HCI Webinar Recap: Red Flags that a Leadership Crisis is on the Horizon for Your Organization, with Phillip B. Wilson
- Jonathan H. Westover, PhD
- Apr 4
- 3 min read
In the latest HCI Webinar, Dr. Jonathan H. Westover talks with Phillip B. Wilson about the red flags that a leadership crisis is on the horizon for your organization. Below is a summary of the main points from their conversation! Check out the full episode and let us know what you think!
Watch the episode here:
Quick Recap
Jonathan and Phil discussed the challenges of leadership in today's complex and rapidly changing world, emphasizing the need for better training and support systems for leaders, particularly frontline leaders. They also highlighted the importance of receiving and giving feedback as a leader, encouraging disagreement and constructive criticism within a team, and the significance of believing in oneself as a leader. Lastly, they touched on the current political and social landscape, suggesting it may be a ripe time for such discussions, and Phil shared his new book, "The Leadership Playbook."
Leadership Crisis in Organizations Discussed
Jonathan and Phil discussed the red flags indicating a leadership crisis in organizations. Phil, a national expert on leadership and labor relations, shared his background and upcoming book launch. They also touched on the current political and social landscape, suggesting it may be a ripe time for such discussions.
Leadership Challenges in Modern World
Jonathan and Phil discussed the challenges of leadership in today's complex and rapidly changing world. They highlighted the need for better training and support systems for leaders, particularly frontline leaders, who are often promoted without any training on leadership skills. They also noted the shift in expectations for leaders to be more empathetic and invest in the emotional and mental well-being of their teams, a role they were not previously trained for. Phil emphasized the challenges of managing a larger team with fewer resources and the potential for a negative culture to develop.
Challenges of Promoting Salespeople to Management
Jonathan discussed the challenges of promoting high-performing salespeople into management roles, citing the example of Michael Scott from the TV show "The Office." He noted that these individuals often struggle to build trust with their new team due to a lack of humility and relationship-building skills. Phil shared his own leadership journey, which started with him at the top of Mount Stupid, where he thought he knew something but actually didn't.
Phil's Leadership Style and Team Dynamics
Phil discussed his experience with a team member, Debbie, who initially refused to work for him due to his leadership style. Phil acknowledged his mistake of not trusting his team and being the chief bottleneck, which led to a dysfunctional team culture. He shared how he worked to improve this by accepting feedback and staying within his designated role, allowing his team to provide input and guidance.
Leadership and Team Feedback Importance
Phil and Jonathan discussed the importance of receiving and giving feedback as a leader. They emphasized that a lack of negative feedback or only hearing positive feedback from team members is a red flag, indicating that team members may not feel safe sharing their concerns. They also highlighted the importance of encouraging disagreement and constructive criticism within a team. Other red flags mentioned included high turnover rates, lack of growth opportunities for team members, and only hearing about crises rather than smaller issues. They concluded that a good leader should regularly seek feedback and encourage growth within their team.
Believing in Oneself as a Leader
Phil discussed the importance of believing in oneself as a leader, emphasizing that one's growth and development significantly impact those around them. He highlighted the need for leaders to recognize their influence and take responsibility for their impact. Jonathan agreed, noting that a good leader can make a significant difference in one's work experience. Phil also shared his new book, "The Leadership Playbook," and encouraged readers to visit his website for more information. He concluded by emphasizing the significance of the "hero assumption," which assumes that team members want to do great work, and that this mindset can transform leadership.
Listen to the webinar here:

















