss of a bonus, no pay raise, a cut in pay, or ultimately termination.
Every organization has its own rules about how to handle this, but a clear statement of expectations and the consequences for not meeting expectations will go a long way toward getting someone's attention.
My experience is that some people will change and some won't. Some people want you to set boundaries, and others will bridle. Getting into action will make this clear.
Finally, if you are so unhappy with an employee that you are considering termination, it seems only fair to tell that person the truth: unless you change, you're in danger of losing your job. Give them a chance to change.

What do you think?
There is much more that could be said on this topic. What are your experiences? How do you handle these situations?