Braving Difficult Conversations in the Workplace

If you’ve made it to this point in your career and have never faced a difficult conversation in the workplace, I’d say you’ve most likely either avoided them or you’re simply a lucky individual! Whether related to performance issues, personality conflicts, or a difficult work environment – these confrontational discussions are by no means easy, but extremely necessary. Learning how to face these direct conversations head on is an important step in everyone’s career, and we’re excited to be chatting with Heather Davis this week to hear about her experience and tactful approach.

You should have an ongoing level of transparency so there are no surprises.

CQ: A May 2016 Upstart Business Journal article by Mindy Mackenzie states, “As a leader, you are paid to be courageous. You are paid to do the hard stuff.” As a leader, what would you include in “the hard stuff?”

HD: The hard stuff is any interaction that you find upsetting, or where the other person is upset. It could be anything, you never know what people are bringing with them to the office each day. And each different situation requires a different level of courage.

CQ: What makes a conversation difficult? What are some of those topics that are hard to discuss?

HD: It’s really anything emotionally charged where you run the risk of potentially offending someone. The situations I see most often are when giving/receiving constructive feedback, or when you are collaborating and there is a difference in opinion.

CQ: How do you keep your cool?

HD: I try to bring empathy with me. You have to take 100% responsibility for what you can bring to the conversation. You cannot control how people will respond to you – only what you bring. Give unconditional respect and go into the conversation seeing the positive intention, and try not to be attached to the outcome. I think about it like this: On a scale of 0-10, how many f*cks do you give? If it’s something you’re really passionate about, then stand by it. But if it’s something that mildly agitates you, then put a pin in it.

CQ: Why is it so important not to shy away from having these tough conversations?

HD: There is too much at stake if you don’t. We’ve all left a meeting feeling like you should have said something or pushed the agenda. And with that mindset and fear, no one will grow.

CQ: What was your learning curve to advance your skillset?

HD: It’s all through practice – you won’t become an expert by reading about it. In the past couple of years, I’ve been in some high conflict situations with very differing opinions. And through such situations, I’m continually developing this skillset as a part of my craft.

CQ: What are you some things you should avoid?

HD: Avoid letting emotions run hot – deescalate conversations that get emotional by hitting the pause button. Avoid creating a zero sum game, where if someone wins the other loses. Rather, find ways to create win-win situations and build common ground. And don’t wait until there is an issue to have a conversation. You should have an on-going level of transparency with your employees so there are no surprises.

CQ: What about the other way around – how do you handle conversations with leadership above you?

HD: I don’t change my approach. I bring transparency and empathy, and make sure that everyone feels valued. And as I said before, bring the same level of respect that you’d expect. If it’s someone I know, I try to be less formal – crack jokes and be self-deprecating. And when it’s someone I don’t know very well, I try to mirror their behavior.

Links and Resources


Want to hear more from Heather? Listen to the full podcast to hear more about her techniques to make difficult conversations less stressful and more meaningful.

Music by SONGO 21 – Studio sessions 2003 by SONGO 21 is licensed under a Attribution-NonCommercial-ShareAlike 3.0 International License.

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ABOUT Heather

Dubbed “cultural ambassador and corporate diplomat,” Heather has a strong track record of building and implementing marketing, communications, branding, and education programs for professional services firms.  As Managing Director of Brand + Culture at MGAC, she leads the firm’s largest change management effort to date. Her areas of expertise include: change management, leadership & professional development, performance management, employee engagement, corporate development, and corporate cultural growth.  She received her B.A. from Bryn Mawr College and her M.A. from the Corcoran College of Art + Design.  Heather is a 2015 graduate of SMPS University and is currently obtaining an HR for People Managers Certificate from the University of Minnesota’s Carlson School of Management.  She uses her passion and skills to invest in her team, and to facilitate business acquisition, engagement, and communication across the company.

Have questions or want to chat more with Heather? Post your comments below or connect with her on Twitter and LinkedIn.


Join us Thursday on the podcast when we’re back with Heather to learn more about her education and career experience.

Music by SONGO 21 – Studio sessions 2003 by SONGO 21 is licensed under a Attribution-NonCommercial-ShareAlike 3.0 International License.


Next week, we’ll welcome Susan Murphy, Principal at Murphy Motivation and Training to discuss the true power of a good presenter.