Everybody disagrees with his or her boss from time to time. The question is how you navigate through that sort of tricky situation—and what you tell a job interviewer when asked about it later. “Tell us about a time you had a conflict with your boss,” is one of those interview questions that prospective employers enjoy tossing at candidates, because it has the potential to reveal so much—including how the candidate deals with authority. And since even the most freewheeling tech company can’t operate without some semblance of authority (no matter how much Valve and other firms try to position a “flat” management structure
as pure democracy), that question has particular relevance. If you find yourself on the receiving end of such a question, here’s your best answer:
Position the Disagreement as Professional
Never, ever frame a conflict with your former (or current) boss as personal; you both wanted the project or initiative to succeed, but thought differently about the actual route to victory. Mention that the disagreement was professional and courteous.
Emphasize Your Reasoning Skills
Your interviewer wants to know if you’re willing to negotiate, and if you have the communication skills to turn somebody’s opinion around. With that in mind, narrate how you walked your former boss through the issue.
Don’t Rub Things In
Let’s say you triumphed, and your former boss agreed to do things your way. When describing your victory to the interviewer, don’t gloat or make jokes at your supervisor’s expense; instead, take a moment to discuss how your solution led to better results for the company.
The Flip Side
Sometimes, job interviewers will frame this question as a hypothetical: “How would
you deal with a disagreement with your boss?” In this situation, the process is similar to the one described above: You’re going to emphasize the need for reasoning and communication… as well as your willingness to ultimately accede to your future boss’s point of view, should things come to that.