Ignoring the rules is not always bad. You can learn a lesson from the Outlaws working for you: Questioning authority and the way things have always been done can give you some new ideas. Nurture curiosity among your staff. Loosen the reins a bit.
FOCUS ON CREATIVITY, NOT COMPLIANCE
Ask the Outlaw to tell you which policies she finds the most cumbersome and unproductive. Ask "Why? How exactly do these rules reduce personal performance and departmental productivity?" Write down her answers. Chances are that old ways of doing things have been hampering others as well.
Set up a time to challenge rules on a regular basis. That way, the Outlaw will have a forum in which to express her dislike of rules - but a forum that you control. If you do get rid of rules that are unnecessary and cumbersome, explain why in a memo to all employees and attribute the idea to the Outlaw who helped you. Receiving recognition as "rule busters" is very important to Outlaws.
Make challenging the rules a department-wide event. Give every wannabe Outlaw a chance to be defiant. Use the energy and momentum that rebels in the organization are capable of generating to your advantage by getting people excited about remaking existing policies. In effect, you are using your employees' rebellious streak to have them come up with ways to manage better.
Start with a town hall meeting. Have some fun with it. Your ultimate goal is to suggest new policies and procedures to enhance the performance and productivity of your department or work area. Review existing protocols and then open the floor for discussion. Demonstrate to the Outlaw that neither you nor her coworkers are hidebound and that everything is subject to discussion.
Challenge team members to suggest alternative policies and procedures that will help them do a better job reaching departmental goals. Give prizes for the best suggestions or those that receive the most support. Write up the meeting ideas as an action proposal that is endorsed by the Outlaw herself. Point out that this document reflects the consensus of town hall participants. Your people have told you how they think things should be run and you're ready to use your authority to carry it out.
CREATE A NEW ORDER
You want your entire staff to feel as if they can operate outside the box. There's nothing wrong with that. But your department's activities are governed by your company's overarching goals, and your department's procedures and rules must reflect that. That's how you complete the circle you've created by indulging the Outlaw. Tie all discussion and activities to the results and outcomes your department needs to achieve.
Create "Rules and Results Teams" to review how policies are enhancing or impeding your work processes. This lets the Outlaw know that she doesn't have exclusive claim to challenging the status quo. But make sure you implement new systems and work processes that the Rules and Results Team recommends. If you don't act on suggestions, team members will feel that their contributions are merely window dressing and the positive benefits will be lost.
Place the Outlaw in charge of maintaining order by including her on the Rules and Results Team. This makes her directly responsible for enforcing rules. That's a paradoxical bind. But if you have set up the over-all goals and outcomes of the department as targets to be hit, the Outlaw has to figure out how to make it happen. She may surprise you with the sense of responsibility she demonstrates when placed in a position of authority.