We recently asked “What has been one of the biggest challenges you’ve faced as a leader and how did you overcome it?” Here’s what we learned…
Leadership is never without its hurdles.
We asked top leaders to share the toughest challenges they’ve faced and the creative solutions they used to overcome them.
From navigating remote work dynamics to motivating diverse teams, their challenges and stories offer a glimpse into the realities of leading with resilience and insight.
Cassandra Josipovic
Marketing Director – Marketing and Events: The Appliance Guys
One of the biggest challenges I faced as a leader was keeping my team consistently motivated. Known by friends and family as a motivated and passionate individual, I needed to find ways to share this energy with my team when I stepped into a leadership role. Having been a leader my entire working career since I turned 18, I understood the importance of maintaining high levels of engagement and enthusiasm.
To overcome this challenge, I focused on transparent communication, ensuring everyone understood our goals and how their contributions were vital to our success. I made it a priority to acknowledge people’s successes and give praise where it was due, celebrating both individual and team achievements regularly. This helped boost morale and foster a sense of accomplishment.
Additionally, I encouraged a culture of inclusivity and innovation, where team members felt valued and heard. By promoting open dialogue and actively seeking their input on decisions, I empowered them to take ownership of their work. Providing tailored opportunities for professional growth and development further kept the team motivated, building a cohesive, high-performing unit that consistently exceeded expectations.
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Kimberley Flood
Intensive Care Unit Associate Nurse Unit Manager: Northeast Health Wangaratta
Change management can be very difficult for a leader. I have always found it important to identify and spend time working with those who are on the fence about the change, particularly staff who are influential amongst the team. If I can have some key staff members on board with the change and talk about it in a positive way when management are not present, it is likely that they will influence and engage other staff who may be hesitant. The idea is that the number of staff who are actively engaged in the change process will overwhelm those who are not, and the change will be successfully implemented.
I try not to use my time on those who are overly resistive because they will eventually be outnumbered and I know that no matter how much time I spend with these staff members I will not be able to change their mind. The other group that I will spend less time engaging in promotion of change with is those who believe in the change from the outset. This group will be drivers of change and therefore there is no need to be “preaching to the converted”. They are likely to be participating in roles such as implementation leads, super users etc.
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Gavin Tye
Founder: Sales Market Fit
One of the biggest challenges I’ve faced as a leader is learning to communicate in a way that truly resonates with others.
Early on, I realised that expecting clients or team members to immediately grasp where I was coming from was a recipe for disaster, especially when speaking on an area I specialise in, like founder-led sales. We wouldn’t be aligned from the outset, which was a real problem that could become worse over time.
My epiphany came when I shifted my approach to meeting people where they first were in their understanding of the subject. Instead of pushing them toward an outcome they couldn’t yet see, I focused on understanding their perspectives and guiding them step-by-step to the right solution or direction.
This approach not only made communication more effective but also empowered others to embrace the change themselves. I learned empathy is really powerful in this regard, making sure the path forward is clear and ensuring everyone is aligned to move in the right direction.
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Heather Gallagher
Head of Training and Education: outsource Financial
I see challenges as opportunities needing solutions. A few years back, I held dual senior roles at outsource Financial, namely Head of Training and Education, and State Manager for NSW/ACT/SA. Balancing national education requirements with state-level broker interactions was a significant challenge. My solution was to recruit good people, provide them with the necessary resources, and motivate them to surpass expectations.
That year, I grew the state team by two. The first recruit, despite her lack of recent industry experience, exhibited all the right behaviours and attributes. The second recruit, with a broking background, brought immediate value to our brokers with her technical skills.
By investing time in their growth through a comprehensive onboarding plan and innovative training tools, they were empowered to take ownership. This not only alleviated my workload but also provided our members with passionate, dedicated resources committed to their success.
Taking the time to invest in good hiring decisions and onboarding practices rather than just hiring the first “match on paper” has paid dividends across the business.
The long-term results of this are an engaged, empowered team who are delivering excellent service to our members and continue to grow within our business.
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JP Purcell
Head of Customer: East Coast Canning + Printing
One of the biggest challenges I’ve faced as a leader is leading a diverse team remotely.
It’s challenging to put myself in my team members’ shoes at a distance, understand their roles in unique working environments, and infuse our small business culture through our work since we don’t often see each other face to face.
Working as an all-remote team, we miss out on casual interactions like daily conversations, lunches, tea breaks, and the banter that builds relationships in a centralized in-person work setting.
To overcome this, I’ve implemented regular virtual check-ins, fostered open communication channels through Slack and Teams, and organized in-field mentoring and coaching sessions IRL when I travel to them.
During the busiest times of the year, we also have in-person team meetings at a central location to help each other remove roadblocks and offer support.
These initiatives help bridge the gap, strengthen relationships, and ensure everyone feels connected and valued despite the physical distance.
The post Expert opinion: How did you overcome your biggest challenges as a leader? appeared first on The Big Smoke.