Grace with Empathy: 3 Strategies To Lead Without Judgment and with Understanding

School leader, author, and keynote speaker Jessica Cabeen gives it to you straight, "Here is the deal," she says,  "when you lead with empathy: you are not always going to be liked. With that said, it isn’t acceptable to harbor resentment or bad feelings due to a past circumstance. Understanding others’ perspectives and circumstances allows you to craft communication that best meets the situation. It doesn’t mean you should worry about how they will respond or what they will say afterward behind your back."

In her book Lead With Grace, she provides frames that will empower anyone–teacher, principal, parent, or superintendent–to lead with grace. Throughout her book, you’ll read stories and strategies that will allow you to walk away with key practices and exercises that will build confidence so you can extend grace with others.

Be yourself, practice empathy for the other person in the situation, and move on rather than holding a grudge. School leaders don’t need to be liked 100 percent of the time to lead. And honestly, if you were liked 100 percent of the time, are you really leading in the way that best supports your school?

Giving feedback and making tough decisions is essential to ensuring we are all working toward a common vision and with the best supports and strategies at our fingertips. That doesn’t mean we should do it in the harshest way possible. Leading with empathy allows us to make those decisions without becoming hard, harsh people. Instead, we must listen, be patient and open to what we are communicating, and remain open to what we are receiving as well.

Here are 3 strategies for leading with grace and empathy you can implement today.

Photo credit J

 1. Lead Forward Strategy: Keep It Real

Leading with empathy and being open to what the other person is saying allows you to listen and learn in every setting and context. This requires that you stick to your authenticity and vulnerability, and continue practicing those soft skills to improve your relationships. It all starts with one simple truth: no matter the situation, be your empathetic self.

  • Be yourself. You can be in a classroom, or at the grocery store in your sweatpants, no makeup, and three-day hair. It doesn’t mean you get to change who you are or your attitude toward your staff or students. Don’t question the decisions you’ve recently made, regardless of who you’re facing. No matter your location or looks, be yourself. Say hi and ask how the recent assessment went or how an older sibling is doing. 
  • Remember to be a person first, a title second. When making tough decisions that impact personal relationships, that thick skin has to shed a few layers. Be sensitive to another after a difficult conversation, and don’t start to isolate yourself or others. While these conversations are uncomfortable, walking away or avoiding the other person afterward means the message is lost. In short, you’re making it personal rather than professional—and that’s not empathy. Instead, amend the relationship however you can, and go out of your way to make sure the person knows that you’ve moved past the unpleasantness. You will improve your relationships and prove yourself as a leader, just by practicing those small, authentic kindnesses. 
  • Avoid awkward silence at all costs. The other person is probably just waiting for you to make the first move, and as the leader, it’s part of your job. Practice empathy here too, and realize that you can’t stand back and wait for them to come to you, no matter how much you might want to. If you’re in a particularly difficult situation, a script might help here as well. Prepare several pieces of small talk, then seek the person out, smile, wave, and start a conversation with them.

2. Show Up, Title Optional

Some of my best moments in leadership happened when I showed up for something without my title, name tag, or business card. Caring for those you serve sometimes means just showing up as yourself, listening, and staying still in their presence. 

  • Listen. What is really going on? Don’t make assumptions from the narrative you hear from others. Ask questions to get the big picture of what has happened, and what the people impacted might need. 
  • Learn. We all experience grief differently. If you are spending time with a family during a difficult circumstance, don’t assume that they experience loss in the same way you would. When you are entering into a situation of deep sadness for others, just show up without judgment. My dear friend and mentor knew right where to find me hours after we learned some devastating news. I had gone into work. While some might judge my decision to complete paperwork and finish emails during the deepest pit of my adult life, my friend knew that in that moment, I needed to move forward and not fall into a deep, dark depression. He sat with me, listened to me, and had no judgment about the way I was dealing with my grief (and state of denial). Nine years later, I can’t quite remember what he said to me, but I do remember that he stayed with me through the darkness. 
  • Care. As you care for others in your school community, do not be afraid to demonstrate care in your own authentic way. Maybe it is sitting with the children while the family completes paperwork, attending a concert with a family who recently lost a mother or father, or making that hot dish for a teacher who is grieving a significant loss. As long as you show up authentically, the other person will see your care the way you mean for them to see it.

3. Show Empathy in the Hiring Process

Listening and empathy aren’t always about the actual action. They also include setting up the space to make it comfortable for the other person to speak.

  • Optimize the physical space. Review the location of the interview. What does the room say about the school? Are you seeking a candidate who is excited about learning and building relationships, and does your space reflect that? I have asked people to come in and sit in the room as if they were being interviewed, and then asked them for feedback on the experience based on room aesthetics. Small details can make a big impact on how people see you and the school, and how comfortable they are in the meeting itself. 
  • Plan ahead for a smooth process. How are you setting the stage for a successful experience for the candidate? Send questions ahead of time, including a link to a video introducing the school. Test any tech equipment in advance to ensure the Google Hangout, Skype, or Zoom session goes off without a glitch. Investing this effort on the front end ensures a successful interview for all parties, and allows everyone to feel part of a collaborative effort.
  • Remember the person behind the position. When was the last time you went through an interview? Do you remember how you felt and what you were thinking before, during, and after? Practice empathy for others and take time as a team to discuss how to make this experience positive for all parties.


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