Best Practices

Why I Don’t Shy Away From Difficult Conversations Anymore

Read Time: 5 minutes
Beth White
Sr. Manager, Educational Content, Teaching Strategies
A school leader has a serious conversation with an educator.
October 26, 2021

I grew up as the classic middle child—an adaptable people-pleaser who often took on the role of peacemaker. For much of my life, I haven’t wanted to rock any boats or upset any apple carts. I was always most at ease when life was quiet. Less drama. More smiling.

Therefore, I presumed myself to be naturally well-suited for the job of kindergarten teacher. Who else is perkier? Quicker to praise? Slower to anger? Who is more patient? Whose dispositions are sunnier? These are the folks who routinely make up jolly sing-alongs about standing in line or washing your hands. These would be my people.

What I didn’t count on, in part because my teacher preparation program didn’t mention it, was that not all exchanges I was about to be a part of would be entirely welcomed ones. I quickly realized that there would be times in my role as a teacher that I would need to lead, or at least participate in, difficult conversations.

That part of the job was hard for me. Really hard.

So, I spent the first couple years telling children’s families that everything was going great. I committed to maintaining a positive outlook in all things. When I met with families, I’d go on and on about every kind word, good deed, and sign of progress that I’d observed. In and of itself, a positive attitude and a focus on children’s demonstrated abilities is a good thing! Right?


Where I Went Wrong, Even Though I Didn’t Mean To

Whenever I did need to address a subject that I thought might upset or worry a parent, I’d tiptoe around any hint of negativity and instead talk about “what we’ll be working on next”— that is, if I addressed a sensitive issue at all. I am ashamed to admit that sometimes I just ignored a complex problem and hoped that it would quietly drown in my sea of good cheer.

By the time I became a school leader, I’d gotten somewhat better about being upfront with families, but I knew I’d have to strengthen my abilities in this area if I was going to be successful in the principal’s office. I also knew that I had just broadened the scope of people with whom I’d probably need to have difficult conversations. It was during this time that I finally learned to find my voice as an educator.

My “voice lessons” didn’t come from talking but rather from listening. And they didn’t come from another educator. They came from my late husband’s medical team.


Finding My Voice

The conversations I was a part of when my husband was diagnosed with and treated for the cancer that eventually took his life were the most difficult I’ve ever been a part of. He and I repeatedly marveled at the empathy, clarity, and grace with which his doctors, and then his hospice nurses, addressed literal life-and-death issues with us. They never minced words. They were always clear and forthright. Along the way, they let us know about treatment options and what the possible rewards and associated risks would be for each. And eventually they let us know when the available options had run out.

Their willingness to engage in such difficult, but necessary, conversations made all the difference in how he and I were empowered to approach his plan of care. Absent these conversations, we would never have been able to make informed decisions.

I remain a peacemaker, but I’m also a lesson-learner. My kindergarten-teacher-level of optimism insists that in everything we encounter in life, even in the most difficult of circumstances, something good can come. One of the good things to come from having been a part of these oh-so-difficult conversations is that I saw firsthand the incomparable power of honesty when delivered with empathy, clarity, and grace.

I began to see comparisons between the roles of hospitals and schools and those of healthcare providers and childcare providers. Correlations between medicine and education are numerous, and one of them is that we are both entrusted with doing what’s best for each person in our care.

I also realized that finding my voice as an educator meant using it to further that goal, regardless of the topic of conversation: if families were to have a complete picture of their children’s growth and development, such that they were empowered to do what was best for their children, they would need the same level of honesty, empathy, clarity, and grace my husband’s medical team had provided for us. Furthermore, they deserved it.

And if teachers were to have a complete picture of the effectiveness of their classroom practices, such that they, too, were empowered to do what was best for children, they would also need that same level of honesty, empathy, clarity, and grace from school leaders Furthermore, they deserved it.


Here are five things I learned about difficult conversations.

  1. There are times that I will need to make and act on important decisions, but no decision of mine is ever final if you can show me something else that is better for children.
  2. Few things in life improve with neglect, and any topic that rises to the level of “difficult conversation” will not be among them.
  3. Every difficult conversation deserves not just honesty but also clarity, empathy, and grace.
  4. Everyone deserves respect and empowerment.
  5. Part of respecting and empowering others is acknowledging their right to make informed decisions.

Our voices as educators allow us to speak on behalf of children in ways that they cannot do for themselves. Not all difficult conversations on their behalf will be the most difficult conversations. But examining the most difficult ones—the ways they transpired and their eventual outcomes—made a difference in how I approached all of them and showed me how to amplify my voice when doing so was most important.

Facilitating Challenging Conversations Successfully

Watch this one-hour webinar where we explore actionable strategies program administrators and instructional leaders can use to facilitate successful challenging conversations with faculty, staff, and families.

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