Some jobs actually require employees to take risks and make mistakes -- jobs that are by nature about being creative and innovative.

If an employee's job is to be creative, the biggest favor you can do for that employee is to be clear about what is not within that employee's discretion.

What do you do? Spell out the parameters within which the employee needs to operate. If you don't want to hold the employee back in any way—no guidelines, no goals—clearly define whatever parameters can be established. Is there a time limit? Or will you pay the employee to brainstorm ad infinitum? How will you know when the employee is "done"? How will you recognize a finished product or result?

If you want an employee to feel free to take risks and make mistakes, then what you need to do is spell that out as a concrete assignment: "I want you to take risks and make mistakes." Maybe you need to tell the employee how many risks to take and how many mistakes to make. Maybe not. But you have to define some parameters in order to create a space in which risk taking and mistakes are truly safe in the context of a job, where somebody is paying you.

Sometimes when managers who give out "creative" assignments, what's really going on is that it's not necessarily a creative assignment but more that the manager doesn't have a clear goal in mind; the manager doesn't really know what he or she is looking for . . . at least yet. So the manager might ask the employee to "take a crack at it." Maybe the manager thinks, ‘once I see something, then I'll have a better idea of what I'm really looking for…' Maybe this manager is really using the employee to work out the early stages of the manager's creative process. In fact, that's fine, that's legitimate. But if the manager has not explained to the employee what the employee's role in the assignment really is, it can become a very frustrating experience. Maybe the employee works hard on a project, only to have the manager send it back to the drawing board over and over again or take over the project in the middle and rework it. The employee feels like the manager has hijacked the project and that his or her work and efforts have been for nothing.

Even if the goals are uncertain, you need to tell an employee what you do know about the assignment and what role you want the employee to play in the assignment. You might tell the employee, "I don't know what I'm looking for yet, but I need you to take a crack at it so that I have something to look at and that will be my starting point. Let me be clear. This is my project and I'm asking you to help jump-start my creative process. I am asking you to come up with a rough draft, which I will probably send back to the drawing board several times and it's likely that at some point I'll take over the project myself and rework it - ok? Ready, set, go, please."

BONUS MANAGEMENT BEST PRACTICE
Choose an employee you manage whose job requires some creativity. Now list all the aspects of the job that are NOT within the employee's discretion. What are the required outcomes, timelines, and parameters of each task and responsibility?

Now figure out what's left. What is WITHIN THIS EMPLOYEE'S discretion? What decisions and actions are truly up to the employee to choose for him/her self?

In your next one-on-one with this employee, explain the analysis you've done. Ask for the employee's reaction. Talk about the limits of his/her discretion in the job. Discuss the decisions and actions that are TRULY within his/her discretion on a regular basis. Ask the employee: "How do you make those decisions? How do you decide what actions to take in that case?"