Main Stage

• Discussion Table 1: Career transitions: Staying, leaving, and designing your next move
  • What are the key signs to stay and stretch in your current role versus time to move on?
  • What has helped you design a career move that better fits your strengths and life?
  • What can you do in the next 6–12 months to stay “move-ready,” either way?

• Discussion Table 2: Finding your niche in insurance 
  
  • When in your work do you feel most engaged and confident? What does that say about the kind of niche that might suit you?
  • What parts of insurance have you ruled out, and what did you learn about yourself from those experiences?
  • What are effective ways to differentiate yourself without becoming too narrowly defined?

• Discussion Table 3: Managing up in insurance organizations 
  
  • What aspects of managing do you find most challenging right now, and why do you think that is?
  • When have you successfully influenced a decision or outcome upward, even in a small way, and what helped make that happen?
  • How comfortable are you advocating for yourself with senior leaders, and what tends to hold you back?

• Discussion Table 4: Talent retention in specialized insurance roles
  
  • Where have you seen strong talent disengage or leave a team, and what do you think drove that decision?
  • What retention efforts have worked for you in the past, and where have well-intentioned approaches fallen short?
  • What signals do you use to identify retention risk early, especially in highly specialized or hard-to-replace roles?

• Discussion Table 5: Practical mentorship: Making it work when everyone is busy
  
  • What has made mentorship difficult to sustain for you in the past, and what would need to change for it to feel manageable this time?
  • What small, consistent practices could make mentorship valuable without requiring a major time commitment?
  • What boundaries or structures could help you stay engaged without feeling stretched too thin?

• Discussion Table 6: Marketing strategies for women in insurance
  
  • What does “marketing” in insurance currently mean to you, and what feels uncomfortable or unclear about it?
  • Which marketing channels feel most natural for you right now, and which feel forced or intimidating?
  • What marketing efforts have you tried that didn’t work, and what did you learn about your audience or yourself from those experiences?

Industry trends & business strategy

• Discussion Table 7: The growing role of ESG in insurance decisions
  
  • What knowledge gaps or resource constraints make it difficult for you to confidently engage in ESG-related conversations with leadership, clients, or partners?
  • Where do you feel tension between ESG goals and traditional insurance priorities like profitability, risk selection, or client expectations?
  • What does ESG currently mean in your role, and where does it feel clear versus overwhelming or ambiguous?

• Discussion Table 8: Emerging risks that keep you up at night
  
  • Which emerging risks (cyber, climate, regulatory, or market shifts) are causing you the most concern in your role, and why?
  • What strategies have you tried to proactively address emerging risks, and which have worked or fallen short?
  • How do you communicate emerging risks to clients, colleagues, or leadership without creating unnecessary alarm but still ensuring action is taken?

• Discussion Table 9: Navigating client expectations vs. operational realities
  
  • Which client expectations do you most often struggle to meet, and what makes them challenging to navigate in your role?
  • When a client expectation conflicts with operational realities, how do you decide what to prioritize?
  • What tools, strategies, or support would help you more confidently set and manage client expectations in your day-to-day work?

• Discussion Table 10: Explaining cost increases to internal and external stakeholders
  
  • What parts of explaining cost increases feel most uncomfortable or challenging for you?
  • Can you recall a time when a cost increase was received well, and what approach or language helped make that conversation successful?
  • When stakeholders push back on cost increases, how do you balance maintaining relationships with communicating the business realities?

• Discussion Table 11: Understanding Canadian vs. US market realities
  
  • What aspects of the US or Canadian insurance market have you found most challenging in your experience?
  • When working across borders, how do you determine what market realities to prioritize without overcomplicating the client experience?
  • What gaps in your knowledge about the US or Canadian market make you feel less confident in advising clients or colleagues?

Culture, well-being & inclusion

• Discussion Table 12: Inclusion, belonging, and being an ally in insurance
  
  • When have you noticed someone feeling excluded or unheard at work – and how did you respond (or wish you had responded)?
  • What does being an ally mean to you in your day-to-day role, and where do you feel unsure about how to take action?
  • If you could change one thing about your organization’s culture to better support DEI, what would it be? How could you contribute to that change personally?

• Discussion Table 13: The human side of technology adoption
  
  • What new technologies or tools have been most challenging for you to adopt, and what made them feel difficult or overwhelming?
  • What strategies have you found helpful for encouraging others on your team to adopt technology, especially when they are hesitant or overwhelmed?
  • How do you personally approach learning and adapting to technology, and where do you wish you had more support?

• Discussion Table 14: Avoiding burnout in high-pressure insurance roles
  
  • How do you currently recognize early signs of burnout in yourself, and what strategies have helped to address them?
  • What boundaries or routines have you tried to set to protect your time and energy, and where have they been difficult to maintain?
  • What activities or practices outside of work help you recharge, and how could you realistically integrate them into a busy schedule?

• Discussion Table 15: Strategies for work/life balance at every stage 
  
  • What parts of your current role or schedule create the most tension between work and personal life?
  • How have your work/life priorities shifted at different stages of your career, and what has helped you adjust successfully?
  • What habits or practices have helped you feel more balanced, even during busy or high-pressure periods?