Almost every business owner has dealt with stale employees who refuse to change with the times. These employees have decided that they’ve learned everything they need to, and now coast by on their tenure without contributing their share to the success of the company.

Unfortunately for you, the boss, these employees probably used to be exceptional in their positions. You probably have a great relationship, and they’re likely your most highly paid employees. But if these members of your team don’t change, you may have to choose between maintaining longstanding relationships or ensuring the success of your business.

Can Stale Employees Be Saved?

As an agency consultant, I have years of experience coaching business owners on handling these situations. While some stale employees can be saved, old habits are difficult to change.

I had a client on the East Coast who owns an agency of about 25 employees. The owner was loyal to an account representative who had been with him for 15 years. Unfortunately, this employee had chosen not to embrace the digital revolution in his industry, and his skills had become irrelevant over the years. The owner felt so attached that he didn’t realize what a burden the stale employee had become on his other employees until his star account executive quit, citing his frustration over covering for the stale employee as his reason for leaving.

As a result, this agency’s biggest client also left, and the owner had to lay off some of his workforce. That finally got his attention. Had he taken action earlier, people would have kept their jobs. He sat down with this employee and gave him a generous amount of time to change and specific progress goals to meet. But he saw little sustainable improvement.

In the end, he gave his employee a choice—resign or be fired. The employee resigned, and on the day of the announcement, the owner learned that several other people had been looking for new jobs to get away from this person. Most stayed, but the damage of the stale employee had taken its toll on the company.

How to Deal with a Stale Employee

Obviously, you can’t afford to wait as long as my client did. If you have a stale employee, start with these three steps:

1. Schedule the conversation. Talk with the employee away from the office. Allow for a couple hours, and brace for a difficult conversation. Give the person credit for work done in the past, then have a candid conversation about the current situation. Back up your points with facts and specific examples from their work.

2. Set an ultimatum. Tell the employee that this can’t continue. Is he or she willing to grow and change for the betterment of the company, or is it time for a job elsewhere that better aligns with his or her skills?

3. Set metrics and a deadline. Provide specific goals that directly correlate to the tasks this employee needs to be able to complete in order to stay. Set a firm deadline for closure (90 days is good), have it in writing and evaluate progress along the way. Allow the employee the necessary resources to make the change, but don’t spoon-feed.

Happy endings aren’t impossible with stale employees, but both of you have to invest the time and effort to make the change. If the employee doesn’t meet the improvements by the deadline, help him or find something new as respectfully as possible, but don’t continue to let a stale employee drag your business down.

This article was written by Drew McLellan and was originally posted on American Express.