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December 09.2025
3 Minutes Read

Avoiding the Worst Mistakes CEOs Make: Insights from OpenTable's Christa Quarles

This Is the 'Worst Thing' CEOs Can Do, According to the Head of OpenTable

Understanding Leadership Pitfalls: A Blinkered View

In the fast-paced world of leadership, it often feels like CEOs are racing against the clock, making decisions that can make or break their companies. Recently, OpenTable's CEO, Christa Quarles, articulated a vital perspective on modern leadership that resonates with upper management across various industries. According to her, one of the gravest missteps a leader can make is the unwillingness to acknowledge the failures or missteps within their organization. Instead of viewing errors as opportunities for growth and improvement, some CEOs bury their heads in the sand, leading not only to their demise but also jeopardizing the very fabric of the company.

The Dangers of Avoiding Accountability

Ignoring problems can result in a toxic corporate culture. As noted in the insights gained from Vistage, poorly communicated accountability leads to a disorganized team where employees may feel disconnected from the objectives of the organization. When a leader refuses to take ownership of mistakes or foster open dialogue about issues, it creates an atmosphere where accountability falls away, and mediocrity can thrive. CEOs need to cultivate an environment where challenges and failures are openly discussed rather than hidden to avoid facing uncomfortable truths.

Lessons from the Trenches: Empathy as a Leadership Tool

Quarles also emphasizes the importance of empathy and connection within a team. A significant issue seen in many companies, especially startups, is the tendency for CEOs to become overly attached to their original vision, leaving little room for employee insights and feedback. By not listening, leaders risk alienating their team members and losing valuable perspectives, akin to the lessons learned by many who have faced company-breaking points. Lessons from fellow leaders, such as those highlighted in the Spero Ventures article, showcase that effective leaders incorporate diverse viewpoints into their strategies, allowing them to steer their companies toward lasting success.

Building a Culture of Learning: The OpenTable Example

Quarles reflects on OpenTable’s own hurdles, indicating that understanding one's total addressable market and actively exploring avenues for growth are critical to preventing a stagnation of ideas. The first phase of any company, according to Quarles, is finding that product-market fit, but it's the second phase where many falter—scaling effectively without breaking down. Quarles’s advice resonates strongly: embrace the inevitable bumps along the way and be transparent about them. Continually asking questions and being open to feedback can shift culture from one of blame to a more constructive environment focused on improvement and innovation.

Practical Steps Towards Empowering Leadership

The path to effective and transformative leadership doesn’t have to be ambiguous. As echoed in both Christa Quarles’s discussions and Vistage’s insights, leaders should strive to:

  • Encourage open feedback to foster communication.
  • Take calculated risks while being open about failures.
  • Promote a culture where learning from one’s errors becomes the norm.
  • Ensure their vision aligns with the team’s shared goals.

To drive meaningful change, every leader needs to adopt a mindset that sees beyond immediate challenges. Accountability and empathy are their best allies in cultivating a cohesive team that rises together.

Your Role as a Leader: Take Action

Understanding the challenges that come with leadership and actively working to mitigate them can transform the business landscape. If you’re a CEO, it’s time to reassess your approach. Are you encouraging robust discussions about errors? Have you created channels for honest feedback? Embrace empathy in your leadership style, because, as Quarles suggests, it’s not just about avoiding the worst mistakes; it’s about fostering a resilient organization capable of thriving even in adversity.

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