1. If you have to ask whether someone is up to the task, you already know the answer. He or she is not. It's not easy to admit this to yourself. After all, as the CEO or owner, you're largely responsible for the fact that the employee is now in over his or her head.
Plus, admitting the mistake means that you'll have to overcome your internal wiring to "finish the job" and "not give up." Persistence is often an admirable trait, but not when it prevents you from making a necessary midcourse adjustment.
2. Create a timetable. Once you've recognized a performance problem with a key employee, you have to decide how to act. If an immediate firing is not in order, then at the very least you need to determine how much rope--that is, how long--you'll give the employee to improve his performance.
Weiner cautions that "there is not a single, uniform answer for this. It all depends on the individual and the situation. Whether one month, three months, six months, or a year, make sure you are doing everything possible within the allotted time to help the individual clear the bar."
You can help the struggling employee by being extremely clear about your timetable and the metrics that you need to see improvement in. You should also offer whatever tools, coaching, and structural flexibility he or she needs to meet the timetable's expectations.
3. The least compassionate thing you can do is to leave someone incapable of doing his or her job in that role for too long. By contrast, the most compassionate thing you can do "is to alleviate their suffering by transitioning them out of the role as gracefully and constructively as possible."
Weiner mentions a person he knows who, after getting let go from his job, returned several months later and admitted that moving on "was one of the best things that had ever happened to them, both professionally and personally." Gary Swart, CEO of oDesk, has told a similar story, about someone he fired later coming back to thank him.
The point is: You may think that letting someone go is one of the most cruel things you can do to a longtime employee. CEOs who've been there and done that will tell you otherwise. And their fired employees may well be there to back them up on it.