What team will your ownership plan need, and what can you support along the way?
You may know the leadership team you want and still be unable to build it all this year. The five-year roadmap connects today’s responsibilities to the people, support, costs and timing behind a workable future arrangement.
Start with your intended role. You might want to remain CEO, continue selected work or move out of operations. The plan should make that choice practical while keeping its trade-offs visible.
Map the work and the people before adding positions
A functional chart shows the work the company needs. A people chart shows who actually performs it. Compare CEO, CFO, CRO and COO responsibilities with the employees, providers and owner time supporting them.
Mark responsibility as assigned, Unassigned or Unconfirmed. Explain work that is not needed here. Check the available time, not just the number of boxes beside a person’s name.
A promotion can create a second staffing decision. In a hypothetical company, the delivery manager is ready for broader operating leadership, but their daily scheduling and supervision still need coverage. The plan includes both the new responsibility and the work left behind.
Use the findings from M19 to choose the priority. An unreliable close may prevent a supported hiring commitment; independent work clarifying roles can proceed while finance resolves that foundation.
Compare arrangements that actually cover the work
You can hold a seat, develop an employee, combine an employee with coaching or fractional help, retain a fractional leader, or hire full time. These are options to compare. There is no mandatory path ending in three full-time executives.
Be specific about who leads, who does the work and who helps them improve. A coach supports learning. A consultant may deliver a project. A fractional executive may accept continuing responsibility. An engagement can combine those contributions when the agreement says who owns each part.
Assess the actual person and agreed scope. A firm’s reputation or an executive title does not prove the work is covered. A long-term fractional arrangement can be appropriate when its availability, capability and continuity fit your company.
Build four connected plans for the same five years
For CEO, CFO, CRO and COO, show the current arrangement and the intended arrangement in each year. Include the person or future role, support, leadership capacity, your own responsibility and the conditions for a change.
A temporary arrangement needs an intended transition year and a nearer decision date. A continuing arrangement needs a reason and review date. A future promotion depends on demonstrated readiness and financial support, not simply the calendar advancing.
Read all four plans together. A revenue expansion may require delivery capacity before it produces enough cash to fund leadership. A person supporting two functions cannot supply the same hours twice. Future capability ratings are targets, not scores already earned.
Compare the complete cost and cash timing
With finance, include compensation, employer costs, providers, support staff, recruiting, development and transition overlap. Separate one-time from continuing costs and distinguish new spending from an expense being replaced.
In a hypothetical comparison, a $180,000 annual salary starting in July adds $90,000 of base salary in that calendar year. It can also require recruiting, benefits, coaching and overlap before or after the start. The $90,000 alone does not describe the complete investment.
Count shared people once, using supported allocations where needed. Keep a combined provider fee intact when its split is unknown. Use the same reviewed three-statement model and forecast as the company plan.
Examine profit, cash timing, working capital, debt, investment and your ownership-income needs. A share of gross profit or a salary benchmark cannot establish affordability. Leadership investment may reduce near-term distributions; the expected benefit and timing need support.
If the preferred hire is not yet supported, compare a narrower scope, different support or a workable interim arrangement. Keep future options conditional. An essential funding gap labeled “to be determined” still needs resolution before a dependent commitment.
Make a decision from the combined plan
Ownership and the CEO review the four plans and make an actual staffing, support, development or continuation decision. Discuss immediate assignments, authority and support with the people doing the work.
Record who participated, the decision, reasoning, cost assumptions, responsible person, conditions and next review. Keep sensitive succession possibilities with the appropriate audience. An uncontacted future hire has not agreed to a role because their name appears in a plan.
| Working tool | What it helps you establish |
|---|---|
| Current function charts and company people view | Today’s work, assignments, gaps and capacity across functions. |
| Four Five-Year Leadership Plans | A connected staffing and support arrangement across the same years. |
| Leadership Staffing Decision | The evidence, options, chosen response and next review for one decision. |
| Leadership Arrangements and Costs reference | A way to compare scope, support and complete costs. |
| Current financial model and supporting schedules | Whether material commitments and their timing fit the company plan. |
Suitable existing company records count. The tools organize decisions; completing every optional format is unnecessary.
What completion looks like
All four supported five-year plans connect to current responsibility, assessments and financial evidence. You have used them for an actual decision and scheduled continuing review. You do not have to wait five years, hire everyone or leave every operating role.
Open the seven completion requirements
1. Set the direction for the five-year plan
Reflect: What operating role do you want, and what must the leadership arrangement make possible for the company?
What to do: Identify the five-year period, ownership direction, company strategy and current forecast edition. Explain the intended role and any open assumptions.
Complete when: The plan’s purpose, periods and relationship to ownership goals are clear.
2. Show today’s responsibilities and people
Reflect: Who carries the CEO and three functions, including work underneath each seat? Where is capacity missing or overlapping?
What to do: Review CEO, CFO, CRO and COO work, actual people, providers, support and authority. Mark a relevant unassigned job and explain work that is not needed. Use the company people view to identify overlap.
Complete when: A supported picture of current work, people and meaningful capacity gaps. A title or count of responsibilities alone does not establish available time.
3. Choose priorities from the evidence
Reflect: What does the current function/person evidence tell you, and which gap matters first given the plan, risk and dependencies?
What to do: Use the three M19 function and person findings, supporting work and dates. Distinguish actual capability from future targets. Review the CEO through their role and work.
Complete when: A reasoned priority using the actual findings. The lowest score is not an automatic personnel decision, and no fourth /81 assessment is required.
4. Plan each seat over the same five years
Reflect: Who will carry each responsibility, with what support and capacity? What must be true before each transition?
What to do: Complete the four seat plans for the same years. Include intended people/roles, support, leadership time and expected changes. For temporary arrangements, name the transition year, readiness/funding conditions and next decision. For a continuing arrangement, state the reason and review date. Include the work left behind by a promotion.
Complete when: Four connected supported plans. Future hires, promotions and capability targets remain proposals; the owner may deliberately retain a role.
5. Reconcile cost and timing with finance
Reflect: What does the entire arrangement cost, when does the cash leave, and what supports the proposed timing?
What to do: With finance, connect compensation, provider fees, support staff, development, recruiting, overlap and other transition costs to the reviewed forecast. Count shared people once, with supported allocations. Show effects on profit, cash, ownership income and owner work. Preserve combined provider fees when their split is unsupported.
Complete when: Material commitments have complete supported financial implications and funding/operating conditions. An essential “funding to be determined” dependency stays incomplete. A workable supported interim arrangement may form part of a conditional future plan.
6. Use the combined plan and agree on immediate work
Reflect: What decision did ownership and the CEO make from the four plans? Do the people responsible understand the immediate work and support?
What to do: Hold the planning/review discussion, make a supported staffing/support/development/continuation decision and record responsibility, timing and conditions. Discuss relevant commitments with the people doing the work while protecting sensitive succession information.
Complete when: One actual decision using the combined plan, with immediate commitments understood. An AI draft or future meeting is preparation; an uncontacted proposed hire has not agreed.
7. Schedule continuing use and keep one current plan
Reflect: Who maintains the current edition? When will the next review occur, and what would bring it forward?
What to do: Name the maintainer and next scheduled review. Connect current commitments to monthly meetings, consequential changes to quarterly review and next-year people costs to annual planning. Include departure, failed-assumption and material forecast-change triggers.
Complete when: The current edition, maintenance responsibility and next review are clear. Scheduled review is part of completion, not an optional to-do after awarding 3.
Review the milestone-specific 0–3 score and evidence test
0, Not Started. You have not begun a supported plan for how the CEO and three functional responsibilities will be covered over time. Current titles and the hope that growth will solve the gaps remain the main guide. Unreviewed evidence is not automatically a zero.
1, Learning. You can explain the difference between the work a seat owns, the people and support carrying it, and the cost and capacity needed over time. You can explain how the plan should support ownership direction. You have not begun the company-specific roadmap and supporting review.
2, In Progress. Substantive work is underway, but one or more of the seven requirements remains incomplete. Examples include unfinished seat plans, unsupported costs or transition dates, missing current assessment evidence, a plan not yet discussed and used, or an unscheduled continuing review.
3, Installed. All four seats have a supported five-year plan connecting current responsibilities, the owner’s intended role, required capacity, staffing/support choices, cost and timing. Current function/person evidence supports the priorities, and material commitments and transitions reconcile with the reviewed company financial plan. Ownership and the CEO have used the combined plan to make and assign a decision, with the relevant people clear on immediate commitments. A maintainer, next scheduled review and ongoing monthly, quarterly and annual connections are in place. Future appointments and results remain conditional, and the owner may intentionally retain an operating role.
Verification test: Open the four seat plans, current responsibility and assessment evidence, financial support and the dated planning decision. Trace a material transition or continuing arrangement from the ownership/company need through the people, support, timing, cost and funding assumptions to the next action and review. Show how the other seats fit the same company plan. A reviewer can follow the work with the records open; recall speed and a forecasted perfect score do not establish completion.
Use suitable existing work. Record each requirement as complete, incomplete or not reviewed, with its evidence and date. You choose the saved score; keep owner, peer, coach and AI assessments separate. Missing access remains unreviewed rather than automatically zero. Preserve prior reviews and identify the next action, responsible person and review date.
Revisit the plan as the company changes
Keep the current roadmap in Your Leadership Team, financial support in The Numbers, and dated planning decisions in The Rhythm. Preserve the approved budget for comparison while using the current forecast to test changes.
Monthly reviews check commitments. Quarterly review revisits consequential staffing and development choices. Annual planning builds the next year’s people and costs into the budget. Reopen the affected plan sooner after a departure, failed assumption or material forecast change.
M21 uses those priorities to develop a person through real practice. A stronger team develops through supported work and review; its future value is not guaranteed by the plan.
Explore the team your plan needs
- 509. The 5-Year Leadership Roadmap, with Ryan and Kim: connect ownership goals and staffing. Use the current written requirements in place of recorded perfect-score or staffing-ratio shortcuts.
- 433. Designing Your Future Org Chart, with Mike Frommelt and Rick Rittmaster: start with future responsibilities before fitting people into roles.
- 405. Breaking Founder Dependency, with Mike Frommelt: define the owner’s intended role and the leadership work that needs coverage.
- Functional Seat: separate responsibility from the title and employment arrangement.
Choose your next step
Review the wider system. Use the Ownership Assessment to consider this work beside your goals and the other milestones. Choose a useful priority from the evidence.
Bring the plan together with support. The 90-Day Boardroom Blueprint connects ownership direction, the financial foundation and decisions in a first usable Playbook. You can explore help directly; taking the Assessment is not a purchase prerequisite.
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