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:
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.