Three life lessons from successful women in the workplace

To celebrate International Women’s Day 2025 I invited two women to share their experience and dig into their experiences as women in senior leadership positions. 

Guest Speakers:

Caroline Sherry, Executive Director and CFO of Hostelworld

Maura Winston, Chief People Officer of Cairn Homes Plc.

We set out to address a few key issues and share our perspectives:

• Breaking Barriers: Women in Leadership

• Equity vs. Equality: Why It Matters

• Balancing Ambition & Well-Being

• The Power of Representation

While we didn’t get to the bottom of every topic, the conversation flowed and Caroline and Maura shared so many interesting points- and loads more for us to follow up on! You can watch the full live stream here, but below I have drawn out three talking points that got all of us nodding.

1. Reframing barriers in the workplace to help you succeed

Time: 6m30s

Don’t look at the barriers, look at what you can control and how you are shaping yourself

As Caroline talked us through her varied career she pointed out that the next step in her journey wasn’t always obvious. She believes that as long as you’re learning and growing the next stepping stone starts to appear organically. If you focus on getting what you can from a job then new opportunities do arise you will have the confidence and experience to say yes to them whether that was a promotion or a new project.

2. Attitude trumps skill every single time

Time: 10m00s

This point came several times during our conversation and really struck a note with all of us whether it’s from our experience building teams or advancing our own careers. When Maura started working for the Federal Court of Australia she initially took the job because it labelled itself as family friendly. After a few months she realised the potential to do some really great work and by the time she left she was Director of Court Innovation. Considering that title didn’t even exist it’s a pretty strong testament to Maura’s hard work, and more importantly, attitude.

I wasn’t backing myself from the beginning but once I was in and I could see it, I was backing myself

It’s a similar theme in her current role in Cairn Homes. “I didn’t really see myself as a HR person” says Maura, but understanding that you might not have all the skills but you do have the right attitude will help you say yes to the job and build the skill profile as you go.

3. Understanding the balance you need

Time: 26mins00s

While we all understand the importance of work-life balance, in practice it can be tricky to vocalise what that means for you on a personal level.

Caroline points out the first step is acknowledging when the scale begins to tip in the wrong direction. As a leader she finds openly discussing balance with her team really beneficial when work begins to spill over.

For me it’s about balancing who I am in and out of work 

Maura summed it up beautifully when talking about juggling being a senior leader and a busy home life. “It’s not about the hours I spend at work vs the hours I spend at home”. It’s about being able to understand what the priorities are and balancing them so you can be authentic at work and at home.

What I learned from this conversation

Ambition is rudderless without my own wellbeing

I learned that there is real power in sharing our experience and this type of conversation is so valuable. Caroline and Maura both confirmed a mantra I keep at the centre of my work at Pinnacle HR. Taking care of yourself first is the best way you can fulfil your ambitions and build the professional life you want.

Honestly choosing only three key takeaways was difficult, there were so many good points,I really urge you to listen to the full thing here. And keep an eye out for more events like this in the future.