Imagine investing $1.5 million in a new sales methodology, only to watch it fail completely because you never understood what was actually broken in the first place. This isn't a hypothetical scenario—it's exactly what happened to one organization that sought help from Teri Long, VP of of Global GTM Enablement at GoTo.
When leadership was asked what specifically was broken with their sales team, they couldn't provide a clear answer. Instead of digging deeper, they threw money at the problem and hoped for the best. The result? A complete failure of investment and a team that remained just as "broken" as before.
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This costly mistake highlights a critical issue plaguing sales organizations today: poor leadership that makes decisions in boardrooms without understanding what's actually happening on the ground. The consequences extend far beyond wasted resources - teams lose trust in leaders, sales reps become disengaged, and enablement programs fail to deliver results.
But there's a better way. In this article, we'll explore the four pillars of authentic leadership that can transform your sales organization and prevent costly mistakes like the one above.
Poor leadership in sales creates a domino effect that touches every aspect of your organization. When leaders make decisions without understanding ground-level realities, they create initiatives that are doomed to fail from the start. This leads to wasted resources, frustrated teams, and ultimately, poor revenue performance.
The problem isn't just about making bad decisions - it's about creating an environment where teams lose faith in leadership altogether. When sales reps see leaders consistently implementing solutions that don't address real problems, they become disengaged and stop contributing valuable insights that could actually drive improvement.
The need for leaders to be more authentic and transparent with their teams is growing significantly. Modern sales teams expect leaders who understand their daily challenges and can provide meaningful support, not just directives from above.
Teri Long's experience working with sales organizations has revealed four essential pillars that separate authentic leaders from those who simply hold titles. These pillars form the foundation for building trust, driving real change, and creating sales teams that actually perform.
"Leaders who are genuine in their communication about both successes and challenges build extraordinary trust with their teams," Teri explains.
This means abandoning the false notion that leaders must have all the answers all the time.
Authentic transparency involves:
Instead of pretending to have expertise you lack, create space for others to contribute their knowledge and insights. This vulnerability becomes the foundation for psychological safety within your team.
Don't sugarcoat challenges or oversell successes. Your team can handle the truth, and they'll respect you more for being straightforward about the reality of your situation.
When issues arise, address them directly rather than hoping they'll resolve themselves. Transparency about problems allows your team to help solve them.
This approach might feel uncomfortable at first, especially if you're used to projecting unwavering confidence. However, this vulnerability actually strengthens your position as a leader by building genuine trust with your team.
Authentic leaders understand that the most meaningful outcomes often emerge from unexpected sources—from people who might not be considered experts on a topic but bring fresh perspectives to the table.
Create systems and opportunities for team members at all levels to share their insights and suggestions. Often, the people closest to the problem have the best solutions.
Don't just listen to your top performers or most senior team members. Sometimes the newest rep or the person struggling the most can provide insights that transform your approach.
Listening isn't enough—you need to demonstrate that you value input by implementing good ideas and explaining why others might not work in the current context.
Creating this culture of contribution leads to better, more diverse solutions that actually address real challenges rather than perceived problems.
This pillar is where many leaders fail, as demonstrated by the $1.5 million mistake mentioned earlier. Before implementing any solution, you must understand the root cause of the problem you're trying to solve.
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Teri recommends using the Sakichi Toyoda 5 Whys Framework:
Don't accept surface-level explanations. If your sales team is underperforming, ask why that's happening.
Continue drilling down to understand the underlying causes.
Each "why" should take you deeper into the root cause of the issue.
Don't implement solutions until you've reached the core of the problem.
This methodical approach prevents the kind of expensive mistakes that happen when leaders assume they understand problems without proper investigation. It also ensures that your solutions actually address the real issues affecting your team.
Data tells one story, but the people living the experience tell the complete picture. Authentic leaders understand that you can't lead effectively from a boardroom - you need to understand what's working and what isn't from the people experiencing it firsthand.
Observe real interactions between your sales reps and prospects. See how your processes actually work in practice, not just how they look on paper.
Listen to actual calls, attend meetings, and watch how your team navigates challenges in real-time.
Your team members deal with obstacles and opportunities that never make it into reports. Regular conversations can reveal insights you'll never find in dashboards.
Getting into the trenches means abandoning the comfort of high-level metrics and diving into the messy reality of daily sales work. This hands-on approach reveals gaps between what you think is happening and what's actually occurring.
When leaders embrace these four pillars, the transformation is remarkable. Teams feel safe to share ideas because they know their input is valued and their leader is willing to be vulnerable. Trust grows exponentially when people see that their leader is genuine and transparent.
You begin to see the real problems affecting your team rather than the symptoms or assumptions you had before. This clarity leads to solutions that actually work because they address root causes rather than surface issues.
People grow under your guidance because they feel supported and empowered to contribute. Change happens faster because your team is engaged and invested in the outcomes rather than simply following orders.
As Teri notes, "You're not just earning a seat at the table anymore, you're redefining what that table looks like."
Authentic leadership doesn't just improve your current situation—it transforms the entire dynamic of how your organization operates.
The $1.5 million mistake that opened this article could have been avoided with authentic leadership. By being transparent, listening to the team, understanding what was actually broken, and getting into the trenches to see the real situation, leaders could have identified the true problems and implemented effective solutions.
Authentic leadership isn't just about being a better person—it's about being a more effective leader who drives real results. When you embrace transparency, listen actively, understand root causes, and engage directly with your team, you create an environment where people thrive and businesses grow.
The four pillars of authentic leadership provide a framework for transforming your sales organization from the inside out. By implementing these principles, you'll not only avoid costly mistakes but also build a team that's engaged, motivated, and capable of achieving extraordinary results.
In this episode of SellMeThisPen Podcast, Michael and Teri dive deep into the critical elements of authentic leadership in sales organizations. They discuss the costly mistakes leaders make when they operate from boardrooms without understanding ground-level realities, and how the four pillars of authentic leadership can transform sales teams and drive real results.
Teri Long is VP of Global GTM Enablement at GoTo, where she focuses on strategic advisory and executive coaching. She shares insights on leadership, enablement, and personal growth, helping sales organizations build stronger, more effective teams through authentic leadership practices.
