The document outlines 5 steps for having difficult conversations: 1) Prepare by considering different perspectives; 2) Check your purpose and decide if the issue needs to be raised; 3) Start from a place of understanding different perspectives; 4) Explore all stories and perspectives; 5) Problem-solve by considering all options and standards. It provides guidance for each step, such as inquiring with open-ended questions, acknowledging feelings, and inventing options for resolution. The overall aim is to have authentic conversations that understand multiple perspectives and jointly solve problems.

1. Difficult Conversations Handouts
Greater New Orleans New Leaders
Step 1: Prepare by Walking Through the Three ConversationsStep 1: Prepare by Walking Through the Three Conversations
• Walk through the Three Conversations 1 2 3 4 5
Step 2: Check Your Purposes and Decide Whether to Raise ItStep 2: Check Your Purposes and Decide Whether to Raise It
• Check to make sure your purposes make sense
• Don’t do it on the fly
1 2 3 4 5
Step 3: Start from The Third StoryStep 3: Start from The Third Story
• Think like a mediator
• Describe the issue as the difference between your perspectives
• Describe your purposes
• Invite, don’t impose
• Make them your partner in figuring it out
• Be persistent
1 2 3 4 5
Step 4: Explore Their Story and YoursStep 4: Explore Their Story and Yours
Inquire and listen to learn
• Authentic listening
• Manage your internal voice
• Don’t make statements disguised as questions
• Don’t use questions to cross-examine
• Ask open-ended questions
• Ask for more concrete information
• Ask questions about the Three Conversations
• Make it safe for them not to answer
1 2 3 4 5
Distinguish blame from contribution 1 2 3 4 5
Embrace both stories, adopting the “And Stance” 1 2 3 4 5
Paraphrase for clarity and acknowledgment 1 2 3 4 5
Acknowledge feelings 1 2 3 4 5
Speak for yourself with clarity and power
• Feel entitled to speak
• Start with what matters most
• Say what you mean (don’t rely on subtext; avoid easing in)
• Don’t make your story simplistic
• Use the And Stance
• Don’t present your conclusions as the truth
• Share where your conclusions come from
• Don’t exaggerate with “always” and “never”: give them room to change
• Help them understand you (ask them to paraphrase back; ask how they see it differently and why)
1 2 3 4 5
Redirect the conversation 1 2 3 4 5
Name the dynamic; make the trouble explicit 1 2 3 4 5
Step 5: Problem-SolveStep 5: Problem-Solve
• Propose crafting a test
• Say what is still missing
• Say what would persuade you
• Ask what (if anything) would persuade them
• Ask their advice
• Invent options
• Ask what standards should apply; encourage mutual caretaking
1 2 3 4 5
AUTHENTIC CONVERSATION SKILLS ASSESSMENT1
On a scale of 1 to 5, with 5 being excellent, how do you rate your skills (or your peer’s if you are using this form following a role
play) in utilizing the following authentic conversation strategies?
1 Adapted from Heen, Patton, and Douglas Stone. Difficult Conversations: How to Discuss What Matters Most. New York: Penguin Press,
1999, p.244-248.

2. Difficult Conversations Handouts
Greater New Orleans New Leaders
1 Adapted from Heen, Patton, and Douglas Stone. Difficult Conversations: How to Discuss What Matters Most. New York: Penguin Press,
1999, p.244-248.
! It is the end of the first quarter of your year serving as a resident principal. You feel you are making a
difference in the resident site and your work with your team of six teachers identified for the Teacher
Improvement Project (TIPS) is started. You are also realizing how difficult and complex change is. You are
painfully aware that this may take longer than you realized and want to be sure you plan your time
strategically so the progress you identified for each teacher is made.
! Your mentor principal has charged you with planning all of the professional development for the year
and with identifying the facilitators for the sessions. The focus for the year is on increasing rigor for all
content areas. When the focus of rigor was shared with the faculty, there were several comments from
teachers stating that daily instruction is already rigorous. Although it was not stated, it became apparent to
you that many teachers are neither aware of what rigor is nor have strategies to increase rigor. There were
other comments that the students in this school are barely able to master what is taught and that to increase
the rigor will only impact students’ self concepts and cause frustration.
! You notice one teacher who arrives at professional development sessions displaying a variety of
behaviors indicating lack of interest and engagement as well as a reluctance to learn. The teacher is one of
the teachers your mentor principal and you identified for the TIPS assignment and she has several goals
requiring professional development. The teacher is Ms. Gilham and she has taught for seven years. Ms.
Gilham arrives late at profession development whether it is a full day, half day, or after school session and
arrives late to staff meetings. She is off task in the sessions and engages in side conversations or grades
paper. Her comments are skeptical or even negative and she appears to be oppositional to both the content
and skill development that is the focus for the session.
! After observing this behavior twice, you talked with Ms. Gilham. Unfortunately the conversation did
not go well. You showed frustration and connected her behavior to the goals she had for improvement in the
TIPS. You basically said that you saw little or no hope that she would meet her goals without a sincere and
obvious commitment to professional development. Ms. Gilham responded by telling you that until you
arrived in the school, she had always been considered to be an effective teacher. She ended the
conversation saying that you obviously had problems with her not jumping when you wanted her to jump
and that she found you to be contradictory in her approach to her and the messages you were giving. She
said that when you described having no hope for her growth that she found this discouraging and that the
message contradicted your other messages about believing all individuals have the potential to get smarter
and to learn. Her last comment in this conversation was that you do not understand that the students in this
school are only able to manage instruction that is at their level and that your focus on rigor only shows your
lack of experience.
What is your plan for an authentic conversation with Ms. Gilham? Use the Authentic Conversations
Preparation Form to think through the issues and what you will say.
Scenario 1 - Professional Development Woes

3. Difficult Conversations Handouts
Greater New Orleans New Leaders
1 Adapted from Heen, Patton, and Douglas Stone. Difficult Conversations: How to Discuss What Matters Most. New York: Penguin Press,
1999, p.244-248.
! You have served in the role of resident principal for four months and are beginning to understand the
culture of the school and the motivation of several individuals on the staff of your resident site. Once your
mentor principal saw the results of your culture assessment, she charged you to take the lead for the
improvement of school culture for the upcoming year. She feels that working with a team of 4-6 teachers will
enable you to grow with coaching teachers and building capacity while working on improving the school
culture will give you the perspective of the whole school which needs to be built in order to be prepared to
be a principal at the end of this year. Your focus is on building high academic standards for all students and
putting in processes and programs to prepare college and career ready students.
! You notice that one of your teachers, Shane, is seen talking with small groups of teachers in the
lounge, in the halls, and in the parking lot after professional development or staff meetings. On a few
occasions when you have approached the group, the conversation stops. There is a consistent group of
teachers that connect with Shane but recently you have noticed that he is expanding his conversations to
include others.
! Shane and you have had several discussions about whether all students can be or should be
prepared for college. Shane expressed his opinions that for many students college is not the right direction
or a possibility. He gives examples of several parents in the community who do not aspire for their children
to attend college and want them to go into the military or assume a role in the family business. Shane
frequently refers to his cousin who did not attend college and has his own plumbing company. Shane
appears to be quite resentful of his cousin when he states that his cousin makes more money than Shane
does as a college graduate employed as a teacher. Your response to Shane has been to ignore his
comments but you think a lot about what you should say to him.
! Your mentor principal attended a conference out of state this past week. One evening during the
week when your mentor principal was at the conference, you got a note that there are a group of teachers
who wish to meet with you the next day to share their concerns about the direction you were taking with
improving school culture and several of the changes you have initiated. Shane is one of the teachers. You
call your mentor principal and she advises you to meet with the group to learn their concerns.
! You schedule the meeting for the next day. In the meeting, you are surprised with the intensity and
the tone of the meeting. The other four teachers do all of the talking while Shane says nothing. You feel
confident that Shane has recruited the other teachers into these viewpoints and have coached them on
what to say as Shane has expressed the same things in individual conversations with you. You decide that it
is important to listen to the group but that Shane needs to be the focus of your upcoming conversations.
What is your plan for an authentic conversation with Shane? Use the Authentic Conversations
Preparation Form to think through the issues and what you will say.
Scenario 2 - Come Join My Team

4. Difficult Conversations Handouts
Greater New Orleans New Leaders
1 Adapted from Heen, Patton, and Douglas Stone. Difficult Conversations: How to Discuss What Matters Most. New York: Penguin Press,
1999, p.244-248.
! The first few months as a resident principal were challenging but productive. You learned to
recognize that there are individuals who are never satisfied. There is one teacher, Mr. Sullivan, who is
causing you great concern. Whenever ideas are presented by others or by you, he finds fault with
everything. No matter how promising the initiatives are for students, he only sees the flaws. When you offer
support and incentives to encourage staff buy-in, he makes comments that this is not enough and that you
do not know how to show appreciation to professionals. Whenever issues come up, he consistently blames
others including other staff members, the students, the parents and of course you. He frequently has
difficulty seeing his role in making an initiative or a situation successful. You notice a pattern when he brings
up issues. He brings up multiple issues, issues from the past, or issues outside of his ability to control.
! In the last staff meeting, you publicly asked Mr. Sullivan to try to be more positive with his comments.
You noticed that the room became very quiet and that everyone seemed to be watching you and Mr.
Sullivan. He did not respond to your request but became silent for the rest of the meeting. After the meeting,
several of Mr. Sullivan’s friends huddled with him in the teacher’s lounge.
! You are concerned that Mr. Sullivan will alienate other staff members and discredit you as the leader
creating problems with your relationships with many members of the staff. You realize that an area of growth
for you is learning how to shift the negative and resistant thinking of others. You are also concerned about
your becoming less tolerant and patient with Mr. Sullivan.
What is your plan for an authentic conversation with Ms. Sullivan? Use the Authentic Conversations
Preparation Form to think through the issues and what you will say.
Scenario 3 - Never Satisfied