Head of School

Trusted Tips from Heads of School on Having Tough Conversations

By The Education Group Consultants and Coaches

This is the third in a series on “Having Tough Conversations” by The Education Group.  

Having tough conversations comes with the territory for heads of school. New heads of school quickly learn that speaking honestly with their school’s constituents about challenging topics isn’t in the “other duties as assigned” category. It's one of the main responsibilities of a head of school.

This is not something that everyone does well, even seasoned heads of school. There are tools and techniques that make tough conversations more productive. If done well and strategically, these discussions can move a school forward.

Almost all of our consultants and coaches have spent decades as a head of school. They have heard it all, seen it all, and have talked to their school communities about it all. Here are our tried-and-true tips for having tough discussions – and for turning most of these conversations into opportunities.

First, be a visible, open, and available head of school. 

Projecting care and concern goes a long way toward setting the right tone for even the most challenging conversations. Welcoming engagement, mastering the art of the cameo appearance, being friendly, and demonstrating interest in the well-being of others have great value and can improve your ability to manage tough conversations effectively. 

How the conversation is conducted can be just as important as the content of the discussion. Avoid fighting battles via email and set a proper tone from the start. Email is probably most effective for exchanging basic information like scheduling matters, statements of policy, or just greetings and ways of sharing school news or staying in touch. 

Emails can also initiate conversations that would work better by person-to-person or even face-to-face contact. Emails, though, allow for way-too-easy escalation of anxieties or concerns and don't always maintain the right level of decorum or civility. The head of school can nip this in the bud early on and request person-to-person contact when it looks as though the initial email exchange has the potential for a conversation going sour.

Be proactive in educating people about school basics. Often, complaints are misunderstandings or are a result of a lack of information. For instance, a room parent who oversteps their bounds may create conflict with the division head or lead teacher. To avoid this, conduct a thorough room parent orientation at the beginning of the year where roles and expectations are clearly laid out. Similarly, a new parent orientation early in the year on your school’s mission, core values, and history can build a valuable context for understanding school policy and priorities down the road. Doing some of this even earlier during the admission process might be even better! Helping constituents understand roles and expectations in advance is a responsibility of school leadership.

Before you schedule any meeting, consider the timing.   

Timing is a challenge to having difficult conversations. Sometimes, there is a benefit to letting an emotional situation cool down, to allow emotions to settle a bit before having a tough chat. However, this cannot be confused with "kicking the can down the road" and avoiding a difficult conversation. After the initial cooling-off period, time doesn't usually improve contentious situations. One solution is to respond immediately with an offer to meet in a couple of days. That addresses the need to make contact without forcing the meeting prematurely.

You cannot afford to have parents or employees be able to say that they contacted you about an issue and you didn't respond promptly. Our consultants and former heads have "refereed" parent/faculty confrontations where the faculty member was absolutely in the right and deserved to be supported, only to have the parent counter that s/he had emailed twice and left a voicemail, none of which received responses. The issue then moved from whatever the initial problem was to one of a failure to communicate.

PRE-MEETING PLANNING

Avoid deciding on an outcome before the meeting. 

As head of school, part of your job is to be neutral before the meeting. If the person you are meeting with has a history of an explosive behavior disorder, ask your school security to be in the hall within earshot of the meeting. No one is allowed to become physical during a meeting. If it occurs, stop the meeting and leave the room.

Should you conduct a meeting solo? 

Deciding whether or not to have a colleague in the room requires some thought. Having a second set of ears (and eyes) is beneficial to debrief conversation later. In the case of a family, the presence of a student's advisor or trusted division head or dean can provide a comfort level that meeting alone with the head of school might not. 

In the case of a personnel decision, it is prudent to have another person, perhaps the human resources professional or school attorney, present to clarify any misunderstandings or misrepresentations later on. However, in some sensitive cases, having a second person is not beneficial, especially if the individual can feel that the administration is against them. You can always ask someone to join you during the meeting.

If the person you meet with is a parent who brings along anyone other than their spouse or partner, refuse to allow the person to join the meeting. If this means postponing the meeting, do it. If the person is divorced, agree to meet with an additional family member who you know.

Create a neutral space.

A neutral space, such as a conference room, can create a sense of a "level playing field" for employees, parents, and students. Talking to someone behind your desk about tough issues makes it uncomfortable for both parties. 


MEETING ETIQUETTE FOR TOUGH CONVERSATIONS

Start the meeting the right way. 

Always start by asking the individual if they intend to record the meeting. If they say yes, you can either stop the meeting or get out your phone and record the meeting, too.

Tell the person you meet with how much time you have allocated for the meeting. If you have an assistant, be sure they know that if you are not back in your office 15 minutes after the allotted time, he or she should come to the meeting room door and remind you that you are needed elsewhere. 

If the meeting is to inform the person of your decision, start by saying something like, "We are meeting today to ..." Give a short recap of what you know and areas of the handbook (or other relevant resource) that might apply, then calmly share your decision. 

Keep the temperature down. 

Allow the other person to talk and do not interrupt. As long as the person/people who are upset don't get to control the agenda completely, there is benefit in letting them express themselves first while listening empathetically. There will be time later to clarify details that they have wrong, but letting them vent their emotions and share their perception of the problem sometimes defuses the situation.

Do not take "blaming" personally. If you are speaking to a parent, remember that when the topic is their child, every parent is capable of being a lunatic from time to time.  

Avoid being confrontational, even if the other person wants it that way. Stiff-arming a parent with counter threats like “your position is contrary to school policy” or “you have no business saying this” (while they may be true!) leaves no room for understanding and discourse and will actually slam the door shut and get hackles up. The head of school should take the high road and be the voice of reason and calm to give the conversation a chance.

Remember: You may be talking to a person who spends their day making final decisions, so don't be surprised if the person wants to argue your decision. If so, say something like, "I am sorry, but I listened to you at our meeting. I carefully considered the options, and this is my final decision.”

Listen and be respectful, no matter what. 

You are the head of school: Be kind and speak in a calm, pleasant voice throughout the meeting.  There is no reason to be anxious, worried, or angry when you know you have the final say. Take a few notes if needed, and never lose your temper! 

Listen intently. Listening involves inviting feedback and letting the person talk. It means acknowledging their concerns and anxieties and being as empathetic as possible. Repeat for the person what you hear them. Say “I just want to be sure that I understand what you’re saying…” In short, find a way to help the person feel heard and valued.

Listen for signals about the real issue. Too often, we dismiss the person and the concern because it seems relatively minor or trivial - a dress code matter or the quality of the hot lunch program, for example - when what may be driving the complaint is much deeper or more fundamental than that. It could have to do with how the school communicates with its parents or a basic misunderstanding of the school’s core values or traditions. Identifying and focusing on the central point can make a huge difference in effectively addressing a concern.

Find common ground and a constructive path forward. Without compromising what the school fundamentally believes or requires, try to find areas of agreement, perhaps about the mission or core values or the good things that are apparent in a program or in a student’s progress, for example. Parties to the conversation might ask themselves, given what is good and valued at the school, is there room for compromise or a phased-in solution? Is there a reasonable path forward? Even doing a balance sheet, weighing what’s good and right about the school against the negatives, can have a calming effect and make some resolution of the complaint possible.

Ending the meeting 

Before you end the meeting, repeat what you heard and ask for clarification where needed. Avoid adding your opinion or statements like "I know how you feel," "A similar thing happened to me once," or "This will be fine." Such statements may make the person feel that they have been pacified. 

A generally constructive dialogue can sometimes end with the sides agreeing to disagree if there is room for this within the bounds of school policy and expected behavior. Sometimes, weighing what the school values or expects against the parents’ goals or expectations clarifies that the school is no longer a good fit for the family. No school can be everything to all people. In situations like this, suggesting a separation and even helping assess other school options is not inappropriate. 

There may come a time when a parent or staff member engages in abusive language or inappropriate behavior, even after a head of school’s best efforts to maintain a civil tone. That’s where respectfully ending the meeting or conversation with “we can’t continue this conversation…” is appropriate. 

Ask for time to consider what you have heard and so you can check on areas needed for more information. Give the person a date when you will get back to them.

Immediately following the meeting, write down what you remember, what you were told and requests for action. In addition, analyze the meeting. For example, were there implications for improving the school handbook?

Be timely with your response. You can call or have another meeting. Decisions about a conflict should not be sent by email or text. 

Consider the other person when emotions are at stake.

It is never easy as both sides of those involved in such situations feel ownership of their feelings and positions. I believe active listening is the most successful characteristic of a person involved in a conversation that may involve conflict, potential personal hurt, and future ramifications of the subject in question. 

There are no guarantees in totally resolving issues involving another person or group's feelings, opinions, etc. Listening and offering respectful and thoughtful feedback may diminish the intensity of a difficult conversation/situation, thus allowing for more productive interaction. If a person who has a different point of view feels listened to, no matter the circumstance or subject, at least a more positive dialogue results. 


Meet The Education Group team.

Need more help with tough conversations? Check out TEG’s other posts in this series:

How can TEG’s Executive Coaching program help you better navigate leadership challenges? Contact Katherine Moncure Stuart, TEG President, at katherine@educationgroup.com.

At The Education Group, we are experts in guiding schools through searches for heads of school and other top positions. Our coaches and consultants are experienced, former school leaders who tailor searches, coaching, and consulting to your school’s needs and goals.

Why a New Head and School Need Executive Coaching

Leadership transition at independent schools is both art and science, systematic and organic. When a board of trustees approaches a newly appointed head of school’s first 18 months with the same strategy and purpose as it did for the search process, the head and the school are positioned for success.