Career progression used to follow a fairly predictable path: gain experience, earn a promotion and climb the ladder. Today, careers are far less linear. They're shaped by unexpected conversations, relationships, lateral moves and leaders who recognise potential before it's fully realised.
For organisations, that means thinking differently about development. Career growth isn't defined solely by promotions or performance reviews, but by the experiences, relationships and opportunities that help people grow. As these stories demonstrate, the moments that shape a career are often the ones nobody planned
The strongest career opportunities aren't always planned
It's easy to assume successful careers are built on carefully mapped-out plans. In reality, they're often the result of staying open to opportunities that couldn't have been predicted at the beginning.
For Cara Kelly, Director of Site Operations at Toast, Inc — ranked among both Ireland’s Best Workplaces for Women™, Best Workplaces for Health & Wellbeing™, Best Workplaces in Tech™ and Ireland’s Best Workplaces™ — the foundations of her career were laid long before she joined the company. After studying international commerce before moving into information systems, she built experience across banking software, telecommunications and technology, but when she reflected on the moments that shaped her career, it wasn't a particular qualification or promotion that stood out. It was the people she'd met along the way.
Working in banking software early in her career meant travelling extensively to countries including Colombia, Nigeria, Kenya and Botswana. Those experiences created close professional relationships that would continue to influence her career years later. Looking back, she realised that almost every role she'd accepted came through someone she'd previously worked with or someone within her network rather than through a traditional application process.
That became particularly evident when Toast entered her career. After noticing that a former colleague had joined the business, she reached out simply to congratulate him. What began as a conversation between former colleagues soon developed into an entirely unexpected opportunity. Toast recognised the value she could bring and ultimately created a position around her experience rather than asking her to fit neatly into an existing vacancy.
It's a reminder that careers are often built long before someone starts looking for their next role. Networking is frequently viewed as something people do when they want a new job, but the strongest professional relationships are usually developed without any immediate expectation of reward. Staying connected with former colleagues, taking an interest in where people's careers have taken them and maintaining genuine relationships creates opportunities that rarely appear through formal recruitment processes alone.
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For Dawn Kearney at Salesforce Ireland — ranked among both Ireland’s Best Workplaces for Women™, Best Workplaces in Tech™ and Ireland’s Best Workplaces™ — career growth was shaped by a different realisation: progression doesn't always mean moving up. After eight years in consultancy, Dawn reached a point where continuing upwards no longer felt like the only measure of success. Instead, she wanted breadth. A conversation with one of her partners encouraged her to think differently about career development, describing it not simply as building depth in one area but expanding across different experiences as well. That perspective ultimately prompted her move into industry and began a series of transitions that would take her through programme leadership, operations, alliances, emerging business and, more recently, back into HR leadership.
Those moves weren't driven by a rigid career plan. Many of the roles didn't even exist before conversations began. Instead, opportunities emerged because she had built relationships across the organisation, remained curious about different parts of the business and made it known that she was willing to help where she could add value. A conversation with a Chief Operating Officer about organisational design eventually became an entirely new role only weeks later, illustrating how often careers evolve through visibility and connection rather than job advertisements alone.
That philosophy is reflected in Salesforce's idea of a "career mosaic", recognising that careers are strengthened by the variety of experiences people accumulate rather than by a single upward trajectory. Rather than viewing lateral moves as pauses in progression, they're treated as opportunities to develop new perspectives, understand different parts of the organisation and build capabilities that become increasingly valuable as leadership responsibilities grow.
It's an important shift for organisations to recognise. For decades, progression was closely linked with promotion, but today's workforce increasingly values development that doesn't necessarily involve a change in title. Cross-functional projects, temporary assignments, internal mobility and exposure to different parts of the business all contribute to building more capable, adaptable leaders. Employees gain a broader understanding of how organisations operate, while businesses retain talented people who might otherwise feel they have to leave in order to continue growing.
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In many ways, the ladder has been replaced by something much less predictable, but ultimately much stronger. Careers now resemble a collection of experiences, relationships and opportunities that gradually build towards leadership rather than a series of perfectly spaced promotions. That also changes the role organisations play. Creating meaningful careers is no longer simply about advertising vacancies internally or identifying successors for senior roles. It requires creating an environment where conversations happen naturally, where employees feel encouraged to explore different paths and where leaders are prepared to recognise potential beyond someone's current job description.
While opportunity matters, it's often confidence that determines whether someone is willing to take it.
The role leaders play in building confidence
Career opportunities only matter if people feel confident enough to take them. That confidence isn't something people either have or they don't. It's shaped over time by the experiences they have, the feedback they receive and, perhaps most importantly, by the people who lead them. The right manager can encourage someone to take on a challenge they would never have considered on their own. Equally, a poor leadership experience can leave talented people questioning whether they're capable of progressing at all.
It's why conversations about women's careers often extend far beyond recruitment or promotion. Access to opportunities is important, but so is creating environments where people feel able to put themselves forward in the first place.
Debra Popplewell, Director at Heineken Ireland — ranked among both Ireland’s Best Workplaces for Women™, Best Workplaces for Health & Wellbeing™, and Ireland’s Best Workplaces™ — spoke candidly about the confidence gap she experienced during the early stages of her career. Having worked across transformation, supply chain, commercial functions and manufacturing before eventually moving into HR, she admitted that capability was never the issue. Confidence was.
Working in industries where she was often one of very few women, she found herself questioning opportunities that were offered to her rather than embracing them. Like many professionals, she experienced imposter syndrome, sometimes convincing herself she had only been considered because she represented diversity rather than because she was genuinely capable of doing the job. Looking back now, she recognises that those doubts existed entirely in her own mind, but at the time they influenced the decisions she was willing to make.
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It's an experience many organisations will recognise. Research continues to show that women are often less likely to apply for roles unless they feel they meet every requirement, while men are generally more comfortable applying without ticking every box. Whether driven by confidence, workplace experiences or social expectations, the result is the same: talented people can unintentionally remove themselves from opportunities before anyone else has the chance to encourage them.
What stood out in Debra's story, however, wasn't simply that she experienced those doubts. It was that she continued saying yes anyway. Her career wasn't built through one carefully planned route into HR. Instead, she spent years moving through different functions, taking on stretch opportunities and accepting roles that broadened her understanding of how organisations operate. At one point she worked as a process engineer on a paper machine, something she openly acknowledged had never featured on her original career plan. Yet those experiences ultimately became the reason she found her way into people leadership. Having worked alongside commercial, supply chain and operational teams, she understood the organisation from multiple perspectives, allowing her to become a stronger HR leader than if she had stayed within one discipline from the outset.
It's a powerful reminder that career development isn't always about moving closer to your destination. Sometimes it's the detours that give people the perspective they'll rely on later. More importantly, Debra reflected on the people who helped her make those moves. Every significant step in her career was supported by leaders who believed in her before she fully believed in herself. They encouraged her to take opportunities that felt uncomfortable, challenged her assumptions about what she was capable of and provided the confidence she needed until her own confidence eventually caught up.
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That experience has shaped how she now leads others. Rather than seeing leadership as directing performance, she described it as creating belief in people who may not yet see their own potential. For organisations thinking about leadership development, that's an important distinction. Future leaders don't only need operational expertise. They need the ability to recognise talent, create psychological safety and encourage people to take opportunities they might otherwise dismiss.
That same theme emerged through Tina Killbride's career story, albeit from a very different starting point. Now Operations Manager at Aura Holohan Group — ranked among both Ireland’s Best Workplaces for Women™, Best Workplaces for Health & Wellbeing™, and Ireland’s Best Workplaces™ — Tina never imagined that teaching swimming while studying in college would lead to a career in the leisure industry more than two decades later. After travelling, working overseas in sales and training, and eventually returning to Ireland, she found herself back in the industry almost by accident before progressing into a leadership role with Aura Holohan Group.
She laughed as she described having what she called a "naïve confidence", agreeing to responsibilities before fully understanding how she would accomplish them. On the surface, it sounds like personal confidence. Listening more closely, though, something else becomes clear. She repeatedly returned to the managers she'd worked for throughout her career. The people who trusted her, coached her, encouraged her and reassured her that she could do more than she believed herself capable of. That confidence wasn't developed in isolation. It was built through leadership.
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Looking back across the four career stories, it's striking how often success is attributed to another person. A colleague who suggested an opportunity. A former manager who stayed in touch. A leader who opened a door. A mentor who offered advice. Careers are deeply personal, but they are rarely built alone.
For organisations, that's perhaps one of the biggest lessons. Leadership development isn't only about preparing people to manage budgets or deliver strategy. It's about equipping leaders to create confidence in others. When people consistently hear, "I think you can do this," they eventually begin to believe it themselves.
Preparing future leaders at every stage of their career
By the time someone reaches a leadership position, many of the behaviours that make them successful have already been shaped over years of experience. That's why the organisations represented during the discussion all described development as something that starts long before promotion.
At Heineken, leadership development is built around a consistent global framework rather than a collection of disconnected programmes. While initiatives are adapted locally to reflect different cultures and markets, they share common principles centred on coaching, feedback, authenticity and helping leaders develop the interpersonal skills that become increasingly important as careers progress. Rather than focusing exclusively on technical expertise, the programmes recognise that leadership effectiveness depends just as much on how people communicate, build trust and help others succeed.
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Debra explained that the aim wasn't simply to deliver training but to create a shared understanding of what good leadership looks like across the organisation. That consistency allows development to continue regardless of where someone works, while still giving local teams the flexibility to make learning relevant to their own context. It's a balance many organisations continue to navigate as they grow internationally, ensuring employees experience the same leadership standards without losing the local culture that makes each workplace unique.
Salesforce approaches development through a similarly long-term lens. Recognising that representation began to decline at senior leadership levels, the organisation introduced its LEAD programme to support women at Director and Senior Director level. Rather than focusing solely on technical capability, the programme explores topics including personal branding, sponsorship, networking and imposter syndrome while creating opportunities for women to build relationships with peers experiencing similar challenges. The emphasis isn't simply on helping individuals develop. It's about ensuring talented people continue to see a future for themselves within the organisation.
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Creating workplaces where careers can flourish
One thing connected every story shared, despite the very different industries and career paths represented - none of these leaders described getting to where they are today on their own.
Some spoke about former colleagues who opened unexpected doors years later. Others reflected on managers who gave them opportunities they didn't think they were ready for or mentors who challenged them to think differently about what was possible. In every case, another person helped shape the direction of their career. That's why development can't sit solely within formal programmes.
Structured leadership initiatives, mentoring schemes and internal mobility programmes all have an important role to play, but they're most effective when they're supported by a culture where learning happens every day. Sometimes that's a planned mentoring conversation. Sometimes it's a leader taking ten minutes to answer a question. Sometimes it's simply someone saying, "I think you're ready for this," before the individual believes it themselves.
Cara Kelly spoke about how willing senior leaders at Toast are to make time when people ask, even admitting that many employees wait for organised mentoring events before approaching someone they admire. Her advice was simple: ask. More often than not, people are happy to help. At Toast, that willingness to share knowledge has evolved beyond traditional mentoring into mentoring circles, informal conversations and even speed mentoring sessions, recognising that development doesn't always need to follow a formal structure to have a lasting impact.
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For organisations, the challenge is creating an environment where those conversations feel natural rather than exceptional. Tina Killbride described this as culture. Working with a predominantly young workforce, many entering employment for the first time, she believes creating a workplace where people feel comfortable asking questions, making mistakes and learning from one another is what allows people to grow.
For Tina, culture isn't something that's written into company values or introduced during induction. It's reflected in the everyday interactions that shape how people experience work. When employees know they can ask questions, admit they don't have all the answers and learn without fear of being judged, they're far more likely to challenge themselves, take on new responsibilities and continue developing throughout their careers.
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Skills can be taught, but confidence develops when people feel trusted, supported and able to be themselves. That's the foundation that creates stronger teams, better customer experiences and, ultimately, stronger organisations.
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It's also why representation matters. Seeing women in leadership positions sends a powerful message to those starting their careers about what's possible. It normalises ambition, demonstrates that progression is achievable and encourages the next generation to picture themselves in those roles.
Career development has changed significantly over the last decade. It's no longer defined solely by promotions or years of service, but by the breadth of experiences people gain, the relationships they build and the confidence they develop along the way.
For organisations, that means creating more than opportunities to progress. It means creating workplaces where people are encouraged to explore, supported to take on new challenges and surrounded by leaders who recognise potential before it's fully realised. Because while no two careers follow exactly the same path, the organisations that help people build them often have one thing in common: they make growth feel possible.
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