Match Charter Public School
June 2026
Execution
Match Charter Public School has just completed a significant strategic planning process. The work of turning that plan into reality now begins, and it begins at a moment of real complexity.
- Key executive positions are in transition, including the COO and CFO, and the Chief of Staff role is evolving. The leadership team that will carry the strategy forward is not yet fully formed.
- The CEO is navigating organizational redesign decisions, executive hiring, and the work of onboarding new leaders into a team that is still finding its footing.
- There are dynamics with the board that deserve attention. If unaddressed, they could constrain the CEO's ability to lead with full authority and confidence.
- Each of these challenges is real on its own. Together, they raise a more important question: does Match have the leadership infrastructure, relational trust, and team effectiveness needed to execute the plan?
This is not primarily a strategic planning implementation challenge. It is a question of whether Match can build the leadership conditions under which implementation becomes possible. That distinction shapes everything about how we would approach this work.
Much culture and leadership work focuses on generating insight, helping teams reflect on how they want to operate, which is valuable. In our experience, leadership teams need more support translating that insight into their day-to-day work, especially when the stakes are high and time is limited. Our work is grounded in how adults actually learn and change.
It's the kind of support I didn't know we needed until we had it. Now I wouldn't do strategy or leadership development without them.
Before proposing a specific body of work, we always begin with discovery. Given the complexity of this moment: leadership transition, board dynamics, and a fresh strategic plan all converging, it is especially important that we develop a clear, grounded picture before charting a path forward.
This is not a generic leadership team diagnostic. It is an assessment designed specifically around the questions that matter most for Match right now. Where available, we also collect existing artifacts: prior 360s, team survey data, board feedback, or other relevant reports, to round out the picture and avoid duplicating work already done.
Discovery didn't just give us a report. It put us on a path to break through and transform dynamics that had us stuck.
- ✓ Leadership team assessment and pattern analysis
- ✓ Strategic execution readiness assessment
- ✓ CEO leadership feedback themes
- ✓ Recommended 12-month roadmap with pathway options
Strategic plans require more than implementation. They require leadership teams that are ready to execute. Here is a rough arc of what this work could look like over the next year.
- Discovery
- Stakeholder interviews
- Readout + recommendations
- Leadership retreat
- Clarify roles and decision rights
- Establish execution rhythms
- Coaching and observation
- Team development
- New leader integration
- Progress review
- Refresh retreat
- Operating model adjustments
Based on what discovery reveals, we will propose a tailored, sequenced set of supports. Below are three pathways we commonly see, though the right combination for Match will depend entirely on what we learn. We share these now to give a sense of what the engagement could look like.
- Leadership transitions are manageable
- Strategy is clear and team is aligned
- Board dynamics are stable
- Leadership kickoff retreat (1.5 days)
- Group coaching and observation (2 hours/month for 1 year)
- CEO advisory (up to 4 sessions)
- In-person shadow day to support real-time learning
- Team cohesion and trust are the primary barriers
- Leadership transitions require active integration
- CEO needs structured support and feedback
- CEO coaching and advisory (2x/month for 1 year)
- Team reset retreat (1.5-2 full days) to introduce new tools and norms
- Team coaching and observation (2 hours/month for 1 year)
- In-person shadow day to support real-time learning
- Trust gaps across the team or with the board
- Leadership patterns limiting the CEO's effectiveness
- Structural tensions requiring facilitated resolution
- CEO coaching (2x/month for 1 year)
- Board advisory (up to 6 sessions)
- Facilitated dyad or small group sessions (up to 10 sessions)
- In-person shadow day to support real-time learning
- Leadership reset retreat (1.5-2 full days)
- Observation and intervention (2 hours/month for 1 year)
We always begin with Discovery, which provides the foundation for everything that follows. The pathway investment ranges below are estimates. The final scope will be shaped by what Discovery reveals and will be proposed before any Phase Two work begins.
When I brought a challenge, Olori didn't just help me solve the problem. They helped me understand what was creating the problem. The work wasn't really about strategy. It was about relationships, beliefs, communication, and how adults work together.
Now comes the work of creating
the conditions to bring it to life.