Executive Summary
What the data reflects is a leadership team with real strengths: deep mission commitment, genuine resilience under pressure, and an unusual willingness to name hard things about how they operate. These assets form the foundation from which everything harder becomes possible.
The patterns that need the team's attention are structural as much as they are behavioral. This is a team that has scaled significantly — from roughly $8M to $20M in organizational complexity — with the same people, the same relationships, and largely the same operating model. What worked at a smaller scale is now creating drag. Leaders who have the capability and the desire to operate at executive altitude are being pulled into execution because the systems, documentation, and decision-making clarity that would allow them to lead differently don't yet exist. The competency framework names the right destination. The work ahead is building the conditions to get there.
This report is organized in three sections. The first names what the team has built that is worth protecting and building on. The second describes the patterns that are limiting the team's collective performance. The third outlines a sequenced path forward. An appendix offers individual development profiles for each team member — a resource for Jill and Pam's planning and, in time, for each leader's own development conversation.
Strengths
What follows are the specific things this team has going for it — the assets that make the harder work worth attempting and that will carry the work forward when it gets difficult. A development agenda built on a team's real strengths looks different from one that starts from a deficit, and the HOA leadership team has more to build from than many.
Across every conversation, mission alignment surfaced as a behavioral reality, not an aspiration. When the organization needs something — a packed warehouse, a recovered project, a crisis resolved — this team finds a way. Leaders described pulling together in moments of operational pressure in ways that cut across functional lines and personal exhaustion. The team is candid about the unevenness, and the effort is real. But the underlying current, a genuine investment in the work HOA does and in the people and communities it serves, holds. It is the thing that has gotten the organization to this scale, and it is the thing that will sustain the harder work of operating at the next level.
"We always get it done. We're holding our breath — and we know we're going to make it — and we get there."
"We did good work. We should be happy."
This team brings candor to its hardest conversations. Multiple leaders described instances of naming uncomfortable truths in real time: calling out patterns in LT meetings, pushing back on timelines, raising concerns about how the team is functioning. Many leadership teams develop an implicit norm of surface harmony that makes honest feedback nearly impossible; this team has largely resisted that pull. The challenge is willingness meeting follow-through. The candor exists. The systems that would make it productive are still being built.
"There is a willingness to name the hard thing. It's about the org — what does happen is a lack of movement when we've worked together, then the frustration, then the shift doesn't happen."
"Most feel comfortable to say and raise concerns. There's a fair level of trust on the team to do that."
One of the most striking features of this data set is the quality of individual self-reflection each leader brought to the process. Across six conversations, people named their own edges clearly, spoke honestly about where they struggle, and in several cases articulated the team's structural problems with precision. The team wants to do this work and, in many cases, has already been thinking about it. That self-awareness is a significant asset: the team can meet the process as participants rather than subjects.
"I would want them to know — entire org — that we do get together and work things out. They may not have the visibility to know."
"Hopefully I grow — higher level of leadership. Wants the team to work together. All passionate. Need to work less siloed — figure out a way to come together."
Patterns Worth the Team's Attention
The patterns below are the predictable pressures that accumulate when a team is navigating a genuine scale inflection: when the organization has grown faster than the operating model, when the same people who built something small are being asked to lead something large, and when the infrastructure hasn't kept pace with the ambition. Naming them is the first act of the development work.
| Leader | CEO Mindset | Collaboration | Set the Pace |
|---|---|---|---|
| Hetal Patel | Area of Growth | Most Natural | Most Natural |
| Joy Hathaway | Most Natural | Area of Growth | Most Natural |
| Pam Bryden | Most Natural | Most Natural | Area of Growth |
| Tom Helwig | Most Natural | Most Natural | Area of Growth |
| Belinda | No survey | No survey | No survey |
| Leah Erickson | Area of Growth | Most Natural | Most Natural |
What the pattern shows: Growth edges in the self-assessment are differentiated — no single pillar is a universal gap. But the team rating tells a different story. Set the Pace scored 2.0 across every single respondent — the only unanimous score in the dataset. That convergence, regardless of whether someone self-assessed this pillar as natural or a growth area, points to an organizational conditions problem more than an individual capability gap. It shapes the group-before-individual sequencing in the Path Ahead.
The most consistent theme across every conversation is that leaders know what it means to operate at the executive level, want to do it, and are being pulled away from it by the demands of execution. Vacancies go unfilled and the leader absorbs the work. Processes aren't documented and the institutional knowledge lives in a single person. A function scales in volume and complexity but not in headcount or tools. In each of these cases, the leader closest to the gap becomes the solution, and in becoming the solution, they stop being the strategic leader their team needs.
The real story here is about conditions, not capability. Across the team, there is genuine executive potential. The team is running a $20M organization with the operating model of a smaller one, and that gap is showing up in every leader's daily experience. Every respondent who completed the survey rated Set the Pace and Operate Effectively at 2 out of 5 — the only unanimous score in the dataset. That unanimity is significant: the conditions are suppressing execution across the whole team, and the pattern holds regardless of individual strength.
The individual development edges in this pillar are real and worth attending to, and they are named in the appendix. But the team-level development work here begins with the structural question: what would need to be true for each leader to be able to lead their function rather than run it?
"Lacking stability, so much is moving, so LT has to be in the weeds to move work. You've built and developed a team that can execute the work, so you can lead more strategically and support them for the growth on the runway, but only one leader can do that right now."
"Can we take things to 90% and have time to do the unplanned? We're at 110%, and we know we're going to make it, but we are holding our breath."
HOA's leadership team gives feedback. That is the good news, and it is real. The pattern worth attending to is what happens next: the feedback doesn't consistently land, behavior doesn't consistently change, and over time some leaders have stopped expecting it to. When feedback becomes a ritual without consequence — something that happens because it should, not because it leads anywhere — it stops doing its job. The team then loses one of its primary tools for self-correction.
The root of this pattern is accountability infrastructure, not communication skill. Feedback works when there are norms, agreements, and some form of shared consequence that makes acting on it the path of least resistance. HOA's team has the willingness; the architecture is still missing. And in the absence of that architecture, the gap between what's said and what changes has become a source of frustration that is eroding trust between some function pairs.
The survey open-text responses reinforce this directly. When asked what pattern gets in the way of operating at the highest level, three of five respondents named accountability in almost exactly the same terms.
"Feedback is not a gift at HOA — it is a re-gift. It doesn't land or create change."
"People are tired of saying the same things and there is no change. Now it becomes about the person."
"Falls short in execution. The issue is not that feedback isn't given; it's fairly good at being shared. It falls short in what follows."
Every leader in this process expressed a genuine desire to think and act beyond their own function. The aspiration is real. What the team doesn't yet have are the structural conditions that make enterprise thinking a daily practice rather than a good intention. Cross-functional literacy is uneven: some leaders can speak fluently about other parts of the business, others cannot. Shared information flows are inconsistent. Documented ways of working don't exist in a form other teams can draw on. And the pull of functional execution is strong enough that, when things get busy, the enterprise lens is the first thing to narrow.
The competency framework asks leaders to internalize the strategy and goals of every function and to act as if responsible for the whole. That is the right aspiration. Getting there requires the organization to create the moments, the tools, and the norms that build cross-functional understanding as a shared habit rather than a personal attribute. The leaders who demonstrate this most consistently at HOA have built it through relationship and proximity. That is a strength in those individuals; it is a gap in the system.
"We all have the capability to do the org-wide thinking, but we don't always have the capacity — some do and some don't, even if it isn't always best."
"Not a deepened understanding currently — this is a gap. Taking the time to learn, document our processes — there's nothing to draw on."
Jill is, by multiple accounts, an exceptional coach and a visible, caring leader. The team's warmth toward her is real, and it shapes how they navigate their own authority. The pattern worth naming is that some of what belongs at the leadership team level — tension between functions, decisions that require cross-functional judgment, questions about prioritization and resources — is still finding its way to the CEO rather than being resolved by the team. The pattern reflects a genuine ambiguity about what the team is authorized to own, compounded by a CEO operating style that has historically involved close engagement with the details of internal operations.
As HOA continues to scale and Jill's attention is increasingly required externally, this pattern becomes a structural constraint. The team will need clearer decision-making authority — not permission to work around Jill, but a shared understanding of what the leadership team is empowered to resolve. That clarity benefits everyone: it gives leaders the confidence to act, reduces the volume of decisions flowing to the CEO, and creates the conditions for the team to operate as a genuine executive body.
"What needs to be brought to Jill versus what we can own — getting more clear on Jill's role with a decision-making matrix."
"The decision maker is Jill. Ask for help, person says no, then still doing it individually, we reprioritize."
"We are growing — you can't know everything and be everywhere. LT ownership."
The Path Ahead
This team brings real assets to the development work ahead: mission alignment, genuine self-awareness, and a shared willingness to do the work, which is more than most teams bring to a process like this. The question is where to focus first, and in what combination. Two considerations shape the answer.
Three of the four friction themes in this report are systemic. The feedback loop that isn't closing, the operating altitude problem, the ambiguity about what the team can resolve without the CEO: none of those move through individual coaching alone. They are patterns the whole team is inside of, and they require the whole team to address them together.
That means the first investment is group work: building the shared agreements, norms, and practices that make the competency framework something the team actually lives rather than aspires to. That includes working sessions designed to establish how feedback gets given and followed up on, how cross-functional tensions get resolved at the LT level, and what cross-functional literacy looks and sounds like in practice. It also means creating the structural clarity that is currently missing: a decision-making framework that defines what the leadership team owns, what goes to the CEO, and how gray areas get navigated.
That framework requires Jill's active participation to build and to hold. Part of what the team is asking for, across several conversations and in different words, is clearer authorization: confidence about what they can own and resolve at their level. Creating that clarity is itself a leadership act, and one that belongs at the top of the development agenda. The group work and Jill's posture as CEO need to move together.
The appendix to this report profiles each team member's development edge in detail. For planning purposes, three broad categories emerge from the data.
Some leaders are ready for individual coaching now and would use it well in parallel with the group work. Their self-awareness is high, their appetite is real, and coaching would accelerate what the team-level work opens up for them.
Others have development needs that are more directly tied to structural or resourcing conditions in their function. Coaching will matter eventually, but the more immediate lever is organizational: clarifying scope, addressing resource gaps, or resetting expectations about what executive leadership looks like in their role. For these leaders, the development conversation is part of a broader management conversation that belongs first to Jill and Pam.
A small number are genuinely differentiated in their growth edges across the three pillars, meaning a targeted individual plan will serve them better than generic group work alone. The individual profiles in the appendix are the starting point for those conversations.
The measure of all of this work is an organization that can carry out its mission at the scale it is reaching, where the schools, students, and communities HOA serves get the best the organization has to offer, and where the people doing that work can lead it sustainably.
Individual Development Profiles
These profiles are intended as a planning resource for Jill and Pam, and in time as the starting point for each leader's individual development conversation. They are drawn from each person's self-assessment survey, their 1:1 conversation, and what the data as a whole reflects about their growth edge.
| Leader | CEO Mindset | Collaboration | Set the Pace |
|---|---|---|---|
| Hetal Patel | Area of Growth | Most Natural | Most Natural |
| Joy Hathaway | Most Natural | Area of Growth | Most Natural |
| Pam Bryden | Most Natural | Most Natural | Area of Growth |
| Tom Helwig | Most Natural | Most Natural | Area of Growth |
| Belinda | No survey | No survey | No survey |
| Leah Erickson | Area of Growth | Most Natural | Most Natural |
| Leader | Clear sense of what I'm developing |
Actively seeking feedback to grow |
Feel supported in my development |
Make time for my own learning |
|---|---|---|---|---|
| Hetal Patel | 3 | 4 | 5 | 2 |
| Joy Hathaway | 3 | 4 | 4 | 3 |
| Leah Erickson | 3 | 2 | 2 | 5 |
| Pam Bryden | 2 | 3 | 4 | 2 |
| Tom Helwig | 4 | 4 | 2 | 2 |
| Team Average | 3.0 | 3.4 | 3.4 | 2.8 |
What stands out: The team average on "Feel supported in my development" (3.4) masks significant variation — Hetal rates this 5, while Leah and Tom rate it 2. That gap is worth attending to: the leaders with the lowest support scores are also among the newest to the team, suggesting onboarding into the development culture may be uneven. "Make time for my own learning" is the lowest team average (2.8), which is consistent with the operating altitude theme — leaders buried in execution have little runway for their own growth.
Survey
Hetal brought precision and high standards to every part of this conversation. She is clear-eyed about what the organization needs, willing to name what isn't working, and operating with a level of organizational literacy that benefits the whole team. Her candor about the frustrations of her role — the ways in which her team absorbs the downstream consequences of other functions' decisions — reflects both self-awareness and genuine investment in HOA's health.
Hetal self-assessed Set the Pace and Operate Effectively as her most natural pillar, and the data supports it. Finance is consistently named by peers as one of the functions that has figured out how to deliver at volume without losing altitude. Her team is high-functioning, her goals are clear, and her operating discipline is a model. Her sense of what it means to think org-wide is also genuinely strong; the challenge is less her own orientation and more the conditions that make that thinking visible to and shared by the rest of the team.
Hetal's growth work is about influence without authority: specifically, how to get the organizational standards she sees clearly to land as shared priorities rather than finance-driven requirements. She has the insight; the development work is building the approaches that help peers receive it. She named wanting development that is substantive and applied — work that addresses the real accountability and process gaps rather than staying at the conceptual level. Notably, she rated feeling supported in her development at 5 — the highest on the team — which suggests real readiness to invest in that work. The constraint is capacity: like most on the team, she rated making time for her own learning at 2.
Survey
Joy is one of the most analytically clear voices on this team. She brought both a strong point of view and a genuine openness about her own edges, particularly around collaboration, that reflects real self-awareness. Her structural recommendations for the organization reflect a leader who is thinking well beyond her own function. She is also newer to the team, which gives her a particular kind of clarity that is worth preserving.
Joy self-assessed CEO Mindset and Set the Pace as her most natural pillars, and her interview confirmed both. She is a driver who moves work forward and holds others accountable, and she brings a systems-level view to how the organization operates. These are significant assets for a team that needs more executive ownership.
Joy named Collaboration as her growth pillar, and the data supports it. Her directness and energy are real assets; the work is calibrating how they land in a team environment where different styles require different approaches. The development edge is around creating conditions where other voices have space and where her high standards register as collective expectations rather than individual pressure. She named wanting facilitated experiences where she can try things and receive real-time feedback, practice-based and grounded in real work.
Survey
Pam brought a long view to this process — the perspective of someone who has seen the organization across several chapters and understands, perhaps better than anyone on the team, the distance HOA has traveled. She is thoughtful, grounded, and genuinely committed to the team's collective growth. She also named her own fatigue honestly, which is worth honoring; she is carrying a lot, and the development work for Pam needs to hold that reality.
Pam self-assessed CEO Mindset and Collaboration as her most natural pillars. Her organizational knowledge is deep and her relationships across the team are strong. She plays an informal connective-tissue role that holds a great deal of the team's functioning together, and that role, while valuable, may be one of the things making it hardest for her to operate at strategic altitude.
Pam named Set the Pace as her growth area, and the development edge beneath it is about leverage. The work for Pam is moving from being the person who holds the connective tissue to building the systems and structures that hold it themselves: documentation, decision frameworks, and organizational processes that reduce her personal load while improving the team's collective operating capacity. She named wanting development that is practical and immediately applicable, with real tools and team-level work that reduces the ambient noise she described as one of her biggest sources of drain. Worth noting: she rated having a clear sense of what she's developing at 2, the lowest on the team — which suggests the development conversation itself, including naming a focused direction, is part of what she needs from this process.
Survey
Tom brought a thoughtful, systems-oriented perspective to his conversation. He is a precise thinker who sees process gaps clearly and articulates them with specificity — the kind of detail orientation that is genuinely valuable in an operations leader. He was also candid about where he and his function are stretched, which reflects self-awareness and trust in the process.
Tom self-assessed CEO Mindset and Collaboration as his most natural pillars. His process thinking and cross-functional awareness are real strengths. He sees how decisions made in one function create downstream complexity for others, and he names it specifically.
Tom named Set the Pace as his growth area, and the picture that emerges across the data is of a leader whose function is under-resourced for the organization's current scale, which means Tom is absorbing execution that limits his ability to lead. The development edge is about managing up effectively: making the case for resources, naming constraints before they become crises, and building the executive presence that ensures his function's needs are visible and factored into organizational decisions. He named wanting practice-based development over conceptual, specifically around feedback and accountability habits built in real time. His rating of feeling supported in his development at 2 — alongside a strong sense of direction (4) and active feedback-seeking (4) — suggests the appetite is there but the organizational support hasn't caught up. That gap is worth addressing directly as part of the development planning conversation.
Survey not completed — development edge drawn from interview only.
Belinda brought a clear-eyed, generous perspective to her conversation — someone who has deep organizational knowledge and is willing to hold both the strengths and the hard truths at the same time. Her read on the team is precise, and her self-awareness about her own development edges is unusually honest. She is also carrying one of the organization's highest-stakes functions, which gives her particular credibility when she names what the team is and isn't doing.
Belinda demonstrates a strong CEO Mindset in practice: she thinks in terms of organizational consequences and downstream effects more consistently than most. Her Development function is high-performing and she is deeply invested in the team's success. Her care for colleagues and the organization is visible and valued.
Belinda's development edge is about operating at executive altitude while managing the execution pressure that comes with running one of the organization's most externally visible functions. The specific work is around building peer influence that gets Development's needs factored into organizational decisions earlier, and creating enough internal leverage that she can lead more and execute less. She named consistency as what she needs from any development investment: the work that sticks is the work that has rhythm and follow-through.
Survey
Leah brought a distinctive vantage point: the cross-cutting view of someone who sits at the intersection of every function and works closest to Jill's agenda. She is oriented toward action, sees patterns quickly, and thinks practically about what the organization needs. She is also newer than most to the team, and her development work has the quality of being both individual and organizational: as the Chief of Staff function finds its footing at HOA, her own growth and the organization's operating model development are closely intertwined.
Leah self-assessed Collaboration and Set the Pace as most natural, and her interview supports both. She moves things forward, navigates ambiguity well, and has a practical intelligence about how to get work done across the organization.
Leah named CEO Mindset as her growth area. She has organizational literacy by virtue of the role; the work is about strategic shaping. The Chief of Staff function at HOA is currently oriented heavily toward operational coordination; the development edge is expanding that toward strategic leverage: helping Jill see around corners, shaping the team's agenda rather than managing it. She named wanting development that is embedded in the work rather than separate from it, and specifically named seeing the competencies come to life in the weekly LT meeting as the form of development that would feel real. Her survey scores tell an interesting story: she rated making time for her own learning at 5 — the highest motivation on the team — while rating feeling supported in her development and actively seeking feedback both at 2. The motivation is there; what's missing is the structure and the support that would let it go somewhere.