Ask an Exec: Dealing with Difficult Conversations at Work

Did you notice? The title of this article is not “Dealing with difficult people” but, instead, it’s about “difficult conversations”. Don’t think there’s a difference? Then you might find some surprises here.

Speaking as a panelist during a webinar regarding difficult conversations, Betty Chan-Bauza explained: “Sometimes, the hardest conversations aren’t with people we would consider ‘difficult.’ They’re with people who like you and respect you; who mean a lot to you.”

Chan-Bauza started out her career as an industrial engineering major. Somewhere along the path to becoming a VP of Product Management, she discovered that transparent communication could be a powerful productivity tool. Now she helps organizations move beyond the stalemates and silos that stifle productivity by fearlessly stepping into coaching the teams and individuals she works with.

Chan-Bauza admits that dealing with difficult conversations can be scary and that, for many people, the prospect of having to have one of these conversations can trigger the proverbial “fight-or-flight” response. “Predominantly, people will take the flight method,” she observed. “But this skill is second only to public speaking as a critical workplace skill, especially for managers.”

Does conflict have to push people apart?

Our other panelist, Erin Chapple, is a Group Program Manager with Microsoft, where she and her team deliver cloud infrastructure based on Windows Server. According to Chapple, “Dealing with difficult conversations is not something to be feared, but something to have in your tool belt.” Chapple, whose bachelor’s degree is in electrical engineering, developed an advanced set of organizational coaching and consulting tools through her MA in Applied Behavior Science.

“In the workplace, relationships are key to getting things done,” she explained. “We often think conflict and differences push people apart, but in reality these conversations can do a lot to strengthen relationships. When I look back on my career and I think about what has helped me be successful, a lot of times, it’s the relationships that I have and the people that I know.”

Chapple has observed colleagues becoming very intimidated by difficult conversations. “They think it’s going to hurt the relationships they’re trying to build or put distance between them and someone else,” she empathized. “But I’ve found that having the difficult conversation can be one of the greatest ways to bond with someone and get closer because you are listening to them and understanding them.”

Chan-Bauza agreed, adding, “Through having these conversations, you actually gain cooperation, strengthen the relationship with the individual, and assist the company in achieving its goals.”

Work at it. It’s a skill.

Chapple noted that people underestimate their ability to acquire this skill. “Oftentimes,” she said, “people say, ‘I’m not good at conflict’ or ‘I’d like to avoid conflict.’ I’d like to challenge both to say, ‘You know what, actually, we’re all capable human beings. We can work at it.’ It’s a skill.”

During the webinar, the speakers shared numerous personal anecdotes, covering scenarios that included difficult conversations with subordinates, peers, teams, leaders, a customer user group and even a boss’ boss’ boss. Here are the lessons they learned, and are eager to share with other women leaders:


• Disarm them with sincerity;

• Build mutual respect by listening and learning;

• It’s OK to take a break then re-engage;

• Decide if it is more important to be respected than liked;

• Take personal accountability to defuse a situation;

• Be true to your beliefs, stating them sincerely and non-judgmentally;

• Put yourself in others’ shoes and respond from that position;

• Ensure people feel heard before moving forward.


• Don’t leave a difficult situation unaddressed;

• Don’t expect instant gratification;

• Don’t react, take time to think/plan your response;

• Don’t assume they have ill intentions.

As you can see, dealing with difficult discussions doesn’t have to become the boogeyman we often make it out to be. Like other leadership skills you’ve mastered, it can – and should – be learned.

The Takeaway: Use conflict as an opportunity

As a closing thought, Erin Chapple encouraged her audience to appreciate what can be gained when they stop avoiding difficult conversations and, instead, face them head on. “Don’t walk away from it,” she urged. “Lean in. Use conflict as an opportunity to practice your skills. I guarantee that if you can get good at this, the relationships that you’ll build and the impact you can have will improve.”

Or, as Betty Chan-Bauza succinctly put it, “Practice makes perfect!”

Jo Miller

Jo Miller is a globally renowned authority on women’s leadership. She’s dedicated two decades to helping women advance into positions of influence by leveraging their leadership strengths. Based on her work with hundreds of thousands of women, she developed a pragmatic and powerful roadmap that guides women to become the leaders they aspire to be. Jo shares this proven process in her book Woman of Influence: 9 Steps to Build Your Brand, Establish Your Legacy, and Thrive (McGraw Hill, 2019.)

Jo is CEO of leadership development, consulting and research firm Be Leaderly. Learn more about her speaking engagements at and follow @Jo_Miller on Twitter.

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