Women in leadership – Boss or bossy?

Our panel, Lizzie Pillinger, Anne-Marie Nicholson, Leonie Stoate and Ashleigh Bryant

This engaging webinar was moderated by Lizzie Pillinger, Partner at Trowers & Hamlins and Director at WiRL,  explored the challenges and opportunities faced by women in leadership. The discussion featured Anne-Marie Nicholson, CEO at amn architects; Leonie Stoate, Principal Planner at Tetlow King Planning; and Ashleigh Bryant, Senior Director at CBRE. The discussion focused on perceptions of female leadership, workplace biases, career progression, and strategies for success. The conversation touched on personal experiences, resilience, and how women can navigate leadership while staying true to themselves.

The 'bossy' label: challenging perceptions of female leadership

For many women, stepping into leadership roles often comes with being labelled as “bossy” rather than “strong” or “assertive.” The panellists shared their own experiences with this double standard and how they’ve reframed such narratives.

Anne-Marie shared a memorable example "No one has ever called me bossy to my face, but I have been told, ‘you know where you stand with Anne-Marie.’ I took that as a compliment, it meant I was finally being heard."

Similarly, Leonie pointed out "I think the word 'bossy' comes with negative connotations, so people try to say things like ‘assertive’ instead. But if you’re in a leadership role, that’s not a bad thing, it’s necessary."

This reflects a broader societal issue, women are often expected to be accommodating and agreeable, while men exhibiting the same traits are seen as confident leaders. It’s time to redefine leadership language to ensure women are recognised for their strengths, not penalised for them.

Workplace biases: the challenge of being seen and heard

Women frequently encounter assumptions about their roles in professional settings, often being expected to take on administrative or supportive tasks.

Leonie shared a personal experience "I was in a public inquiry, advising a barrister on affordable housing, and a client walked in and asked me to go and grab lunch. I had to remind them that I was next up in the session."

Likewise, Ashley discussed the subtle yet persistent biases in workplace dynamics "For years, I was always the one making tea in meetings. Then one day I realised, why is it always me? So I stopped, and no one questioned it."

These moments highlight how ingrained gender expectations can be. The panellists agreed that overcoming these biases requires speaking up, setting clear boundaries, and ensuring their expertise is recognised.

Balancing leadership and personal life

Motherhood and caregiving responsibilities continue to be major challenges for women in leadership. The discussion addressed the importance of flexible working policies and changing workplace cultures to accommodate family life without compromising career progression.

Anne-Marie recalled a particularly frustrating moment, "I was told after maternity leave that I shouldn’t expect to be promoted. My response? ‘That’s illegal.’ And I got my promotion. But it shouldn’t have been a battle."

Similarly, Ashley shared her experience,"When I returned from maternity leave, my role had completely changed to something I didn’t recognise. It was a reminder that, as women, we sometimes have to fight harder for stability in our careers."

Meanwhile, Leonie had a different perspective based on her upbringing, "My father was the main caregiver at home, and that upbringing made me realise that leadership has nothing to do with gender, it’s about capability and confidence."

This highlights the evolving perceptions of caregiving and leadership. More men are taking on active parenting roles, but workplace structures still have a long way to go in truly supporting working mothers and parents.

Building confidence and resilience in leadership

One of the key themes of the discussion was the importance of confidence and resilience in leadership. Many women feel hesitant to assert themselves in meetings, but the panellists offered valuable strategies to overcome this.

Ashley shared a piece of advice that transformed her approach,"The best advice I was ever given was simple: ‘Make sure you speak in every meeting.’ Even if it’s just a question, you need to make your voice heard."

Leonie agreed, adding "I ask senior colleagues to invite me into discussions. Once you’re in, it’s much easier to keep contributing."

Anne-Marie highlighted the need for a mindset shift "Realising that everyone in the room is just another person, regardless of title, helped me overcome my fear of speaking up."

Their insights reinforce that confidence is built through action, whether that means making small contributions in meetings, seeking mentorship, or proactively advocating for oneself.

The role of compassionate leadership

The panellists also discussed the shift from authoritative leadership to compassionate leadership, which prioritises listening, understanding, and supporting team members.

Anne-Marie emphasised the importance of equality in leadership "Think of people as equals. Whether they’re senior or junior, we are all human and we all bring value."

Ashley echoed this sentiment "Listening is one of the most underrated leadership skills. If people feel heard, they will trust and respect you."

Leonie added that outdated, autocratic leadership styles no longer serve modern workplaces "Autocratic leadership styles don’t work in today’s world. The most successful workplaces are those that support and understand their employees."

This approach benefits not only women in leadership but all employees, fostering a workplace culture that values collaboration, empathy, and growth.

Final words of advice

The panellists left attendees with powerful advice for women striving for leadership roles:

Anne-Marie "Tough times will pass, take control of your career and make changes when necessary."

Leonie "Don’t let one negative experience define your career—seek out supportive mentors and peers."

Ashley "You are never alone in your challenges. Be open, be honest, and build strong networks."

These takeaways reinforce the need for resilience, mentorship, and self-advocacy in navigating leadership challenges.

The workplace is changing, and women today have more opportunities than ever to reshape leadership on their own terms. The journey is far from over, but through mentorship, advocacy, and community support, women are breaking barriers and paving the way for future leaders.