Byte of Prevention Blog

by Jay Reeves |

How to Have “Stay Conversations” With Your Team

There’s never been a more pressing need for having a “stay conversation” with members of your team – particularly new associates.

A stay conversation is an in-person discussion with a focused agenda. One goal is to offer empathy and support in these uncertain, stressful times. A larger goal is to let each employee know how you envision their future at the firm.

“On a regular basis, some part of an ambitious professional’s brain is ruminating on their position on the career ladder, whether it’s an ambitious Millennial trying to make partner, a mid-career Gen X trying to drum up more business, or a well-established Baby Boomer wanting to solidify his or her legacy,” writes Lindsey Pollak for ABA Law Practice Today. “As a law firm leader, you can help people at all levels know their options and achieve their personal and professional goals. While frequent input is vital to feeding this need, consider occasionally initiating a more formal, deliberate discussion, often known as a stay conversation, where you discuss each individual’s future at your firm and help them achieve their unique goals.”

When you’ve got professional liability insurance with Lawyers Mutual, you’ll want to stay forever. We’ve been keeping North Carolina lawyers and firms safe and successful since 1977. It’s who we are and what we do.

The number one reason lawyers leave a firm is not pay or benefits. It’s because they have a poor relationship with their boss. During this pandemic, that relationship is more crucial than ever.

“The cost of building relationships can be next to nothing compared with the cost of the turnover when talented employees leave,” writes human resources expert Lynn Cowart for SHRM. “The Work Institute’s 2018 Retention Report shows that U.S. organizations spent $600 billion on turnover last year. That figure is expected to be nearly $680 billion by 2020.”


6 Tips for a Successful Stay Conversation

  1. Schedule them in advance. The conversation doesn’t have to be lengthy. Fifteen minutes might be plenty. It can occur anytime and anyplace. Just make sure the time and location are convenient and comfortable for the employee. After all, they’re the star of this show.
  2. These are not one-and-done events. “Stay conversations are most effective when repeated often, with follow-up steps along the way to build an ongoing dialogue with a purpose and meaning,” writes Cowart. “Stay conversations can take place over a cup of coffee, on a walk around the workplace campus, over lunch—anywhere that you can make the connection. When choosing a time and a place, remember that privacy is important for your employee to feel free to be open and honest.”
  3. Start by saying thank you. “Don’t wait for a formal stay conversation to let your team know how much you appreciate their efforts,” says Pollak. “Acknowledgment and praise are vastly underutilized management tools across all generations. Sometimes we are sparing in our praise with younger generations because we don’t want to be seen as giving out participation trophies. Or we forget to offer kudos to more experienced professionals because we think it doesn’t matter to them. If your team is currently working virtually, this appreciation is even more valuable as it can be hard to gauge your contribution when working in isolation.”
  4. Don’t make assumptions. Ask questions, then listen to the answers. Here are some questions suggested by Cowart: What about your work is most exciting? Least interesting? What do you want to learn? What are some of your short and long-term professional goals? How do you like to be recognized for contributions and accomplishments? Where do you feel you need more (or less) feedback from me? What would make you feel more successful at work? What has been your biggest surprise about our culture? What do you know now that would have been helpful to know earlier? What do you think this organization values?
  5. Don’t ignore the elephant in the room. Ask how they’re coping in the pandemic. Let them know if the firm’s future – and their individual future with the firm – has changed because of it.
  6. Follow-up. Write down action items. Follow up in one month, six weeks and six months for accountability. Keep the conversation going.


Jay Reeves is author of The Most Powerful Attorney in the World. He practiced law in North Carolina and South Carolina. Now he writes and speaks at CLEs, keynotes and in-firm presentations on lawyer professionalism and well-being. He runs Your Law Life LLC, a training and consulting company that helps lawyers add purpose, profits and peace of mind to their practices. Contact or 919-619-2441.



About the Author

Jay Reeves

Jay Reeves practiced law in North Carolina and South Carolina. He was Legal Editor at Lawyers Weekly and Risk Manager at Lawyers Mutual. He is the author of The Most Powerful Attorney in the World, a collection of short stories from a law life well-lived, which as the seasons pass becomes less about law and liability and more about loss, love, longing, laughter and life's lasting luminescence.

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