Difficult Conversations Power Balance
Florent "Flo" Groberg, Medal of Honor Recipient and Business Leader, U.S. Army and Fortune 500 Companies

Case: Power Balance 

Leader: Florent “Flo” Groberg  

Topic: Difficult Conversations

Reference: Medal of Honor Leadership Series

Case Challenge

As a new leader in a corporate job, Groberg must manage up and assuage frustrations with his manager by establishing communications and building a relationship to work together regardless.


Taking on a new corporate role, Groberg must develop a relationship with his boss even though he has the buy-in and support from his boss’ boss.  After the situation worsens with his boss, Groberg must establish communication and rebuild the relationship with his boss who feels undermined and eventually stops talking to him.


Hired by a more senior leader than his direct manager, there is friction from the start.  When Groberg does not have the approval from his direct manager on a project idea, he proceeds to gain approval from his boss’ boss.  Although the project is successful, he struggles with building a relationship with his direct boss.  Flo Groberg’s boss feels undermined and stops talking to him. At this point, Groberg must determine how to work with his boss moving forward. Groberg is a Medal of Honor recipient, having received this prestigious award for his acts of valor in Afghanistan.  The Congressional Medal of Honor is the United States Armed Forces' highest military decoration and is awarded to recognize American soldiers, sailors, marines, airmen, guardians and coast guardsmen who have distinguished themselves by acts of valor.

Case Design

These leadership cases are designed to be discussed in a group so that divergent viewpoints can be debated. This enables participants to broaden their perspectives and gain insights into the values and instincts that drive decision- making. Each video pauses to allow for discussion at key points in the leader’s presentation

Keep in Mind

The cases do not always provide the correct or ideal solution. Rather, they present one person’s experiences and judgment based on the circumstances faced at the time. Some critical facts may also have been unintentionally omitted. 

Facilitation Tips 

To help create a trusting, open atmosphere:

  • Establish ground rules for the discussion, such as setting up a safe space.
  • Feedback should not be personal but directed at behavior.
  • Encourage participants to state and defend his or her opinion.
  • Refocus participants by raising broad questions and themes.
  • Reassure your group that leadership is an art that can be learned through practice, feedback, and experience.
  • In closing, provide a theoretical context for the discussion and takeaway lessons.

Teaching Insight - Leadership Background Content

Developing relationships with supervisors and managing-up takes strong communication skills, commitment, humility, and empathy.  In this video case, there are two challenges.

Challenge 1: Groberg did not accept a hiring offer from his supervisor, but instead accepted it from his supervisor’s boss.  He then must determine how to proceed when his supervisor does not support his project proposal.

Challenge 2: When Groberg is hired and then seeks buy-in for a project from his boss’ boss, he leaves his boss out of the loop and undermines his authority.  As a result, the boss feels powerless, Groberg perceives his boss feels threatened, and communication stops.  Groberg must rebuild the relationship with his boss.

This video case is about a leader who must balance personal and team success with his relationship with his supervisor.  Regardless of the support a leader may have within the organization, it is still important to establish trust and communications with a direct manager.   In contrast, some leaders may think simply getting the job done is the only thing that is important regardless of relationships. Groberg realized the importance of having a relationship with his boss and had to use empathy, communication, and commitment to earn his trust.

Video Segment 1: Initial Challenge 

Background and Initial Challenge:

As a new leader in a corporate job Groberg does not have a strong relationship with his direct boss after being hired by his boss’ boss.  When he does not get the approval he wants for his project, he must consider how to proceed.

Initial Challenge Discussion Questions:

At the first Discussion stop (time 2:48), ask these questions to the class at large or to particular students.  Encourage everybody to participate by seeking a variety of different opinions.

  1. When Groberg does not get the approval he wants from his boss for his project proposal, what should he do?  What are his options? Evaluate each option then take a vote and discuss. 
  2. How can Groberg address and manage the feelings that he is seen as a threat?
  3. How can he build a better relationship with his boss to gain the support he needs?

Video Segment 2: Second Challenge 

Challenge 2: In a difficult situation, Groberg must reconcile with his boss who is frustrated after a series of events in which  his boss’ authority was undermined. 

Discussion of Challenge Questions:

Ask these questions to the class at large or to particular students.  Encourage everybody to participate by seeking a variety of different opinions.

  1. What does Groberg risk as a leader by not establishing a relationship with his boss?
  2. Groberg sees his boss as having “bad leadership.” Do you agree or disagree? Discuss.
  3. When Groberg says he doesn't care if his boss dislikes him or not, do you think this attitude is helpful?  Discuss.
  4. Are there any other options or alternatives Groberg should consider in an effort to build a relationship with his boss? (besides confronting his new boss; continue working without his support; or leaving the company?)

Video Segment 3: Decision

Decision: Groberg decides to meet his boss in person, address the problem, share context, and work to build a new relationship. Groberg must apologize for his actions and reinforce that he had never spoken badly of his boss.

Discussion Questions:

Ask these questions to the class at large or to particular students.  Encourage everybody to participate by seeking a variety of different opinions.

  1. Do you think Groberg should apologize to his boss? Discuss.
  2. Do you agree that Groberg should have talked about ways he made his boss look good in spite of the boss not initially supporting his proposal? Why or why not.
  3. How else could you manage this conversation with the boss?  
  4. What other actions could he take to improve the relationship with the boss moving after the conversation?  

Video Segment 4: Results and Lessons Learned 

Results: After three months Groberg’s boss started talking to him again and Groberg continued to perform well with his team.  Groberg continued working for his boss for 18 months yet he never had a strong relationship with his boss in spite of his efforts.

Results Discussion Questions:

Ask these questions to the class at large or to individual students.  Encourage everybody to participate by seeking a variety of different opinions.

  1. Do you agree that having a project win is more important than building a relationship with a boss?
  2. When the boss suggested the need to create a better professional relationship, what steps could be taken?
  3. How could the boss have better managed this situation and relationship with Groberg, especially considering Groberg’s lack of experience in a corporate setting?

Lessons Learned:

  • In difficult conversations it is important to take the “high road” and acknowledge what may be your fault.
  • There are always two sides to a story and sometimes a good idea may not be appreciated because of poor communication.
  • It is important to put yourself in someone else’s shoes to understand where the other person is coming from.
  • Learn from examples of poor leadership to know what not to do yourself.  Sometimes you can learn more from bad leadership than good leadership.

Lessons Learned Discussion Questions:

  1. Do you agree with the lessons learned here? (Note: An instructor will need to mention the above lessons learned.)
  2. How do you balance looking good in a new role with building relationships with the people around you?
  3. In a world of hybrid or remote work, how can you build relationships when people may be skeptical of you or feel threatened?


The lessons shared by this leader are based on his own experiences. These lessons are not necessarily substantiated by academic research but are shared to spark consideration and insight.