Best Friends Don't Make For the Best Bosses
Where Should We Begin? with Esther Perel
Deep Dive
Why did the friendship and professional relationship between the bookstore owner and his employee deteriorate?
The relationship deteriorated because they lacked formal systems for discussing job performance, leading to misunderstandings and tension. The owner would make snippy comments about the employee's performance, which made the employee feel defensive and tense.
Why did the employee decide to leave the bookstore?
The employee decided to leave to preserve the friendship after several altercations and to avoid further tension. She felt that the professional and personal boundaries were too blurred and that the relationship was becoming toxic.
Why is it important to have a professional off-boarding conversation when leaving a job, especially with a friend?
A professional off-boarding conversation is important to clarify what worked and what didn't, to set clear expectations, and to address issues of competence and performance. It helps both parties learn from the experience and can pave the way for a potential future collaboration.
Why did the employee feel intimidated by her friend and boss?
The employee felt intimidated because her friend was very smart and often dismissed her ideas. This created a power dynamic where she felt her contributions were undervalued, leading to a lack of confidence in sharing her thoughts and ideas.
Why did the employee feel the need to leave the job to preserve the friendship?
The employee felt that the professional and personal boundaries were too blurred, leading to a toxic work environment. She believed that leaving was necessary to preserve their long-standing friendship and to avoid further conflict.
Why did the employee think it was important to have a debriefing conversation with her friend?
The employee thought a debriefing conversation was important to clear the air, learn from the experience, and potentially improve their future professional and personal interactions. It would help them understand what went wrong and how to prevent similar issues in the future.
Why did the employee feel that the relationship was too fragile to handle difficult conversations?
The employee felt that the relationship was too fragile because the familiarity and long-standing friendship made it difficult to have productive, professional conversations. She reacted strongly to criticism and felt that the relationship was at risk of breaking down.
Why did the employee think her friend was more focused on criticizing than improving?
The employee felt that her friend focused on what was wrong or what he didn't like, rather than setting clear expectations and goals. This lack of constructive feedback made it difficult for her to improve and led to a sense of frustration and defensiveness.
Why did the employee believe it was important to have a conversation about their collaboration, even if they don't want to work together again?
The employee believed it was important to have the conversation to learn from the experience, improve their communication skills, and ensure that their friendship remains strong. It's about personal growth and being better equipped for future relationships and collaborations.
Why did the employee suggest starting the conversation with what worked well?
Starting with what worked well helps set a positive tone and acknowledges the successes of their collaboration. It provides a foundation for a constructive conversation and makes it easier to address the areas that need improvement.
- Lack of systems for discussing job performance
- Snippy comments and defensiveness
- Absence of professional boundaries
- Blending of friendship and professional roles
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