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Alignment Offsite Agenda and Prework

A half-day working session for Habib and Shahysta. Prework questions, agenda blocks, and the three decisions that must come out of this session before any Phase 1 work begins.

1.1 · Founder Alignment Lead · artifact id: alignment-offsite-prework-v0.html · 2026-05-28 · v0 draft

Why this session matters. The Watch page explains the alignment question in full. The short version: every downstream decision about pricing, positioning, hiring, and market entry resolves differently depending on whether SmartOne stays self-funded or raises capital. The offsite session is the conversation that lets you make those downstream decisions with confidence. It should happen before the HARBOR engagement begins in earnest, not during it.

Session design

Parameter	Value
Format	Working session, not a retreat. Structured agenda with a facilitator (HARBOR or a trusted third party). Paper and a whiteboard, not slides.
Duration	Half day (3-4 hours) with a break. Can be done remotely on video if in-person is not feasible, but in-person is meaningfully better for this kind of conversation.
Attendees	Habib and Shahysta only, plus facilitator. No staff, no advisors, no guests. This is a founders' session.
Prework	Both founders answer the prework questions independently before the session. Answers are not shared in advance. The divergence between the two sets of answers is the starting point for the session.
Output	Three written decisions (see below). Not a 20-page strategy document. Three decisions, written in plain language, signed by both founders.

Prework: Habib's questions

Answer these independently before the session. One to three sentences per question is sufficient. Longer answers are welcome; exhaustive ones are not necessary.

What does SmartOne look like in five years if everything goes right?
Describe the company: scale, ownership, team size, market presence. What are you proud of?
What would make you feel like the last 14 years were worth it?
Not the exit price or the revenue number. What outcome would make you feel the work mattered?
If you raised $10M tomorrow with no strings attached, what would you do with it?
Be specific: headcount, products, markets, equipment. This reveals what you believe the constraint is.
What is the one thing you would not want to change about how SmartOne operates today?
This identifies the non-negotiable in the next phase. Whatever the answer is, it is a constraint on any restructuring plan.
What is the technology layer you want to build, and who builds it?
On the May 15 call, you described a platform built from 10-20 open-source tools. How important is that, on a scale of 1-10, to the version of SmartOne you want to run?
What is your honest assessment of the two failed senior hires?
What went wrong: the hire, the onboarding, the mandate, or the company stage? The answer tells you what you need to fix before hiring again, regardless of which path you choose.

Prework: Shahysta's questions

Same instructions. Answer independently. The session starts with both of you sharing your answers.

What does "securing revenue as fast as possible" look like when it's done?
What metric or milestone signals that survival mode is over and you can make structural decisions?
What is your commitment to the Madagascar workforce, specifically?
Not in general terms. If a decision came up that would make the business more valuable but would reduce the Madagascar headcount by 30%, what would you do? Knowing your actual answer to this shapes every workforce and pricing conversation that follows.
What does Habib want that you think is unrealistic right now?
Say it plainly. Not a critique; an honest description of what you think needs to wait until the foundation is more stable.
What would change your view on raising capital?
Is there a specific milestone, an investor type, a term structure, or a market signal that would make the VC path feel less like a risk and more like an opportunity?
Europe Growth: is it Phase 2 (months 4-9) or later?
Your assessment on the May 15 call was that the French market is ready and you already have a team there covering Europe. Do you have the bandwidth to lead a structured French enterprise sales motion while also managing Phase 1? What would need to be true for you to resource that motion at month 4?
What role do you want to hold in the company in two years?
If the two failed senior hires were attempts to put operators under you who could take on day-to-day execution, what would you want to be doing once the right operator is in place?

Session agenda

Block	Duration	What happens
Block 1: Prework share	45 minutes	Each founder reads their answers to the other. No debate during this block. Facilitator notes divergence points without resolving them yet. The divergences are not problems; they are the agenda for the rest of the session.
Break	10 minutes	Facilitator organizes the divergence points while founders take a break.
Block 2: Path conversation	60 minutes	Work through the decision memo (Path A vs. Path B). Not a debate about which is right in the abstract. A conversation about which matches what each founder said in their prework answers. Facilitator's job: keep the conversation grounded in the prework answers, not in hypotheticals.
Block 3: Non-negotiables	30 minutes	Each founder names two non-negotiables. Things that cannot change regardless of which path is chosen. Write them on the whiteboard. These become the constraints that any plan must respect.
Block 4: Three decisions	45 minutes	Write the three decisions (see below) as draft statements. Revise until both founders agree with the plain-language phrasing. Sign both copies. These are the operating agreements for Phase 1.

The three decisions this session must produce

Decision 1

Capital path

Write a plain-language statement: "We will / will not seek outside capital in the next 18 months. If we will, we will target [type of investor] for [use of proceeds]. If we will not, our growth constraint is [specific threshold] and we are comfortable with that pace."

This decision gates: hiring plans, marketing budget, speed of European growth motion, platform development timing.

Decision 2

Madagascar workforce commitment

Write a plain-language statement: "We commit to [specific workforce protection: no layoffs below X headcount / headcount protected through revenue stabilization / full flexibility as business requires]. This is the floor below which we will not allow strategic decisions to take us."

This decision gates: AI augmentation investment, pricing model (if augmentation reduces delivery cost but also headcount), and the authenticity of the "institutional workforce" positioning claim.

Decision 3

Primary hill for the next 18 months

Write a plain-language statement: "Our primary hill for the next 18 months is [specific market / customer segment]. Everything we build and every hire we make serves this hill first. Secondary hills are [list], and they activate when [specific trigger: robotics deal signed / committed revenue above $X / French entity activated]."

This decision gates: every positioning, pricing, and hiring conversation in Phase 1. Without it, the company tries to chase all four hills simultaneously and makes insufficient progress on any of them.

After the session

The three decisions get shared with the HARBOR team within one week of the session. They become the operating brief for every artifact and role in the Phase 1 team roster. If the decisions change after the session (which happens), the founders update the team. No decision made during the engagement should surprise the founders because it contradicts a decision they made at the offsite.