On April 2, 2025, John Clements hosted the sixth session of the New Managers program titled Supporting Your Boss and Organization. Facilitated by Ms. Grace Alcid, Ed.D., the session dissected the HBS case study Thomas Green: Power, Office Politics, and a Career in Crisis, offering actionable insights into managing upward and aligning with organizational goals.
The 5 Essential Conversations Every Manager Needs with Their Boss
The “5 Conversations” framework was central to the session, designed to bridge gaps between managers and their superiors. These conversations are:
- Situation: Align on role expectations and organizational priorities.
- Expectations: Clarify short- and long-term goals.
- Style: Adapt communication and workflows to complement your boss’s preferences.
- Resources: Identify tools, budgets, and support needed to succeed.
- Personal Development: Seek growth opportunities aligned with organizational needs.
Dr. Alcid emphasized that neglecting these conversations can lead to conflicts like those seen in the case study.
Lessons from Thomas Green’s Career Crisis
The case study highlighted Thomas Green, a senior market specialist at Dynamic Displays, whose rapid promotion led to clashes with his boss, Frank Davis. Green dismissed Davis’s 10% growth targets as unrealistic, focusing instead on a long-term software project. He avoided Davis, relying more on charisma than on data-driven strategies, and failed to leverage available tools or update critical reports. During the session, groups analyzed these failures through the lens of the 5 Conversations.
Group Exercise: Tackling the “Resources” Conversation
Assigned to the Resources group, participants role-played as Thomas Green and identified five critical needs. They emphasized the importance of finding the right work tools and references to help Green meet expectations, requesting additional staff for market research, obtaining real-time analytics to justify strategies, and upskilling in data-driven decision-making. They also recognized the need for mediation from upper management to address communication gaps and balance both Green’s and Davis’s concerns.
Dr. Alcid expanded on these points, stressing that proactive resource negotiation prevents conflicts and builds trust.
How the 5 Conversations Could Have Changed the Outcome
Had Green applied the framework, he could have aligned with Davis on kiosk sales versus software priorities. He might have presented data to negotiate more realistic growth targets and adapted his communication style to meet Davis’s preference for detailed updates. He could have secured the necessary tools to validate his long-term vision and requested training to strengthen his strategic skills.
Smart Strategies for New Managers
- Align Early: Clarify priorities before conflicts arise.
- Data Over Charisma: Use analytics to support proposals.
- Adapt Communication: Mirror your boss’s style for smoother collaboration.
- Leverage Resources: Advocate for tools that drive results.
Final Thoughts
The New Managers Program session underscored that supporting your boss isn’t about compliance—it’s about strategic collaboration. By mastering the 5 Conversations, managers like Thomas Green can turn potential crises into opportunities for growth.
Master the Art of Supporting Your Boss
Effective upward management can transform your career. The “5 Conversations” framework shared in John Clements’ New Managers Program offers invaluable strategies for building better relationships with your boss and driving organizational success.
Need personalized advice? Reach out to John Clements Consultants to explore tailored solutions for your leadership journey. Contact us today.
