How to Have a Tough Conversation

An unavoidable duty of moving into the assistant principal role from the teaching staff is having difficult conversations with the same teachers you used to work alongside. Addressing conflict with, or supplying feedback to, colleagues may even be something you try to avoid.

However, if you “Eat the frog”—handle your worst task first—the rest of the day will seem easy, says productivity expert Brian Tracy. Procrastination may even result in avoiding the issue altogether, and any conflict may worsen if you wait too long to intervene.

Addressing tough situations with teachers promptly and professionally is a good place to start, and here are a few additional tips for having a productive and successful “tough” conversation:

Be Prepared

Thinking through what you want to communicate and how you’ll go about it can make all the difference, says James Bowen, director of NAHT Edge, a teachers’ trade union for aspiring leaders. It might even help to consider in advance what the likely response will be.

However, it’s also critical to maintain the flexibility necessary to respond as the conversation develops. An inflexible approach or sticking too rigidly to your script may give the impression that you aren’t really listening or engaging with the person to whom you are speaking.

Start With Respect

Communications consultant and leadership coach Jennifer Abrams offers this advice: Don’t begin with a phrase such as, “We have an issue.” Instead, start with a sincere acknowledgment such as “You have my respect for…,” “I appreciate you and want you to know that…,” or “We have worked together for more than a decade, right?”

Further, she recommends, don’t insert your feelings into professional situations by exercising power or becoming too “parental” in conversation. Only mention your feelings if the source of conflict is an interpersonal issue (“When you said this to me/about me, I felt…”).

Be Kind

Maura Clinton-Jones, an assistant principal at Griffin Memorial School in Litchfield, New Hampshire, draws upon her teaching skills when faced with tough conversations with adult colleagues including teachers.

“When I was a teacher, I tried to be kind, understanding, empathetic, and a good listener when dealing with a student,” Clinton-Jones says. “I wanted to work with the student to get to the root of the problem and then make changes, if needed. I think that the same approach works when addressing issues with adults now that I am an administrator.”

She always tries to remember that the person to whom she is speaking has feelings, too. “I can be direct while also being kind and understanding,” Clinton-Jones says. “I might have to be tough, however, there is a person behind the issue. Again, kindness and empathy are needed and go a long way in helping to resolve the problem.”

Find a Way Forward

Concluding tough conversations can also be difficult. The end goal should be to explore various options and solutions together before agreeing on a plan, Bowen says. Also, it’s important to agree on a time and date to meet and review how things are going together.

As the best leaders know, she says, it is possible to remain kind, polite, and communicate a genuine sense of care and concern for the person they are speaking with, while also addressing the issue at hand with real clarity.

Belinda Lichty Clarke is director of alumni engagement at the Medill School of Journalism at Northwestern University and a freelance writer based in Evanston, Illinois.