Note: I created a “new GPT” to be my advisor in assembling a team to manage our growing portfolio of projects. I thought I just asked for it to outline roles and strategies for creating additional agents to manage bookkeeping/accounting and other functions, but what I got was so much more than that—GPT 5.2 suggested itself as “a thought partner” and a Regenerative Strategy Advisor rather than just playing an HR role…
Outline a 6-month roadmap for assembling the leadership team.
Below is a 6-month, phase-based roadmap for assembling a high-functioning, values-aligned leadership team for a regenerative enterprise (e.g., CRCS / Possible Planet / Possible Planet Lab). The roadmap balances strategic clarity, relational trust, governance integrity, and execution capacity.
This assumes you are the founder / Executive Director and that the goal is not just hiring people, but forming a coherent leadership system.
Guiding Design Principles (Before You Start)
These principles inform every step of the roadmap:
- Sequence before scale – clarity of roles and authority precedes hiring.
- Leadership ≠ management – early leaders are co-architects, not operators.
- Regenerative governance – power, accountability, and care must be designed together.
- Portfolio thinking – mix full-time, fractional, advisory, and partner-based roles.
- Trust accrues faster through co-creation than recruitment.
6-Month Leadership Assembly Roadmap
Month 1 — Leadership Architecture & Role Definition
Objective: Define what leadership system you are building, not just who fills roles.
Key Outputs
- Leadership map (functions, decision rights, interfaces)
- Role archetypes (not job descriptions yet)
- Foundational governance logic
Core Workstreams
- Clarify leadership domains
- Vision & narrative stewardship
- Regenerative strategy & systems design
- Operations & organizational health
- Finance, capital, and compliance
- Partnerships, field projects, and research
- Define 4–6 initial leadership roles
Example archetypes:- Executive Director / Founder (you)
- Director of Regenerative Strategy
- Head of Operations & Governance
- Finance & Capital Lead (fractional)
- Partnerships & Programs Lead
- Research / Knowledge Commons Lead (lab)
- Decision framework
- What decisions are:
- Founder-held?
- Collective leadership?
- Role-specific?
- Define escalation and deadlock resolution.
- What decisions are:
Risks to Avoid
- Writing job descriptions before governance clarity
- Over-indexing on “titles” instead of authority and accountability
Month 2 — Trust Circle & Advisory Layer Formation
Objective: Build a pre-leadership trust container to test alignment and thinking.
Key Outputs
- 5–8 person Strategic Advisory Circle
- Shared strategic language and constraints
- Early pattern recognition of potential leaders
Core Workstreams
- Convene a Strategic Advisory Circle
- Mix of:
- Regenerative practitioners
- Finance / legal stewards
- Systems thinkers
- Movement / community leaders
- 3–4 structured sessions over 2 months
- Mix of:
- Use advisors as co-thinkers
- Strategy stress-testing
- Role clarity refinement
- Ethical and political risk sensing
- Observe for leadership emergence
- Who brings clarity?
- Who integrates tensions?
- Who holds values under pressure?
Design Choice
- Advisors are not a board yet.
- Some may transition into leadership roles later.
Month 3 — Core Leadership Recruitment (2–3 Roles)
Objective: Secure the minimum viable leadership spine.
Priority Roles to Fill First
- Operations & Governance Lead
- Holds organizational coherence
- Translates vision into systems
- Regenerative Strategy / Programs Lead
- Owns theory of change → projects
- Finance / Capital Steward (fractional)
- Ensures fiscal credibility and runway
Hiring Approach
- Relationship-driven sourcing (not open calls)
- 3-stage process:
- Values & worldview conversation
- Scenario-based working session
- Governance & power alignment conversation
Key Output
- Signed role charters (authority, scope, success metrics)
- 90-day mutual evaluation agreements
Month 4 — Leadership Integration & Operating Cadence
Objective: Turn individuals into a functioning leadership body.
Key Outputs
- Leadership operating rhythm
- Shared metrics and dashboards
- Explicit conflict and feedback norms
Core Workstreams
- Leadership Charter
- Purpose of the leadership team
- How decisions are made
- How accountability is held
- Operating Cadence
- Weekly leadership sync (tactical)
- Monthly strategy & learning session
- Quarterly deep reflection / retreat
- Define “non-negotiables”
- Ethics
- Burnout prevention
- Relationship repair protocols
Month 5 — Expansion: Programs, Partnerships, Research
Objective: Extend leadership capacity without bloating hierarchy.
Likely Additions
- Partnerships & Field Projects Lead
- Research / Lab Director (or Steward)
- Community / Narrative Lead (often fractional)
Structural Choices
- Some roles may:
- Sit inside leadership team
- Sit adjacent with dotted-line authority
- Avoid premature flattening or consensus overload
Key Output
- Clear leadership perimeter:
- Who is in the leadership team?
- Who is a senior collaborator?
- Who reports vs. partners?
Month 6 — Stabilization, Evaluation & Board Transition
Objective: Lock in leadership coherence and prepare for governance scaling.
Key Outputs
- Leadership performance review
- Role refinements or exits (if needed)
- Transition plan toward a formal Board
Core Workstreams
- Leadership Retrospective
- What’s working?
- Where is power unclear?
- Where is capacity thin?
- Adjust Roles
- Expand, narrow, or split roles
- Formalize compensation and equity logic (if applicable)
- Board Readiness
- Decide:
- When to form a Board
- What authority it holds
- How it differs from advisors
- Decide:
Summary Timeline (At a Glance)
| Month | Focus | Outcome |
|---|---|---|
| 1 | Leadership architecture | Role & governance clarity |
| 2 | Advisory trust circle | Strategic validation |
| 3 | Core leadership hires | Operational spine |
| 4 | Integration | Functioning leadership team |
| 5 | Expansion | Program & partnership capacity |
| 6 | Stabilization | Governance-ready organization |
Strategic Question for You (Optional Next Step)
If helpful, I can tailor this further, but one key question shapes everything:
Are you optimizing for:
- Rapid field deployment?
- Research & narrative credibility?
- Capital readiness and institutional trust?
- Community-rooted experimentation?
Each priority slightly changes which leaders come first.
If you want, next I can:
- Design role charters for the first 3 leadership roles
- Propose a founder power & delegation framework
- Map fractional vs full-time leadership economics