Leadership and management are core pillars of any successful organization. As CEO of Leadbox, I’ve had the privilege of leading diverse teams and reflecting deeply on the philosophies that guide effective leadership. In this blog, I’ll share some of my perspectives on core management principles, lessons from the pandemic, and the importance of personal and professional growth.
How Did You Go From “Working In” the Business to “Working On” the Business?
Shifting from working in the business to working on the business is a gradual process. As a CEO, it’s crucial to take a step back, gain perspective, and plan for the company’s future. Yet, staying connected to daily operations is equally important.
For instance, I still work closely with some of our dealer partners. This hands-on involvement helps me stay attuned to their needs and the challenges our team faces. At the same time, I consciously avoid micromanaging departments I used to oversee, like marketing and sales. Empowering department heads to make decisions fosters trust and innovation.
One of my favorite ways to work on the business is to step away—literally. I often take my iPad and sit by a river with my dog, using this time to strategize and envision our five-year goals. These moments of solitude, away from the daily distractions of notifications and meetings, are crucial for long-term planning.
What is similar or different between small and larger businesses?
I’ve had the opportunity to work with both large corporations, like Rogers and Postmedia, and smaller, more agile businesses like Leadbox. Each environment offers distinct learning experiences.
In large companies, you often specialize in a particular role, gaining deep expertise in a specific domain. The challenge is staying curious and proactive, as the scale of operations can sometimes stifle cross-departmental learning.
Smaller companies, on the other hand, require you to wear multiple hats. When I joined Leadbox, I was simultaneously involved in HR, marketing, product development, and sales. This breadth of responsibility accelerates learning but can also lead to overwhelm if not managed carefully.
Ultimately, success in both settings depends on one’s curiosity. Whether you’re in a Fortune 500 company or a 50-person team, the willingness to ask questions, seek knowledge, and adapt is a fundamental predictor of growth.
Do You Focus on Results or Processes?
This is a classic debate in leadership: should we prioritize results or trust the process? While results are undeniably essential—they are, after all, the measure of success—they shouldn’t come at the expense of process and culture.
Over the years, I’ve seen individuals generate fantastic results while cutting corners or disregarding company values. This short-term success often leads to long-term challenges, including team dissatisfaction and operational inconsistency. At Leadbox, we’ve embraced a value-driven hiring and management process. Core values like growth are non-negotiable; we look for individuals who actively seek self-improvement, whether through reading, podcasts, or new skills.
Ultimately, if we trust the process—hiring the right people, setting clear expectations, and fostering growth—results will naturally follow. And when people feel supported and valued, they’re more likely to go the extra mile for clients and colleagues alike.
What Did You Learn Leading Through the Pandemic?
The pandemic was a difficult period for everyone, including our team. Beyond the tragic loss of lives, businesses faced unprecedented challenges. Yet, as an optimist, I believe in finding silver linings.
Before the pandemic, Leadbox operated from multiple offices, which unintentionally created a sense of hierarchy and disconnection between teams. When the pandemic hit, and we all shifted to remote work, something remarkable happened: we found unity. Suddenly, everyone was on a level playing field, engaging through their screens from home. This new dynamic fostered a stronger sense of camaraderie and alignment.
The financial impact was significant; our advertising management fees—comprising 50% of our revenue—dropped by 75%. Despite this, we made the decision to retain all 26 employees. We believed that investing in our people, even during tough times, would pay off when the market rebounded. And it did. By the end of the year, we made everyone whole, except for the executive team, who willingly took a financial hit. This decision cemented a culture of loyalty and resilience within the team.
What Advice Would You Give Your Younger Self?
If I could hop into a time machine, I’d tell my younger self a few things. First, I might encourage myself to take on a leadership role sooner. There’s immense growth that comes from stepping into positions of responsibility early in one’s career.
Secondly, I’d remind myself to enjoy the journey. I’m naturally responsible and tend to prioritize work, often rushing back from business trips without taking time to explore new places. In hindsight, I realize that life’s richness often lies in these moments of curiosity and experience.
Additionally, I’d caution against the pitfalls of social media comparison. It’s easy to be disheartened by others’ curated highlights while overlooking the hard work behind their success. My advice to anyone feeling this pressure is simple: focus on your growth and cherish meaningful relationships. Professional achievements matter, but the bonds with family, friends, and colleagues define true success.
Where Do You Go For Advice?
Leadership isn’t about having all the answers—it’s about knowing where to find them. When I need guidance, my first instinct is to look inward. Our team members, who are closest to daily operations, often have the most insightful perspectives.
To encourage this, we’ve implemented a “red card” system, inspired by Toyota’s Kaizen methodology. Anyone can metaphorically pull the red handle to flag issues or suggest improvements. However, as leaders, we must repeatedly emphasize that we value these contributions—and follow through by implementing the best ideas.
Externally, I turn to mentors and peers. Over the years, I’ve benefited immensely from conversations with experienced professionals across industries. Joining CEO forums and networking groups provides access to diverse viewpoints and invaluable advice. For aspiring leaders, I recommend finding mentors early and staying open to feedback throughout your career.
Final Thoughts
Leadership is an evolving journey, shaped by experiences, challenges, and continuous learning. While this post might deviate from the usual marketing insights, I hope these reflections offer valuable lessons for your own leadership path.
Thank you for joining me at my desk. I look forward to sharing more insights in the future—and remember, leadership isn’t just about the results. It’s about the people, the process, and the impact you create along the way.
The post Leadership Insights from Ian Cruickshank: Lessons from the Leadbox CEO appeared first on Leadbox HQ.