Leadership Is a Game of Snakes and Ladders - RegInsights

For decades, we were told to climb the corporate ladder. The path seemed clear: take one step at a time, work hard, and eventually, you’ll reach the top. But today’s leadership journey isn’t that simple. It’s no longer a straight, predictable climb, it’s more like a game of Snakes and Ladders.

You roll the dice, make your move, and just when you think you’re soaring, a snake sends you tumbling down. Or you stumble into a ladder, a sudden opportunity and catapult forward. The modern workplace is filled with twists and turns, and success depends less on steady upward progress and more on your ability to navigate uncertainty with agility and purpose.

Why the Corporate Ladder No Longer Fits

Why the Corporate Ladder No Longer Fits

The traditional concept of a corporate ladder worked in an era defined by predictability and tenure. Leadership roles came with clear expectations and a step-by-step route to the top. But the rise of globalisation, digital transformation, and shifting organisational dynamics has replaced stability with uncertainty.

Executives are now expected to lead teams through continuous disruption, adapting to challenges like artificial intelligence, hybrid workplaces, and global market shifts. A McKinsey study revealed that over 60% of senior leaders say their roles require constant reinvention to remain relevant. This shifting landscape demands leaders who can pivot quickly, build diverse skills, and inspire confidence during unpredictable times.

Programmes like the Postgraduate Diploma in Business Management are equipping future leaders with these vital capabilities—helping them prepare for the realities of modern leadership beyond the outdated ladder metaphor.

The Snakes That Undermine Progress

enemy of progress

In the context of leadership, snakes represent the unexpected setbacks that derail momentum. Organisational politics, for example, can undo years of hard work if relationships sour or alliances shift. Likewise, technological disruption continues to upend industries, requiring leaders to constantly adapt or risk obsolescence.

There is also the growing challenge of burnout. The pressure to perform in high-stakes environments has left many leaders emotionally and physically exhausted, threatening not only their careers but their overall well-being. Research from Harvard Business Review shows that nearly 70% of executives experience symptoms of burnout, underscoring the importance of resilience and self-care in leadership roles.

The Ladders That Propel Leaders Forward

The Ladders That Propel Leaders Forward

While the board is filled with snakes, there are also ladders—moments of chance, choice, or preparation that allow leaders to leap ahead. These often take the form of mentorship, crisis leadership opportunities, or strategic networking. Leaders who embrace continuous learning and develop strong emotional intelligence are best positioned to recognise these ladders when they appear.

At Regenesys, courses such as the Master of Business Administration (MBA) help aspiring leaders build a mindset of lifelong learning and adaptability, preparing them to seize opportunities in a competitive and ever-changing environment.

Winning in a Snakes and Ladders World

Winning in a Snakes and Ladders World

To thrive in this unpredictable landscape, leaders must shift their perspective. Instead of viewing success as a single upward journey, they need to embrace a dynamic, non-linear path where setbacks and breakthroughs are part of the game.

Resilience becomes the cornerstone of this approach. Leaders must develop the ability to recover quickly from setbacks, learning and adapting so that every fall becomes a stepping stone. Emotional intelligence also plays a critical role, helping leaders to understand team dynamics, navigate complex relationships, and inspire trust even during turbulent times.

Investing in leadership development is another crucial strategy. Programmes like Regenesys Corporate Education are designed to help organisations equip their leaders with the tools and confidence to navigate uncertainty effectively.

Turning Setbacks Into Strategy

Every leader will encounter a snake at some point. The question is not whether you will fall, but how you will respond. Reflecting on setbacks, rather than avoiding them, transforms failure into growth. This reflective practice strengthens a leader’s ability to make better decisions and prepares them for the next ladder they encounter.

As leadership expert Dr Marko Saravanja often reminds us in his Secrets of Success series, “It’s not what happens to you, but how you respond that defines your leadership.”

Keep Rolling the Dice

keep rolling the dice

In a world where leadership feels like a board game, the goal is not to avoid snakes entirely—it is to keep moving forward, no matter how many times you slide back. Success belongs to those who stay in the game, continue learning, and recognise that every setback holds the potential for a greater leap ahead.

So when you hit a snake, take a breath, learn the lesson, and look for the next ladder. Leadership isn’t about getting to the top once. It’s about having the courage and vision to keep climbing, again and again.

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Author

Dip Media Practices Content Writer | Regenesys Business School Neo is a Content Writer at Regenesys Education with a passion for crafting engaging, purpose-driven content. She contributes to various Regenesys platforms, including the RegInsights blog and Regenesys Business World Magazine, focusing on leadership, education, and personal development. With a background in marketing communications, Neo brings creativity, strategy, and a strong sense of purpose to her work. Outside of the office, she’s committed to using her voice to advocate for education, wellness, and opportunities for neurodivergent individuals.

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