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The 6 Phases of a Difficult Conversation: A Strategy Guide for Teachers

By Margaret Steen

A parent catches you at drop-off one morning and wants to know why her son got in trouble the day before, since he never misbehaves at home.

A colleague presents a proposal at a staff meeting that you are certain will not work.

At the end of a long day of parent-teacher conferences, you are scheduled to meet with the parent of a student who consistently misses assignments, with a different excuse each time.

Getting through these conversations with your relationships intact — while still getting your point across — can be difficult. “With parents, the difficult conversations are when you clearly see the child in two different ways,” said Jan Stewart, a career coach with Emerge: Coaching for Success. “What the parent sees is not necessarily what you see in the classroom. You have to convey that to the parent without making them feel wrong about the way they see the child.”

Colleagues — whether they are fellow teachers or administrators — present a different type of challenge. Sometimes experienced teachers may think newer teachers, who are enthusiastically advocating for new approaches, don’t appreciate the lessons their more seasoned colleagues have learned over the years. And the newer teachers can feel that their ideas are being rejected without being given a chance.

“Teachers may also have to have difficult conversations with students — about classroom behavior, for example,” said Douglas Stone, co-author of Difficult Conversations and a lecturer on law at Harvard Law School. Administrators, too, can end up having difficult conversations with all of these audiences.

It can be useful to approach these difficult conversations in stages:

1. Before the conversation

Consider your goals and how best to achieve them. “Ask yourself, ‘What’s my purpose in this conversation?’ ” Stone said. “Make sure that the actions you are planning are aligned with achieving that purpose.” This starts with deciding who will take part in the conversation — or even if a conversation is the best way to approach the issue. Occasionally, an email message would work better as an initial approach.

And, although difficult communications are usually best handled in person, the setting and people present can make a big difference: “Is it best to have a one-on-one conversation, or to invite a set of people?” Stone said. “Think about what makes sense before you get started.”

2. At the beginning of a conversation

“Start the conversation by stating the purpose,” Stone said. He suggests using a template:

  • Start by observing a difference in perspective — doing your best to describe that difference without judgment in either direction.
  • State an interest in understanding the other person’s views and sharing your own.
  • Propose that you problem-solve together.

For example, in a one-on-one conversation with a parent, that template might be filled in like this: “I’d like to talk about your son’s experiences in my classroom.  I know from prior conversations that you and I see things a bit differently — you’re concerned that I haven’t taken into consideration the challenges he’s experiencing outside the classroom, and for my part, I’m struggling with ways to give him the attention he needs while still teaching the other students.

“I’d like to hear more about your perspective on this, and I’d like to share mine, and see if we can come up with some ideas for how to improve the experience for your son.”

3. When others present their views

It’s critical to listen — not just stop talking — when the other person or people in the meeting are talking. Stewart suggests “really listening to the other person and focusing on whatever emotion they’re conveying.” When the other person is clearly upset, try a response like, “I’m so surprised to hear that — can you tell me more?” This “allows the person to expand on what they have said so you can really listen.”

Stone offers other questions that can help you understand other points of view: “What has been the emotional impact of that?” “What are you most concerned about?”

To make sure you’re understanding, it can also help to repeat what you hear the other person saying. For example, try saying, “So this is what I’m hearing you say…” Stewart said. “Ask open-ended questions to get more information, while reframing or clarifying as much as you can.”

4. When it’s your turn to respond

Stewart recommends asking for permission if your point of view is substantially different from the one you have just heard: “‘Do you mind if I share another perspective?’”

Give specific examples rather than conclusions, Stone suggests: “Don’t say, ‘Well, it’s just a fact that your son is disruptive.’ Instead, offer an example: ‘Here’s an example of what has been challenging for me’.”

It’s also important acknowledge if the conversation has given you new information or changed your mind in some way, Stewart said. “This draws it back into being a partnership and not an adversarial relationship.”

5. When you’re problem-solving

Once everyone at the meeting has presented their view of the issue at hand, it’s time to brainstorm together about how to solve the problem. “Some problems may disappear through deeper understanding, and other problems will remain,” Stone said. “Share some possible solutions or ways to approach the challenges, and ask for the other person’s ideas as well.”

6: When the conversation ends

The conclusion depends on what has been resolved. “You may be able to figure out a way that if something like this should happen again, it doesn’t build up into a big deal,” Stewart said. For example, you could say, “In the future, if something like this happens, I’d appreciate it if you would…”

If there is no agreement, it can help to acknowledge that and to thank the person for having the conversation. It may also make sense to set up another meeting, either to continue the discussion or to check on how things are going.

Staying on the right track

It’s important when having these difficult conversations — whether they’re carefully planned or impromptu — to avoid some common pitfalls:

  • Not listening: “We assume we understand what the other person is going to say, for example, because we dealt with what seemed like a similar situation in the past but, in fact, the current situation may be different in important ways,” Stone said.
  • Not being candid about your own views: “Sometimes we listen well, but fail to share our own views and concerns,” Stone said. “For example, we might be thinking, ‘Well, that’s a good idea in theory, but I’ve already tried that and it doesn’t work.’ But instead we say, “Well, we’ll see how it goes.’ And then, of course, nothing improves because we aren’t doing anything differently.”
  • Not thinking through solutions: “Sometimes we’re just not aligned with our own purposes,” Stone said. “Our goal may be to understand what’s going on with a student and to problem-solve, but we make a speech to the parent about how the child needs more supervision at home. We might think that the child does need more supervision, but a one-way speech to an over-burdened, worried parent who doesn’t feel heard is not going to move the conversation in a positive direction.”

Thinking carefully about each stage of a difficult conversation and avoiding common mistakes will not guarantee success in every conversation.

“Nothing can turn a difficult conversation into a fun, easy conversation,” Stone said. But these steps can “increase the chances that the conversation will be productive, while at the same time helping to preserve the relationship.”

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