Career Coaching, Diversity, Equity, and Inclusion

How to Get Comfortable with Uncomfortable Conversations

Michele Meyer Shipp
By Laura Quaglio

According to Michele Meyer-Shipp, chief people and culture officer of Major League Baseball, last year marked a turning point with people more willing than ever to have uncomfortable conversations about subjects like race, religion, and politics—not only in their personal lives but also in the workplace.

“Early in my career, when I was practicing employment law, I counseled clients to avoid discussing topics like race, religion, and politics at work,” she says. “Over the last year, I’ve seen these types of conversations grow exponentially. I have never seen anything that is so powerful and so authentic in my entire career.”

Having spent the past decade as a human resources and diversity and inclusion executive, Meyer-Shipp UCN’89 had already noticed a gradual opening of mouths and minds. First, there was an increase in watercooler talk about formerly taboo topics. Then a few years ago, corporate awareness took a leap forward with the creation of a group called CEO Action for Diversity & Inclusion, which engaged CEOs squarely in these conversations. It took George Floyd, a nationwide racial reckoning, and “one hell of a year in 2020” to really get people talking.

For workers who are wary of engaging in uncomfortable conversations, Meyer-Shipp attests that the payoffs can be powerful, as she has seen firsthand many times. In one case, a colleague in a wheelchair showed Meyer-Shipp how inaccessible a new office building was, and the builders were brought back to make some changes. Another time, after Meyer-Shipp’s sons were invited to play “manhunt” at night with the neighbors, she approached it as a teachable moment—explaining to their mom why it could have been deadly for her Black sons to play hide and seek at night in neighbors’ yards—without shutting the door on their friendship.

Meyer-Shipp offers some strategies for navigating such difficult topics.

For starters, do your homework

Being a good ally means putting in the work to learn about people from underrepresented groups before you start jumping into a potentially uncomfortable conversation. This might mean reading a book, watching a webinar, or taking a course at work, for example. “Doing your own work may generate thoughts and questions,” says Meyer-Shipp. You can even use those insights as conversation starters.

Ask permission before asking questions

Meyer-Shipp suggests saying something like, “Hey, Michele, I just read this book and I really want to understand this or that. Can we grab a coffee and chat about it?” If the other party agrees, she says, open-ended questions (ones without a yes/no answer) are usually the best at drawing out meaningful insights. From there you can ask for clarity about a particular point or for their thoughts on related topics.

Then simply listen and soak it in. Meyer-Shipp will often wrap up her own informal uncomfortable chats by saying, “Thanks for your candor and willingness to share. I didn’t know you were dealing with that. Is there anything I can do to support you?”

Be cautious when you’re the one sharing

Depending on the topic at hand, you may be the one in the underrepresented group, so be prepared for that, too. Meyer-Shipp says that she generally won’t decline to answer a question, but she sometimes is more reserved with her answers. “If I don’t know somebody, I’m extra cautious until I start to hear some of their thought processes,” she says. That’s why she suggests asking as many questions as you answer. “This way, you’re learning about their viewpoint along the way, so you will get to know who you’re talking to and exactly how candid you can or should be.”

Know where your fill line is

Everyone has a fill line, says Meyer-Shipp. That’s the point that you reach when you can’t take any more. When you get to that place, or preferably before you do, it’s OK to step away or even to take a break from uncomfortable conversations entirely. “Last September, I was mentally exhausted,” she admits. “I just stopped watching the news for a few weeks. Repeated images of George Floyd’s murder haunted me. Self-care proved critical.”

Keep the conversation going

“I’m of the mindset that I’ve never met a stranger,” says Meyer-Shipp. “So, when anyone needs anything, I’m going to help.” What’s more, once she’s begun a conversation with someone, she ends it with an act of kindness and a call to action. For example, she might share a list of books to read, then say, “If you want to talk about them, just let me know.”

The best part about this approach? It makes the next conversation less uncomfortable and, in time, maybe these conversations won’t be uncomfortable at all.

From Michele Meyer-Shipp’s Reading List: Looking for some homework? Here are three books Meyer-Shipp recommends on the topic of conversations:

For more of Meyer-Shipp’s insights, along with those of other Rutgers alumni, watch Alumni Workplace Engagement Business Forum: A Conversation on Diversity, Equity, and Inclusion.


This article is part of a series developed in partnership with Alumni Workplace Engagement and Alumni Career Resources that feature prominent Rutgers alumni providing expert knowledge on timely topics.