At The Roundtable, we know life doesn’t always go smoothly—especially when serious challenges arise, whether at work or at home. We recently hosted a webinar called “Tough Topics: How to Manage Real Life and Others When Things Aren’t So Okay.” Our panel featured three incredible perspectives:
- Lisa Cyr (Sibley), an HR professional who turned her experience of a profound loss into a mission to help others navigate grief;
- Ainslie Law, who shared her lived experience recovering from an eating disorder and offered insights on supporting youth through mental health challenges;
- Christine Burych, a seasoned mental health expert specializing in workplace well-being and leadership.
Here are three key takeaways out of so many.
1) Grief Is a Journey, Not a Checkbox… Grief doesn’t follow a predictable timeline, and it can’t simply be “fixed.” As leaders, if you have a team member who’s navigating grief, one of the most important things you can do is be present without trying to solve someone’s pain. Listen more than you speak, offer consistent support, and avoid tiptoeing around the topic. If it feels right, mention the name of the loved one who was lost—acknowledging their significance can help them feel less alone. Recognize that grief can surface unexpectedly and often lingers far longer than we anticipate. A two week bereavement policy isn’t going to ‘make them better’.
2) Curiosity Beats Judgment Every Time… Often when someone is struggling with their mental health at work, they show up differently. When you notice a shift in someone’s behaviour, start by gently noting what you’ve observed: “I’ve noticed you seem different lately.” Open-ended questions let them share freely and show that you’re there to listen, not to judge. By leaning into curiosity—rather than jumping to “quick fixes”—you invite honest dialogue that can lead to more supportive, constructive outcomes.
3) Your Own Past Shapes Your Present…Mental health struggles are often hidden behind outward success or familiar routines. This can make them easy to overlook. Reflecting on your own past and any unresolved issues helps you become more empathetic and patient with those facing a crisis. Self-awareness fosters genuine understanding, creating a steadier presence when someone else is in need. To be the best leader you can be, work on your own self-awareness to support others.
At the core of each insight is a call to empathy, compassion, and self-awareness. Whether you’re supporting someone through grief, addressing a mental health challenge, or confronting your own feelings, remember that authentic connection and gentle curiosity can be powerful tools.
How You Can Help
In the spirit of raising awareness and offering tangible ways to make a difference, we encourage you to consider supporting these charities that are particularly meaningful to our panelists:
- Teddy Bear Project: Provides comfort and support to children facing health or mental health challenges.
- The Recovery Project: Focuses on recovery programs, outreach, and education for individuals facing eating disorders and other mental health concerns.
- Jack.org: Canada’s only charity training and empowering young leaders to revolutionize mental health across the country.
If you missed this webinar and want to watch the full conversation, you can find the recording here.
On March 27th from 9:00 a.m. to 10:00 a.m. ET, join us for our new series Roundtable Talent Talks featuring Dr. Liane Davey, Co-founder and Principal at 3Coze Inc., in conversation with our own Glain Roberts-McCabe, Founder and President of The Roundtable. Together, they’ll dive into strategies for accelerating team focus and flow so you can thrive amid change and uncertainty. Reserve your spot today.
We’re designing a new service at The Roundtable focused on supporting the whole life of leaders including mental health and career support. We’d love your input to help us shape this new service offering. Please let us know if you would like to be a part of our advisory panel.
