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10 tips for handling difficult conversations at work

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Good communication is a skill. Like any other, it requires knowledge and practice. A recent episode of the UC Alumni Career Network brought together a panel of UC experts to share their advice for better workplace conversations, including setting yourself up for success, navigating challenging topics, finding common ground and more.

Moderated by author Jaime Carias (’08, UC Santa Barbara), civic engagement coordinator and fellow, USC Annenberg School of Communication & Journalism, this event featured:

  • Nicole Cox (’13, UCLA), manager, EY
  • Annalyn Cruz (’00, UC Santa Barbara), senior manager of leadership & management development, Electronic Arts
  • Sunny Lee (’97, UC Irvine), assistant vice chancellor & dean of students, UC Berkeley

Here’s their advice.

1. Don’t psych yourself out

When Annalyn Cruz realized that she was ready to make a career pivot, she was nervous. Her parents, who were immigrants, had taught her not to “rock the boat” at work. And, although her managers and mentors had always been supportive, she worried that they might disagree with her new plan. To help overcome her anxiety before speaking with them, she focused on preparation. She reflected on her path, outlined specific goals and envisioned her ideal outcome. Over time her confidence grew, and when she did speak with them, the conversations were a success. “Everyone was completely supportive of my plans,” she says. “It turned out that overcoming the negative mindset I had developed was the most difficult part.” 

2. Prepare, prepare, prepare

Sunny Lee agrees with Annalyn’s forward-thinking approach. “Having difficult conversations takes courage, and even fierceness sometimes. Before you set things in motion, consider the cost/benefit analysis of having the conversation versus not,” she recommends. If you decided to proceed, make sure you’re ready. Practice if you need to, and set a time. Consider how it might go. “If possible, try not to have the conversation in the moment. Give yourself time to prepare,” Sunny says. Also: Know and be ready to manage your triggers. Set your non-negotiables before you go in so that you can stay focused on the outcome.

3. Consider your audience

“I always try to start by finding a commonality between myself and the person I’m talking to,” says Nicole Cox, who regularly works with multicultural and multidisciplinary teams. She also tailors her messaging based on her audience — high-level recommendations for executives vs. detailed explanations for junior-level staff. And, she gets to know her colleagues, so she can mirror their communication style, joking with some and getting straight to the point with others. These actions demonstrate familiarity and respect. “Establishing a baseline of trust is extremely important — whether you’re validating your credentials or considering cultural factors that may influence how you come across,” Nicole says.

4. Model conversations you want to have

“If you want people to open up to you, to have a meaningful conversation, you need to be willing to be vulnerable as well,” says Annalyn. “After all the racial injustices that happened in 2020, I challenged myself to show up authentically; to share my experiences and not be complacent.” Since taking this approach, colleagues have thanked Annalyn for her openness, as it has allowed them to follow her lead. Their interactions have become more meaningful and rewarding. And, says Jaime, take time to check in. “Before starting a conversation, particularly on Zoom, take a minute to check in to see how everyone is doing,” he says. This can help kick off the conversation on a positive note.

5. Make space for everyone to speak

Pay attention to who is participating in a conversation and who is silent. If a participant has not spoken, ask for their perspective; if someone begins to dominate, encourage other voices. A crucial part of encouraging open dialogue is adopting a welcoming tone that conveys your receptiveness to different points of view, says Nicole. “People tend to underestimate how much tone can impact what we’re communicating. Self-awareness is a big part of creating a space where everyone can be valued and heard. For example, if you know you tend to come across as passive-aggressive or authoritative, try to address these traits.

6. Pay attention to your body language – and smile

“You’d be surprised at how much people become at ease when you smile and have a pleasant expression on your face,” says Nicole. Body language can communicate whether you are receptive to a conversation. Try adopting an open posture and making eye contact to signal you’re ready to connect. “I tend to have my arms crossed because I’m always cold,” says Nicole. “Since I know this may make me look like I’m displeased, I usually let people know the reason for my posture so that they understand it’s not related to our conversation.”  

7. Address the root issue

If a conversation seems overly contentious, something else is likely going on. “We spend a lot of time talking about things above the water [of a metaphorical iceberg], when the underlying problem is that someone is not feeling valued or respected at work,” says Sunny. Annalyn agrees. “If a situation is challenging for you, consider what feelings it is bringing up,” she says. “And, if there’s an issue with a particular person or a dynamic within the team that’s not sitting well with you, push yourself to address it.” By acknowledging your feelings and sharing how a situation is negatively affecting you, you allow the other person to understand your point of view and share their own.

8. Be proactive in identifying needs

In the wake of the George Floyd, Ahmaud Arbery and Breonna Taylor killings last summer, the Black Professional Network at EY initiated regular forums where Black professionals and allies could share their feelings and come together as a community. Local leadership did not initially take part, and Nicole could tell that this absence was limiting the events’ impact. She took a chance and reached out to her location manager to explain that leadership presence was essential for demonstrating EY’s commitment to anti-racism and inclusiveness. “It was a difficult conversation for me in the moment — I was intimidated due to our difference in rank,” Nicole said. “But afterward, he thanked me for being candid and transparent.” Since then, their relationship is stronger, and her manager has become a key advocate for leadership involvement in anti-racism efforts.

9. Follow up — and reflect

“After a difficult conversation, show your appreciation and ask what the next steps are,” says Sunny. Whether a conversation goes well or poorly, consider the factors that led to this outcome — What did you do well? What could you have handled better? — and keep them in mind when you’re prepping for future exchanges. If you’re unsure where things went wrong, consider talking it over with a colleague or mentor before reaching out for a follow-up conversation. Then, communicate that you are eager to continue to work towards a resolution.

10. Ask for help if you need it

Navigating challenging conversations is a skill; like most workplace skills, it helps to have training and guidance. “Many of us haven’t been coached on how to have challenging conversations. It’s important for us to seek mentors who can help us learn how to frame these talks — and when it’s a good idea to take a chance on initiating them,” says Jaime Carias. And, adds Sunny, it might not be your place to resolve some forms of workplace conflict. For example, if you are part of or witness a contentious conversation, especially one that violates a protected class, loop in someone who can help — your supervisor, Human Resources, Title IX officer or ombuds office.

Save the date for our next episode on Feb. 17: Leveraging social media to launch or grow your business

Need some advice for getting your passion project off the ground? Register to attend this interactive, workshop-style session led by UCLA alumna Bonique Edwards, owner of Kaleidoscope Consulting Group — a full-service digital marketing agency specializing in website development, graphic design and social media. We’ll cover the fundamentals of using social media to grow your business and offer tangible tips to help you reach more customers. Attendees will have an opportunity to meet UC alumni and community members through breakout activities during the event.

About the UC Alumni Career Network

The UC Alumni Career Network is a high-impact, online series designed to provide UC alumni and community members with the insights, information, and connections to launch, grow and expand your career opportunities. Each month we’ll tackle a different career topic by providing you with insider tips and advice to help you make the most of your UC network. Join us online to gain the latest information and to ask questions relevant to your own professional journey.

Sign up for the email list to receive monthly invites! For more information about the UC Alumni Career Network and links to recordings of past episodes, visit our website.

Contact alumni@ucop.edu with questions.


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