Canada’s insurance industry is not short on capable, ambitious women. Across broking, underwriting, risk advisory, and carrier operations, female professionals are highly visible and increasingly influential. Yet when the most senior decision-making roles open up, representation still narrows. The issue is less about the supply of talent and more about how readiness for leadership is perceived and assessed.
Denise Hall (pictured), managing director at Aon Risk Solutions, has spent nearly 25 years in the industry observing how leadership transitions unfold. From her vantage point, the barriers today are often subtle rather than structural. Organisations may genuinely believe they are promoting on merit, yet perceptions of leadership style and confidence can shape who is viewed as the natural successor.
Competition for senior roles has intensified in recent years, both internally and externally. As executive searches widen and expectations rise, candidates are evaluated not only on performance but on executive presence, communication style, and perceived strategic maturity. Those criteria can be subjective, and small biases can compound over time.
“I see tremendous female talent in the insurance industry today, which is encouraging. Yet when senior roles open up, the competition (both internally and externally) is intense, and several subtle but significant obstacles can still stand in the way of women progressing.”
One of the most persistent obstacles, Hall suggests, is the image of what a leader “should” look like. While overt discrimination has diminished in many firms, unconscious preferences for traditional leadership styles can still influence hiring and promotion decisions. Leadership traits historically associated with assertiveness or a particular communication style may be rewarded more readily, even when alternative approaches are equally effective.
At the same time, advancement is not solely about qualifications. Visibility and self-advocacy play a significant role in how leadership pipelines are formed. Talented professionals who wait to be invited into opportunity conversations may find themselves overlooked in favour of those who actively signal their ambition.
The challenge is compounded by a tendency among high performers to hold themselves to exceptionally high standards before seeking promotion. When women feel they must meet every listed requirement before applying, while others are comfortable stretching into a role, the pipeline can appear thinner than it truly is.
“Talented women may be less likely to put themselves forward or may assume they need to be 100% ready before raising their hand, which can limit the perceived pipeline,” Hall said.
Beyond hiring bias and self-advocacy, questions around flexibility and work-life integration often surface in conversations about leadership. Senior roles are assumed to demand constant availability, heavy travel, and limited room for personal priorities. Yet Hall’s experience suggests that while balance may not be perfect at every moment, sustainable leadership careers are possible.
She emphasizes the importance of proactive communication – not only within the workplace but at home. As professionals consider larger roles, expectations around travel, return-to-office requirements, and workload should be discussed transparently with both hiring managers and family members. Leadership transitions require adjustment, and planning for those shifts can reduce stress and increase long-term success.
Rather than silently opting out of opportunities based on assumptions, Hall encourages direct conversations. Clarity around flexibility, wellness, and performance expectations can dispel uncertainty and open doors that might otherwise feel closed.
“My experience is that flexibility to manage both work and personal responsibilities does exist – even in senior decision-making roles. It won’t always feel perfectly balanced, but over time, it is possible to achieve a sense of wellness in both areas. If female colleagues are concerned about flexibility, I would strongly encourage them to voice those concerns and have open conversations with leadership.”
While individual agency matters, Hall is clear that systemic improvements are also essential. Formal DEI programs and women’s networks have become commonplace across the industry, but their effectiveness varies widely. Some initiatives create real skill development and sponsorship; others risk becoming symbolic if they lack structure, leadership buy-in, or measurable outcomes.
Mentorship programs, for example, can provide valuable guidance, yet chemistry and authenticity determine their impact. Informal sponsorship – where senior leaders actively advocate for high-potential talent behind closed doors – often proves even more decisive in who receives stretch assignments and promotion opportunities.
Organisations that invest in structured leadership development, measure representation at senior levels, and hold themselves accountable for transparent hiring processes are more likely to see durable change. Without measurement and executive endorsement, progress can stall.
“It can be difficult to precisely quantify the impact of formal DEI initiatives, mentoring programs, or women’s networks, but from what I’ve seen, some elements are far more effective than others.”
For CEOs and senior leaders, Hall points to two practical levers that can shift outcomes within the next 12 to 24 months. First, hiring and promotion processes must be transparent, consistently fair, and visible to all employees. Informal taps on the shoulder limit access and reinforce existing networks.
Second, sponsorship must be intentional. Rather than waiting for women to self-nominate, leaders can proactively identify high-potential talent, encourage applications for stretch roles, and advocate during selection discussions. Diverse interview panels and consistent evaluation criteria further reduce bias in screening and selection.
“If CEOs and senior leaders focused on just these two areas – fair, transparent hiring and intentional sponsorship of high-potential women – we would see meaningful progress in who sits at the decision-making table.”
Join the Women in Insurance Summit Canada 2026 on June 2 at Universal Eventspace in Vaughan, ON, to turn representation into leadership. Hear from industry leaders, build your network, and leave with practical strategies to advance women into decision‑making roles.
