Navigating Difficult Conversations: Insights from Leadership Expert Henna Pryor

Navigating Difficult Conversations: Insights from Leadership Expert Henna Pryor

In today’s hyper-connected work environment, young people—especially those who are under the age of 30—are deficient in the most basic communication skills. Henna Pryor, founder and CEO of the Philadelphia-based leadership coaching firm Pryority Group, encourages leaders to be willing to get comfortable having uncomfortable conversations. She’s convinced that this skill is key for their professional development. Pryor stresses that with the right preparation and strategic wording, advocates can empower these individuals to more successfully navigate those situations.

Pryor emphasizes the importance of memorizing go-to phrases which can really help take the heat out of the conflict. One of her other favorite phrases is “I am looking for clarity.” She thinks that this phrase is a really great way to open the discussion. Address the real problem being discussed. Replacing the confrontational “you versus me” mindset with a collaborative “us versus the problem” approach. This smart strategic reframing creates a better conversation.

The Importance of Preparation

Whether it’s race, gender, or something else, preparation is essential when navigating difficult dialogues. Pryor agrees, but says that even the most basic of conversations takes real preparation. She offers this suggestion to everyone before an important conversation — take a few moments to center yourself and gather your thoughts.

“I’m about to have this conversation … can you provide three counter-perspectives from someone who might see it differently?” – Henna Pryor

Not only does this approach strengthen your overall understanding of the topic at hand, it keeps you more level-headed throughout the meeting. Additionally, Pryor often reassures herself with an out-loud pep talk:

“You’ve got this Henna. You’re uncomfortable, but you can do this.”

These messages are a good quick confidence-boost, yes, they get people into the right headspace to tackle what comes next.

It’s a view shared by Alison Wood Brooks, an associate professor at Harvard University, who strongly agrees with Pryor. She says the key to navigating these tricky conversations is taking just 30 seconds to center yourself and remain grounded. This brief pause allows for reflection on how to approach the topic constructively.

Building Confidence Through Practice

Pryor advocates for speaking up when the stakes are low as an effective way to build confidence in navigating conflict. By addressing small problems first, people prepare themselves for when a more serious or high-stakes discussion arises. That steady introduction may make participants more comfortable speaking up about bigger issues down the road.

Pryor occasionally uses technology to advance her talks. This practice helps her to hone her pitch and foresee objections, building her confidence for actual real-world encounters even more. She understands that many young professionals say they feel awkward in office encounters and sometimes will even choose to disengage from an issue entirely to dodge contention.

“This is really hard for me to say, but I know it’s important we talk about it.” – Henna Pryor

By accepting the discomfort and showing a commitment to the conversation, one can build productive relationships with peers and leaders.

Strengthening Connections in Remote Work

In an era where remote work has become increasingly common, Pryor emphasizes the importance of deepening bonds with colleagues through casual interactions. She recommends having virtual coffee chats or recording voice memos as other methods for building relationships even when you’re not in the same room. These back-of-the-napkin conversations are great ways to humanize dialogue and make tricky conversations less daunting.

Pryor’s research documents that young people regularly experience discomfort on the job. This discomfort can lead them to avoid facing conflicts. To counteract this, she advocates for preemptive engagement and relationship-building exercises that can sharpen communication strategies.

“My comfort is more important than enhancing my relationship with this person.” – Henna Pryor

This recognition shines a light on the challenging choice many women must make between personal ease and professional advancement. With a little more attention to both, anyone can work to create a more positive and productive workplace.

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