Know What You Want from a Difficult Conversation

Summerconf_logo_100x98As a teacher who moved into the role of an assistant principal and then acting principal, author Robyn Jackson knows a few things about challenging conversations with educators. During her “Strategic Conversations for Instructional Leaders” session at ASCD Summer Conference, Jackson evoked personal lessons she’s gleaned from uncomfortable conversations inside the school building.

After learning from some hard knocks, Jackson wants educators–specifically administrators–to realize that difficult conversations can be conducted strategically, with a purpose and desired outcome. It’s not always easy, but if administrators take the time for proper preparation and execution, Jackson guarantees it will be one of the best skills in their leadership toolbox. Jackson introduced her formula for developing targeted, individualized conversations to engage teachers as partners and create joint ownership over problems and solutions.

“When having strategic conversations with teachers, plan a series of interactions rather than just one,” said Jackson. She introduced four types of conversations to have with teachers:

  • Reflective: Help teachers make connections between their attitudes and approach and student achievement.
  • Facilitative: Help teachers make commitments to improve their instructional practice.
  • Coaching: Help teachers make corrections to their teaching behaviors to improve student achievement.
  • Directive: Help teachers make changes in their teaching behaviors that will improve student achievement.

Each type of conversation has a precise outcome, which can help administrators stick to the goal of a conversation. Although Jackson believes administrators can layer types during one conversation, the administrator should always know what he or she wants from the conversation. So instead of trying to go from a reflective conversation to a directive conversation during one sit-down, Jackson suggests scheduling a succession of different conversations that build into an overall goal.

Jackson realizes that these conversations could easily be ignored, but that leaders are not in the position to ignore painful tasks. “At some point, I had to become comfortable with being uncomfortable.” Her ultimate reward was gaining trust with her teaching staff and tapping into shared knowledge and expertise to create greater team building inside the school.

How do you deal with difficult conversations?


  1. Having been an administrator and math coach, I agree with what Jackson says. My first year as a principal was when I first worked with Cognitive Coaching; the skills I learned through that training enabled me to carry on the kinds of conversations Jackson talks about. The Directive type, of course, is the responsibility of the administrator, not a coach. In my experience only having the skills of coaching enables an administrator to push through the discomfort of difficult conversations. I believe these skills should be mandatory training for all administrators.

  2. I tend to focus on the reflective conversations. I think it is vital that teachers work to improve self awareness. A teacher that can readily evaluate his or her own performance is more likely to work cooperatively with a coach or administrator to improve student learning

  3. As a math coach I try to be facilitative- by asking teachers what they think stands in the way of stucent achievement- directly from the classroom. Often they pause because they want to blame outside factors. I tell them we can only improve what happens here. Then they become reflective and we begin. Focusing on student work eliminates the threat and anything that might be considered directive. We focus on how the skills they teach in 3/4 grade is such a foundation to student success later, ike in algebra. I have found elementary teachers tobe in awe of how the basic algorithms they teach are so important and directly linked to agebra. Best part is they are all so receptive to learning the math themselves! Then I help them write good questions and tasks to use in class and next we focus on the student work that resulted. I love my job!

  4. I wholeheartedly agree with Ms Jackson’s perspective of engaging teachers as partners and creating joint ownership. As a “traveling” math coach I serve under many different administrators and administrative teams. Leaders that have some training or awareness of the coaching skills needed to plan and carry out this type of strategic conversation are always miles ahead of those who don’t.

  5. I often find that administrators make some drastic assumptions. One such is assuming that teachers know what good teaching looks like, and when this does not occur in their classroom, we often assume they are unable to teach effectively. Remember, coaches and administrators come from the fortunate perspective of being able to observe many teach. This multi-class experience helps us recognize teaching success and areas in need. Our teachers do not usually get this chance. Explain and dialogue about effective teaching practices, and have those tough conversations, but also make sure teachers see and experience effective practices with students involved. Participation goes a long way towards discovering potential.

  6. As a coach I use many of the skills to relate to teachers that I used as a classroom teacher with my students and parents. I reflect before I speak and then start out with a positive to engage in conversation. I want the teacher to be in an emotional state that is relaxed rather than tense. I like to ask questions to give the authority to the teacher first and then speak to the situation always with students achievement as the goal.

  7. Having difficult conversations is part of an administrators job and although I agree with the article, I didn’t see anything regarding listening. Many times educators do not have great communication skills and have a hard time getting to the real issue of what brings on this difficult situation. I feel that often times people are brought into this role of principal via different vehicles and training is often time put to the side. Administration should be given the opportunity to learn about communication and people skills.

  8. I’ve gone from classroom teacher to coach and now I am returning to the classroom. I’ve found the coaching PD (especially that on conversation and questioning skills) very valuable. As an administrator, you have an opportunity to create time for rich conversation. It is very difficult to take time for courageous conversation with all the plates we currently spin. Building discussion time into the day for Professional Learning Communities (PLCs) is a great way to encourage staff to share. Guided by an agenda and an overall vision to improve student achievement—great things will happen. Just a little food for thought…


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