_{What if the secret to building an award-winning company culture wasn't about having all the answers, but about having the courage to say "I don't know"? In this episode, Lindsay Dodd, CEO of Cashco Financial, shares how vulnerability, core values, and purpose-driven leadership transformed his organization into one of Alberta's Best Workplaces for five consecutive years. Tune in for honest, actionable insights on hiring to values, embracing AI, and leading with authenticity.}

What Makes a Leader Truly Authentic in Today's Business World?

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What if the secret to building an award-winning company culture wasn't about having all the answers, but about having the courage to say "I don't know"? Lindsay Dodd, CEO of Cashco Financial, has proven this counterintuitive truth by leading his organization to become recognized as one of Alberta's Best Workplaces for five consecutive years by embracing vulnerability, authenticity, and a relentless commitment to core values. His journey offers a refreshing perspective for leaders tired of pretending to be superhuman and ready to build trust through honest, values-driven action.

As a self-described introverted leader with, as he describes himself, "the empathy of a garden slug," Dodd's story challenges every stereotype about what great leadership looks like. Under his guidance, Cashco Financial has achieved a remarkable 91% employee engagement score, far exceeding the 65% company threshold for good engagement, while simultaneously pursuing a bold social mission to end financial exclusion for underserved communities. This dual commitment to people and purpose demonstrates that profitability and social impact aren't competing priorities, they're complementary forces that drive sustainable success.

The foundation of Cashco's culture rests on a counterintuitive hiring philosophy: hire clients for their lived experience and empathy, then train them in technical skills. Combined with 200 hours of annual training per employee (nearly an hour every workday), this approach creates a workforce uniquely equipped to serve customers with dignity and understanding. By flipping the traditional organizational hierarchy upside down, placing frontline employees at the top and the CEO at the bottom, Dodd has created a support structure where leadership exists to serve those who serve customers.

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Purpose-driven leadership strategies for business success

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If you've ever felt like you don't fit the mold of a "natural born leader," you're not alone, and you're not disqualified. One of the most liberating insights from Dodd's approach is his emphasis on leadership behaviors over innate qualities. While traditional leadership development often focuses on charisma, extroversion, or confidence, these traits can actually become barriers if they're not paired with the right actions.

What behaviors actually matter? Dodd identifies courage, curiosity, empathy, and consistency as the cornerstones of effective leadership. These aren't personality traits you're born with, they're practices you can learn, develop, and refine over time. Courage shows up when you're willing to have difficult conversations, make unpopular decisions, or admit you don't have all the answers. Curiosity means approaching disagreement or tension with genuine questions rather than defensiveness. Empathy requires truly understanding the experience of your team members and customers, even when it's uncomfortable.

Here's the game-changer: anyone can develop these behaviors. You don't need to transform your personality or pretend to be someone you're not. Instead, focus on showing up consistently with actions that build trust, even when it feels awkward or uncertain. When Dodd walks into tense situations, he leads with curiosity: "Help me understand where you're coming from". This simple behavioral shift transforms potential conflicts into collaborative problem-solving.

The real magic happens when leaders model these behaviors consistently over time. Teams learn to trust not because their leader is perfect, but because they know what to expect. When vulnerability, honesty, and curiosity become the norm, psychological safety flourishes, and with it, innovation, engagement, and loyalty.

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Operationalizing Values: How to hire and fire based on company values

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Values on a wall mean nothing if they're not operationalized in daily decisions. This is where most organizations fail, they craft beautiful mission statements and core values, then ignore them the moment it's inconvenient. Dodd's approach is radically different: at Cashco Financial, values aren't aspirational, they're operational.

The hiring and firing litmus test: If you won't hire or fire based on your values, they're not really your values. Cashco's hiring process explicitly screens for alignment with core values, not just technical skills. They look for lived experience, empathy, and a genuine desire to serve underserved communities. Technical competencies? Those can be taught through their extensive 200-hour annual training program. But values alignment? That's non-negotiable from day one.

Equally important is the willingness to fire to values. When someone repeatedly demonstrates behaviors that contradict your organization's core principles, no amount of talent or tenure justifies keeping them around. Tolerating values violations sends a clear message to the rest of your team: these principles are negotiable, and that's when culture starts to crumble.

But operationalizing values isn't just about consequences, it's about celebration. Cashco starts every meeting with a core value story: a real example of someone on the team living out one of their principles. This practice does three powerful things:

• It reinforces what "good" looks like in concrete, tangible terms
• It publicly celebrates and recognizes team members who embody the culture
• It creates a shared narrative that unifies the organization around common purpose

When values drive decisions at every level, from who you hire to who you promote to what you celebrate, they transform from words on a poster into the living DNA of your organization.

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Trust-building through vulnerable leadership practices

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"I don't know, let's figure this out together". These seven words might be the most powerful leadership tool in your arsenal, yet most leaders are terrified to say them. Dodd's willingness to embrace vulnerability has become one of his greatest strengths, not despite his role as CEO, but because of it.

The vulnerability paradox: We're taught that leaders must project confidence and have all the answers. But in reality, pretending to know everything creates distance, erodes trust, and shuts down collaboration. When leaders admit uncertainty, they open space for others to contribute, problem-solve, and take ownership. Vulnerability invites people in rather than pushing them away.

Dodd describes navigating some of the most polarizing issues of our time, social justice, politics, pandemic responses, by leading with curiosity and openness rather than rigid certainty. When faced with diverse perspectives on his board and within his team, he doesn't shut down disagreement or assert his authority. Instead, he asks questions: "What are you worried about? Help me understand your perspective". This approach defuses tension and transforms potential conflict into productive dialogue.

Vulnerability doesn't mean weakness or indecision. It means being honest about what you know, what you don't know, and what you're still figuring out. It means being willing to change your mind when presented with new information. It means trusting your team enough to show them you're human.

The result? Teams that feel psychologically safe to share ideas, challenge assumptions, and bring their full selves to work. When leaders model vulnerability, they give everyone permission to do the same, and that's when innovation, creativity, and breakthrough solutions emerge.

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Purpose-Driven Leadership: Balancing Profit with Social Impact

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Can a business be profitable and purpose-driven? The answer is a resounding yes. Purpose attracts and retains top talent. Dodd points out that people join causes, not just companies. When employees understand the "why" behind their work, when they see how their daily tasks contribute to a larger social mission, engagement skyrockets. It's no coincidence that Cashco's 91% engagement score coincides with their crystal-clear purpose.

But purpose-driven leadership isn't just about feel-good mission statements. It requires structural alignment.

Cashco's entire business model is designed to serve the underserved:

• They hire clients who understand financial hardship firsthand
• They train extensively to ensure dignity and empathy in every interaction
• They measure success not just in profit margins but in lives changed.

The upside-down triangle: Traditional org charts place the CEO at the top and frontline employees at the bottom. Cashco flips this model entirely. Frontline employees, the people directly serving customers, are at the top. Leadership exists to support, resource, and remove barriers for those on the front lines. This isn't just symbolic, it's a daily operational reality that reinforces the organization's commitment to its purpose.

Purpose also creates resilience in challenging times. When organizations face pressure, uncertainty, or difficult decisions, a clear sense of purpose acts as a north star. It helps leaders make values-aligned choices even when they're unpopular or costly in the short term. And it gives teams something bigger than themselves to rally around when things get tough.

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Ready to Build a Values-Driven Culture?

• To get practical tools and actionable tips that will jumpstart your journey, download the Values-Driven Leadership Kick Starter Booklet here.
  
  

• Join the newsletter to be notified when a new episode is ready for you to listen and get every Kick Starter Booklet for all future episodes.
  
  
• And if you’re looking to elevate your entire C-Suite leadership team, learn how Craig Dowden can help your leaders perform at their highest-level visit https://www.craigdowden.com/executive-mastermind
  
  
• For a deeper dive, listen to the full-length episode of the Do Good to Lead Well podcast featuring Wes Adams & Tamara Myles:
  
  • Spotify
  • Apple Podcasts

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Did you like this article on the state of Ai therapy in organizations? Does it help you become a better leader? Then check out these articles to help hone those skills even further:

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• Sharing at Work with Craig Dowden: The Science of Sharing at Work: Leadership Lessons for Better Connection, Trust, and Wellbeing
• “Having it All” with Corinne Low: Achieving “Having It All” as a Working Mom: Evidence-Based Insights from Corinne Low
• Curious Leadership: The Power of Curious Leadership: Todd Kashdan's Revolutionary Approach to Self-Leadership and Principled Dissent
• Uncertainty: Turning Uncertainty into Advantage: Scott Stirrett’s Leadership Blueprint
• Group Dynamics: Unlocking Team Success with Colin Fisher’s Insights on Group Dynamics and Positive Leadership
• Noticing and Hearing in the Workplace: The Importance of Noticing and Hearing in the Workplace with Zach Mercurio
• Leading with Purpose: Core Qualities and Practices for Positive, Inclusive Leadership with Angela Bonfant‍
• Leadership in Uncertain Times with Elizabeth Weingarten: How Questions, Vulnerability, and Community Fuel Leadership in Uncertain Times with Elizabeth Weingarten‍
• ‍Positive Leadership for Innovation and Resilience with Jason Tham: Leading with Authenticity, Agility, and Purpose in a Fast-Changing World‍