How to Deftly Handle Conflict With Your Boss

Conflict fuels drama. Think about it: Would we be as captivated by the story of Romeo and Juliet (or by The Real Housewives, for that matter) without the family feuds, fractured friendships and forbidden love? But unlike these often-entertaining escapes, knowing how to handle conflict with your boss can have serious implications for your health and career path. 

Here are a few tips to help you navigate differences in opinion while demonstrating your value and saving the drama for your favorite Bravo-lebrities.  

Given that future opportunities and a positive working relationship could hinge on the outcome of a conversation, it makes sense that there’s a large undercurrent of fear when it comes to confronting your boss.

Entrepreneur Serena Kerrigan also believes this fear could be a trauma response from childhood.

“But the conversation never ends up being as scary as your idea of it,” Kerrigan says. “You think you’re keeping the peace by not doing anything—but it’s the opposite, I would argue. When you’re not honest, open and don’t communicate what you want, then you can become passive- aggressive, resentful and gossipy.”

Industrial-organizational psychologist Dr. Nicole Scott, founder of EvoExec, LLC, believes when, how and even if you bring up conflict is related to the level of psychological safety you feel.

“If leaders haven’t created a space where employees can push back, fail and use it as a learning experience, then a person’s motivation is to stay under the radar.”

“Men always lean in, they don’t have to have a million accolades to do so, whereas women are constantly feeling like they’re not ready,” Kerrigan says. And this could become a self-fulfilling prophecy.

Researchers have found that women tend to have an expectation of having less influence, which can translate into a resistance to insert themselves even in situations where their skills are valuable. Women also can be more likely to avoid confrontation in the workplace because conflict tends to affect them more negatively than men. In addition, studies have shown that people are predisposed to believe that women are more prone to workplace conflict with one another, which can lead to lower commitment and poorer working relationships.  

Setting expectations and asking questions at the outset can go a long way toward mitigating workplace conflict.

“When you start working with a new boss, tell them you really want to kill it and ask, ‘What do you expect from me? What could I do to eventually get a promotion? How can I be a team player? How can I impress you?’” Kerrigan says.

Scott encourages employees to learn their boss’s rules of engagement.

“Ask them what their preferred method is for you to raise questions or flag issues. Email? A separate conversation? Bring it up in your regular one-on-one’s?”

She also recommends choosing your battles wisely and encourages people to explore their workplace values.

“Am I motivated by money, rewards and recognition or job security? Understanding what you need can help you address issues and even determine whether you should stay or go. But if you’re constantly the naysayer, eventually your concerns become background noise and nothing will get heard.”

So, Scott says to consider the following aspects of your specific situation:

If you decide to have a conversation, knowing how to deal with conflict at work is essential. Scott says you don’t want to attack your manager’s position. Instead, you should authentically generate new insights into the why and into what they are doing and saying. “Then share your perspective so you can come to a mutual understanding.”

If you’re at fault, Kerrigan recommends taking the loss and apologizing. “The more you harp on something or defend it, the bigger it becomes. Take responsibility and move onward.”

And give your manager the benefit of the doubt and enough time to adjust. 

“I want the best for whoever works for me,” Kerrigan says. “What I need is communication and transparency and enough time to pivot.”

While there are a wide array of conflict situations that can arise at work, Kerrigan highlights three key scenarios  that commonly arise for employees. 

Upset in your personal life has the potential to wreak havoc on your career. Kerrigan knows this firsthand. After college, she started interning at Refinery29 amid a personal crisis. “My first love had just broken up with me, and I was a zombie at work,” she says.

Kerrigan was so in her own feelings that she began making errors like mistakenly charging personal Uber rides to a corporate card and being late to a shoot.

“It was an amazing place to work, and I wanted to get hired, but my boss told me it felt like I didn’t want to be there.”

So Kerrigan owned up to the personal situation and decided to use the experience as a turning point.

“I didn’t want to make the same mistake again. There are constant lessons and learning taking place, so the real mistake, what would be on me, would be repeating my mistakes.”

When it comes to direct feedback on your work, Scott says to get curious about what’s behind the boss’s perspective. “Is it based on recency or based on performance where they have multiple instances that support that score?”

Come in ready to supplement the information your boss has and fill in their blindspots.

“Also, ask for specific actions and examples of how you can improve your performance or what you should stop doing that’s negatively impacting it,” Scott adds.

A woman who worked for Kerrigan compiled a PowerPoint presentation on everything she had done over the past year to demonstrate that she was ready for a promotion.

“You want the money, prove it,” Kerrigan says. “You have to advocate for yourself.”

If the boss is taking credit for your work, Scott says you need to have a hard conversation with yourself. “Do you need to stay in that environment or is it time to launch your job search?”

“Ask if you can present next time as a development opportunity or offer to field any follow-up questions,” Scott says.

And if it comes time to walk out the door? 

“There is never going to be a good time to quit,” Kerrigan says. “If you have the ambition and drive to make what’s next happen, you will.”

Photo by AYA images/Shutterstock.com

Jill McDonnell is a Chicago-based content writer and communications professional. She has a bachelor's degree in magazine journalism from the University of Missouri-Columbia and a master's degree in public relations and advertising from DePaul University. She is currently at work on a psychological thriller novel.