There were many aspects of being a school leader that I loved but one thing I loathed more than anything was initiating a hard conversation. I wore many hats in my role, but one of the biggest parts of my job was being the Official Haver of Hard Conversations.


“You have been 10 minutes late two days in a row. What’s going on?”


“I have heard you raising your voice in the classroom several times this week. I’m concerned for you and for the children. Let’s talk about the support you need.”


“I notice that you are not wearing a bra today and I can see your nipples through your shirt. Here is a hoodie for you to borrow for today and a fresh copy of the dress code. I expect your attire to be more professional tomorrow.”


Yes, these are all actual conversations I have had with teachers.


While I initially dreaded these talks about policy, protocol, and personal growth, I eventually began to appreciate them. There is great power in just “going there” and having a hard conversation about something that is a problem. I found that people were often relieved and grateful at the end of these talks. Once I learned how to have a hard conversation, my leadership was elevated to a new level.


I also realized that people respected me for being willing to do this hard work. There are many ways to have a tough conversation without it becoming an emotional disaster. Here are some of the strategies I used along the way.


Prevention is the Best Medicine


If you can, the best thing to do is build a school culture in which hard conversations don’t have to be had very often. Some of these conversations are inevitable because a group of people are existing in the same space and that will always lead to challenges. However, there is a lot that you can do as a leader to make the hard conversations few and far between.


Build an environment where context is part of the culture. The universe abhors a vacuum. If you don’t give information to your staff, they will fill up that vacuum with their own stories about what is going on at the school. The stories they create are likely to not only be inaccurate, but probably make the situation out to be worse than it actually is. Give as much information and context as you can so that the staff is not left with a vacuum to fill. The truth is so much easier to work with.


Have regular contact and communication plans. If your school has more than two classrooms, you should be sending a weekly update to your staff. Build a template with the important things you want to touch on every week and make it a point to send it religiously. Staff will know it is coming and will look for the information they seek there.


Email communication is great, but you also need to have frequent personal contact with your staff too. Set up regular office hours or another system that clearly shows staff that you are available to connect with them individually if they need it.


Model professionalism by owning your stuff. If you want your staff to trust you and be open to your feedback, you have to be a person worthy of respect. That doesn’t mean being perfect, it means being open. Admit openly when you have made a mistake and talk about what you learned from it. Be genuinely open to hearing feedback from your staff. Publicly discuss what changes you are going to make in response to the feedback. Thank and give credit to staff members who are willing to call you out on your stuff respectfully. Let down your defenses and provide context on how you arrived at certain decisions.


Having a Hard Conversation


While there is a lot you can do to prevent the need for constant hard conversations, you must also accept that sometimes they have to happen. As the leader, it is your responsibility to embrace this part of your role and facilitate the conversations that need to happen.


Here are some of the ways that I have learned to successfully initiate hard conversations:


Be calm and direct. You know that old advice saying to deliver hard news by saying something super nice right before and right after you say the hard thing? GARBAGE. This is emotionally manipulative and confusing to the recipient. They often don’t understand the seriousness of a situation when the information is “sandwiched” like this.


Be respectful and honest. Sometimes it can be hard to keep our big feelings out of these conversations. As the leader, you must do your best to avoid emotional confrontations. No matter how bad the behavior you are addressing is, this individual is still a human. The best resolutions happen when we set the way our employee makes us feel to the side and instead focus on the facts of the situation.


Mean what you say. Want to be sure that nobody at your school ever respects you? Make threats and promises and then don’t deliver on them. If you are writing up an employee and you tell them that they will be let go after the next infraction, you damn well better fire them the next time the behavior rears its ugly head.


I once fired a person for being two minutes late. No joke. She was chronically late and had been written up several times for leaving her classroom short-staffed at a busy time of day. At the last meeting I told her, “Not even two minutes.” Three days later she rolled in two minutes after her shift started and I fired her on the spot.


There is never a convenient time to fire or discipline a teacher, you just have to commit to leading with integrity and holding people accountable to your reasonable expectations. Your staff will respect you for being the type of leader who says exactly what you mean. They may not always agree with you, but they won’t question your integrity.

When You Have to Have a Conversation with the Whole Staff…


Sometimes big, unexpected things happen that can rock our world. When a beloved teacher suddenly quits, a grave incident occurs at the school, or a terrible rumor is spreading like wildfire, you might need to meet with the whole staff to clear the air, build context, and move forward as a community.


Here are my tips for having a hard conversation with a group:


Bring in a facilitator. Usually when meetings like this are needed, it is because trust in school leadership is low or something big and emotional has happened. An outside facilitator with no attachment to the situation is your best bet for making this conversation productive and smooth. The facilitator can set clear ground rules for respectful communication during the meeting and he or she will also be able to see the situation with clarity that those in the midst of it might not be able to.


Sit amongst the staff. As this meeting plays out, you should be sitting amongst your teachers. Equal to them. One of them. Just one part of a much bigger whole. The psychological power of this is immeasurable.


Set your defenses aside. If this group meeting is to be effective, you must prepare yourself to be open. It is highly likely that something that triggers you emotionally will be said during the meeting. Your job is to sit with those feelings and receive the feedback with grace and gratitude. Easier said than done, I know, but if you want to re-build trust you had better be willing to hear some hard things and accept them as potentially true. It is really hard to not respect someone who is open to hearing challenging things and willing to admit their own faults.


Be open to what is said. Your staff may have ideas, perspectives, or needs you could have never imagined. Be open to what they have to say and show willingness to explore possibilities that you weren’t previously open to. In the end, you may not decide to make a change, but your staff will respect you immensely for considering their perspective and exploring new possibilities.


Want to know the secret for how I flipped my anxiety into excitement for digging into meaty, challenging conversations? I read the book Fierce Conversations by Susan Scott. This book changed my whole perspective on connecting with my staff as a leader and using direct conversation as a tool for growth in the school. I highly recommend every school leader read this book and use the tools and guidance inside. It completely changed my life as a leader.


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