When teaching employees to meet deadlines, start with one small goal with a short deadline and all the specifications. If they deliver, then set a little bigger goal and a slightly longer deadline. And so on. Gradually increase the amount and importance of the work you assign, until you reach the employee’s appropriate scope of responsibility…for now.
Once the employee reaches that point, you can continue to empower them by coaching them and by using project planning tools together. Help them develop long-term project plans, complete with clear benchmarks along the way. Focus your regular one-on-one meetings on evaluating their progress toward each benchmark.