Reader questions on governance and leadership, answered. Have one? Email me at ask@greenwichleadershippartners.com — I read every one.

A Question from a Board Chair:

Stephanie:

This is a great question. When I took my first not-for-profit board seat, I was told to “listen and observe in year one, and begin to speak up once up to speed.” This is common guidance, and I believe it’s bad advice. Even if that message is not communicated in early days of service, the notion that a new board member can’t make meaningful contributions out of the gate is a limiting assumption.

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Happy August! My most recent blog post “When the Goal Posts Move...” addresses a topic that’s been on my mind for some time now, and serves as the perfect introduction to this month’s Blueprint. Here goes:

Even before Covid and the cultural and political crises we’ve endured in recent years, many executive directors and heads of school shared a sense that their jobs were undergoing fundamental change; that the goal posts were always moving and nothing they did was enough. And the reality is that the goal posts have moved. The job of leading mission-based organizations has changed, and a failure to name this reality and to adapt how we define and design leadership is a recipe for stress and even damage to the organization.

I love to reference Mr. Chips, the beloved teacher who becomes the emotional heart of his school in James Hilton’s novel. In so many minds, Mr. Chips is the iconic school leader — ever-present on campus, a philosophical and wise academic, and the living repository of institutional memory. In this model, leadership is shouldered by one central figure. The model persists, but it’s not realistic for the large majority of schools we encounter. Similarly, in not-for-profits, we see organizations falter when charismatic founders transition, and when new leaders ascend to the top without adequate preparation, a well-developed team, or a board that is ready to support them properly. The quest for scale and impact often outshines the fundamental need to build high-functioning systems and capabilities in a resource-constrained organization.

Today, leaders must hold a wider view and set of responsibilities that extend beyond their organization and their own leadership. They can no longer do it all. Four new realities jump out, the last of which is the key lever for success.

1. Shorter tenures and greater complexity mean that depending on one leader for continuity and institutional memory adds significant risk.

2. New unknowns and their attendant challenges require leaders to ask better questions and have the courage to make predictions. They must be future-focused as they manage what’s in front of them.

3. The necessity of a broader perspective and the importance of building relationships and fundraising in sustaining the business model demand that the leaders spend more time away from the office or campus.

4. The increased scope of responsibility means that leaders must first and foremost be an expert in developing and deploying talent.

Rather than seeing the new goal posts and asking, “How can I get there?” successful leaders ask, “How can I help develop the talent and the capabilities we need to go the distance and address problems we can’t yet see?”

The reality of this new job description has implications for boards too. When a board fails to understand the new role of the leader, or communicates mixed messages on expectations, it will consistently damage the leader’s ability to fulfill vital responsibilities. It may be time for a rigorous conversation, a realistic redesign of the role, and a reset of expectations.

What can Executive Directors and Heads do?

The standard career paths inside nonprofits and schools are not designed to help you learn talent management skills — and much of your preparation happens organically or in the hands of capable mentors. You might get trained in finance and in fundraising. You might get a master’s in leadership. But almost nowhere along that path do you get practical experience on how to develop talent, delegate and communicate effectively, provide people agency, and give them the personalized coaching and support they need. This experience is vital for your work with employees and with your board.

Start with an assessment of your experience and abilities. Being charismatic, visionary, and well-liked is not the same as being good at talent development. In fact, an over-reliance on motivating others through sheer personality can block rather than support the development of a team and the growth of others. Even if you are not new to the role, it can be helpful to ask the questions Michael Watkins highlights in “The First 90 Days”:

• What are you really good at and love doing that you need to do less of in your current role?

• What are you perhaps not so good at or not enjoying doing that you need to do more of?

• How fast am I trying to change things before I truly understand them?

Clarity will help you avoid spending time on tasks that are more familiar but less important.

Delegate and provide the opportunity for agency. In the HBR article “Why Aren’t I Better at Delegating?” Elsbeth Johnson identifies four challenges that may stop you from delegating:

• An addiction to the dopamine hit of easy productivity

• A disinclination to reject requests for help

• A desire to meet their own bosses’ or clients’ unmanaged expectations

• A misunderstanding of what “work” should mean for a manager

Activity-based work is what helped you rise to the top. Now your responsibilities require the ability to establish the conditions that enable others to be successful. Johnson calls this “context-setting” which “includes explaining why the work needs to be done (following an organizational strategy, entering a new market, onboarding a client, or investing in a project, for example); the results the person or group is expected to deliver; the deadline for the work; and how people should behave (with one another, other colleagues, clients, and others) to get it done.” Clarity of this sort enables:

• Each member of your team to grow in the process of doing their work.

• The team to accomplish more than what you can do alone.

• Your focus to be on areas that only the head/CEO can attend to.

When anxiety rises (and it will), you may feel the temptation to micromanage. Rather than pulling the activity back into your own “to-do” list, double down on support by improving the practices and systems that help everyone align their work with the organization’s mission and strategy.

As highlighted in “The Surprising Success of Hands-on Leaders”:

“What distinguishes the leaders of these high-performing firms is their sustained and close attention to behaviors and systems. They are not inserting themselves into every decision or displacing their teams. Instead, they act as teachers and system builders: They’re present in the work not to control it or make every decision themselves but to model standards, sharpen problem-solving, and establish behavioral norms that enable others to act with autonomy and discipline. They don’t meddle—they coach. They don’t override—they elevate.”

Commit to becoming a good coach. Gallup research identifies the skills that great managers do differently and what those coaching skills look like in action:

Embed talent development in everyday work. Too often leadership and talent development is limited to sending a few people to an off-campus conference. While conferences and speakers can certainly be worthwhile, that approach lacks the frequency, relevance, application, and immediate feedback necessary to fully develop your high-potential people. In our paper “Everyday Succession Planning,” we emphasize the importance of connecting daily learning with the strategic needs of the organization. This learning can take the form of apprenticeships, shadowing, functional rotations, special projects, and serving on task forces or teams. This is also how you break the cycle of leaders rising to the top of your organization without the skills to distribute leadership and develop talent.

Spend time and energy improving how your team works. Teams are more than a group. A team is interconnected and interdependent, working in service of a common goal. Like a crew boat, unless everyone rows together in a way that harnesses their individual contributions to advance the whole, no one wins. Google’s multi-year research identifying the characteristics of a great manager (Project Oxygen) noted:

“We analyzed over 10,000 data points about our managers, taken from performance reviews and feedback surveys, as well as taking hundreds of pages of notes from interviews with Googlers. The findings were clear: Teams with highly effective managers were more likely to achieve better results, be happier, and experience lower turnover.”

This finding may seem obvious, but for a study that started with the premise that managers are not needed, it is meaningful.

The key insight from Google’s subsequent research on what makes effective teams (Project Aristotle) is more surprising: “The study’s key insight is that how a team works together is more important than who is on the team. An effective team sets meaningful, clear, impactful goals, and blends open communication with a culture of continuous learning.” For a deeper look at teambuilding, see our blog series “We Call Ourselves a Team, But” Part 1, Part 2, and Part 3.

Be a learner and sense-maker, rather than an all-knowing expert. In this Google article, their chief learning officer notes, “In the AI era, our teams don’t need us to be all-knowing. What they need is transparent learners, working right alongside them to architect a future that we’re building together.”

One of the multiple benefits of not being the “source of all answers” is that you allow room for others to develop decision-making and solution-building skills. The BigThink article “Stop giving advice, start asking better questions” takes it a step further: asking someone on your team a real question means you value their perspective enough to look for their answer and be changed by it. Asking better questions is a skill you can hone, notes Alison Wood Brooks and her colleagues at Harvard in “The Surprising Power of Questions.”

“Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards.”

Be willing to accept the sense of loss that can accompany not being the center of everything. You may wish for a time when the work was intense but not impossible for one person. A time when you could oversee one domain and tune out the noise around you. When you rarely had to leave your office or classroom and every significant decision that affected you ran through you.

In order to harness the power of distributed leadership, you have to give up being the larger-than-life figure at the center of everything. There are lessons from scaling in the corporate world that are relevant even though your organization may not have increased the number of clients, students, or employees, because the scope of what you are responsible for as head of school or CEO is vastly larger than in the past. In the Forbes article “Why Successful CEOs Can Struggle at Scale,” the author writes:

“I know because I lived it.​ In the early days of building my business, I was involved in everything: clients, hiring, strategy. It worked until it didn’t, and at a certain point, the business couldn’t grow any further without changing how I showed up. I had to step back from being the driver of every outcome and become the integrator of the system. That meant building a stronger leadership team, trusting people before I was fully comfortable and letting go of control in places where I used to hold it tightly. It wasn’t intuitive or easy, but it was necessary.”

The way you reach the new goal posts isn’t always about doing more. First, you have to identify where you add value. Then you need to actively develop the abilities of your broader team. And keep an eye out for where the roadblock is you.

This requires a ruthless level of clarity about where you should spend your time.

And, at each step, you will need to partner with your board — and help educate your board — on the new responsibilities of the leader and the new capabilities that must be developed throughout the organization.

What can you and your board leadership do?

Start with managing the board’s time well. One of the greatest challenges leaders face is managing time — and the board that is navigating complex issues and heavy agendas can find it hard to allocate time effectively. I have sat through many board meetings where the single most consequential question facing the organization never reached the table. In our blog post “Reporting or Future Building: What Happens in Your Board Meeting?” we offer a reframe that may help: the purpose of a board meeting is not to be informed. It is to think together about what cannot be thought about anywhere else.

This shift in mindset has two positive outcomes: it encourages the board to practice better time allocation, and it enables the board to improve the quality of its own work (which directly benefits the leader’s work too).

Make education a priority. Boards that take responsibility for learning — about the work of the leader, the work of the organization, and approaches to high-performance governance — are generally better at governance.

Look for practical ways that the board can partner with the chief executive or head. Together, you can explore and address expanded responsibilities, especially the work that extends beyond day-to-day operations, such as fundraising, advancing the brand, external affairs, and cultivating a wider perspective.

Establish guardrails. Wise boards are alert to politics and well-meaning but misguided efforts by individual board members and stakeholders that can place a tremendous burden on the leader. They support decisions and act as a buffer so the leader doesn’t shoulder these pressures alone.

Turn the board into an engine for R&D and talent development. Build the board with practices that facilitate distributed leadership within the board — exemplifying the talent development mindset that you want to cascade throughout the organization. Support the head or CEO in establishing practices that embed practical learning in career paths, as we highlight in “Reframing the Work of Succession Planning: Making Leaders”:

“Real succession planning is about talent strategy and leadership development work. It is the ongoing work to answer the question: what approach to talent acquisition and development will make our strategy and our organization successful?”

Hire for the new job description — and recognize that the board’s role in transition continues long after the contract is signed. In “A New Approach to Leadership Transition,” we emphasize that purposeful attention to the transition is as crucial to a successful transition as the search process itself. Effective transitions plan well beyond the first ninety days.

Celebrate progress, not only wins. Most boards reward big milestones and stay silent on the quiet, less glamorous work in between, but as we share in “The Work of Hope: A Note for Boards” the months between milestones are where motivation is won or lost. Recognizing the work associated with a strong process and management acumen is how you keep a team in the game long enough to reach the milestone — learning together as you go!

We hope that The Blueprint regularly helps you pursue and celebrate progress!

We’re excited to expand the resources we offer and hope you will continue the journey with us at our new home on Substack: The Blueprint by Greenwich Leadership Partners.

Greenwich Leadership Partners forges powerful partnerships with not-for-profit and educational institutions to support excellence in governance and leadership.

Independent schools and not-for-profits have learned to read length of tenure as evidence: a long tenure means the leader was good and the board was wise, and a short one means something went wrong. It is a tidy shorthand. It is also wrong often enough to do real damage to the way we think about a successful tenure.

The worry underneath it is legitimate. Searches are expensive and exhausting. Turnover interrupts momentum, unsettles organizations and their constituents, and takes a genuine toll on the person leaving and on the people who stay. A revolving door for leadership is rarely a good thing. So the question I hear often from boards is some version of “how do we keep our leader longer?”

I have come to believe it is the wrong question, and that the way we usually answer has the potential to diminish rather than create value.

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Succession planning is the most underdeveloped muscle in most boards and leadership teams. Often the most common approach sits in a single question from a board to a leader: “What is our succession plan in case of an emergency?” Strong leaders always have an answer at the ready, but it’s often an emergency plan dependent on one individual. This may reas…

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Reader questions on governance and leadership, answered. Have one? Email me at ask@greenwichleadershippartners.com — I read every one.

A question from a not-for-profit governance committee chair:

Stephanie:

This is a common problem within boards, and it can persist to the point of real damage.

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Hello Blueprint Leaders and Readers! At GLP, we are happy to welcome warm summer days, summer Fridays, and summer plans with family and friends. But we are still working and we imagine you are, too. Summer often brings time for leadership retreats so we wanted to explore a few topics that may be helpful as you take time to reflect and plan with your teams.

We also imagine that many of you, as you steer into summer work, are wondering how to coalesce a new team, integrate new folks, and/or address emerging needs and opportunities. Frankly, great leaders are always leading through change because no organization can afford to stand still. Challenges come from inside and outside. Usually they collide!

Whatever the context, we are reminded that leadership is a deeply human activity. This Blueprint explores how to uncover roadblocks and make progress on problems in ways that consider how we, as humans, respond to change and to one another. We hope these resources are helpful—whether you are leading through tough times, beginning transformational work, or building a healthier, adaptive, and more resilient organization.

- Stephanie

Leadership is Rooted in Connection

So much of today’s news focuses on rising rates of burnout, eroding trust, and a doubling down on standard advice for leaders: skill building. Great leadership certainly demands the purposeful development of your abilities, but what if the tendency to overly focus on your—the leader’s—role is part of the problem?

What if instead we start by asking the question in this HBR article: “Are You Meeting the Needs of the People You Lead?”

Focusing on your connection to others, on the relationship itself, can often be the key that unlocks solutions:

“Leadership is treated as a property of the leader, rather than as a relationship shaped by what followers need at a given moment. That shift in perspective changes everything.”

To help you see the relationship from the other end of the telescope, the authors outline six needs that your team has—and relevant questions to examine for each:

Though the article speaks of “leaders” and “followers”—which is helpful for clarity—we think these ideas are equally relevant for leading across teams with peers, managing up, and leading through networks.

Certainly, anyone in a greater position of power, authority, and title has a proportionately greater responsibility to approach leadership thoughtfully. For example, how you respond in a meeting when someone on your team offers a critical assessment can determine whether your team is willing to continue sharing the feedback that is essential for success. You model (or don’t) how human relationships have primacy when you create an open, respectful, and safe container for candor.

In “Why Your Team Won’t Speak Up (And How to Fix It),” Charles Duhigg, author of Supercommunicators: How to Unlock the Secret Language of Connection, says:

“[W]e can say that we want candor, but unless we reward people for being candid, then they won’t do it. And the truth of the matter is, if you go into a meeting with your senior VP and you’re the one who’s second guessing him and offering all these different alternatives about other plans we should use, you’re probably not going to get rewarded for it. Unless that SVP takes a step back and says, ‘Look, just want to say at the end of this meeting, thank you so much, Charles, for bringing up all those issues because the more we question ourselves, the better we’re going to get at doing this job.’ So we have to reward candor rather than punish it, which is what happens most of the time.”

There’s one more important reason to consider the relationship in how you lead. Duhigg adds an important layer of nuance: extensive research in neuroscience has revealed that when we engage in conversation there are actually multiple kinds of conversations happening at the same time and that these conversations tend to fall into three categories.

• Practical conversations—where we’re making plans or solving problems

• Emotion conversations—where you share what you’re feeling and want the other to empathize (rather than try to solve the feelings)

• Social conversations—about how we relate to each other and the outside world

“And what researchers have found is that supercommunicators, the people who communicate best, they really focus on having the same kind of conversation as the person they’re talking to at the same moment,” says Duhigg.

Pause for a moment and think about what this means. How might the identification of the conversation type shape your leadership playbook, and how you respond. If your teammate is in an “emotion conversation” or a “social conversation,” you have to pave the way to a “practical conversation” by building a bridge that recognizes where they are, names it, and then offers pathways forward.

Turning Connection into Teamwork

What if you have a talented group of individuals, but they’re not coming together as a team? This is one of the most common reasons GLP is engaged to lead retreats: to help bring talented people together in ways that actually change how they work.

While an outside facilitator can move the needle for you in key moments, you really want to build this capacity within. Look for what this HBR article calls “super-facilitators”:

“In recent years, a new wave of research has revolutionized our understanding of group success, and it showcases facilitators as much more than just talented team members. If the supercommunicators described by the best-selling author Charles Duhigg help people understand one another optimally, super-facilitators are architects of group performance who bring people together optimally.”

Unlike the “wisdom of crowds,” this model of collective intelligence is not about finding insights in the average answer. Rather it enables each member of the team to excel at their unique expertise and skills while maintaining the ability to bring it all together in support of the team’s results.

“The idea is this: After you launch a project or initiative, don’t merely carve up the work and distribute it across your team. Build out each person’s tasks with an eye toward what drives them and where they function best. Ideally, bring the entire team into the process of role-crafting. When people have agency over their part of the job and knowledge of everyone else’s, they commit more deeply and are less likely to duplicate effort—allowing collective intelligence to bloom.”

The power of super-facilitators underscores again that leadership and teamwork happen in relation to one another. Super-facilitators understand the importance of dialogue and enabling each member of the team to have a voice.

Read more on this in GLP’s whitepaper “How to Build a Great Team.”

Keeping Connected Through Change

Transitions, new leaders, new team members, and change in general are especially likely to create conversational mismatches—and even to inadvertently eliminate much-needed conversations. The MIT Sloan Management Review article “When Employees Are Drowning in Change” notes, “Dialogue is one thing many leaders cut back on during periods of change.”

Whatever the nature of change, the tendency is to focus on the change rather than on the people living through it. When you think of it as “leading change,” you’re likely to start with practical conversations—focused on the why, what, and how for solving problems and creating plans. Instead, thinking of it as “leading people through change” will help you remember that in many cases people will come to the conversations—even conversations that are supposed to focus on solutions—with emotion top of mind. For example, if you say, “Let’s test out how we might implement AI into our workflow.” You might be focused on solutions. But others are likely to immediately wonder, “How will this affect my job?” or “How does this threaten my identity as a professional?” or “How much time is this going to take?”

Focusing on emotions is purposeful, but it’s not an end in and of itself. A couple of key points:

Meeting people where they are doesn’t mean you have to agree. The focus is maintaining connection—throughout both agreement and disagreement. Part of this is establishing the conditions for psychological safety.

Finally, it’s not enough to say “we want people to be comfortable.” Disagreement is both necessary and an ingredient of progress. You have to actively cultivate what this McKinsey article calls “professional dissent” defined as “the courage to voice a contrarian view.” The article highlights five ways:

As a leader, how you ask questions will also play a key role in facilitating helpful responses. This MIT Sloan article explains:

“One of the most common missteps leaders make is asking broad, nonspecific questions like “What do you think?” or “Does anyone have any input?” While these questions might seem open and inviting, our research found that they had just a 51% chance of receiving any dissent. … More effective questions directly invite disagreement. Instead of asking, “Does anyone agree with this plan?” consider asking, “What could go wrong with this approach?” or, “What are the potential risks we haven’t considered?” Questions like these make clear that the leader is actively seeking alternative and potentially challenging perspectives.”

Thoughtful choices in language can make a difference both when you are asking the questions—and when it is your responsibility to respond to your boss’s questions.

Connections Are a Part of “Leading Up”

We’ve been focusing on how to lead others, but what about how to lead your leaders? All of the above tips apply, but let’s steer straight into how to deal with those above you. In “Managing Up: A Skill Set That Matters Now,” the authors write that many struggle to connect with superiors:

“We define effective managing up, or upward leadership as ‘listening to those higher in rank and influencing them to assist you and your team to better embody the organization’s values and fulfill its mission, strategy, and goals.’ … Leading upward does not come naturally to most people. In fact, in his 2001 book, Leading Up: How to Lead Your Boss So You Both Win, Wharton professor Michael Useem suggested that just one-third of managerial employees had the necessary skills and desire to do so. … Turning your own or your team’s reactions, concerns, or feelings into words that a superior can understand may be all it takes to shift that leader’s position, tweak an idea, or change a disagreeable behavior; it’s one step short of advocacy. This requires an underappreciated ability to convey emotional reactions in a respectful manner.”

Leadership in all its forms requires a commitment to translating, to spanning the distance. If you are a chief executive, this is deeply important to how you work with your board. Whether you are encouraging your team to share insights that may be uncomfortable or whether you are the one taking the risk to share those insights with your boss, that translation takes courage.

Governance as Leadership: 
Connection in and Beyond the Boardroom

When working with, and within boards, connection is equally important. Indeed, there will be times when it is the people rather than the practices or procedures that are difficult, impeding progress, and causing friction.

In “Managing Difficult Directors,” the authors describe a common situation:

“It happens in every boardroom. Hours into a marathon meeting, the conversation on the critical strategy topics has not yet started, and that one director won’t stop circling around a minor issue no one else finds relevant. As discussions continue, the same director pushes back on every idea. Momentum stalls, focus blurs, energy dissipates, and frustration mounts.”

They identified three main types of difficult board members:

• Passive Passengers—who stay silent and hope to go unnoticed

• Dominators—who take control of every discussion

• Misguided Experts—who focus too much on the details

Even boards that establish norms in their board charter, build important factors such as the value of teamwork into their selection process, and sustain ongoing board education may encounter this issue.

“Diagnosing difficult behavior in directors begins with disciplined observation. Effective boards look for patterns, and they assess them through three simple but powerful lenses: engagement (Do directors come prepared, show curiosity, and lean into the conversation rather than hovering at its edges?), interaction (Do they listen, build, and challenge constructively, or do they derail, interrupt, or retreat into silence?), and impact (Does their participation strengthen debate, sharpen judgment, and help the board reach sound decisions, or does it slow progress and dilute focus?).”

It is helpful to recognize that each of these difficult board member types can arise from experience and good intentions. Passive Passengers may be expert in narrow fields and hesitant to participate on other topics—so clearly invite them to do so. Dominators may have a long history of success and a genuine enthusiasm for the work—so help structure the meeting with protocols so that it doesn’t become a platform for lecturing on their opinions (and help them understand their role as one member of a team). Misguided Experts may continually bring the conversation back to their area of knowledge, even if it is not the most important for the task at hand—so help them recognize that, like Passive Passengers, they have a responsibility to elevate or release their experience to bear on all aspects of the governance work.

And as Duhigg suggests, knowing what kind of conversation you are having is step one to managing these types. GLP works with boards to discipline and structure conversations, by identifying and managing the differences between dialogue, debate, and decision-making. A wise board chair can manage members with a clear protocol. We describe this in greater detail in our whitepaper: The Adaptive Board, and offer a few tips described in the paper here:

• Uphold your board norms.

• Appoint a facilitator.

• Use protocols to manage discussions.

• Come prepared with open-ended questions to facilitate dialogue.

• Use tools for inclusion.

• Examine options and make decisions through the lens of mission and values.

Sometimes you just can’t affect personality or behavior.

“If a board member persists in disruptive behavior despite repeated efforts to address it, escalation becomes a matter of good governance, not preference. The process must be clear and fair. It should be overseen by the nominating and governance committee, working closely with the chair and the lead independent director.”

When leadership is understood as happening in relationships, in connection, it plays a vital role in transforming a group of individuals into a team with a common purpose. As the authors of the HBR article above note:

“Boards work best when every director pays attention to how the group functions: who speaks, who hesitates, when conversations drift, when the room needs a reset. The chair sets the tone, but how a board behaves collectively is what determines whether it performs or stalls. It’s every director’s job to stop minor tensions from growing into real problems and keep the board grounded. Every director has to show up prepared, contribute with intention, be aware of how their style affects the room, help quieter voices be heard, and lead wandering discussions back to a purpose. Effective boards develop the ability to self-correct.”

Finally, in boards, like teams, it begins with who is in the room. How you build your board is your most powerful tool. In “Building a Board That Adds and Creates Value,” we explore how the process of board composition is itself an ongoing education and team-building practice for both your current and prospective board members.

This is true for every team—not just for boards. Leadership is everyone’s responsibility.

Greenwich Leadership Partners forges powerful partnerships with not-for-profit and educational institutions to support excellence in governance and leadership.

What happens when your organization is optimized for yesterday?

We know that for most schools and not-for-profits, business as usual is a recipe for decline—gradually and then suddenly. This is what keeps most of our clients up at night.

Boards and leaders are the first line of defense when the stakes are high. We might sound like a broken record, but we are convinced that to lead change, there must be a clear and committed alignment of board and leadership about when to change, what to change, how to change, how to communicate change, and how to course correct when change brings unintended consequences.

Change leadership is tricky. And sometimes quite risky. In this Blueprint, we examine three examples of how systems and mindsets that brought success in the past can put your organization at risk today.

- Stephanie

Optimized for Obsolescence: 
Mathematics Education as an Example

During a recent podcast conversation, when asked how he would describe American education right now, my dear friend Ted Dintersmith—author, venture capitalist, and executive producer of the film Most Likely to Succeed—said:

“People will say it’s not working. It actually is working really well. It’s just with an obsolete model.”

So often we hear that the education system is “failing” or “broken.” Reframing is helpful because it answers the question “How did we get here?” and points the way to possible solutions—that have implications far beyond our schools.

Dintersmith offers his perspective (one we’ve been articulating since I had the honor to premiere Most Likely to Succeed with Ted at Sundance in 2015):

“We adhere to the model that goes back to 1893, and that model was designed to equip young kids with rote skills and intentionally erode their creativity and curiosity and audacity and agency. And our decision, which I think was quite fateful, was as technology started to really shift things and move us out of the industrial era to the innovation era, we just doubled down on obsolete. And so it’s working in terms of its goal. It just has the wrong goal.”

The study of mathematics is a great example. Describing what inspired him to write his new book Aftermath: The Life-Changing Math That Schools Won’t Teach You, Dintersmith said:

“I think that’s a gross mismatch between what we not only insist on in school but devote thousands of hours to, versus a world that doesn’t care about that anymore, but cares about all these really powerful, interesting math ideas, ideas that absolutely shape our lives. You know, the more we do that, the longer we persist, the more kids leave school with really dismal prospects and hallowed-out sense of purpose.”

Relatedly, the Deloitte report on 2026 Higher Education Trends, emphasizes that “​​By embracing today’s transformative trends, higher education leaders have a remarkable opportunity to reimagine their institutions as agile, resilient centers of learning and innovation.”

Relevance and value are the most important considerations: “To do so, leaders must reconcile two realities: Students overwhelmingly seek degrees that lead to meaningful employment, and employers need graduates who not only have immediate skills but also the agility to adapt as work continues to evolve—especially under the influence of AI.”

If schools of the past were optimized for rote jobs and “being good at doing tasks you are assigned,” then today we need to optimize for the capacity to continually and rapidly learn. And every organization—not just schools—needs to think about how to facilitate continual learning.

Lifting this discussion back up to our larger thesis about change, we ask: How often is the “why” of what you do unclear? Start by testing some long-held assumptions—and notice what you do that is no longer relevant or valuable. Increasingly, schools and organizations that fail to adapt are seeing consequences in the bottom line—if they know where to look.

Change Your Focus: 
What the Numbers Aren’t Telling You

In “The Looming Crisis” and “Your Local College Is Running Out of Cash,” Michael Horn highlights that many colleges are on the brink of becoming insolvent unless dramatic steps are taken. One of the most alarming aspects is that colleges can seem fine and then suddenly announce crisis and closure. We see similar problems in not-for-profits and private schools that find themselves constantly strapped for cash.

Drawing upon a new study by Steven Shulman, Horn writes,

“Instead of focusing on operating budgets or net assets that are often illiquid, Shulman’s research examined a basic but critical financial question: Given current cash flow, how long could each college survive based on the cash and equivalents available for operations? For a surprising number of institutions, the answer is: not long.

Even assuming enrollments remain steady—an optimistic scenario given the coming demographic decline—more than one-third of the colleges studied have less than five years before becoming fiscally insolvent without significant changes. That means they will have less money coming in annually than they are spending, and will need to start drawing down their unrestricted endowments, or borrowing—if they can—to keep operating. On average, those schools have less than a year before their financial position falls into that territory. Colleges can appear stable right up until the moment they are not.”

There are many parallels for K-12 schools and nonprofits—in both the source of the issues and the potential solutions. Horn’s description of the forces impacting colleges is highly relatable:

“The cause of these challenges isn’t one single factor, but a set of pressures building from demographic changes, shifts in the public’s perception of the value of a college education, increased operating costs, emerging alternatives to traditional colleges, and, of late, possible changes in federal policies and programs.”

The question is: with multiple external forces breaking the old model, what do we deliberately build in its place?

Change is Human Work: 
Leading People in an Age of Technology

Change leadership is tricky and risky because the human dimension of change is at the center of the work. It’s often the most crucial element in successful transformations.

As one example, this BCG article “AI Has Made Work Reinvention a CEO Mandate” highlights the critical role of the leader in relation to AI advancements:

“Too many leaders see AI as a technology transformation rather than a work and people transformation. They’re thinking about today’s work, and today’s processes—simply overlaying technology on top of them. The critical mindset shift is this: We must rethink why we do this work in the first place. What value does it create? Who should do this work? How must we redesign the work to unlock enterprise value, not just individual productivity?

This kind of transformation must be driven by the CEO because these shifts cut directly across existing structures, incentives, and power dynamics. They challenge roles, organizational boundaries, and professional identity. In many cases, the people closest to the work itself, and most impacted by how it will change, are also the ones being asked to help redesign it.”

In change work, people need to know answers to three big questions:

• Why are we changing?

• What are we changing?

• How will this affect me?

This work requires as much (if not more) attention to the people as to the technology.

The Stanford Social Innovation Review article “Welcome to the Age of Relational Intelligence” offers helpful insights. Enter Ms. Ricks, a retired office manager who volunteers at 74th Street Elementary School in South Los Angeles as part of Generation Xchange, and Celeste, a fourth grader, who feels like her school work has more value because Ms. Ricks takes the time to care. “I feel like I know somebody is counting on me,” said Celeste.

Writes the author: “As artificial intelligence grabs headlines and investment dollars, Ms. Ricks and Celeste are practicing an intelligence that cannot be automated. It’s the intelligence of attunement, of care, of knowing, and knowing how to know each other. We might call it relational intelligence (RQ), the deeply human ability to build trust, navigate tension, repair ruptures, and create meaning with others.

Relationships are the foundation when we do work with other humans: when we focus there first, we can pursue the work with greater efficacy, purpose, and meaning.

The Emotional Work of Change

Strategic clarity and relationships are just the start. Emotions and reactions will shape your organization’s ability to pursue its strategy in real time—and when you embark on changing long-established structures and processes, you are guaranteed to encounter a range of emotions: often these emotions are experienced as resistance, opposition, or a lack of accountability. Let’s reframe this by examining underlying emotions, and how that can dramatically improve your ability to lead.

Reframing Resistance

Resistance is often experienced as defiance and criticism. The HBR article “Leaders Treat Resistance as Valuable Data” unpacks why it is helpful to shift your view and see what the resistance can tell you:

“A colleague recently asked me a question about change that seemed so normal: ‘How do you tell the difference between legitimate concerns about a change and kneejerk resistance to it?’ At first glance, it sounds like a practical leadership question. But the more I sat with it, the more I realized it’s not actually answerable. It rests on a flawed assumption: that some resistance is legitimate and some isn’t. That assumption is exactly what gets leaders into trouble.

But here’s what years of studying and guiding organizational change have taught me: All resistance is meaningful data. … In my experience, what we call resistance is almost always something else: fear, loss, confusion, overload, or sometimes a legitimate flaw in the change itself.”

The author outlines four emotional responses to help leaders understand and respond to resistance:

While this is where leaders must begin with change, seeing resistance as data is not a blank check for ongoing behavior that undermines the well-being of the team. We are not encouraging you to drag your feet when someone is actively undermining progress—to the detriment of all. There is a point at which behavior that consistently undermines forward movement demands that leadership step in. Our guiding principle is to invest the majority of your energy in the people who can lead you forward.

Own and Choose Accountability

Another powerful reframing that supports leading through relationships is offered in the HBR article “Accountability Must Be Chosen Not Mandated”:

“Leaders should stop asking ‘How do I hold people accountable?’ and start asking ‘What’s preventing them from choosing it?’”

When you enable your team to shift from a defensive stance (“Will I get blamed for this?”) to a mindset where they see themselves as essential to the outcome, you unlock the potential for growth, shared problem-solving, practices that create psychological safety, and a sense of ownership that drives positive outcomes.

As the author notes, it starts with clarity about the “why”: “When the meaning is clear, accountability stops being about compliance and starts being about care and commitment. At the individual level, meaning might come from values like integrity or reliability. At the team level, it’s often a shared goal that transcends any one person’s contribution.”

Trust and connection cannot be rebuilt with words that don’t match the realities. Looking at difficult realities is not easy. And no matter how thoughtful we are about how we lead and communicate, transformations of this scale involve loss and change—in ways that are personal as well as structural. You can’t duck the emotions associated with loss or change—but you can offer new pathways of purpose, productivity, meaning, and impact.

Greenwich Leadership Partners forges powerful partnerships with not-for-profit and educational institutions to support excellence in governance and leadership.

In our previous Blueprint Roundup, we explored leadership and board evaluation as talent development tools. Here we’ll dive deeper into a systems approach to developing talent throughout your organization.

We know that people are your most important asset. While conversations with boards and leaders about the future often center on issues like funding volatility, political uncertainty, and AI, what soon follows are questions about talent: do we have the people we need to address the challenges ahead? Is our organization ready, and will we be able to effectively respond?

Many of you have shared with us that while change is a constant, finding people who can lead through change is your biggest challenge.

A talent culture, one where people are engaged and actively learning, is the foundation of an organization that thrives through uncertainty and change. How do you build it?

Lots of sports analogies here (which is funny because I know nothing about sports), but I hope they resonate with you as they do with me!

- Stephanie

Talent Development: Model the Way

“You’re not a leader simply because you have a rank or a title,” noted Simon Sinek in a recent conversation on the podcast Aspire with Emma Grede. “Leadership is a choice, and it’s a lot of work. It’s the choice to see another person rise and grow—that you’re going to be a part of that journey.” One of the keys, Sinek says, is to “be a student of leadership” because the factors—culture, generations, politics, challenges—are always changing. What stays constant are basic human principles: “People want to know that they matter. People want to know that their work matters. People want to feel trusted and trusting.”

As a leader, the process begins with you. In “How to Build a Superteam That Keeps Getting Better,” Ron Friedman writes, “At the center of every learning culture is a leader who makes growth a daily priority.”

Fittingly, with the NBA playoffs starting this month, the example highlighted by this HBR article is the dramatic turnaround and sustained success of Oklahoma City Thunder. In just three seasons, the Thunder went from being near the bottom of the league to winning the 2025 NBA Championship. This season, OKC once again has the best record heading into the playoffs.

In investigating the question: “What do the best teams do differently?” Friedman found a number of common elements, including:

• A commitment to constantly improve over time.

• A willingness to experiment more often.

• Leaders working alongside their teams.

• Team leaders who excel at feedback.

Constantly improve. When asked by Sports Illustrated about OKC’s approach to the 2025 draft, general manager Sam Presti said,

“[W]e’re never rigid in anything we do, so we don’t say this is the way we’ve done it so we’re always going to do it this way. We’re always looking to update the way we look at things, try to figure out as much as we can learn. Every draft that we have is an opportunity to reflect back on the others and figure out what we can do better.”

His next remark sheds light on a key factor: in order to constantly improve, you have to build with people who are willing to grow. Presti said,

“But the one thing we’ve never really strayed from, and I don’t think we will, is the focus on drafting people and not players. I think the characteristics of winning players, they multiply at a greater level than just talented players. They scale up better.”

At GLP, we regularly emphasize the importance of hiring for mindset. That’s what Presti means by “winning players”: it’s not just their skill today that matters. When you’re building your board and leadership team, start by identifying non-negotiable mindset factors that every member of the team needs to have. How curious are they? Are they willing to grow? Do they value teamwork as core to success? Do they have what it takes to learn quickly and apply that knowledge creatively?

Our paper “Board Composition: Building a Board That Adds and Creates Value” offers a deeper look at actionable steps for assessing mindsets, and, while the paper is focused on boards, many of the insights will apply to leadership teams as well.

Experiment more often. Does your team experiment when things are going well? The most successful teams “evolve by trying new approaches.” Friedman’s research suggests that rather than spending the majority of meeting time on progress reports, high-performing teams shift the focus to problems that need solving by asking, “What are you stuck on?” This one question does two powerful things: 1) it makes it okay to identify what isn’t working well and 2) it drives your team to continually experiment in order to solve new problems.

Working alongside their teams. “The Surprising Success of Hands-on Leaders” reminds us that leaders need to understand the work, to model the standards, and to stay close to those who are directly working with the people your organization serves. In the Thunder case study: “Even now, with a full scouting department, Presti still spends most of his year on the road and in the film room, studying players most fans have never heard of. It’s a choice that sends a clear message to the rest of his team: No task is beneath him,” writes Friedman. “When people see that their leader is willing to do hard and tedious tasks, responsibility feels shared and collaboration deepens.”

Leaders who excel at feedback. The faster you learn what isn’t working, the faster your team can improve. But it takes creativity to analyze mistakes without sending everyone’s nervous system into fight/flight mode where learning is blocked. In the OKC example, watching the game tape is not always easy. Thunder’s head coach Mark Daigneault recalled, “We had a game where we had 30 turnovers, and I did a film edit of the turnovers to a Springsteen song. I told them, ‘If I’m gonna have to watch 30 turnovers again, I at least want to be listening to Bruce Springsteen while I do it.’”

Sports teams watch game film after every game. What would that look like for your organization?

Succession Planning is Leadership Development

We often ask heads and boards: Do you make succession planning an expectation for yourself and your leaders? Do you require that leadership development strategies and succession plans be updated and assessed annually for all critical positions?

You can likely predict the answer: No. If this is where your organization is today, you have a tremendous opportunity to reduce risk and strengthen your organization’s greatest asset: its people.

To build an architecture that supports and sustains an effective organization, as highlighted in our paper “Everyday Succession Planning,” we recommend five steps:

• Start with Strategy

• Link Strategy to People

• Assess the Organization and Mind the Gaps

• Make Succession Planning an Expectation

• Identify Potential and Steward Talent

• Start with Strategy

Knowing where you are going and what you need to do to get there is what informs who (what kinds of talent and capabilities) you need. For boards and leadership, this is first-order work—because you can’t build an effective organization if you are not clear on what you are trying to accomplish. Strategy is often misunderstood in schools and not-for-profits: don’t confuse it with planning!

In McKinsey’s study on practices to retain non-profit talent, clear mission and strategy was the number one factor for successful retention. When people know why their work matters, they are able to direct their efforts more effectively—and to find that effort more rewarding.

Link Strategy to People

Real strategy begs important questions to succeed:

• What capabilities do we need?

• Do we have the right people focused on the right work (roles and responsibilities), and are they supported by the right systems and resources?

• What do we need in our Head/CEO and what does that leader need around them to work at their highest potential?

As noted in the HBR article “Where Traditional Succession Planning Falls Short,” starting with strategy guides you to hire (and develop) leaders for the future—not just leaders who fit current needs:

“Rather than focusing just on which candidates could step into existing roles, the real opportunity for strategic succession planning is to identify the leaders who can take your company into the future. One way leading companies are starting to do this is through “scenario-driven” succession. … By considering the most likely strategic scenarios of where the company would place “big bets” in the next three to five years, the board evaluated which leader would most effectively succeed in each scenario, then made their selection based on their predicted direction. In this way, succession planning can answer the question, “Who should lead if we take this path?”

Assess the Organization and Mind the Gaps

A well-designed approach to assessment of the organization and its talent is a crucial form of ongoing education and effective oversight—for the board and for leadership. It answers questions that day-to-day demands rarely allow the space to ask: Where are our capacity gaps? Which roles are most vulnerable? Who is ready to grow into greater responsibility, and what do they need to get there?

Assessment is the foundation of intentional talent development. A third-party audit of organizational leadership (talent and structure) can surface opportunities as it spots serious gaps and misalignments. Often, you have the talent you need but they are encumbered by ineffective systems or they are simply in the wrong spot.

Finally, build your own ability to assess. As we emphasized in the earlier Blueprint on evaluation: when you establish evaluation practices, you normalize learning, growth, feedback, and analysis on a regular basis—not just when there is a crisis or things go wrong.

Make Succession Planning an Expectation

At GLP, we’ve coined the term “Everyday Succession Planning” to encourage organizations to shift their focus and approach from reactive (“John is leaving, and we need to replace him—fast!”) to proactive (“When John leaves, we have a strong bench and know how we will address his departure both immediately and for the future.”)

Whether you think of it as “everyday succession planning” or as “leadership development,” it is crucial to frame it as an ongoing part of your leadership responsibilities—not as a response that’s triggered when a key position needs to be filled. Making this shift connects succession planning with the vital, ongoing, “everyday” work of leadership, talent development, and aligning your people and resources with your strategy.

In this McKinsey article, Intuit’s former CEO Brad Smith recalled advice from legendary executive coach Bill Campbell:

“The first day I was in the job as CEO he said, ‘I want you not to think of succession planning as replacing yourself. I want you to think about it as leadership development of your team. And we’re OK if we groom CEOs, and you’re not ready to leave or we don’t want you to leave, and they go someplace else. Because then Intuit will simply be known as a leadership factory.’”

This approach has four powerful components:

• Make it about the position.

• Make it about growth for your team.

• Make it about the future.

• Make it okay to have so many outstanding leaders that they carry the reputation of your organization far and wide.

Your biggest risk right now is not having the talent you need to solve the most vexing problems your organization will face in the future.

As the McKinsey article illustrates, it is worth pausing to reflect on the dynamics encapsulated in the common phrase “passing the baton.”

“Like track and field, the goal of the handover is to ensure the next person gets off to a great start and is well positioned to perform even better after the baton is handed off. … In a successful relay, the person receiving the baton starts running well before the baton reaches them. The same can be said for succession planning.”

Is your organization trying to do the handoff from a cold start? As we emphasized in A New Approach to Leadership Transition, a failed leadership transition can set an organization back both financially and strategically.

Let’s take a look at ways to help your high-potentials start running before they receive the baton.

Identify Potential and Steward Talent

The best part of this work is signaling to your valued high-potential people that you see them and are excited to invest in their future. The pathways and opportunities you open up to them will be informed by your organization’s strategy—and the awareness that not all high-potential people aspire to enterprise-wide leadership roles. Be clear that you have aspirations for them, and check that they are aligned with your perspective. Invite their full participation in developing learning opportunities.

In the 2026 Deloitte study on human capital trends, “Leaders also report that the two most important drivers of success are accelerating how people and resources are orchestrated to perform work and increasing their organization’s and workforce’s ability to adapt to change and speed.” A key part of that is helping people learn better and faster by providing them with the range of experiences and responsibilities that help them grow the relevant skills.

One of the best ways to develop talent is to expose and involve them in enterprise-wide initiatives, helping them see into the work you do as a CEO, Head of School, or functional leader:

• Take rising stars with you to meet with clients, funders, and donors. Introduce them and give them opportunities to plan for the meeting, participate in it, and help with follow-up planning.

• Expose them to board members and other functional leaders. If your leader is program-focused, get them on a team that analyzes the economics of programs, and help them see how program value supports economic health.

• Invite them to board meetings to present, observe, and build relationships. Make sure to explore with them boardroom dynamics and how leaders work effectively with boards.

• Think about what you didn’t know when you stepped into leadership. And help your rising stars fill those gaps now!

Don’t leave leadership to chance; an effective human capital strategy takes less time and money than the alternative.

Greenwich Leadership Partners forges powerful partnerships with not-for-profit and educational institutions to support excellence in governance and leadership.

At this time of year, we field a lot of questions about leadership and board evaluation—and these inquiries lead us into conversations with clients about their overall approach to talent and leadership development. As you can imagine, we sometimes uncover the absence of internal strategy or systems to ensure this work happens with intention. Alternatively, we find haphazard approaches that diminish the efficacy of assessment, evaluation, and development.

We appreciate how hard it is to establish healthy evaluation practices that turn goal setting and assessment into a platform for deeper dialogue. Many organizations shortchange the process because they lack systems—and they lose the benefits of effective assessment: growth and development, aligned goal setting, reduction in turnover, an inventory and pipeline for talent, proactive succession planning, strengthened teamwork, and a culture that models the way for the entire organization.

In this Blueprint, we explore why assessment matters and how to approach it in a way that advances leadership, cultivates a depth and breadth of talent, and drives organizational performance. Next month’s Blueprint will dive deeper and swim further on talent matters—into developing learning cultures, supported by effective talent strategies and system-wide succession planning—what we call “Everyday Succession Planning.”

- Stephanie

Why Does Assessment Matter?

Institutional performance is directly related to both CEO/Head and board performance. In GLP’s work with non-profits and schools, we consistently see better results when the board and CEO/Head share a consistent approach to assessment; one that strengthens their partnership and informs how each grows and develops—so that they can scale this approach throughout the system.

Relatedly, the importance of a strong partnership between the board and CEO/Head, characterized by effective communication and collaboration, seems obvious—but in the whirlwind realities of life and leadership, it is easy to fall into the trap of focusing only on outcomes at the expense of building the everyday systems that support or enable the outcomes you want. This focus can inhibit the earlier, informal, and more helpful feedback loops that promote effective adaption—before you experience outcomes that disappoint.

Designing and implementing an evaluation process for your board and leadership is one of the most powerful foundations for effective collaboration because it provides the opportunity to:

• Define criteria for success

• Identify (and negotiate) clear expectations and goals

• Determine how both actions and outcomes will be measured

• Establish ongoing communication, information sharing protocols, and feedback loops

• Discuss what the CEO/Head needs from the board and vice versa

• Educate the board on the work of the CEO/Head and educate the CEO/Head on the roles and responsibilities of the board

• Align both leadership and governance work to the mission and strategy of the organization

• Diagnose the dynamics in the board–Head relationship that support or hinder success

At its best, the evaluation process gives you actionable insights and builds momentum (rather than increasing fear and defensiveness). Importantly, you are normalizing learning, growth, feedback, and analysis on a regular basis—not just when there is a crisis or things go wrong.

Knowing where you are today is essential to key board responsibilities—such as succession planning and managing effective transitions. As we noted in our paper A New Approach to Leadership Transition, it is the combination of board performance and leader preparedness—not just one or the other—that matters:

At a glance, you can see why it is important to evaluate your board as well as your leadership: an under-performing board may result in the loss of an excellent leader, and the combination of an under-performing board and an under-prepared leader can cause lasting damage to your organization.

Clear-eyed assessment is not always easy or comfortable, and it can face additional challenges in nonprofits and schools—where the work of leaders and board members is done with great heart. In these situations, it can be tempting to avoid critical feedback in an effort to be supportive. But this approach can backfire because it disguises the feedback people need to excel, harms mission delivery, and can result in unspoken friction and limited growth.

The best solution is to build an evaluation process that inspires positive action and strengthens collaboration—rather than making people feel judged unfairly or misunderstood. And evaluation (tools and processes) is meaningful only if it is supported by evidence, examples, and specific recommendations for improvement. Which brings us to the power of putting dialogue at the center of each step.

The Power of Dialogue

The best evaluation processes harness a “dialogue” mindset. As Georgy Ann Peluchiwski noted in this GLP blog post,

“Start by talking to each other. Sounds simple, but this is often the step we see skipped or bungled. Enter the goal setting process in a spirit of partnership and collaboration. Talk less and listen more. Goal setting should be a joint endeavor with the leader. Boards should not ‘present’ goals to the leader, nor should leaders be drafting in a vacuum and ‘presenting’ to the board. Begin with a dialogue about what your shared priorities are, how that will inform the work of leadership, AND the work of governance. Boards should also be asking their leaders what they need and expect and should hold themselves accountable for delivering.”

Carry this commitment to two-way communication throughout every part of the process—especially by using follow-up conversations to understand and unpack the formal evaluations. In the HBR article “For Your 360-Degree Feedback to Be Effective, You Need to Discuss It,” the authors emphasize that the evaluation report on its own does not provide the full benefits:

“The 360 itself didn’t change anything. The follow-up conversations were what made the difference. Indeed, research shows that the biggest predictor of increased leadership effectiveness after a 360 is whether you discussed the feedback with the people who gave it to you.”

Discussing the feedback helps you more accurately understand—and more accurately decide how and what to change.

“Move from assumptions to conversations. When you read your 360 report, you’ll naturally draw assumptions about what people meant. But the worst thing you can do is stay in your own head, interpreting feedback through your own lens and never testing whether you got it right.”

The authors emphasize that it is beneficial to approach these conversations in a structured way to reduce blocks to communication (such as defensiveness and justification) and to avoid hastily making promises of change:

Another context for helpful dialogue is a frank exploration with your leader, Head of School, or CEO about how they see the job and assess themselves. This McKinsey article reveals how the conversation may illuminate different perspectives—and build a stronger shared understanding of what matters most in evaluation. The focus is on CEOs mostly from Asia—but the applications to schools and NFPs are immediately recognizable. Not surprisingly, engaging the board and staying connected to external stakeholders rank as the biggest challenges:

When you put dialogue at the heart of your evaluation process, you create the conditions for strengthening partnership, teamwork, and understanding. You shift away from a one-time “scorecard” approach to an iterative process that truly advances growth and performance.

Avoid Feedback Fatigue—Turn It into Action

In “Turn Employee Feedback into Action,” the authors note, “People won’t speak up if they don’t believe their input will be genuinely considered.”

“Many HR executives we interviewed said that ‘survey fatigue’ is a misnomer. Rather, employees experience ‘inaction fatigue,’ and harnessing their voices requires a long-term investment in building and sustaining trust that their feedback will make a difference.”

As the HBR article on discussing feedback emphasized, start by thanking people who took the time to give feedback—be specific and reflect back to them insights they shared.

This is not to say that all input is equally accurate or useful. Don’t base assessment only on how people feel. Make sure you have examples and evidence for the criteria or goals on which to assess. Consider ways to identify and counteract less than accurate assessments. Measure progress by gathering specific perspectives, examples, and information about leadership that can then be quantified. And don’t make feedback anonymous (you want to encourage a culture of honest and constructive feedback) but do ensure confidentiality.

Designing an Effective System

Engagement with conversation and listening are not enough—they are best offered within the structure of a well-designed approach to evaluation with effective assessment tools. Successful evaluation processes are systematic, customized, and practical—providing you with the evidence and data to diagnose issues, find opportunities, improve, and make good decisions.

For key steps, let’s return to the GLP blog post:

We’ve learned that assessment needs to tie itself to measurable goals, and effective assessment gathers relevant examples and evidence of progress. But so often what gets assessed doesn’t actually measure what matters most. The more clear you are about what matters, and the better able you are to measure effectively, the more you empower everyone in the organization to contribute to the results you want.

Watch out for what this HBR article calls the “superhero scorecard”:

“Boards often create unrealistic expectations—listing 12 ‘must-have’ experiences instead of focusing on the four that truly matter or demanding five core competencies when two would suffice. This makes evaluation less meaningful because decision-makers lack the hard step of ruthless prioritization. As an executive, you need to push back. ... Ask: What must I personally excel at versus what can be augmented through my leadership team and outside support? If everything is a priority, nothing is.”

The authors highlight four essential questions prospective CEOs should answer before taking the job—and these questions are also helpful to consider when negotiating goals and measurements of success.

Don’t Get Trapped in the Rearview Mirror

When designing assessment, you need to balance your consideration of results with what you want to see happen for the future. To ensure you are growing towards what’s next, a key question is: “What assessment drives learning so that the board and leadership feel supported and ultimately advance in their leadership and roles?”

In 2013, Strategy + Business published an article called “Are You Leading Like It’s 1980?” highlighting old approaches to performance management that were no longer relevant. The authors noted:

“A key element to making this shift is changing the focus of the annual performance review process from a backward-looking, narrow perspective that answers, ‘What have you done for me lately?’ to a forward-looking, productive conversation that asks, ‘How can you contribute to the company, and how does this benefit your career?’”

More than a decade later, a 2025 Harvard Business School case study underscores that this outdated mentality is still affecting performance reviews:

“[M]any managers make the mistake of doing backward-looking assessments of an employee’s work during the previous year and fail to initiate forward-looking discussions about career advancement opportunities.”

In contrast, they write, the new system “encouraged feedback in both directions, with employees and managers charting a path together.” Again, the dialogue that follows evaluation is as important as the evaluation itself.

How would your approach to assessment change if you asked, “How can we make assessment a tool for talent retention and leadership development?”

Board Members Are Professionals and They Need Feedback Too

Formal assessment of board performance is a more recent development in the last few decades (an HBR article published in 1998 noted that board assessments were rare but arguably the most important). As we emphasized in 5 Essential Mindsets for Board Members, board members must see themselves not as volunteers but rather as unpaid, professional talent hired to lead and govern an organization with a very serious mission.

GLP’s paper on board composition highlights how this mindset shift will help you build a board that adds value. Transforming how you “hire,” assess, and develop board members provides a powerful route to high-performance governance.

Although there is no single “best practice” for assessment that works for all boards, our May Blueprint, described key aspects, including:

• Assess the key criteria for board members, and assess the collective needs of the board

• Assess culture, composition, structures, and function with questions that are clearly stated

• Ask senior administrators to assess the board and compare results

• Use a well-designed tool to provide evidence of year-over-year progress

Better Together

We have found that when assessment processes are aligned, the board-leader partnership is strengthened, and governance deepens its understanding of institutional performance as a function of both CEO/Head and board performance.

The McKinsey article “Better Together: Three Ways to Boost Board/CEO Collaboration,” notes that “As the board’s role becomes ever more complicated, stronger partnership with management, especially the CEO, can help directors create the most value for their organizations.” Highlighting a survey that asked board members how they have been managing the growing complexity, over half said that their main tactic is to strengthen the collaboration between the board and management team.

The authors note, “In our experience, management teams and boards most often need advice on how to create a good team dynamic in the boardroom, sometimes with support from a coach, and many CEOs aren’t clear enough about what insights and expertise they need from their boards.”

Establishing and implementing an integrated evaluation process provides numerous opportunities for strengthening trust and collaboration across and within leadership and the board.

Diagnose and Decide: The Roadmap for What’s Next

The evaluation itself is not a roadmap—and even the discussions to unpack and understand the evaluation won’t automatically produce actionable insights. Effective evaluations are a result of effective tools and processes. You will need to translate what you learn through diagnostics, assessment, and discussion into a road map for what’s next.

When you focus on the stakeholders and strategic context—rather than focusing solely on the tools—you can transform qualitative research into an inclusive learning experience that benefits all. By exploring the evidence and feedback offered within the tool, you uncover new insights and better solutions, creating conditions for deeper relationships and the culture you want. The process itself educates your board members, leaders, and broader organization by asking questions that target the key elements of high-performing leadership and governance.

Building a learning culture helps develop your organization’s most essential asset: its people. Effective assessment is a key building block in learning, and it enables your organization to steward high-potential talent, address gaps in key positions, and proactively plan for the future. In the March Blueprint, we’ll dive more deeply into the purpose and practices of “Everyday Succession Planning.” If you’d like to get a jump start, here is our most recent paper!

Greenwich Leadership Partners forges powerful partnerships with not-for-profit and educational institutions to support excellence in governance and leadership.