I had many, many years of those sleepless nights myself.

There is a certain mix of energy, anxiety, and excitement that keeps you awake regardless of how much you need the rest . There were years where I was frustrated seeing the clock at 2am, and other years where I did a better job of accepting that a sleepless night was inevitable .

This year, though, I’ve been wondering more about what we can learn from this phenomenon.

It’s worth pausing a moment to think about why teachers, principals, and school heads cannot sleep the night before school starts.

Yes, there’s some level of basic nerves. A new year is starting. We’ve prepared for some time. And we are both excited about the prospect of things going very well and nervous about what could go wrong, or what we might have forgotten to prepare.

But if that was all there was to it, the feeling would fade over time and at some point veteran heads would sleep soundly. There must be something more at play.

I believe that the root of what keeps us awake the night before school is a deep, sometimes even subconscious, awareness of the magnitude of what we are about to begin.

The school leaders I work with tell me that they chose this profession because it called them. It might have been the desire to care for the youngest and most vulnerable children in our schools, the hope of improving some of the flaws in our educational systems, or the goal of connecting teenagers with the beauty of knowledge and critical thinking. Whatever it was, there was a spark there which drew us to this work, and kept us here for years and even decades.

As we move through the school year, though, that spark can sometimes get buried under the day-in day-out work of managing stakeholders, navigating conflicts, and pushing forward school improvement efforts. The work gets done, often quite successfully, but our connection to what originally called us to this work can fade into the background.

During the summer we get the chance to take a step back, reflect, and plan for the coming year. We reconnect with our leadership teams and dream about the coming year. As we do so, the spark often starts to rekindle, yet not fully.

Because as wonderful as summer can be, one thing is still missing…

It is precisely when this final element is added back into the mix; that is, when the students finally return to the building, that something in us is re-awakened. Of course, I mean that metaphorically, but on the night before school it is also true quite literally.

The night before school is the one moment in the year when the power of the work we have chosen comes rushing back to us. While the students have not yet walked through the doors, we can sense their return. And with them, the power of what originally called us to this work comes back as well.

I used to think of those hours as something to endure, a problem of nerves to be managed or breathed through until sleep finally arrived. This year I am less sure.

Maybe sleeplessness is not related to the pressure of the work, but to the fact that the spark is indeed still lit.

And so this year, rather than managing it, I am suggesting we listen to it more closely.

What is the sleeplessness telling me about why I am still doing this, all these years in?

What do I remember on this night that is in danger of fading in the months ahead?

What first lit the spark for me and how can I care for it this year?

The goal is not to sleep soundly the night before school. Quite the opposite. The goal is to stay awake to that same sense of energy long after the first day has passed.

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I always learned that senior leaders need to respect this hierarchy. There’s nothing more disempowering for a middle manager than to have their own boss regularly intervene with frontline staff.

While I continue to believe this, there’s an important counterpoint that is worth some thought, and that is the idea of “skip level” meetings.

Skip level meetings are where you meet with your direct report’s staff team, without the direct report present. If you’re a Head of School or CEO, that might mean meeting with the business office staff without the CFO in the room.

What is the argument for holding these meetings?

As Kim Scott lays it out in Radical Candor:

1. Our job as supervisors is to offer rich, meaningful feedback that helps our direct reports grow.

2. Meaningful feedback requires real data.

3. Our direct reports’ own teams are a crucial source for data. One that goes beyond quantitative metrics and self-reported progress.

Based on this argument, Scott highlights that “the intent of these sessions is to be supportive of the managers who report to you, not to undermine them.”

While acknowledging the dangers involved, Scott argues that the benefits of being able to give meaningful feedback to your direct reports makes the skip level meeting worth the risk.

So how can we hold skip-levels that are actually supportive of our direct reports?

It starts with a caring and respectful relationship with our direct report. If we hold ourselves to that kind of relationship, we will never meet with someone’s team without first asking for their permission to do so. Ideally it will then be the manager themselves who explains to their staff what the meeting is and why it is happening, framing it as part of a joint effort for everyone in the organization to grow.

Of course, that framing can only happen if it is authentic. A skip level should not be conducted as an investigation to catch poor performers. In fact, we should not even consider holding skip level meetings unless we already have the kind of relationship that includes regular direct and honest feedback.

Inside the skip level meeting itself, it must be clear to everyone that we are here in order to help this manager grow, since the team sees things that a single supervisor cannot. We are not there to collect grievances but rather to learn, and we must continually reinforce the importance of that learning process in everything that we do. Scott actually suggests taking notes on a screen that everyone can see during the meeting, so that participants can weigh in and correct us when we get something wrong.

The final piece is how we share what we have learned with our direct report. Here too, the key is to focus not on what person a, b, or c might think of their manager. Rather, we convey what we learned from this meeting that can help the manager grow in the future. What was surprising about the feedback? What new insights have emerged?

Put differently, a skip level meeting needs to be seen by all involved as a formative rather than a summative assessment process. Popham defined formative assessment as “a planned process in which assessment-elicited evidence of students’ status is used by teachers to adjust their ongoing instructional procedures or by students to adjust their current learning tactics.” Here too, the goal of the skip level meeting is to help leaders adjust how they guide, and staff shape how they pursue, growth and learning.

Even with all of Scott’s careful caveats in place, I’m honestly not sure whether most of us should be instituting skip level meetings in our organizations. Nonetheless, I believe the concept is worth thinking through, because it forces us to confront whether our organization in general, and our feedback processes in particular, are aimed at enhancing learning or simply at producing evaluations.

If the former, then we can explore many creative ways to get the data we and our staff need to enhance growth and learning. If the latter, then maybe it is time to rethink more than just which meetings we hold.

Don’t miss our recent podcast episodes Lessons from Launching a New School Abroad with Rabbi Rick Schindelheim | Spotify | Apple | YouTube

Wherever we are in our tenure as school leaders, though, that opening meeting can be an intimidating task. Two school heads I work with shared the challenge with me from opposite perspectives.

One head is starting his first year in a new school. He wants to set out an inspirational vision and build the faculty’s trust and confidence in his leadership, but he knows that if he promises too much in this first year he is likely to disappoint down the road - or to generate skepticism just as the year is beginning .

The other head is starting year five in her school. Her tenure has been successful overall, but last year the school faced some significant governance, enrollment, and financial challenges. She wants to start this year on the right foot, and she needs to show the faculty that she will be able to lead in this changing environment , but why should they believe her?

This opening meeting quandary is a nutshell version of the core issue we face as leaders: we want, and need, to inspire our staff with an uplifting vision - without being overly optimistic or out of touch with the reality on the ground.

So how can we present a vision for growth that lands as a credible plan rather than aspirational fluff?

1. First name the challenges honestly. Nothing kills believability faster than pretending the past was already perfect. Start by naming, specifically and without defensiveness, what didn’t work last year and what challenges are still present this year. Demonstrating that we understand what went wrong, and how that negatively impacted our people, shows that we are aware of the realities and helps us earn the trust of the staff. Hiding or glossing over the negative, on the other hand, creates a sense that we are either oblivious or just don’t care about our people.

2. Frame the plan as a hypothesis, not a promise. Instead of “this year we will raise engagement,” try “here’s our plan for how we will move the needle, and here’s how we’ll know if we’re right.” Leaders who present in this way are not lowering the bar, they’re showing that they are planning realistically rather than declaring victory in August. Eric Reis (Lean Startup) has shown that growth metrics work better than vanity metrics in building a company, and the same is true for engaging your staff.

3. Tie the aspiration to something concrete and near-term. A clear sign that your plan is a hypothesis rather than a dream is that you can connect it to specific actions in the near future. Talk vision, but connect the vision to 2-3 specific changes in the coming weeks. It could be a schedule change, new meeting structure, coaching or PD model, but it needs to be concrete, coming soon, and a reasonable ask of those around you. (Hence 2-3 changes, not 10!)

4. Implicate yourself, not just them. As leaders, we need to be clear about what we plan to do differently this year - not just what we are asking others to do differently. Here again, we need to be careful to outline realistic steps rather than empty promises. What are we going to change in our own behavior as leaders that will support the vision we are outlining for our staff? If there’s something that has been difficult for us in the past, whether it’s showing up on time for meetings, spending enough time in classrooms, or communicating effectively with all staff, we should not simply assert that it will be different this year. Instead, we need to present the concrete steps we will take, and be open about how we will hold ourselves accountable.

A mentor of mine once told me that there is a fine line between a leader of the pack and someone out on a walk by themselves. If we want our staff to come with us, we need to craft a grounded vision rather than an aspirational promise.

I’ll admit that this is a lot less fun and can come out sounding less poetic. But the goal of our opening meeting, and all of our leadership, is not merely to craft a beautiful vision - it’s to galvanize those around us to take a challenging journey together.

This does not mean you shouldn’t be inspirational. Vision is necessary, and leaders need to inspire and uplift. But that inspiration needs to be both thoughtful and credible in order to be effective.

For leaders who tend towards the visionary side, consider the four tips above a helpful self-check to make sure that you are actually bringing your staff along and not just taking a stroll by yourself.

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We know that many routine meetings can be a poor use of staff time. However, we are loath to cancel these meetings because we also know that we genuinely need to get our people together. Caught between those two pulls, the status quo usually wins and we keep meeting exactly the same way we have been in the past.

The POP framework was my suggested way through that tension. The first two parts, Purpose and Outcome, suggest that the question is not whether or not to meet but, rather, for what purpose are we meeting?

If we challenge ourselves to clarify the purpose and intended outcome of each meeting, we will quickly see which meetings are worth keeping and which should be cancelled. More importantly, if we know why and to what end we hold each meeting, we will be well on our way to ensuring that the meetings we do keep are poised to be meaningful and effective.

To be clear, saying that each meeting must have a purpose does not mean that each meeting must deal with concrete or tactical issues. As I noted last time, purposes may include strategic decision making, collaborating around challenging issues, as well as cultivating team relationships, or building staff morale. The same is true for the desired outcome, which flows from each of these purposes.

Once we have decided which meetings to keep, and once we are sure about their purposes, we come to the third P, process. Process is where we make sure the way a meeting is run is aligned with what we hope to accomplish.

I saved process for its own post because it is a different kind of work. Purpose and outcome require conceptual clarity. Process is where the rubber meets the road as we challenge our deeply rooted meeting habits.

Think for a moment about how most of our team meetings run. We start with an agenda consisting of assorted items added by team members. We go around the table, people share updates, we open it up for discussion, and near the end we try to arrive at whatever decisions are necessary. The open discussion format is comfortable, and it often works just well enough to lull us into complacency. In many cases, however, it is not the best pathway to our chosen outcomes.

The secret to a great meeting is that form must follow function - or, in our case, process must be aligned with purpose.

For example, if the purpose is strategic decision making we can design a standing process around the Identify-Discuss-Solve paradigm. In this process, the meeting agenda should state that step one is to clearly define the issue at hand. This also may mean sharing background information in advance so that we can make the best use of our time in the meeting room. The meeting leader/facilitator’s role is to ensure that the discussion focuses on the crucial first step of developing a shared definition of the issue before moving on to any discussion.

Once the issue has been defined, we can move on to the discussion stage. Here too, the facilitator’s role is to ensure that the group stays in discussion mode, raising key questions, exploring multiple perspectives and pathways, and fleshing out relevant issues before moving on to adopt a specific solution. Depending on the group, we may also set a defined amount of time for the discussion, or determine that all team members must share an opinion before we move on to adopting a solution.

In the final stage of this process, we move to a solution. The most crucial aspect of this phase is stating clearly and in advance who will own the decision. The senior leader in the room needs to ensure the team understands whether this is a case of “I will decide, and I want your input” or “we will decide this together.” If the latter, the protocol needs to protect enough time for making the actual choice, rather than letting the discussion run until the meeting is over.

In my coaching, I have found that leaders who view themselves as kind and collaborative often have trouble stating clearly when they will own decisions. But what we hear from leadership teams is that they want to be heard, they want their opinion to carry weight, and at the same time, they fully accept that in some cases the senior leader will be the one making the decision based on input, rather than attempting to achieve consensus. This acceptance, however, flows much more freely when the team has clarity on who will make the final call. As a leader, it is OK to make the final decision - it is not OK to pretend something is a group call when in reality it is not.

To take another example, when the purpose of the meeting is building relationships or morale, the default discussion format serves us worst of all. A round of status reports does very little to build relationships. Instead, this kind of meeting benefits from prompts and activities that stimulate human interaction (think icebreakers, but less dorky). It may also benefit from something like the consultancy protocol, which allows a team member to share a challenging issue and receive support and guidance from the group. An effective process for this kind of meeting also requires limiting group size and picking a setting other than the conference table.

What should be clear from this brief description is that we are not assuming relationships or morale will be strengthened just because people are in a room together, we are building a process that proactively ensures it will happen.

There are many more examples to explore, but the common thread remains the same.

First we need to get clear about where we are going by identifying the purpose and outcome of each type of meeting.

Next we need to thoughtfully plan a process which can get us there.

Last but certainly not least, we have to hold ourselves accountable to actually running that process in the room, even when our old habits pull us back toward the way we have always done things.

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This is particularly true for routine meetings.

We set up a meeting because it seems like a good idea, whether it’s a leadership team, departmental, or faculty-wide group. Then we get together weekly or monthly, often without a clear idea of what exactly we are trying to accomplish.

On some level, we know that the meeting is not the best use of everyone’s time. And we might even recognize that much of what happens in the meeting could have been accomplished by email. At the same time we are reluctant to do away with the meeting because it feels like something we should do. Stuck between those two pulls, the status quo tends to win out and we just continue getting together.

I am not in favor of letting the status quo continue. But that does not mean I am telling you to cancel all of those meetings. Our reluctance to have an unproductive meeting is valid, but so is the feeling that we need to get our people together.

Instead of feeling paralyzed between those opposing pulls, we need to take the tension as a sign that we have some work to do.

Here’s where a simple concept, originally taught by Leslie Sholl Jaffe & Randy Alford at the Rockwood Leadership Institute, can be helpful.

The approach is called POP, which stands for Purpose, Outcome, and Process, and it has been applied to everything from decision-making to strategic planning. I believe it also gives us the key to navigating the meeting tension.

The summer is a great time to take stock of all of our routine meetings. In fact, I recommend creating an actual written chart for this purpose to keep ourselves disciplined.

Once we have listed out all of our key, ongoing meetings, we can carefully apply the Purpose-Outcome-Process framework.

First, we look at each individual meeting and ask what broad purpose this meeting is meant to serve. The key point here is that we need to be both clear and honest about the purposes of the meeting. What we note here must be the actual purpose(s) for which we hold this meeting, not a purpose stemming primarily from wishful thinking.

Purposes may include strategic decision making, collaborating around challenging issues, or ensuring all team members are up to date on key developments. There may also be purposes that focus more on the people than the tasks at hand, such as cultivating team relationships, or building staff morale.

The purpose is the broad, underlying reason for the meeting, and we should not ask anyone on our teams to devote their time to an ongoing meeting that does not have one. In other words, if we cannot come up with a legitimate, meaningful purpose, it’s time to consider turning that meeting into an email .

Moving along the POP framework, once we have clarified the broad purpose of the meeting, we must define the specific outcome(s) the meeting will achieve. The difference between a purpose and an outcome is that a purpose is the motivator, the reason we are having the meeting; while an outcome is what we expect to result from the meeting.

For example, if the purpose of the meeting is to discuss challenging student issues, the outcome may be updated and effective student support plans. If the purpose is cultivating team relationships, then the outcome will be more along the lines of the specific partnerships, collaborations, or forms of teamwork we expect to see.

As with purpose, if we cannot come up with reasonable and meaningful outcomes that we expect from this ongoing meeting, we may need to consider cancelling the meeting altogether.

Once we have challenged ourselves to identify both the purpose and expected outcome for each meeting on our list, a number of insights will emerge.

First, we will see which meetings may indeed be unnecessary or unjustified given a lack of purpose or outcome. Second, we may begin to see that we have multiple meetings with overlapping purposes and outcomes, and we may benefit from merging or otherwise adjusting attendance or frequency of these. Third, we may be struck by important purposes or outcomes that are absent from our list and begin to think about new frameworks we need to add to our routine.

These insights may lead us to adjust and refine which meetings we choose to continue, stop, or start in the coming year. Then, once we have our final list, it is time to get to the final P - process, which is where we make sure that the way the meeting is run matches the goals we want to achieve. That becomes a more detailed process, and it’s what we’ll deal with in next week’s post.

Don’t miss our recent podcast episodes Building a Different Kind of Jewish Day School with Rabbi Dr. Gil Perl| Spotify | Apple | YouTube

If this is not part of your leadership routine yet, I sincerely recommend that you consider incorporating it.

If it is part of your routine, you know that it is often trickier than it sounds. At the heart of the challenge lies a fundamental confusion about precisely what kinds of goals we are setting.

Take a head of school working with a high school principal for example. When they sit down for the annual goal-setting meeting, the head of school may have in mind a number of ways in which they would like to see the high school improve - teaching quality, parent communication, student engagement, etc. In the meeting, these goals for high school improvement will then be framed as performance goals for the principal.

At the same time, the head may have in mind a number of ways in which they would like to see the high school principal themself improve their professional practice, which may include how they lead meetings, supervise their staff, collaborate with the leadership team, etc. These too will be framed as performance goals for the principal.

At the end of the meeting, the principal emerges with an undifferentiated list that mixes together both school improvement and personal/professional growth goals. All the goals are important, but if we are not clear on the distinction between the two, our principal will have a much harder time achieving either set.

The first step in tackling this challenge is to explicitly distinguish between the two kinds of goals. The easiest way to do this is by dividing each goal setting meeting with a senior leader into two parts.

In the first part, we focus on the growth we hope to see in the division/department in the coming year. This can be anything from enhancing day to day routines to accomplishing special projects or remedying an ongoing problem. The director/principal is charged with achieving these goals, including marshalling whatever other staff and resources may be relevant and necessary in order to do so. While it is tempting to turn this into a laundry list of areas for improvement, we must bear in mind that a more intensive focus on a small number of priority areas will be much more effective.

At this point in the meeting, we need to pause and mark the transition before we begin our discussion of the professional growth of the director/principal themself. Goals in this second area can include anything from delegation skills to communication techniques or conscious leadership practices. The key distinction is that we are now focusing on the professional capacity and practice of the leader, rather than on the improvements in their division. The director/principal is still charged with achieving these goals, potentially with the support of a coach or other professional development resources we can provide. It is even more essential that we keep this list focused on a small number of priority areas if we want to be successful.

Distinguishing between these two kinds of goals brings a number of key insights to the forefront. First, it allows both the supervisor and the direct report to see clearly in what ways their own professional practice may need to grow in order for them to create the sought after improvement in their department. For example, if we are seeking enhanced staff coordination in the department and we also note delegation skills as a growth area for the professional, it quickly becomes clear that a change in the individual professional practice must precede the improvement on a departmental level.

Second, it enables us to apply a distinct and appropriate lens to guiding and measuring each category. For example, a departmental improvement need may have preexisted the current director’s tenure, and there may be a variety of rate-limiting factors that we need to take into account in setting appropriate and realistic expectations for growth. In these cases, the supervisor and direct report can analyze those factors together and determine a reasonable bar for success while taking the full landscape into consideration. Once the goal is set, the change plan will be focused on the system or some portion of it, including action steps that are owned by the director and by the other staff members in the department.

When it comes to individual professional growth goals, on the other hand, external factors will be less relevant in determining how we set the bar. For this category, the professional’s own capacity for growth is the rate-limiting factor. I may want them to go from 50 to 100, but if I put the bar at a height that is out of their reach I am simply setting them up for failure. In fact, what we know about human learning, at all ages, is that we make the most progress when we create an optimal degree challenge. In this case that means setting goals that are a meaningful stretch, but not out of reach.

In many ways, this is the most difficult lesson for us to learn as managers. We are usually promoted into supervisory roles precisely because we care deeply about outcomes, and that same drive tempts us to set the highest possible bar for the people we lead. But a goal that a direct report cannot reach does not motivate growth, it erodes confidence and trust.

So the next time you sit down for a goal-setting session, try splitting it in two. Spend the first part on what the department needs to get done, and the second part on how the person needs to grow to best lead it. Keep both lists short, and note explicitly when you’re moving from one to the other.

Most importantly, when you get to the second kind of goal for your direct reports, ask yourself the harder question: are you setting a bar they can actually reach, or one you just wish they could?

Don’t miss our recent podcast episodes Building a Different Kind of Jewish Day School with Rabbi Dr. Gil Perl| Spotify | Apple | YouTube

A lot of my time this summer has been devoted to helping organizations reassess their leadership structures. As part of that work, I have been analyzing org charts and doing a deep dive into more job descriptions than I care to count.

The first phase of the work is to ensure that each job description is reasonable, coherent, fit for purpose, and appropriately situated within the overall organizational structure. When we pull out a current employee’s job description, we tend to realize that what they are doing in practice is not exactly what was originally written - for good and for bad.

Many of us look at staff job descriptions only when we are in the midst of a hiring process, and that is a lost opportunity. Reflecting together on the differences between what was written and what happens in practice is a great way to recalibrate workloads and ensure that expectations are aligned between staff and supervisor.

The second phase of the work is where organizations encounter even more challenges. Beyond looking at each individual staff member’s responsibilities, we now look at how they fit together. On one level, this helps ensure that no crucial task will fall between the cracks.

On a more important level, though, we look at the jigsaw puzzle of job responsibilities alongside the org chart, in order to discern whether the staff team is structured for success in moving the organization forward. We know that clear staff role structures, which complement but do not overlap with one another, and well-understood lines of responsibility and supervision are necessary for team success. Necessary, that is, but far from sufficient.

We sometimes assume that if the org chart is drawn clearly, responsibilities delineated, and supervisors assigned, then we have done our job. If that’s all we have done, though, the team is not likely to go anywhere.

In The Advantage, Pat Lencioni underscores what goes wrong in many leadership teams. Each person in the group has been assigned responsibility for a clear area within the organization - they understand that responsibility and carry it out faithfully. They have also been asked to take part in the organization’s leadership team. When they join the leadership team, however, they often do so while still wearing the hat of the individual department head. When you gather a bunch of people wearing their own departmental hats in the room, the result is a team of leaders and not a leadership team.

To create a leadership team we need two things. First, we need each person in the room to understand that they are being asked to take on a new role, above and beyond the department or division they lead. That additional role requires them to put the good of the organization as a whole above any department. Second, we need all the people in the room to see themself as inextricably partnered with one another. Not just individual leaders within the organization, but a connected leadership team.

That is the part that can’t be found on an org chart. The chart handles the vertical relationships well enough. Combined with job descriptions, it shows who reports to whom and where one job ends and the next begins. It does not show whether the finance director and the operations director actually work as one team or as two departments each guarding their own turf.

The relationships between staff matter more than the reporting lines in determining whether the organization really moves forward. We can get the boxes and lines right and still miss what happens between them. The spaces between the boxes, the relationships team members have with one another, are what hold the leadership team and the organization together.

If you want to know what kind of team you have, watch the room when the pressure is on. When someone reports a problem in their area, a team of leaders braces: the news gets framed defensively, and everyone else leans back an inch, feeling uncomfortable about someone else’s problem. On a leadership team, often before the news is delivered, someone in the room asks “how can we help?”

The same dynamic plays out in a budget meeting when money is tight. On a team of leaders, everyone arrives convinced their own area is the essential one, and the meeting becomes competing cases for whose area should take priority. On a leadership team, a director can name which of their own priorities could wait a year if another department needs the funds more.

The distinction here is not between selfish professionals and altruistic ones, though it is often tempting to explain it that way. It’s not about the individuals at all; it’s about the relationships between them.

Redrawing an org chart is satisfying, and clear lines, roles, and structure is necessary for an organization to succeed. But when I redo a chart, I know that is really just the first step of the process. I have never drawn a line that made two colleagues trust each other, or a box that turned a set of department heads into a true team. A good chart simply clears the path for the people in the room to focus on what really matters: the way they relate to one another.

Don’t miss our recent podcast episodes Building a Different Kind of Jewish Day School with Rabbi Dr. Gil Perl| Spotify | Apple | YouTube

Fortunately, each of our jobs have their routines and seasons, including the times we get to step back and reassess the way we do things. While summers are not exactly a quiet time for school leaders, they can be a great time to review and reset many of our routines before the start of a new year.

In particular, a recent conversation got me thinking more about how our leadership routines impact our relationships.

In Deal and Peterson’s comprehensive analysis of how leaders can impact school and organizational culture, perhaps the least appreciated and most challenging is the effect we can have on relationships. Each of the relationships we build with our senior team members, staff across the school, lay leaders, parents, and students, is intrinsically important. And each of these connections produce additional ripple effects across school culture.

That ripple effect is where Todd Whitaker’s observation that “when the principal sneezes the school catches a cold” comes from. Leaders typically understand that the way we relate to our direct reports will influence the way they relate to their own teams, and that will carry down the line. But the phenomenon extends well beyond those with whom we have regular meetings and a formal relationship - it includes the parents we speak to when they happen to be in the lobby, the Board member we schmooze with before the meeting starts, and the kids in the classrooms and hallways.

The challenge is that when it comes to regular meetings and a formal relationship we can plan, adjust, and hopefully enhance our approach over time. That can be much harder to do when it comes to the informal relationships that dot our days in sporadic and sometimes unpredictable ways. This is where we come back to our leadership routines.

We cannot plan each hallway encounter, but when we are reassessing our routines we can look clearly at whether the patterns of our days will lead to the kind of relationships we hope to build. If, for example, we find ourselves running (or speedwalking) from task to task over the course of a day we are much less likely to say more than a cursory hello to the child in the hallway or parent in the lobby.

On the other hand, if we want to build our days so that they facilitate relationship building, we may decide to add a new routine of being at the front door during arrival, getting coffee at the time that most teachers are taking their break, or taking a slow walk around the school every day after lunch.

Put differently, we must ask ourselves what we are optimizing for when scheduling our days. Are we aiming for efficiency and completing all of our management responsibilities, or are we optimizing for relationships? Setting aside time for things like walking around the school and poking our heads into the offices, classrooms, or faculty rooms can be difficult. These are not tasks we can cross off our list, and most days our list overfloweth with tasks. Yet these little routines, compounded over time, are among the powerful ways to build both relationships and school culture. They create space for ongoing small moments of connection, and those moments compound over time to create the culture of relationship across our organization.

One of the nice things about routines is that once we have established them, they take on a life of their own. Once you start getting your coffee in the teachers’ room, hanging out in the lobby during high-traffic times, or showing up early for meetings to schmooze, these become a force of habit. Relationship-building routines in particular tend to generate their own momentum - the informal times in the faculty room, the classroom, or the boardroom fill us with the energy of connection and remind us why we do this work.

Of course not every visit to the front lobby will generate a meaningful moment with a parent or volunteer. But over time, shifting our routines to allow for these connections will move us in the right direction. For those of us who find ourselves running from task to task, this may start as simply as a slow walk, and even some pit stops, on the way to our next meeting.

Don’t miss our recent podcast episodes Leading Through Transition with Rabbi Jordan Soffer| Spotify | Apple | YouTube

When leaders talk to me about navigating the challenges of their job, their concerns often fall into two broad categories: (1) quantitative challenges and (2) qualitative challenges.

Quantitative challenges are the challenges of overwhelm. There is too much to do: too many people to respond to, emails and messages to answer, meetings to attend, and tasks to accomplish.

When leaders are dealing with these kinds of challenges, I typically recommend systems and techniques for managing workload, refining schedules, and delegating effectively. These are not always easy to implement, but generally speaking we understand and accept that they are necessary.

The picture is different, though, when we are dealing with “qualitative” challenges. By qualitative, I mean those leadership tasks that demand emotional bandwidth or pose a psychological challenge. Tasks like navigating conversations with angry stakeholders, delivering bad news, or sharing negative feedback with staff.

Unlike the quantitative challenges, when it comes to the emotionally demanding tasks we often resist the idea that a system or technique could help us. That resistance makes a lot of sense. A tough conversation is going to be tough. Delegating it to someone else might help ease the burden, but it can be hard to see how a system or technique could help reduce the discomfort. As a result, we often stay stuck in our ways of dealing (or not dealing) with these parts of the job, and the longer we do that the harder it all gets.

The truth is though that managing the emotional challenges of leadership is a skill. Perhaps a different type of skill than managing your calendar or empowering your staff, but a skill nonetheless. And as a skill, it is something that we can improve over time - particularly if we learn to apply key systems and techniques.

Consider the example of tough conversations with staff members. This one is sufficiently difficult that many leaders simply avoid it altogether. Unfortunately, as Dan Rockwell notes, “You can avoid tough conversations. You cannot avoid the consequences of avoiding them.” And those consequences include weakened relationships, poor performance, and broad damage to morale, culture, and trust.

Often we approach this as an emotional problem that requires an emotional solution. Having those tough conversations is intimidating, even downright scary. So we fall into thinking that the best approach is to work on managing our own emotions - tactics like grit your teeth and bear it; treat yourself to a cup of coffee (wine?) as a reward for getting through it; make sure you have a trusted colleague to support you when you’re done; or, more broadly, make sure you have enough positive experiences in your work/life to balance the negative.

I’m not against any of these, and I think the last two are actually good ideas in general. However, the mistake in each of these is that they do not help us improve our ability to have the conversation itself - and so the conversations never become any easier.

But what would happen if we focus on how to have the conversation itself? If we can overcome our resistance and skepticism, there are a number of techniques that help us improve our approach to the toughest face to face interactions.

Perhaps the simplest one comes in the form of conversation starters. Here are some examples provided by Dan Rockwell.

“I need to discuss something difficult because our relationship matters to me.”

“I care about your success too much to stay silent about this.”

“I respect your potential. That’s why I need to address something that isn’t working.”

If these conversation starters resonate with you, great. Print them out and put them in your desk drawer (or add them to your notes app). If you’re looking for alternative formulations, there are more here, or you can write your own.

The reason these are powerful is that they remove a key stumbling block in our avoidance. Once we already have the first line, it’s much easier to imagine the rest of the conversation. We move from having no idea how the conversation will go, to a clear sense of at least how it will start.

Having general conversation starters is the first step. Once you have the hang of that, the next level is to write specific, tailored starters for each tough conversation. Doing so will force you to decide the purpose and goal of each conversation before you begin. Many hard conversations go wrong in the first minute because we are not crystal clear on what we are trying to accomplish. Are we correcting a behavior, repairing a relationship, or both? If we have not answered that for ourselves, the other person will most definitely not understand what we are after.

When we’re done with each conversation, it’s important that we don’t delete or throw away the starters we’ve written. Keep them on file and they will become a record of how we’ve approached conversations over time; a way of chronicling the development of our own skills in an emotionally challenging area.

More broadly, they will become a reminder that the qualitative challenges of leadership will always be there, but that developing our skills, techniques and systems can eventually make the emotional weight easier to carry.

Don’t miss our recent podcast episodes Cracking the Affordability Code in Jewish Day Schools with Melissa Rivkin| Spotify | Apple | YouTube

Of course, she found that item placement – rather than any intrinsic factor like taste or health – exerted a significant impact on student dietary choices.

Carolyn, in Thaler and Sunstein’s telling, is an amalgam designed to make a point, and the research behind it is clear - and does not only apply to children. We know that stores from supermarkets to Walmart use similar techniques to influence our purchasing decisions with significant success.

This holds true well beyond the seemingly minor choice of what to buy at the store or eat for lunch. Research shows that the order in which potential insurance plans are communicated greatly influences healthcare choices, and the “default” option is the single largest factor determining whether people contribute to a retirement savings plan, or even sign up for organ donation!

The common denominator in all of these cases is what Thaler and Sunstein call “choice architecture.” Just as the arrangement of rooms in the building determines how we get from point a to b, and just as the placement of the coffee machine influences who is more likely to socialize with whom in an office, the underlying structures across organizational life exert a constant, powerful, and often unseen, influence on our behavior.

So what does this mean for leaders?

Fundamentally, it means that we have a lot more power than we sometimes imagine.

Most principals I speak to don’t think that they have much impact on what their students eat for lunch, but a careful review of the cafeteria serving counters shows they have more influence than they realize.

The same logic can be extended to any other challenge we may be facing. Staff morale and collaboration? Parent interactions? Board behaviors? Each of these has its own architectural parallel to the cafeteria counters. It may be a bit more difficult to see, but our job as leaders is to uncover the matrix that lies beneath each area we want to shift.

If you’re struggling with staff morale and collaboration, think about what patterns influence when, where, and how people talk to each other and work together in the building. Using the summer break to adjust the layout of the staff room, rebalance how you assign teaching, duties and free periods, and reassess how you schedule meetings can go a long way towards shifting staff interactions.

If parent interactions are not where you want them, think about the very first touch a family receives from the school each year and what tone that sets. Try making sure the first series of messages and interactions each year are specifically personal and relational, rather than transactional and logistics focused. If you’re troubled by how, and to whom, parents express their complaints, try setting up a default pathway where the path of least resistance leads to the right address (usually the teacher) and reinforces ongoing communication with that address.

If you need to improve the way your board functions, think about the structure of meetings. The way chairs are arranged in the room, the order of agenda items, timing allotted, and even the number of options presented for each decision-making item can fundamentally shift board meeting culture.

If you’re struggling more with how board members engage with parents or professionals outside the meetings, think about what happens when a trustee gets stopped at pickup, or at synagogue, or in the grocery aisle, by a parent with a grievance. In that moment, most trustees choose the easy path - they nod, promise to look into it, and carry the complaint back to the administrator as if it were a directive. But imagine what would happen if we give trustees a short, warm, pre-agreed-upon line that can be easily put to use. Something like, “I hear you, and the person who can actually help with this is the head/principal/teacher. If you call the office they’ll make sure to connect you.” If we simply make the redirect easier than the micromanaging approach, many more trustees will default to that more appropriate option.

There’s much more here than any of us can address at one time, but the underlying point should be clear. Pick any area of organizational or school life, and you can be sure that there is an underlying architecture which influences behavior more than any of us realize. Part of our job as leaders is to unearth these hidden structures, and carefully adjust them so that the path of least resistance is also the most productive one for our culture and mission.

Don’t miss our recent podcast episodes The Art of Donor and Parent Relations with Raimy Rubin| Spotify | Apple | YouTube

As I said the word “trust,” I saw a number of team members shift in their seats. The pushback came quickly.

“I don’t think we have a trust issue.”

“It’s actually more of a communication problem.”

“Of course we trust each other. I don’t think anyone in this room would lie to me. We’re all good people.”

The first time I heard pushback like this, many years ago, I believed it. Even now, I have to hold myself back from believing it again every time.

Most teams are fairly certain they do not have a trust issue. Or, to put it more accurately, they certainly do not want to admit that they have a trust issue.

Why?

To many leaders, particularly in the world of education and nonprofit world, trusting and being worthy of trust is a core value. It’s synonymous with integrity, honesty, and basically being a good person. All of which means that we are highly resistant to the idea that we may not actually trust others on our team, or that they may not trust us.

The reality is, though, that in a professional environment trust is about a lot more than telling the truth. Many wonderful people who are kind, honest, and filled with integrity may face trust issues at work, in both directions.

Feltman and Hammond explain this clearly in The Thin Book of Trust. When it comes to professional relationships, trust is actually made up of four equally important and necessary ingredients: Care, Sincerity, Reliability, and Competence.

Care and sincerity are the more self-explanatory of these, and closer to what we would colloquially associate with trust. We need to believe that our colleagues care about us as people, and we need to believe that the sentiments they convey are honest and forthright (sincere).

Most teams I work with are filled with caring and sincere individuals. The challenge they encounter, however, is often in expressing that caring. A caring leader who is also dealing with a very full plate may easily forget to express and convey their care for team members on an ongoing basis. Ironically, as work pressures rise leaders are driven to focus on just getting the job done - but it is exactly at those times when teams need more expressions of care not less. This does not mean we need to take our team out to lunch, it means we need to ask them how they are doing - and we need to care about their answer .

Reliability and competence are often the overlooked components of team trust, yet they are just as crucial.

For example, a colleague may sincerely care about our wellbeing. They may always interact with us honestly. But if they miss deadlines, show up late for meetings, or don’t return emails, we will not consider them to be reliable .

Alternatively, a colleague may be punctilious and diligent about their responsibilities, but if they do not have the necessary skills or knowledge to accomplish their core responsibilities we will not deem them competent .

For a team to have trust at work, it is not enough to know that our colleagues sincerely care about us. We also need to believe that they are both sufficiently reliable and competent to come through for us on a regular basis.

When a team has a hard time believing they are having trust issues, the problem often can be traced back here. We don’t want to think that there is a trust problem, because we believe that our colleagues are good people - they are caring and sincere.

The truth is, though, if we cannot count on our colleagues to come through for us then we do not just have a functional problem - we also have a trust issue.

This is the part that catches good people off guard. In our personal lives we can carry a friend’s unreliability indefinitely. We love them, the stakes are low, we plan around it, and we accept them for who they are.

At work, though, the stakes inevitably impact the team as a whole. A colleague’s missed deadline becomes my problem with my board, and their skill gap becomes one more thing I have to cover. The generosity I can extend to a friend does not survive shared accountability. At work, my colleague’s lack of reliability and competence is not just their issue, it is mine as well and, therefore, it fundamentally impacts our relationship.

So yes, our teams are filled with good, honest, and caring people. And yes, we may also have a trust issue that we need to acknowledge before we can move forward.

Don’t miss our recent podcast episodes Sustaining Excellence: A Community Approach to Jewish Education with Dr. Miriam Heller Stern| Spotify | Apple | YouTube

And yet, when it comes to understanding how people actually perceive us in our leadership roles, many of us are operating with little real information.

This is not entirely surprising. When we do get feedback, it often comes from those who supervise us, be it our CEO or our Board. It is much more rare that we get real, meaningful feedback from those whom we supervise - and those are the people who most directly experience and understand who we are as leaders. Tools such as a formal 360 degree review, which collects data from our subordinates as well as our supervisors, can be very helpful, but these require significant effort and are usually implemented once a year at most.

In addition to the time constraint, getting feedback as a leader can be further complicated by the power differential. When leaders ask direct reports for an overall assessment of our strengths and weaknesses, many direct reports will demur, gloss over, or sugarcoat difficult areas. Recently, I’ve been thinking about how leaders can cut this problem down to size. And I mean that literally.We often think about feedback as a holistic report which outlines our strengths and weaknesses and highlights areas for improvement. Perhaps we received this kind of feedback in our initial years on the job, or perhaps this is just what we imagine as “real” feedback.

But feedback can be useful in smaller chunks as well, and it may be much easier to obtain it that way.
If we spread our feedback requests into ongoing routine asks instead, we may find ourselves with both more meaningful data and more trusting relationships. Rather than asking broad questions like, “How am I doing?” or even, “What should I do more/less of?” leaders can focus our feedback requests around specific events.

For example, after a difficult conversation with a faculty member, we can ask a colleague who was in the room, “What would you have done differently there?” Or, after a meeting that felt off, we might say to a trusted team member, “What did you notice that I might have missed?”

The smaller the ask, the easier it is to answer honestly. People can respond to a focused question without feeling like they are delivering a verdict. They are less likely to fear negative consequences, purposeful or not, that may come from giving an honest critique. Since the ask is about one concrete instance, our team members are also less likely to be afraid of hurting us, damaging our relationships, or being seen as disloyal.

Since these are smaller asks they need to happen on an ongoing basis, and that’s a good thing. The first few times we make the request it may not come off as we intend, and our people may not know if we really mean it. When we start to incorporate mini-requests into our day to day routines, we give ourselves the opportunity to practice how we ask, and we help our team see our commitment to actually getting this feedback.

If we stick with this approach, a few things will start to happen. First, our colleagues will begin responding to us more openly, with helpful, real-time feedback related to our questions. As we hear their feedback, we will have the opportunity to be more deliberate in what questions we ask and how. Rather than trying to look back on the year and understand our strengths and weaknesses broadly, we can look ahead at each day, week and month, decide what we would like to learn about our own practice, and then translate that into small daily questions that elicit authentic answers.

Second, as the practice of mini-feedback integrates into our routine, we will see others on the team starting to ask similar questions. Once the leader goes first, others will start to see this as a cultural value and feel the psychological safety they need in order to solicit their own feedback. As asking for feedback on a day to day basis becomes part of what we do, we can guide team members as well to be deliberate in what they are asking and how.

Admittedly, implementing this approach can feel challenging at first. Asking for feedback demands a level of vulnerability that causes many of us to hesitate, and doing so on a daily basis can be daunting. And, as with any daily practice, it will take some effort until it becomes a natural part of the routine. If we do stick with it though, mini-feedback can open the door to a deeper understanding of our leadership, our teams, and ourselves. In my mind, that makes it well worth the effort.

Don’t miss our recent podcast episodes What the Data Says About Great Leadership with Gali Cooks of Leading Edge| Spotify | Apple | YouTube and Building Lifelong Torah Learners with Rabbanit Dr. Yosefa Fogel Wruble| Spotify | Apple | YouTube

Most of us have been there. The bylaws say you have to hold the meeting. Parents or members show up, often in modest numbers. A few questions are asked, board minutes are approved, and new trustees are elected. Everyone goes home vaguely unsure why they bothered coming, and that often includes the leader who planned it.

In The Art of Gathering, Priya Parker argues that most get-togethers fail for a simple reason: the host never seriously considered why they were gathering in the first place. Instead, they replicated what had always been done - whether it was a party, a meeting or a conference. The form stayed the same long after anyone could remember the supposed function- just as it has with many of our organizations’ annual meetings.

Parker’s corrective is to go back to basics. Before you plan the agenda, before you book the room, and definitely before you invite anyone, ask yourself what this gathering is actually supposed to accomplish.

This is hard to do for any gathering, and it is even more challenging with annual meetings because we often get stuck in the mere fact that we are obligated to hold them.

What we need to be asking, however, is not what we are obligated to do but rather:

What do we want people to know, or feel, or take with them when they leave?

I spoke with two leaders over the last week who took a step back to ask that question, and I was amazed at where it led them.

One head of school determined that what really mattered at this moment was their school’s connection to the community. As they thought about the gathering from this angle, they were inspired to integrate the annual meeting into a larger community-wide gathering. Attendance grew exponentially and the school’s work was recognized in front of its precise target audience. Rather than just electing new trustees, the reimagined meeting meaningfully enhanced one of the school’s strategic goals.

Another leader determined that the core goal of their annual meeting was to inspire and motivate board members. They decided to keep the participant list the same, but rescheduled the annual meeting from a weeknight in the board room to a Sunday brunch in a board member’s backyard.

Rather than a dry list of annual reports, the brunch was filled with meaningful thank yous to those completing their service and a heartfelt welcome to new board members. The leader was shocked that many of their past presidents, who were always invited but rarely appeared, decided to join as a show of support. During the mingling, the past presidents spoke with the newer members about the importance, value and meaning of board leadership. It definitely took more planning, but the pride on board members’ faces as they wrapped up that morning was exactly what this leader had hoped to achieve.

Hearing this leader’s story, it struck me that annual meetings could actually be a lot more like a middle or high school graduation.

A good graduation is not just a goodbye ceremony, and it is certainly not two hours of boring speeches. It is one of the few moments in the school year when you get to say, out loud and in front of everyone, what the place is about. You recognize the people who gave something to it, and you do so with specificity. Perhaps most importantly, you send people off with a sense of shared direction. When a graduation works well, everyone in attendance leaves knowing that they are a part of something that matters.

Our annual meetings can be a grown up version of the same thing. The components are remarkably similar: People are transitioning off and on to the board, a year of meaningful work is ending, and a new one is about to begin. Relationships that sustained the organization through a challenging stretch deserve to be recognized, individual and group growth needs to be marked, and the transition point gives leaders an opportunity to tell members old and new the story of the community they belong to.

You do not necessarily need a backyard brunch or a community gathering, and you do not need to give your board members caps and gowns. But for many of our organizations the current format of our annual meeting is a missed opportunity.

If we push ourselves to take that step back and think about what this meeting could accomplish, and only then determine the setting, participants, and program, we can find our way to an annual meeting that truly serves our goals.

Don’t miss our recent podcast episode From Consultant to Head of School: Leadership Lessons with Rabbi Maccabee Avishur | Spotify | Apple | YouTube

I continue to encourage my school and organizational leaders to do so this year as well. But this time, I’ve started guiding them to take a new approach to how that meeting goes.

Typically, our end of year reviews look at what happened over the last 12 months with an aim to identify what went well and, even more significantly, what did not work. Based on this analysis, the leadership team then prepares potential interventions to roll out in the coming year.

If we are not satisfied with student culture, we might decide to adopt a new behavior management program. If we see issues in classroom pedagogy we might invest in a new curriculum or instructional coaching.

I am not against any of these approaches, but in recent years I have begun to see that the way we conduct our reviews may lead us to miss the most crucial path to improvement.

Instead of the classic review, I now suggest a flipped version based on the core concepts from Positive Deviance. In this approach, we begin our review by asking:

• Where did something work better than expected this year?

In doing this, it’s crucial to note that we are not looking for the superstar who is more talented or charismatic than others. In fact, we are not looking for people at all. We are looking for practices. This is why we ask “where” did something work, rather than “who” made something work. We are looking for different practices, approaches, techniques, behaviors, etc. that led to better results.

Identifying these “positive deviant” cases is the first crucial step. The next steps are preserving and, eventually, expanding them.

First, preserving.

Leading researchers Michael Fullan and Larry Cuban, among others, have shown that the biggest mistake we make in educational change is dropping an idea or approach before it has truly taken root. We need to find those teaching practices that worked this year and, first and foremost, ensure that they continue to happen next year.

Second, expanding.

Rather than planning our own intervention efforts over the summer and introducing them to the faculty when we return, we can focus the summer on distilling the practices that were most effective last year. Ideally, we can engage the teachers who implemented them to help us understand exactly why they worked - and how they can work for others. When we do so, we need to push past any personality-specific pieces to get at the specific moves and determine how they could be implemented in other classrooms.

The moves themselves may look as simple as an unusual approach to assessment cycles, lesson timing, student grouping, or classroom setup. But, unlike most new approaches we bring in from outside our school, we will be working with specific, grounded practices that we know have already worked well within the particular environment of our school.

Our task over the summer is to understand where and why these practices were effective, to ensure that they are poised to continue, and to chart a path for them to expand gradually into other relevant classrooms.

When we come back to school in the Fall, we won’t be coming back with a shiny new curriculum or different approach to professional development. We will be coming back with an already-tested set of practices, and pathways grounded in teacher experience to help these practices spread across the school.

This “positive deviance” style review makes our end of year meetings more enjoyable and inspiring. More importantly, it leads to ideas that actually work.

Instead of using the review to decide what we need to fix, let’s use it to discover what has already begun to solve the problem.

Don’t miss our recent podcast episode Building Teams That Actually Work with Dasee Berkowitz | Spotify | Apple | YouTube

As a head of school, I heard the same question from parents every Spring, “So, is the year winding down?”

Granted, it was a much more innocuous question than, “Can you make sure my daughter is in a class with her 4 best friends next year?” or, “How do you plan to fix the math curriculum/athletic program/bus routes by the Fall?”

At the same time, whenever people asked me if the school year was winding down, it was clear how little they understood about the life of a school leader. Spring is the season of performance reviews, contract renewals, teacher recruitment, end of year trips, holidays and special programs, graduation preparation, IEP reviews, report cards, and more. It is the season of wrapping up this year and preparing for next year, all while keeping the regular routine going.

So no, the year is not winding down. Spring is when a school leader’s year winds up, and up, until the minute that students leave the building for summer, when it finally slows down . Only then do we exhale.

The fact that the end of the year is intense is not necessarily a problem. For many of us though, the beginning of the year is pretty intense too, and so is most of the middle.

The challenge is that when we are in the midst of these intense periods, it’s often hardest to take a step back and think about whether there is anything we can (or should) do to ease the intensity.

While I truly believe that some leaders thrive on the forever sprint, that’s not a path that most of us can tread if we want to do this job well. It is not healthy for ourselves and those around us in the long term. And so, when a leader tells me that they’re having another one of those weeks, it’s my cue to ask, “What could we do differently?”

There are typically a number of scheduling habits and practices that can help to reverse this problem . However, I am finding more and more that to meaningfully impact the leadership overload, we need to take a fresh look at the administrative structure itself and consider what is often called distributive leadership.

Take the long list above as an example. It’s Spring and we as school leaders are juggling preparation for next year, end-of-year special programming, year, and the regular day to day routine which most certainly does not stop. Distributive leadership argues that all of these tasks should not rest on the school leader, or even the senior leadership team, alone.

Simply put, this argument reasons that sharing leadership among a wider group is a powerful way to engage staff and elevate morale. Additionally, meaningfully distributing leadership is one of the most powerful ways to share the burden beyond an individual leader or a small team.

When they first hear about this approach many leaders have an instinctive resistance.

“I know I’m very busy, but I really need to do all of these things myself. That’s what people expect of me as a leader.’

“If I give any of these to my staff, I’ll have to spend more time teaching them than I would doing it myself. And they probably won’t do it as well.”

“It’s not really their job to do this work, and they will resent it - even if I could compensate them for the extra time.”

While each of these concerns represents a valid obstacle and a real risk,the risks of the overload status quo are just as dangerous.

Using our Spring wind up as an example, if we examine each category, we can start to identify concrete opportunities to distribute the leadership load.

Year wrap-up: Graduation planning is often treated as an admin project when it need not be. A senior teacher can potentially serve as a project manager, owning the logistics, venue, program, rehearsal schedule, family communications. Similarly, end-of-year trips and special programming can be coordinated by a faculty committee with a designated lead; and student reviews and placements can be led by department heads, learning specialists, or other teachers with appropriate experience..

Next year prep: Teacher recruitment is among the most time-consuming Spring tasks. A teacher-led recruitment committee, common in many schools, not only reduces the head’s load but often produces better cultural fit. Department heads or team leads can conduct first-round interviews and bring vetted finalists to the head.

Day-to-day management: This is the category leaders most resist delegating, and understandably so. But consider the weekly all-staff email, the parent meetings, teacher observations, etc. Depending on the culture of each school, some of these can certainly be shared with senior teachers or department heads.

The key, however, is to understand that distributive leadership is not simply a smarter way to manage a to-do list. Done well, this is a shift in mindset that fundamentally reshapes how leadership works in a school. That shift requires investment. Teachers and staff who take on meaningful leadership roles need to be coached through early missteps, and debriefed so that their capacity grows over time. They need to be recognized, formally and informally, for the expanded role they are playing.

When leaders make that investment, which often works best by focusing on one area at a time, we can shift both our own experience and the culture of the staff around us. Staff who lead feel more ownership over the institution. They understand decisions better because they are closer to making them. They grow professionally in ways that routine teaching alone does not provide. And the senior leader, no longer the sole engine of institutional momentum, becomes a leader of leaders, rather than a manager of everything.

Rebalancing the fundamental structure of school leadership is indeed an ambitious goal. There are many real obstacles in the way. But if we are willing to experiment with this new perspective - as a mindshift not a bandaid - we may find ourselves feeling much differently the next time Spring rolls around.

Don’t miss our recent podcast episode Using AI to Lead Smarter with Dr. Sarah Rubinson Levy | Spotify | Apple | YouTube

Around this time of year many coaching calls turn to discussions of increasingly urgent staffing needs for next year. Unfilled teaching and administrative positions have leaders feeling more and more pressure as summer draws near.

Many of these positions remain open because that superstar (or even “very good”) candidate we were hoping for has not yet appeared. Unfortunately, the pressure to hire combined with a less-than-ideal field make it even more difficult to get to the right decisions.

The temptation in these kinds of situations is to look at the available candidates, confer with the senior leadership team, and then make a gut decision on who might be the best fit for our school. I understand the pull towards this approach. I have reverted to it many times myself.

The problem is that trusting our gut, however enticing, is scientifically proven to be the wrong way to make a hiring decision.

Why is going with our intuition so enticing?

Nobel prize winning behavioral economist Daniel Kahneman, who pioneered much of this research, recounts the opposition he faced from decision makers who were quite sure that their experienced eye could provide the most accurate assessment of a candidate’s likelihood of success in any given position. He then recounts how, time and time again, they were proven wrong.

Underlying this perennial mistake is that our intuition, which Kahneman calls System 1 thinking, leads us to prioritize what is immediate and emotionally compelling over the quieter factors that ultimately matter more.

This is particularly relevant in hiring. When we face a difficult question like, “Will this candidate be a successful teacher or administrator in our school?” System 1 employs a subtle trick that Kahneman calls “attribute substitution.”

Instead of answering the hard question, we unconsciously replace it with an easier one. We ask ourselves whether we like the candidate, whether the conversation felt natural, or whether they showed charisma in the classroom. We then answer that easier question, all while believing we have answered the original one.

The result is that we become confident in judgments that are not actually grounded in the evidence that predicts long term success. We overweigh things like social presence, charisma, and fluency, and underweigh less visible indicators which may ultimately matter more in teaching and leadership.

Kahneman proposes a simple approach to overcoming the “attribute substitution” error. Instead of making an intuitive decision, force yourself to use logical, rational System 2 thinking by creating a decision rubric in advance. It works even better if you do this with your team.

For hiring, the process may look something like this.

• Delineate the core elements of great teaching or leading in your school, and list these in the first column. You may (and should) already have such a rubric which you use with your current teachers/leaders.

• Outline what evidence you would hope to see of those in the second column.

• Force each rater to give the candidate individual grades on each core element, rather than an overall summary.

If you want to level up, you can differentiate between the elements a candidate must have when they walk in the door from those you can help them grow and develop over time. For example, my colleague and current head of school Maccabee Avishur notes the ability to hear and implement feedback (“coachability”) as a core component in his school’s hiring process because it is the key to unlocking all other growth.

Once you have the rubric, ensure that it is used in each and every hiring process. Forcing yourself to contemplate evidence of individual elements pushes you towards a thoughtful and balanced process, avoiding false positives and negatives alike. And when the candidate pool is slim, differentiating core elements from those which can be developed over time broadens the field in a way that is tailored to your goals.

This is relatively simple, but it is not easy. Expect that your intuition will keep telling you that you are better than a rubric and enticing you to just go with your gut. That’s what System 1 is built to do. Your job is to resist that temptation and implement the rubric even when you don’t feel like it.

This approach will not create candidates from thin air, but it has been proven to enhance your decision-making ability in an area where it matters the most. For leaders constantly looking to refine and enhance their shared school vision of great teaching and leading, it is a natural - and crucial - next step.

Don’t miss our recent podcast episode Lessons from 36 Years of Day School Leadership with Rabbi Eli Rubin | Spotify | Apple | YouTube

Hit reply or email me at barry@kislowiczconsulting.com with your name/position and we’ll take it from there .

This description of the teacher-to-principal trajectory is as common as it is heartbreaking.

When teachers decide they want to become principals, it is almost always with children in mind.

They want to improve instruction. They want to support great teaching. They want to build a culture where students thrive. They imagine high-fives in the hallway. Thoughtful classroom walk-throughs…

But here is the uncomfortable truth we rarely say out loud: A shocking amount of school leadership is not about students. It is about adults.

Conflict. Morale. Ego. Performance concerns. Professional jealousy. Resistance to change. Documentation. Confidentiality. Rumors. Burnout. (Meagan Booth, Edweek)

I’ve seen the parallel trajectory for those who move into the Head of School role for the first time. New leaders walk into the position dreaming of growing the school and inspiring a community. They are often surprised to find how much time must be spent on finance, fundraising, facilities, and governance.

Meagan Booth argues for better principal preparation programs, ones which focus on the job principals will do rather than on the job they imagine themselves doing. I’m all for continued enhancement of pre-service and inservice training for educational leaders, but I think we need to look further upstream if we want to meaningfully impact this challenge.

We need to reach potential leaders before they have formed an understanding, or misunderstanding, of what school leadership roles really entail. Rather than taking someone who is inspired about improving school culture, elevating teaching and learning and showing them the hard knocks of personnel management, we need to create pathways that allow potential leaders to form their vision of school leadership - from the earliest stages - in a way that includes the beauty of personnel and operations management.

Yes, I said the beauty of personnel management. And yes, I believe that educators in particular are poised to see the beauty of this and other adult-focused and operational aspects of school leadership.

I remember my own transition from teacher to leader. The beginning months were filled with a sense of frustration.

• There are too many kids coming to my office. Why can’t these teachers handle discipline problems on their own?

• Why is my admin team bickering? Do they need me to referee every conversation?

• Another parent phone call? Another Board member meeting?

Fortunately, in my case, those frustrations led me to spend a lot of time sitting in a senior colleague’s office, asking for advice. At first, the advice was case-by-case. It helped me deal with individual issues, but it did not do much for my overall sense of annoyance about where my time was going.

Over time, I started to notice a pattern in the advice I was getting. As a new leader, I was approaching adult stakeholders as “finished products.” They were here to do a job, or to be good constituents, and they should be ready, willing, and able to do so.

At the same time, I was encouraging my teachers to see children as “works in progress.” I would often tell teachers: Don’t complain about what the kids can’t do and understand when they walk in your door. Our job is to understand where they are today and figure out how to move them forward tomorrow.

My colleague was saying the same thing to me: Don’t complain about what the adults can do and understand when they walk in your door. Our job is to understand where they are today and figure out how to move them forward tomorrow.

That was the paradigm shift that enabled me to see the beauty of all those unexpected management responsibilities. Like many teachers, I went into education because I believed in growth. My time in the classroom focused on inspiring and guiding that growth in children. My time in the admin office was most satisfying when I understood that my work was to inspire and guide growth in adults.

Within that frame, the frustrating parade of adults walking into my office with conflicts, resistant attitudes, budgetary issues, and more becomes the parallel of the 8th grader who walks into my algebra class not understanding fractions, or the 6th grader struggling with appropriate social interactions.

A caveat is in order. Adults are often much more resistant to change than children. Boundaries are harder to draw, and we are understandably more concerned about our own job security.

I am not arguing that this paradigm makes educational leadership easy. I am arguing that it returns it to being meaningful, and that it aligns the work of leadership with the reasons we got into the classroom in the first place.

Booth poignantly suggests that “students are the moral center of the work, but adults are the operational reality.” I think that is exactly the perspective which needs to change.

Adults, too, are the moral center of our work. Whether they are teachers, board members, or parents. Educational leadership means developing a growth-oriented vision for all of the “operational” aspects of our work.

School leaders who cultivate this perspective face all the same challenges, but they do so with the conviction that comes from understanding why they got into this in the first place.

Don’t miss our recent podcast episode Lessons from 36 Years of Day School Leadership with Rabbi Eli Rubin | Spotify | Apple | YouTube

We had just finished brainstorming a challenging situation with multiple stakeholders, and the Head had identified a pathway that would likely be successful. But it would not be easy.

That wasn’t the only time that week, or that day, when a leader I work with said something along those lines.

It’s not only struggling leaders or those who are new to their role who are aware of these challenges. When it comes to school leadership in general, and the head of school role in particular, it’s often the best of us who are most aware of the struggles and challenges inherent in the job.

While a coaching session is not usually the place for sharing my own emotions, I have to admit that this conversation led me to a strange mix of sadness and joy. Sadness, because the moment made clear that no matter how good we are at our jobs, school leadership is hard. It can be draining, challenging, and sometimes it can feel like too much to carry. That part is pretty simple to explain.

But what about the joy?

When I say joy, I should clarify that I don’t mean the clicking-your-heels and singing-from-the-rooftops sort of joy. I mean a quieter, more soft-spoken, inner joy.

Every time I speak with a leader, I remember how challenging it was and how lonely it could feel during the years I sat in that chair. And I remember that what helped me navigate those challenges, and what kept me sane while doing so, were the conversations I had with my own coach. I recognize that I am paying forward the support, guidance, and kindness which I was privileged to receive - and that is a very special kind of joy.

All of this got me thinking about exactly why leaders need coaches.

When you become a senior leader you enter a world of structural isolation. You no longer have colleagues in the building. You may partner with a board, supervise a senior leadership team, and engage with an array of stakeholders. These are all important, and complex, relationships, but they are not colleagues in the true sense of the word.

Similarly, you do not have a supervisor in the traditional sense of the term. This means that feedback, both positive and negative, is more difficult to come by, and your ongoing professional growth becomes your responsibility alone.

At the same time, you are tasked with thoughtfully navigating emotionally charged situations on a daily (hourly?) basis, making difficult decisions which often make people unhappy, and you must do so without letting your own emotions get the best of you.

When senior leaders navigate this on their own, there is a cost. The cost might be developing armor so tough that you forget how to take it off, or slipping into a destructive pattern of conflict avoidance because it makes life easier in the short run. It may mean going home drained and not having the emotional energy left for your family and friends, or never uncovering your own blind spots. One way or another, it often prevents leaders from becoming the kind of professional - and the kind of person - they know they can be.

This is what coaching is designed to rebalance. Many leaders engage a coach because there is a specific challenge they want to navigate or skill they hope to develop. Once they begin coaching, though, they realize that adding this relationship as a tool in their arsenal fundamentally shifts the landscape of leadership.

No, it does not suddenly make the job easy, but it creates a space where you as a leader are not alone. It means there is someone in your corner; a confidential thought partner who can support, guide, and challenge you, and even give you difficult feedback when necessary.

Coaching creates a rhythm of pausing before you act, and the ten minutes you spend talking through a decision often saves you weeks of cleaning up after a mistake. It helps you stay honest with yourself by ensuring that you mind the gap between reality and the story you tell yourself (for good and for bad). And it helps you catch patterns before they become problems, noticing what people/conversations you may be avoiding or what cycles you are inadvertently perpetuating.

Perhaps most importantly, leadership is a meaningful but often heavy mantle to carry. A coach gives you a place to set down some of that weight and take a breath before you jump back into the arena.

For me, the bottom line is that coaching gives you a better shot at becoming the kind of leader - and the kind of person - you want to be.

If you are not yet working with a coach, I encourage you to consider doing so. And if you want to explore what it would be like to work with me, just hit reply or email me at barry@kislowiczconsulting.com. No commitment, just a conversation.

Don’t miss our recent podcast episode What It Takes to Lead Schools Over 25 Years: Lessons from Rabbi Dr. Mitch Malkus | Spotify | Apple | YouTube

I’ll admit that for some time I bought into this assumption. I would often reply that it is true that teachers do not necessarily make the best school leaders, just as doctors are not necessarily the best hospital administrators and lawyers are not necessarily the best firm managers. Teaching, like medicine or law, is a specific professional skill. Honing that skill helps you be a great practitioner, but it does not necessarily prepare you to be a great leader.

But I began to think about this differently after I read Roland Barth’s explanation.

Teaching and leading are not innate for most of us. We teach and lead better when we constantly learn how to teach and lead. (Learning by Heart)

Here’s how I see the argument:

#1 - There is a common denominator between teaching and leading.

#2 - That common denominator stems from the fact that both teaching and leading are roles fundamentally focused on helping groups of people change, learn and grow.

#3 - If you want to have any shot at helping someone else change, learn, and grow, you better be doing some learning of your own.

To some extent this is true in every profession. Ongoing advances in medical science mean that doctors need to keep up with the latest research, and ongoing technological development means engineers need to stay abreast of new systems. But there is a key difference. Most other professions require the practitioner to learn for extrinsic reasons, to keep up with the times. Both teaching and leading require us to constantly learn because only learners can teach, and only learners can lead.

Educational change guru Michael Fullan calls for every principal to be the “Learner in Chief” of their school. Some misinterpret that as a simple call for principals to be role models for their teachers and students. Role modeling is important, but that’s not what we are talking about.

Successful teachers and leaders must constantly place themselves in the stance of a learner, because doing so shifts the way that they teach and the way that they lead. The teacher-learner approaches every class with a curiosity that fundamentally alters the lesson; the leader-learner approaches every dilemma and challenge with an openness that changes the experience for all of their stakeholders.

The problem, though, is that when we step into the role of teacher or leader, we feel that others are looking to us for confident answers - not more questions. In many cases, we are correct. It’s much more comfortable for a student when the teacher gives them a clear, unambiguous answer to their questions, and it’s much more comfortable for our stakeholders if we as leaders point them confidently in the right direction. (My children used to marvel at my leadership skill of confidently telling them exactly how long we still had to walk on one of our family hikes. An answer I dutifully provided regardless of how completely lost I knew we were at that moment.)

Giving those confident responses may be comforting, but it does not lead to much learning or growth for students or stakeholders. Even more importantly, for our purposes, it has a negative impact on us as teachers and leaders.

People expect us to know the answers and respond confidently → We fake it so we don’t let them down → Pretty soon we believe it ourselves.

That belief runs directly counter to the learning stance which we need to teach and lead. It leads to a top-down approach that benefits no one and stultifies growth across the board. This is yet another example of what Amishi Jha means when she says “leaders’ pressures and demands eat away at the very qualities they need most.”

The only way to avoid this trap is to cut the cycle off at the very beginning.

People expect us to know the answers and respond confidently → We share honestly what we know today and what we are hoping to learn → We learn together.

I realize that this may seem polyannish, and I know many leaders will worry that they will come off as incompetent if they respond this way.

But the antidote to overconfidence is not weakness, it’s curiosity. Curiosity which can be delivered in a calming and reassuring manner; without pretending to have all the answers and with an emphasis on what we hope to learn - together.

This is the approach that the best teachers and the best leaders have in common, and it is why all of us teach and lead better when we constantly learn how to teach and lead.

Don’t miss our recent podcast episode Turning Accreditation into a Leadership Tool with Dr. Amy Platt| Spotify | Apple | YouTube

I’ll quote her bold wording,:

“Let’s face it: Parent culture is getting uglier. There. I’ve said it. And I’m not the only one to say it. Large, longitudinal, national and international studies of teacher and administrator retention point to constant criticism and judgment from parents as one reason people leave the field or never enter it.” (“What Kind of Parent Do You Want to Be?”, HaYidion)

In my coaching practice, I speak with about 20 principals each week. I’m fairly certain that they would all agree on this point. I’m also fairly certain that most of them could not say so out loud in their communities, for fear of what it would do to their relationships and to their job security.

And what’s more, if these leaders would speak directly to the challenges of running in school in a grievance-based culture with parents who are of consumer mindset, we can be fairly certain that the most problematic parents would not be paying close attention.

So what do we do?

By no means should we remove the responsibility from where it squarely belongs: on the shoulders of those people/parents who choose to act inappropriately. Parents who use money as a weapon, who poison a head of school search on social media, and who gang up on teachers rather than speaking to them directly, are making unacceptable choices that harm all of our children. No perceived shortcoming of a school, leader, or teacher excuses that.

Parent behavior is not our fault. And yet, it remains our role as leaders to shape the institutions and communities we serve. So while we cannot control the behavior of parents, we still have a responsibility to act.. Brown suggests that “a school leader’s job is to create better stakeholders.” I want to look a bit more closely at just how we might do that.

To begin, before we ask parents to become better stakeholders, we need to ask ourselves whether we have built institutions that truly invite them to do a better job.

Over the last decades, many of our schools have developed from mom and pop organizations into polished, professional institutions. We’ve upped our game in communication, social media, fundraising, and we have learned that we must demonstrate the value parents receive for their tuition dollar. All of this is necessary for our schools’ survival and growth.

But there is a real downside here as well. Many of our schools have leaned into demonstrating value, rather than demonstrating our values. We want parents to understand and appreciate what they are getting, and so we talk about “value for your tuition dollar”. But in doing so, we inadvertently reinforce the idea that parents are consumers. Layer on top of that the Covid holdovers of reduced parent time in the building, and professionals now handling many of things once done by parent volunteers, and we start to understand that both parents and educational leaders have reluctance around the stakeholder idea.

I find myself wondering what it would be like if instead of trying to demonstrate value, we leaned into a less-polished stance focused on our school’s educational, communal, and religious values.

It might open the door for leaders to be clear with parents, early and often, not only about what they should expect to receive but about what we believe, and about what genuine partnership actually requires of both sides.

It might also open the literal doors of the school to consistent, low-stakes contact between families and school life, recruiting parents to help with programs or mentor students. Asking parents to give in this way is messy and unpredictable, but it is also one of the more reliable ways to develop stakeholder identity.

This will not resolve the harder problem. Some parents will not respond well to any suggestions, and negative behaviors will still need to be named and addressed directly when they occur.

But if we are to have any chance of moving from a consumer-culture to a true community, we need to reexamine how all sides approach this relationship.

Don’t miss our recent podcast episode From Alumna to Head of School: Leading Community Day Schools into the Future with Dr. Casey Weiss| Spotify | Apple | YouTube