This research paper explores and reveals the dynamic relationship between employees and their bosses as this relationship influences retention. Employee unhappiness has been cited as a common reason that an employee may leave his or her job; but unfortunately, a boss does not often realize that it is his or her own management style which may cause a valued employee to quit. Bosses who fail to retain their staff, end up costing the company anywhere from 90% to 200% of that employee’s annual salary. A primary conclusion of this research is that managers need to be educated; they are the link between a high potential employee staying or leaving the job. Managers have a large impact on their employees’ attitude toward their jobs, and their relationship with the employees remains the single greatest reason why employees leave organizations.