Leadership Team Discovery Report · Confidential

Coney Island
Prep

Leadership Team Discovery Report

The Olori Network · June 2026

Organization

Coney Island Prep

Respondents

6 LT Members + CEO

Assessment Date

May – June 2026

A Note to the Team

What This Report Is and How to Use It

Across May and June 2026, The Olori Network held confidential interviews with seven members of the Coney Island Prep leadership team and reviewed survey responses from all seven, including the CEO's responses gathered through a parallel instrument. Our goal was to understand the team's experience: its strengths, its patterns, and what it will take to operate at the level CIP needs right now.

The themes in this report do not capture every individual perspective. They reflect what surfaced most consistently across conversations, and what the team named as most important to address as it moves into the year ahead.

These patterns are co-created. Everyone on this team is both responding to the conditions described here and, in some measure, reinforcing them. The goal of this report is to offer a clear view of the current state so the team has an opportunity to engage it directly.

We are grateful for the candor of everyone who participated. We encourage you to read with curiosity and a focus on collective learning.

The Olori Network · June 2026

How to Read the Data

The Scale

Responses range from Strongly Disagree (1) to Strongly Agree (5). Team averages are the mean across all valid respondents for each domain. CEO scores come from a parallel instrument with equivalent statements.

1.0–2.9 Area to Strengthen

3.0–3.9 Generally Effective

4.0–5.0 Clear Strength

The Gap

The snapshot table shows team member averages only. The appendix includes a full statement-by-statement response spread inclusive of all respondents, including the CEO's responses, so you can see the complete picture domain by domain.

The Spread

Response distribution bars show the count of each response type per statement. The green circle marks the CEO's response position on each bar. Wide spread across a bar means the team is not experiencing that dimension consistently — divergence is itself a finding.

CEO Position on bar

How to Read This Report

The Six Domains

The report is addressed to the team collectively. The data section provides a snapshot of where the team stands across all six domains, with CEO and team scores shown together. Strengths and patterns are drawn from both quantitative ratings and qualitative interview themes. The appendix provides a statement-by-statement breakdown of each domain for those who want to go deeper.

The scores in this report reflect a moment in time. They are a starting point for conversation and a tool for learning, not a verdict.

The Six Domains

Domain 1

Vision & Purpose

The extent to which the team shares a clear and consistent understanding of where the organization is going and why.

Domain 2

Roles & Composition

Whether the right leaders are in the right seats, with clear responsibilities and the capabilities the organization needs right now.

Domain 3

Systems & Execution

Whether the team's meetings, decisions, and communication structures move work forward or create friction and ambiguity.

Domain 4

Team Dynamics & Culture

The level of trust, candor, and shared accountability that shows up in how this team actually works together.

Domain 5

Reflection & Adaptation

How intentionally the team pauses, learns, and converts individual insight into collective improvement.

Domain 6

CEO Leadership

How the team leader sets direction, models expectations, and creates the conditions for others to contribute fully.

Team Snapshot

Domain Scores at a Glance

Scoring bands:

1.0–2.9 Area to Strengthen

3.0–3.9 Generally Effective

4.0–5.0 Clear Strength

Scores below reflect team member responses only. The appendix includes a full statement-by-statement response spread inclusive of all respondents, including the CEO.

Domain	Team Average
Vision & Purpose	3.17
Roles & Composition	3.17
Systems & Execution	2.83
Team Dynamics & Culture	3.33
Reflection & Adaptation	2.83
CEO Leadership	2.33

Response Distribution — Overall Statement Per Domain

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

Vision & Purpose

OVERALL: Our executive team has a shared understanding of why we exist and what success looks like.

3

2

1

1 respondent selected N/A

Roles & Composition

OVERALL: This team is well structured for what the organization needs right now.

1

3

2

1 respondent selected N/A

Systems & Execution

OVERALL: Our systems enable clarity, coordination, and consistent execution.

1

2

1 respondent selected N/A

Team Dynamics & Culture

OVERALL: This team operates with trust, candor, and shared accountability.

1

4

1 respondent selected N/A

Reflection & Adaptation

OVERALL: Our team is intentional about learning and improving as a leadership group.

1

2

1 respondent selected N/A

CEO Leadership

OVERALL: The CEO's leadership enables the executive team and organization to perform at a high level.

1

2

1 respondent selected N/A

For a full statement-by-statement breakdown of each domain, see the appendix beginning on page 9.

Strengths to Build From

What This Team Has Going For It

The assets below are worth naming carefully because they are the foundation from which all of the harder work becomes possible. A team working through real difficulty is in a different position when the people in the room trust one another, believe in the mission, and have already shown they can do hard things together.

01

People who like each other and believe in each other

7 of 7 respondents

Across every interview, people described their colleagues with real warmth. Even leaders who named significant frustrations with how the organization is functioning rarely questioned the intentions or capabilities of the people in the room. What came through consistently was a team that genuinely enjoys working together, approaches collaboration openly, and extends real good faith to one another. People described colleagues as trying their best, showing up for each other, and caring about the work in ways that show.

That kind of goodwill is not a given, and it is not something that can be manufactured later. It is the foundation from which all of the harder work becomes possible.

"We have good people on the leadership team. We don't always set them up. I'm excited to see everyone at their best."

"The team is great. I haven't left a day feeling like I don't want to do it or that I don't want to do it with the other people in the room. I like and appreciate the people. Even in intense conversations, you still laugh."

02

A college promise that is operational, not aspirational

5 of 7 respondents

CIP's commitment to sending every graduate to college for free is not a tagline. It is a delivered outcome: 87% of students now enroll in four-year programs, and the post-secondary support infrastructure that makes that possible has been built and sustained over years. Several interviewees described students they taught who are now in college because of the work CIP did. That track record is one of the strongest in the sector.

It is also an underutilized asset. The organization has not yet fully translated what it does into the kind of clear, consistent external identity that drives enrollment. The substance is there. The translation is the gap.

"We already do a thing really well. We don't need to change our mission. 80% of students go to college for free. It makes sense to dig in there."

"CIP is a genuinely rare institution. In seventeen years of building something exceptional in a community that is vibrant and diverse in ways that exist nowhere else in this city or the world. We started in public housing. I don't think we lead with that or embrace it enough."

03

Candor in the room

4 of 7 respondents

One of the most consistent notes across all seven interviews was that the leadership team meeting is a space where people will say what they think. There is a clear willingness to raise difficult subjects, and a norm of alignment once a decision is reached. Several interviewees noted that the team has shown it can have hard conversations without the relationship falling apart afterward.

That culture of candor is the precondition for every other improvement the team might want to make. It is worth protecting.

"No one is afraid to say the thing that's on their mind in that meeting."

"When there are tough decisions to make about school leadership, everyone on the team weighs in and shares their honest perspective. Some of the best ideas come from team members who are not directly involved in the decision."

Challenges

What the Data Surfaces

The patterns below are systemic. They have been building for some time, and they connect to one another in ways that make each one harder to address in isolation. What links them is a single underlying dynamic: CIP has not yet made the full transition from how it operated under prior leadership to what it needs to become under the current CEO's leadership.

Pattern 01

The team has not yet built the muscle for making hard decisions together

7 of 7 respondents

The high school principal challenge appears in nearly every interview. It has been discussed for over two years. The performance data is clear. Near-universal agreement exists on the problem. And the team has not acted. That fact, repeated across seven conversations, carries meaning beyond the specific personnel question.

What leaders described is a meeting culture where problems get named, perspectives get shared, and then, with no clear decision right, no timeline, and no designated owner, the conversation ends without resolution. Decision paralysis in values-driven organizations is extremely common. The instinct to ensure fairness and consider the person's humanity is not a weakness. It becomes an obstacle when it replaces, rather than informs, clear decision rights and timelines.

"As a leadership team, we don't have the autonomy to make decisions and our CEO isn't making decisions."

"There's no ownership of failures. Kids leaving, violence, kids with low GPAs. There's a tendency to sweep things under the rug."

"We were talking about this issue for two and a half years. I'm trying to figure out if this team acts or doesn't act."

Safety concerns, declining GPAs, and enrollment challenges are connected challenges that call for a systemic answer. A two-year unresolved personnel question communicates something specific about what CIP does when things are hard, and it is important to understand that pattern in order to interrupt it moving forward.

Pattern 02

Financial opacity is creating risk the organization cannot see clearly

5 of 7 respondents

Most members of the leadership team describe the budget as a black box: something they know exists but cannot see into, cannot influence, and cannot use to make informed decisions about their own functions. Chiefs make resource decisions for their functions without the shared financial context those decisions require.

"This is the first time I've been in an org where chiefs don't see the budget, don't have their own budget, school principals can't see their budget."

"Finance has been a black box. I'll field questions about whether team members can do something and I say 'I don't know.' It's crazy that I don't know."

The addition of new campuses, continued enrollment challenges, and a shrinking reserve position create a trajectory that requires shared urgency and shared understanding to navigate. A leadership team without a common picture of financial reality cannot make the trade-offs that picture requires.

Pattern 03

How the CAO and CSO departures were communicated eroded trust in ways that linger

6 of 7 respondents

Across conversations, team members lifted the reality of late notification of the CAO and CSO departures as genuinely frustrating, particularly given that the CEO knew many months in advance. The result was a compressed hiring window, a pool of internal candidates who felt undervalued, and in some cases received no direct communication at all, and a team now entering the new year with two critical seats either newly filled or still vacant. This moment landed as a significant one for the team, and understanding what it surfaced matters as much as the logistics it created.

"If we had acted on that information earlier, we wouldn't be where we are now. I never asked why. I'm just so annoyed by it."

"We knew about the CSO job earlier. We didn't need to be in this process."

The incoming CSO will enter an organization with little to no overlap with their predecessor, a middle and high school with significant performance and culture challenges, and a school year about to start. That is a harder entry point than it needed to be.

Pattern 04

A leadership model that is still taking shape

6 of 7 respondents

Across conversations, team members described the CEO with warmth and care. At the same time, many noted a gap between the operating model they currently experience and the one they feel the organization needs at this stage. The CEO came to the role through deep operational mastery, and those instincts, while real assets, are at this stage getting in the way of some of the higher-order leadership the team is looking for.

What the team describes is a leadership posture that remains close to the operational detail, while the work that is distinctly the CEO's to hold — cultivating external relationships that drive enrollment, setting a clear strategic direction so chiefs can make aligned trade-offs, and taking decisive action on key challenges — does not yet have consistent ownership. The distance between those expectations and the current operating pattern is where much of the team's frustration lives.

"People are going to do things if the CEO says to do it. That's the function of positional power. People want KJ to be the visionary."

"She's most comfortable with spreadsheets and project plans. She struggles with big picture and strategy."

"When she's at her best, she's a bright light and an innovative leader. The same ops mind that can be a hindrance can show us a better way to do things. I want her to have joy in the work that she does."

The gap between the CEO's self-assessment on the CEO Leadership domain (4.0) and the team's assessment (2.33) is the largest divergence in the entire instrument. It is a signal that the current operating model may not yet have a complete picture of how it is landing. This presents an opportunity to step into leadership in new ways, with the full support of a team that is rooting for it to succeed.

A Note to the Team

How to Use This Report

Each member of this team experiences the leadership team from a particular seat, shaped by their role, experiences, relationships, responsibilities, and perspective. No single interview captures the full picture on its own.

Like the familiar story of several people describing different parts of an elephant, individuals can experience the same team very differently and still each be describing something real. The opportunity ahead is not to determine whose perspective is correct, but to strengthen the team's ability to listen across differences, make sense of patterns collectively, build shared understanding, and move forward together in service of students and staff.

As the team reflects on this report together, a few mindsets may be helpful:

Focus on patterns rather than trying to identify who may have shared specific comments.

Treat the report as an opportunity for collective reflection and growth rather than evaluation or blame.

Assume that everyone on the team both contributes to and is affected by the current dynamics.

Approach differences in perspective with curiosity and openness.

Use the retreat as an opportunity to strengthen shared understanding, relationships, and clarity about how the team wants to work together moving forward.

The themes in this report do not capture every individual perspective. They reflect what surfaced most consistently across conversations, and what the team named as most important to address together. We are grateful for the candor of everyone who participated, and we look forward to working through this with you.

Domain 1 / Appendix

Vision & Purpose

The extent to which the team shares a clear and consistent understanding of where the organization is going and why.

Team Avg

3.17

CEO Score

5.00

Gap

+1.83 ▲

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

CEO Position

Clear and consistently communicated vision, mission, and strategy.

3

1

3

Team priorities directly derive from that shared vision and strategic direction.

1

2

3

1 respondent selected N/A

I understand the distinct work and responsibilities of the executive team, separate from my functional role.

1

2

3

1

The executive team holds itself responsible for modeling and embodying the organization's values.

1

2

3

1

OVERALL: Our executive team has a shared understanding of why we exist and what success looks like.

3

2

1

1 respondent selected N/A

What the Data Shows

The D1 gap of +1.83 is the widest in the survey, driven entirely by the CEO's Strongly Agree on the overall item against a team average anchored by three Disagrees. Where the team is more aligned is in understanding their distinct executive role (four of seven agree or strongly agree) and in valuing the organization's mission. The fracture is in whether that mission has been translated into a consistently communicated strategy that the whole team experiences as shared. It has not.

Domain 2 / Appendix

Roles & Composition

Whether the right leaders are in the right seats, with clear responsibilities and the capabilities the organization needs right now.

Team Avg

3.17

CEO Score

4.00

Gap

+0.83

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

CEO Position

This executive team has the right leaders in the right seats for this stage of the organization.

4

1

We have the right mix of skills, perspectives, and leadership capabilities on the executive team.

3

1 respondent selected N/A

When roles or responsibilities need to shift, gaps are addressed clearly and in a timely way.

3

2

1

1 respondent selected N/A

Roles and responsibilities across the executive team are clear and well understood.

2

1 respondent selected N/A

OVERALL: This team is well structured for what the organization needs right now.

1

3

2

1 respondent selected N/A

What the Data Shows

The sharpest signal in D2 is the "right people" question: four of seven disagree that the right leaders are in the right seats, with one strongly agreeing and the CEO agreeing. This reflects the context of simultaneous departures and unfilled roles more than a settled judgment about the team's long-term composition. Where the team converges with the CEO is on transition management: three disagree and two are neutral on whether gaps are addressed clearly when roles shift. The overall D2 picture is a team suspended between stability (some roles are strong and clear) and significant structural uncertainty.

Domain 3 / Appendix

Systems & Execution

Whether the team's meetings, decisions, and communication structures move work forward or create friction and ambiguity.

Team Avg

2.83

CEO Score

4.00

Gap

+1.17 ▲

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

CEO Position

Our executive team's systems, including meetings, planning, and communication, are designed to move our work forward.

2

1

2

1 respondent selected N/A

Information and decisions at the executive team level are appropriately communicated out to teams.

1

3

Decision-making rights within the executive team are explicit, and we consistently follow through on agreed processes.

1

2

1

1 respondent selected N/A

We have sufficient protected time as a leadership team to focus on the highest leverage conversations and decisions.

1

2

1

1 respondent selected N/A

OVERALL: Our systems enable clarity, coordination, and consistent execution.

1

2

1 respondent selected N/A

What the Data Shows

Systems and Execution is one of the two lowest-scoring domains, tied with Reflection and Adaptation at 2.83. The CEO-team gap of +1.17 is significant. Decision-making rights is the sharpest friction point: three of six respondents disagree or strongly disagree, with only one agreeing. Protected time for strategic conversations is similarly weak. The one relative bright spot is information flow: three agree that decisions are communicated outward, though Eugene's Strongly Disagree and one N/A complicate that picture. The overall portrait is a team spending more energy navigating ambiguity than the system requires.

Domain 4 / Appendix

Team Dynamics & Culture

The level of trust, candor, and shared accountability that shows up in how this team actually works together.

Team Avg

3.33

CEO Score

5.00

Gap

+1.67 ▲

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

CEO Position

We have clear, shared norms for how the executive team works together and use them to hold ourselves and each other accountable.

1

3

1

1 respondent selected N/A

When trust is breached or norms are broken within the executive team, members address it directly and constructively.

1

2

3

1 respondent selected N/A

The executive team practices inviting and offering dissenting points of view and engaging in productive debate.

1

4

1

1 respondent selected N/A

Members of this team act on behalf of the full organization, not just their own departments.

6

1 respondent selected N/A

Once a decision is made, the executive team collectively supports it across the organization, even when there was initial disagreement.

1

4

2

OVERALL: This team operates with trust, candor, and shared accountability.

1

4

1 respondent selected N/A

What the Data Shows

D4 is the highest-scoring team domain at 3.33, and the CEO-team gap of +1.67 reflects the CEO's Strongly Agree on the overall item against a more nuanced team view. The data's most consistent signal is the organizational orientation item: all six responding team members agree that people act on behalf of the full organization, not just their departments. That is a real strength. The gap between the CEO and the team on the overall item is driven by what the team sees more clearly: one Strongly Disagree and widespread acknowledgment that shared accountability, while aspirationally held, is not yet consistently practiced.

Domain 5 / Appendix

Reflection & Adaptation

How intentionally the team pauses, learns, and converts individual insight into collective improvement.

Team Avg

2.83

CEO Score

4.00

Gap

+1.17 ▲

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

CEO Position

I actively reflect on how my own behavior contributes to the effectiveness of this team.

6

1 respondent selected N/A

The executive team regularly pauses to reflect on our results and adjust our approach.

1

2

1

2

1 respondent selected N/A

Feedback, whether upward, lateral, or downward, is encouraged and acted upon.

1

3

1 respondent selected N/A

The executive team creates space for honest conversation about what's working and what's not.

2

4

1 respondent selected N/A

Our executive team models continuous learning and adaptation for the organization.

1

3

1

1 respondent selected N/A

OVERALL: Our executive team is intentional about learning and improving as a leadership group.

1

2

1 respondent selected N/A

What the Data Shows

D5 shows the clearest split between individual and collective practice. Personal reflection is the single strongest item in this domain: all six responding team members agree they actively reflect on their own contributions. Collective practice is the inverse: the team rarely pauses together to reflect on results, and the modeling of continuous learning scores weakest, with three neutral and two negative. The CEO rates this domain at 4.0 against the team's 2.83. The team is composed of self-aware individuals who have not yet built the shared habits that translate that self-awareness into collective learning.

Domain 6 / Appendix

CEO Leadership

How the team leader sets direction, models expectations, and creates the conditions for others to contribute fully.

Team Avg

2.33

CEO Score

4.00

Gap

+1.67 ▲

Strongly Disagree

Disagree

Neutral

Agree

Strongly Agree

CEO Position

The CEO communicates a clear and compelling strategic direction that anchors the organization's priorities.

2

1 respondent selected N/A

The CEO maintains focus on a few, high-impact priorities and aligns the team's attention accordingly.

2

1

1 respondent selected N/A

The CEO models high standards for both results and culture.

1

2

1

2

1 respondent selected N/A

The CEO proactively addresses team dynamics and reinforces expectations through consistent words and actions.

1

2

1

2

1 respondent selected N/A

The leader demonstrates openness to feedback and uses it to improve.

1

2

1

1 respondent selected N/A

OVERALL: The CEO's leadership enables the executive team and organization to perform at a high level.

1

2

1 respondent selected N/A

What the Data Shows

CEO Leadership is the lowest-scoring domain in the survey at 2.33, and the CEO-team gap of +1.67 is among the largest. No responding team member agrees that the CEO's leadership enables the team to perform at a high level on the overall item: three are neutral, two disagree, and one strongly disagrees. The sharpest individual signal is strategic focus, where four of six disagree or strongly disagree that the CEO maintains focus on a few high-impact priorities. The data is not a verdict on capability. It is a clear signal that the current operating model is not yet matching what this team and this moment require.

Thank you.

We are grateful for the candor and thoughtfulness everyone brought to this process. The willingness of this team to examine itself honestly is itself a form of investment in CIP's future and in the students and community it serves.

The themes in this report do not capture every individual perspective. They reflect the patterns most worth the team's collective attention as you prepare for the work ahead. We look forward to being in the room with you.

Seventeen years of building something exceptional is worth protecting. The work ahead is deciding together how to do that.

THEOLORINETWORK.COM