October 2026 · A note from Ryan
A new leader can give you time back before the business earns enough to cover the cost.
That is a real planning decision. How much time would the hire free up? Which decisions would move out of your hands? What happens to distributions while the company grows into the expense?
Those questions belong beside the revenue target in your annual plan.
Put the trade-off in the numbers
Take a simple example. Suppose a leadership role costs $180,000 a year including salary, benefits and employer costs. That is $15,000 a month before any recruiting or transition expense.
The hire may be worth it. The plan still needs to show how the company pays for it, when the person begins and what responsibility changes. If revenue takes longer to arrive, what happens to cash and the money you intended to distribute?
This is an illustration, not a hiring recommendation. Your company’s records, compensation requirements and expected results supply the actual assumptions.
The Owner’s Scorecard gives the decision its purpose. Your month-by-month budget tests how it could work. Your leadership plan makes the responsibility clear.
Take one decision into your planning work
Choose a decision you expect to make in 2027. It could be a hire, an investment, a distribution or a change in your operating role.
Write four short answers in your current planning notes:
- The ownership outcome: what should this change about your time, cash flow or wealth?
- The company work: what has to happen, and who would own it?
- The numbers: what does it cost, when does cash move and which assumptions need support?
- The review: when will you compare actual results with the plan and decide what to change?
Use the work you already have. If an assumption is missing, name it and assign the follow-up. Keep the decision provisional where it depends on that answer.
Your North Star connects the coming year’s ownership goals with company direction and capability priorities. Your 90-Day Game Plan selects the next quarter’s work. They have different jobs, and both stay in the same Owner’s Playbook.
A conversation about the time behind the plan
In Episode 500, Kim interviews me in Time Is the Only Thing You Don’t Get Back. It is a useful companion to the ownership questions in this month’s note.
Listen to Episode 500 · Explore conversations about ownership goals
Bring value into the annual-planning conversation
Our next public workshop is Business Valuation for Annual Planning, planned for the first week of November. The exact date, time and registration details are still to come.
You can begin now with the three lenses of business value. What keeping the company is worth to you, its estimated market value and what a particular sale leaves you with answer different questions.
Put the question that matters to your decision into the plan. Then give it an owner and a date to return to it.
Ryan