By Katherine Moncure Stuart
President, The Education Group
This is the first in a series on Having Tough Conversations by The Education Group.
For independent school leaders, especially a head of school, having challenging conversations about complex issues is a very big part of the job. No one likes to have tough conversations, at work or at home.
As an independent school consultant for almost two decades and now, as president of The Education Group (TEG), a national search and consulting firm, I understand that having tough conversations rarely gets any easier. But I have seen first-hand what happens when school leaders and search candidates avoid these conversations. Only through challenging discussions can schools peel back the layers to get to what matters most.
A key point for those of us who have chosen the education profession: Having tough conversations does not mean sacrificing our kindness. We are in the education arena because we care about people and community. Tough conversations help people – students, parents, faculty, board members, heads of school – improve so schools can improve.
Tackling Challenging Conversations During a Head of School Search
Creating a successful search process has many elements but none is more critical to the process of recruiting a new head of school than ensuring that the board of trustees, search committee, search consultant and candidates are able to navigate candid, difficult conversations. Doing so paves the way for the best outcome of your search: a new head of school that has a clear, honest understanding of your school’s strengths and weaknesses. This demands trust and transparency, which means stepping out of your comfort zone.
The search consultant must understand the intangibles that a school might have and its approach to and aspirations for some of the more complex issues that schools face today. Boards and search committees should be honest about how the school has successfully and not-so-successfully navigated issues. These include everything from the school’s culture of community and important discussion on diversity, equity, and inclusion to how the school handles any concern by students, parents, alumni, faculty, and staff.
Issues that the school leadership might not view as complex should be discussed with the search consultant.
Talk about your school’s communication of and community reaction to any pandemic issues from remote learning, testing, masking, etc.
Discuss the role of the honor code at your school, on paper and in practice.
Dig deep and share recent ripples in your community perhaps caused by smaller issues, such as a recent mascot change or shift in parent association governance. What’s at the root of that ripple? Was it solved? If so, successfully? What were the outcomes?
The more the search consultant understands the complexities of a school's culture, policies, and community, the better they can develop a list of candidates best suited to lead a school. Not having tough conversations early in the search process and with candidates may result in a poor appointment for a school and its incoming new head of school. The best hire for a school’s top leader is one fully versed on the opportunities and challenges that lie ahead, with a deep understanding of the school’s history, approach, and aspirations.
Helping a New Head of School Navigate Tough Conversations
Congratulations! Your school has conducted a thorough search for a new head, a process that included an honest assessment of how your school has tackled complex conversations and areas in which it can grow. You’ve found a great new head, and it’s time to move on from tough conversations, right?
Hardly. Ask any head of school (and I am married to one), having tough conversations every day is part of the job. Like any leadership skill, it is a learned one. Practice won’t make perfect because there is no set of conversational phrases that will work for every challenging conversation, but there are ways a new head of school can hone their skills.
This is where a seasoned executive coach is an invaluable resource, especially one who has led a school. The Education Group coaches are former heads of school and can advise a new head on how to handle tough conversations. Giving a new head the gift of coaching offers an unbiased mentor who can address issues well within their wheelhouse of leadership.
Read more on how coaching helps a new head of school and a school.
Yes, coaches can help a head of school develop key skills – listening with empathy and patience, being direct and clear – but they also can help leaders feel more comfortable out of their comfort zone. This is where most heads of school will operate, even with careful planning. The nature of the job is the constant, unplanned knocks on the office door.
Coaches can talk a new head of school and other school leaders off the ledge by removing emotions and working through a solution. They are a calming third party, experienced in seeing all the different angles and having a seasoned grasp of the nuances of independent school governance.
Being a head of school is lonely. Often, a head of school is alone when having tough conversations. There may be others in the room, but the emotional weight and institutional responsibility for the conversation lie with the head of school. A coach offers expert guidance, a seasoned perspective, and a much-needed pep talk for handling a challenge in a human-centered, mission-driven way.
Understanding a New Head of School’s Leadership Wheel
The best leaders have good self-awareness. Having a full, honest assessment of one’ strengths and weaknesses as a leader is one of the first things a new head of school should do. At The Education Group, our coaches use a variety of tools to assess and understand the new head of school. This is essential for leadership growth, even for experienced heads of school.
Assessing your leadership skills and identifying areas to work on isn’t just for new heads of school. About half of TEG coaching clients are experienced heads who want to continue to grow as a leader. Honest skill assessment is the road map for effective coaching. This immediately helps both coach and head of school identify potential blind spots during tough conversations.
A consultant can help a new head of school develop what best-selling author Kim Scott calls “radical candor” in one of her books. She coined the phrase after lessons she learned as a Google and Apple executive. Her advice: “Never dodge a difficult conversation…avoid any hint of superiority or judgment….skip the long wind-up….be kind and clear.”
There is, of course, more to leading during a challenging time or conversation, but when schools choose to have tough conversations at the beginning of a search, they are modeling for a new head of school that honest conversations based in trust and mission are the way forward. Equally as impactful, when a board provides a new head of school (or another leader who needs it) the gift of an experienced coach to hone this skill, the better the school’s culture becomes and the greater the school’s strides forward are.
Connect with a TEG coach today. 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.
What is your best advice for handling tough conversations at an independent school? Chime in on the conversation!