When You Work with a Rule-Breaker?

Working with someone who sidesteps the rules can be frustrating, especially when they’re good at what they do. How can you address it constructively?

Put their rule-breaking in perspective. Before your frustration builds, consider why they’re cutting corners. External pressures or old work habits might be at play, rather than a disregard for the rules.

Have a curious conversation before a confrontation. Start with open questions, like “I noticed you’re taking a different approach—what’s your thought process there?” You might uncover overlooked reasons behind their actions.

Explain the purpose of rules. Share how the processes make things easier for everyone. For instance, mention how reviews prevent last-minute problems, framing the process as a tool rather than a hurdle.

Offer flexibility where possible. When you can, meet halfway by suggesting adaptations, like shorter check-ins or batching updates. These adjustments can make processes feel less restrictive without sacrificing accountability.

Stay firm if they ask you to break the rules. If they push back, reinforce your boundary respectfully. A line like, “I get that time is tight, but this process ensures fairness,” reinforces the rule with understanding.

(This tip is adapted from “5 Ways to Deal with a Colleague Who Doesn’t Respect Rules,” by Melody Wilding)