Leading Through Ambiguity: Building Teams and Careers That Thrive: Jordan Schwartz

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Summary

This episode of The Eh List features a thoughtful conversation with strategy leader Jordan Schwartz, who shares how leadership, growth, and human connection shape successful organizations. With more than a decade of experience at the intersection of technology and business, Jordan reflects on his journey from university to his current leadership role at Caylent, explaining why following instinct and staying open to opportunity can be more valuable than rigid career planning.

Jordan discusses the importance of building strong relationships, investing in personal development, and creating cultures that support long-term growth, especially in fast-changing business environments. He also highlights why hiring for cultural fit matters and how leaders can balance strategy with execution when expectations are high.

Drawing from his early career experiences, including his time at Traction on Demand and its acquisition by Salesforce, Jordan explains how an exploratory approach helped shape his path. He introduces the idea of delayed gratification, encouraging young professionals to focus on long-term development rather than short-term rewards.

Throughout the episode, Jordan emphasizes the role of company culture, the value of meaningful connections, and the impact of finding leaders who challenge you to grow. He reminds listeners that every organization has its own subcultures, and understanding them can play a major role in career success.

Overall, Jordan’s story is a reminder that careers are rarely linear. Success is driven not by job titles or company names, but by the experiences you gain, the relationships you build, and your willingness to adapt as opportunities arise.

Takeaways:
  • The journey of career exploration often involves making instinctual decisions rather than following a predetermined path.
  • Fostering relationships within an organization can lead to unexpected opportunities and growth in one’s career.
  • Delayed gratification is a vital principle for younger generations to understand in their career development.
  • Building teams with the right cultural fit is paramount for creating a successful and cohesive work environment.
  • Leaders must act decisively when faced with underperformance or challenges within their teams to ensure continuous improvement.
  • Investing in oneself and prioritizing personal growth over immediate gains can yield long-term career benefits.

 

Companies mentioned in this episode:

 

Books mentioned in this episode:
  • Good to Great by Jim Collins
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