Event Cancellation and Organizational Clarity Discussion - Gary Sheng & Jonathon Stewart

Date: June 6, 2025 Participants: Gary Sheng, Jonathon Stewart Context: Follow-up to June 4th conversation regarding Gary's June 14th "Alphas Activate" event Duration: Extended strategic discussion about event cancellation and organizational positioning

Executive Summary

Jonathon Stewart made the decision to cancel Gary Sheng's planned June 14th "Alphas Activate" event, citing concerns about event readiness, potential low attendance, and significant overlap between Gary's mandate and existing Alpha Schools expansion team operations. The conversation revealed organizational confusion about Gary's role within Alpha Schools and established a framework for repositioning Gary's responsibilities to avoid duplication.

Event Cancellation Decision

Jonathon's Assessment and Rationale

Quality and Readiness Concerns:

Jonathon: "I don't feel like your event is ready to go. I say that with with full humility and respect for the work that you have done on it. And the reason for that is I just I have been a part of the last several events that have been put together over the course of May. I know exactly how much work has gone into them. I know exactly how hard it has been to get people to show up for them."

Recent Event Performance Context:

Jonathon: "These were, you know, pretty high profile things. One of them was the, you know, the Stanford dean event and everyone was the tax."

Decision Framework:

Jonathon: "This was sort of a which is which is the worst bad situation, you know? And unfortunately, this one falls on the side of I just don't think it's ready to go and I need to pull the plug on it."

Gary's Response and Understanding

Acceptance of Decision:

Gary: "What should I do with the so by pull the plug, do you mean I should let people know that we it's just not happening?" Jonathon: "Correct."

Acknowledgment of Process Issues:

Gary: "I would say if I were to do this again, I would just ask a lot more questions about who's already doing what versus making assumptions."

Organizational Mandate Overlap

Expansion Team Conflict

Direct Mandate Duplication:

Jonathon: "In looking through all of your materials, including some of this stuff from your last event, I'm a little concerned that your mandate is basically the same thing as the expansion team for alpha that exists and is staffed and has, you know, basically a group of employees working hundreds of hours a week on already."

Specific Overlap Identified:

Jonathon: "One of the things I read in your materials was, you know, expanding to 25 schools in 24 months. And but that's our mandate on the expansion side."

Resolution Framework:

Jonathon: "That means we either need to be working together or you need to be doing something entirely different."

Quality Control and Brand Consistency

Website and Representation Issues:

Jonathon: "Your website itself has a lot of mistakes on it already. I mean, just like outright in like errors in information."

Brand Management Responsibility:

Jonathon: "My job, my the very tip of my job is to make sure that we're representing alpha out in the in the in the universe in a way that is consistent and compelling and tells the same sort of regardless of where you're getting that information from."

Gary's Organizational Position Confusion

Role Clarity Issues

Gauntlet vs. Traditional Employee Status:

Jonathon: "I wanna leave you at the as much autonomy as you want or need, given, you know, how you come up, you know, through through gauntlet and have, you know, a different a, you know, by definition, a different mandate than a, you know, a typical employee of the company."

Structural Misalignment:

Gary: "Discussions with Arthur previously, like I've kind of been implying that being under superbuilders didn't really make sense. I did not get where where I probably should be by now of finding a home."

Organizational Limbo:

Gary: "I've been kind of waiting for this kind of level of decision making, honestly, because I just felt like kind of in a limbo stage."

Initial Expectations vs. Reality

Original Vision Mismatch:

Gary: "I got, you know, brought on ostensibly to do events. I think Davos for the US with an education bent was basically, like I said the last conversation I had. I'm not saying that that was a, you know a job description, right? And there wasn't exactly an orientation."

Leadership Decision-Making Context

Executive Consultation Process

Comprehensive Stakeholder Review:

Jonathon: "I also have had conversations with uh not solely about you, but in the last few days I have had conversations with Joe and Kenzie and Artie and Steph. So when I say I talked to a lot of people in the organization, I typically talked to a lot of people in the organization."

Joe Liemandt's Quality Standards:

Jonathon: "I just settled a long conversation with Joe today about, um, you know, content in the caliber of content in general and he sort of doubled down on the like, if there's anything that you feel like is not gonna be or is gonna be anything short of completely amazing, then it's your job to make sure that doesn't happen, essentially."

Content and Event Strategy

Jonathon's Broad Responsibilities:

Jonathon: "One of the things that I am the, you know, directly responsible individual for is content, and, you know, that content takes the form of pretty much anything, but events are one of them for all of alpha schools."

Relationship Management and Damage Control

Travel and Commitment Obligations

Existing Travel Bookings:

Gary: "Talk to my, you know, people that I started working with on this for a few weeks and see what we can do about the invites that were sent out already and some people that booked travel."

Alternative Accommodation:

Jonathon: "If you have folks that have book travel and are just interested in, you know, seeing alpha, like, you know, that's something that we could probably arrange a tour for."

International Relationship Considerations

Asian Government Connections:

Gary: "The group that is pretty tapped into governmental leaders in Asia that want [to see Alpha Schools]."

Sales Team Coordination:

Gary: "I believe that a member of that team is connected to the head of sales through an earlier conversation. So maybe that can just proceed, however, that needs to proceed."

Jonathon's Concern:

Jonathon: "I don't know who this head of sales is, and what that relationship is and what the expectation is there. But certainly if that becomes an issue or it is an issue, please point me in the direction of that person so that I can have a full conversation with them."

Future Planning and Repositioning

Gary's Pivot Strategy

Scaled-Down Alternative:

Gary: "I think what I may do is maybe just like pivot to a dinner I organized with some of the people that are coming out of town and then maybe just figure out someone like one of the guides I know, well, that could give a tour on that day and just scale it down a lot."

Strategic Reflection:

Gary: "I'll give it some thought about where I want to where I kind of see myself fitting in, given my skills and where I want to go in my career."

Collaborative Planning

Upcoming Austin Meeting:

Jonathon: "I'm actually in Austin on Monday and Tuesday, so there might be a little full, but if you want to meet for, you know, breakfast, one of those two days, actually not Monday, maybe Tuesday, I could do that."

Mutual Commitment:

Jonathon: "I'd love to work with you to get an event for you or whatever you are looking for in order to help you be successful moving forward."

Operational Context and Vendor Relationships

Event Production Infrastructure

Approved Vendor Network:

Gary: "The event production agency is best served called. They were brought on as an approved trilogy vendor after the first event."

Relationship Preservation

Damage Control Approach:

Jonathon: "I did my best to try to make sure through Joe Mackenzie, Stephan and Artie that I, you know, by making this decision, I'm not, uh, undermining any relationships that they're aware of."

Gary's Understanding:

Gary: "I appreciate that. Thanks for the honestly understanding the full context and making that decision."

Strategic Implications

Organizational Structure Clarity

The conversation revealed significant gaps in Alpha Schools' organizational structure and communication, particularly around:

• Role definition for Gauntlet participants vs. traditional employees
• Mandate overlap between different teams and initiatives
• Decision-making authority and accountability chains
• Brand consistency and quality control processes

Leadership Decision-Making Process

Jonathon's approach demonstrated:

• Comprehensive stakeholder consultation before major decisions
• Clear quality standards enforcement aligned with executive expectations
• Willingness to make difficult decisions to protect organizational reputation
• Collaborative approach to finding solutions for affected parties

Gary's Position Evolution

The discussion highlighted Gary's need to:

• Clarify his unique value proposition within Alpha Schools
• Avoid duplication with existing organizational capabilities
• Find appropriate structural positioning for his skill set
• Develop better organizational intelligence before launching initiatives

Key Quotes

On Event Quality Standards:

Jonathon: "If you have an event and it turns out underwhelming, that could kill you in a heartbeat. And for anything moving forward."

On Organizational Learning:

Gary: "I would say if I were to do this again, I would just ask a lot more questions about who's already doing what versus making assumptions."

On Decision-Making Authority:

Jonathon: "My spidey sense is that you could stand to have a little more clarity of purpose and clarity of audience and a little more time, a little more of a ramp to be able to build the next thing."

On Collaborative Approach:

Jonathon: "I'm not really not trying to sabotage anything for you. I'm really trying to because if you have an event and it turns out underwhelming, that could kill you in a heartbeat."

On Organizational Autonomy:

Jonathon: "I wanna leave you as much autonomy as you want or need, given, you know, how you come up through gauntlet and have, you know, a different mandate than a typical employee of the company."

Future Actions and Next Steps

Immediate Priorities

1. Event Cancellation Management: Coordinate with affected parties and manage travel/booking impacts
2. Relationship Preservation: Ensure international connections and sales relationships are properly managed
3. Role Clarification Meeting: Scheduled breakfast meeting in Austin to discuss Gary's organizational positioning
4. Alternative Event Planning: Develop scaled-down dinner/tour option for committed attendees

Strategic Repositioning

1. Mandate Differentiation: Define unique value proposition that doesn't overlap with expansion team
2. Quality Standards Alignment: Ensure all future initiatives meet executive-level quality expectations
3. Organizational Integration: Find appropriate structural home within Alpha Schools
4. Stakeholder Communication: Establish clear communication channels and approval processes

Long-term Considerations

1. Event Strategy Development: Build capability and infrastructure for future high-quality events
2. International Relationship Development: Leverage Asian government connections through proper channels
3. Brand Consistency: Align all external-facing materials with organizational standards
4. Autonomy vs. Integration Balance: Define optimal level of independence within organizational structure

Organizational Insights

This conversation revealed several key dynamics within Alpha Schools:

Decision-Making Hierarchy: Clear authority structure with Joe Liemandt setting quality standards, Jonathon Stewart managing content and events, and careful consultation before major decisions.

Quality Control Priority: Strong emphasis on maintaining high standards and protecting organizational reputation, even at the cost of canceling planned initiatives.

Structural Complexity: Challenges in integrating autonomous contributors (Gauntlet participants) within traditional organizational hierarchies and mandates.

Relationship Management: Sophisticated approach to managing multiple stakeholder interests while making difficult operational decisions.

Growth Management: Tension between rapid expansion goals and maintaining quality control across diverse initiatives and team members.

The conversation demonstrates both the challenges and benefits of Alpha Schools' approach to integrating entrepreneurial talent while maintaining organizational coherence and quality standards. Gary's experience highlights the importance of organizational intelligence and stakeholder alignment when operating within complex, rapidly-growing educational enterprises.