Working closely with a trusted team member for years can make the need for a difficult conversation particularly difficult.

In working closely there is a strong possibility that the two of you have become very comfortable with the relationship and the need for exercising positional authority, as the leader, may well have become non-existent.

Unexpected Issues

Unexpectedly, the complaints begin to emerge from other team members about the person you most trust. It may be about the behavior of this person, it may be how they represent their relationship with you, or simply that they have become insensitive. They may have forgotten repeatedly to follow norms and core values, or simply have become stale in their role.

Whatever the reason, a hard conversation with a trusted partner can be something that most leaders dread and simply wish would go away.

Solving the Problem

As we all know as leaders, “no issue ever resolves itself” and “avoidance means that we will pay twice”. So, we are left with the task of addressing such a situation in a manner that will resolve the issue and get the work with the team back on track. Secondly, we deal with the need to preserve the relationship and the trust that has proven in the past to be so successful.

Phase 1: The Cookie Approach

A very successful strategy for such conversations, although it sounds a bit simple and formulaic, is the “Cookie Approach”. Beginning the challenging conversation with positive accomplishments and attributes of the person to whom you are directing your concerns, essentially a list of great contributions they have made.

Phase 2: A Difficult Dialogue

In the middle, the greasy, nasty, difficult truths must be addressed. Taking time to fully explain the concerns and challenges that recent behaviors have elicited.

During this period, you may well need to be prepared to address reactions, deflections, and counterclaims from your trusted team member.

It is important that, as the leader, you stay above commiseration and taking sides. Your goal is the outcome that will work for everyone.

Phase 3: Finish with Positivity

Lastly, concluding the conversation with examples of the positive behaviors and interactions that you have seen the person exhibit and would very much like to see again. Finishing with a positive!

Bringing such conversations to a close with messages that you believe in them, that you continue to need their help, and very clear expectations for how the behavior expected will look to the other team members going forward.

Separation in the Preparation

There is no question that such conversations feel very uncomfortable. There is also no question that issues left unaddressed will fester and a much larger issue will await the leader in the future. If needed, this may be a place to enlist a trusted thought partner in preparation for such a conversation. Preparation, by the leader, for such work is essential.

It is not recommended that “hoping for the best” in such an important interaction will be a strategy for success. As with all decisions and interactions for leaders, proper planning and preparation will give the outcome a much better chance of being positive and enhancing the future capacity of the team as a whole.

To get personalized support for your organization, contact us here!