Courageous Conversations

Posted April 7th, 2021 by Urban Legal Recruitment

Let's talk

Challenging conversations take place in both our personal and professional lives. Regardless of where they occur, and in what context, people typically avoid these difficult exchanges out of fear. Fear of conflict, embarrassment, hurting others, failure, repercussions, change - there are an endless number of reasons we fear potentially provocative conversations.

“In our work we see the benefits of respectful, productive conversations every day, but we also see the opposite,” says Stacy Cowan, founder of Urban Legal Recruitment (ULR). “Difficult conversations require transparency and safety, but in many cases they can be avoided altogether if all parties are clear about their needs and expectations upfront."

If you find yourself in a situation where you need to initiate an uncomfortable conversation, keep in mind that these conversations have the potential to catapult the relationship to the next level in a good way. Here are some things to consider in your next “let’s talk” scenario.

Timing It. It's natural to want to delay, or avoid, a difficult conversation but time is of the essence. Holding on to issues because you’re not comfortable discussing, or hearing, them is disrespectful and erodes trust.

Heart. Assess your intent. Treat the other person the way you would want to be treated. Respect and vulnerability do not equate weakness but rather set the stage for a productive dialogue. Put yourself in the other person’s shoes and connect with empathy and understanding.

Prepare. When initiating the conversation, you may be tempted to jump in and get it over with as quickly as possible because it’s uncomfortable. Don’t. Prepare for the conversation like you would any other interaction that requires care. You shouldn’t be doing all the talking anyway.

Listen. Respectfully ask questions (don’t ‘interrogate!) and explore the situation for information you may not have. Be prepared to give the person an opportunity to take time to consider what you are saying.

If you are the receiver, keep listening and watch your fight or flight response. The feedback may be touching a deep sensitivity so thank the person for being open with you and ask for time to think about what was said. 24 hour rule - if you are feeling upset, angry or disturbed in any way, take the time to process so you can reply from a clear and respectful place.

Follow up. Come to an agreement about next steps. Then check in regularly to offer support or ask for feedback and adjust as necessary to ensure you are moving toward resolution. Today, the virtual work world makes crucial conversations even more challenging and they require more time and thought, and are more difficult to follow up.

Feedback is a gift

“We are here to help, not to judge,” says ULR’s Director of Executive Recruitment and Professional Support, Shona Tischner. “Be open and don’t make assumptions. Ask for feedback and clarification to ensure you understand, and be open and truthful about your situation so we can help.”

Feedback really is a gift when shared with genuine care. How can anyone ever change or be the best versions of themselves without feedback? Despite how thoughtfully and skillfully difficult conversations are managed, however, sometimes it’s hard not to personalize the feedback. In his groundbreaking book, The Four Agreements, Don Miguel Ruiz explains the importance of not taking things personally.

Which, like navigating courageous conversations, is far more easily said than done.


Life. Career. Opportunity Awaits. If you have any questions, are considering a change, or just want to chat, we would love to hear from you.

At Urban Legal Recruitment, we have experienced, along with our clients, the impacts of COVID-19. We’ve made the necessary adjustments to ensure the safety of our team members and our clients.