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Coaching Concepts: Why And How You Need To Have Difficult Conversations With Your Boss

Updated: Dec 18, 2023

Having difficult conversations is…well…difficult. This is especially true if you need to have a difficult conversation with a supervisor or someone else at a higher level in your organization.

I was recently coaching a young executive who had been struggling with a direct report, who had a history of creating challenges among the team even back to a previous manager. But, this person was also highly valuable because of their skills and experience, and no one wanted to lose them. The young executive with whom I was speaking had sought advice and support from his superior to deal with the issue. In an attempt to help, his boss said that the problem employee could just report directly to him and he would deal with it.

Even with the best intentions and that positive sense of collective required in the hustle of a startup, this attempt to help created far bigger problems for the young executive. Now, the rest of his direct reports believed that if they disagreed with him or if they didn’t like what he said then they too could go around him and directly to his superior. The workaround intended to relieve this young executive had accidentally neutered his ability to lead the rest of his team and as a result multiplied his stress.

We were talking through how he might have this conversation with his boss. Sparing additional detail, here were some key principles we landed on:

  1. Approach with gratitude: We talked about how he could acknowledge the good intent of his supervisor’s move and open the conversation with that appreciation. This would ensure that nothing came across as complaining or personal or ungrateful, which were things he was really worried about. He valued and wanted to protect his positive relationship with his boss.

  2. Appeal to common interests: This young executive was hired because of his own skills and the belief that he could lead this team and the company to a new phase of growth and maturity. He knew that he and his boss could agree on this premise. With that out in the open, he needed to describe the unintended consequences of changing the reporting structure. Clearly, neither of them wanted this young executive to not be able to perform the job he was hired to do.

  3. Focus on outcomes, not people: We talked about making sure the conversation with his boss never became about the valuable, but problem employee. It couldn’t become personal. It had to be about process and performance. So, this young executive needed to show with examples how his leadership was being undermined with other direct reports and how that was impacting performance.

  4. Define an agreeable path forward: This was not a situation that could linger. This young executive was losing authority and credibility by the day and as a result was also developing a lot of frustration and anxiety about his role and the work and so forth. So, he needed to use steps 1-3 to make sure the conversation was primed for: so what do we do now?

Within a few hours of our conversation, I got an email back. The young executive and his boss had agreed that an announcement would be made to the team about the change in reporting structure, so it no longer looked like a workaround that others could also take. They also defined specifically when that announcement would be made. This path forward not only would help solve the authority problem but would also relieve the stress valve for the young executive who now knew something would happen. This wouldn’t linger.

Perhaps most importantly in the long run, I suspect that this young executive’s approach and willingness to have a difficult conversation with his boss only reinforced why he was hired in the first place. I have a feeling his opportunity and authority will only grow as a result of the experience.


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