Navigating Difficult Conversations: Insights from Mentoring 1600 Women

Through my work with over 1600 women in focus group discussions and mentoring sessions, I’ve gained deep insights into the nature of difficult workplace conversations, particularly those tied to mental well-being, performance, and the intersectionality of diversity. These conversations are often nuanced and challenging, particularly for leaders tasked with fostering inclusive environments.

Highlights of Difficult Conversations

Some of the most challenging conversations I’ve observed during these sessions include:

1. Discussing Mental Health: Employees may struggle to openly discuss stress, burnout, or mental health issues due to stigma or fear of judgment.
2. Addressing Performance vs. Stress-Related Behaviors: Managers often find it hard to differentiate between poor performance and behaviours stemming from work-induced stress or personal challenges.
3. Gender and Cultural Barriers: Women, especially in male-dominated environments, find it hard to voice their needs or concerns, often feeling that their experiences of discrimination, unconscious bias, or microaggressions are not fully understood.

Why These Conversations Are So Difficult

1. Lack of Awareness and Training: Many leaders and managers are not equipped with the tools to handle sensitive issues like mental health and well-being. Without proper training, they may feel unsure about how to approach these topics or fear making the situation worse.
2. Intersectionality and Bias: In a diverse workforce, employees bring varied experiences shaped by their gender, race, socio-economic status, and more. Conversations about well-being, performance, or inclusion become more complicated when these multiple identities overlap. For example, a woman of colour facing both gender and racial discrimination may experience stress differently than others, making it more difficult for managers to offer appropriate support.
3. Organizational Culture: In many organizations, conversations around well-being and diversity are still stigmatized, and often reduced to "check-the-box" initiatives. This creates an environment where employees feel unsafe or discouraged from discussing their struggles openly.

Examples of Such Difficult Conversations Women Face in the Workplace include:

• Negotiating Salary or Promotions: Women often face challenges when negotiating higher pay, promotions, or better benefits in environments where assertiveness is negatively perceived due to gender-based modesty stereotypes.
• Addressing Gender Bias or Discrimination: Confronting gender bias, microaggressions, or outright discrimination in hiring practices, daily interactions, or project assignments can be emotionally charged. Women may hesitate to address these issues for fear of damaging relationships or being labelled as overly sensitive.
• Balancing Work and Family Life: Women with caregiving responsibilities often struggle with conversations about balancing work and family commitments, such as requesting flexible work arrangements. They may become defensive due to concerns that prioritizing family needs could be viewed as a lack of commitment to their careers.
• Dealing with Harassment or Inappropriate Behavior: Conversations about sexual or other forms of harassment can be the most challenging and sensitive. Fear of retaliation, disbelief, or ostracism can make these discussions particularly daunting for women.
• Providing Feedback to Male Colleagues or Superiors: Offering feedback to male colleagues or superiors can be tricky in male-dominated environments, where assertive women might be unfairly labelled as difficult or aggressive.
• Requesting Time Off for Health or Personal Reasons: Women may need time off for menstrual health, menopausal concerns, or other personal reasons. These conversations can be difficult due to the stigma associated with reproductive health issues.
• Dealing with Conflicts or Interpersonal Issues: Addressing conflicts or interpersonal issues stemming from personality clashes or differing work styles can be uncomfortable for women, who may fear being perceived as emotional or overly sensitive.
• Setting Boundaries: Establishing boundaries around workloads, work hours, and personal space can be challenging, especially in high-demand environments that expect constant availability. Women may worry about being seen as less dedicated or not a team player, leading to anxiety about potential backlash.
• Advocating for Opportunities: Seeking leadership positions or prestigious projects can be particularly difficult in male-dominated industries. Women often hesitate to advocate for themselves due to the perception that self-advocacy equals immodesty, which is deeply ingrained in social conditioning.

How Organizations Can Foster Inclusivity and Equity

Based on my research and mentoring work, I’ve identified a few key steps organizations can take to make the workplace more inclusive and equitable:

1. Awareness Campaigns and Training Modules: Organizations need to design training programs tailored to the unique challenges of their workforce. These initiatives should focus on educating managers and employees about the importance of mental health, stress management, and the company’s resources for well-being. At Expedia Group, for instance, we are customizing our training to align with employees' needs, ensuring the inclusion of stress-related resources.
2. Training for Managers: Managers should undergo specialized training to learn how to distinguish between performance issues and stress-induced behaviours. This training can help managers identify when an employee is under stress and requires support rather than disciplinary action. In addition, empowering managers to navigate difficult conversations and connect employees to support systems like Employee Assistance Programs (EAP) is critical. However, 20% of women appreciated having an in-house counsellor over virtual EAP assistance.
3. Counselor Availability: Access to professional mental health resources is key. By partnering with benefits teams, organizations can ensure that counsellors are available on-site, even if for a few hours each month. This approach not only offers employees direct access to help but also normalizes the conversation around mental well-being.
4. Wellbeing and Mindfulness Initiatives: Beyond addressing issues when they arise, organizations should proactively foster an environment that supports well-being through sound therapy, yoga, meditation, and similar initiatives. By encouraging such practices, companies can create a culture where mental health is seen as part of overall success, not a taboo topic.

Moving Forward

The intersection of diversity, equity, inclusion, and mental well-being must be approached strategically. Leaders must prioritize training and awareness to help employees feel safe, supported, and understood. By doing so, we not only improve individual well-being but create a more equitable and inclusive workplace for all.

Let’s take these steps forward, ensuring that our teams have the support they need and that conversations around mental health and inclusion become a standard part of our organizational culture.