From a planning conversation
What would count
as progress?
I’m designing a diversified frontier firm with dot, my Chief Operating Agent. I’m the CEO, responsible for the direction and the decisions. Our conversation brought the ambitions back to a practical question: what would let us know the work was paying off?
Sets direction. Makes the decisions.
Helps turn the direction into inspectable work.
The ambitions on the board
These are the broad objective themes. The working key results and commitments stay private.
Business viability
Prove the firm
can earn income.
Give the business a reason to exist beyond the appeal of the idea.
Reliable delegation
Build an agent team that reliably finishes delegated work.
Make completion something we can inspect and trust.
Customer value
Prove a repeatable customer offer for a business line.
Learn whether an offer can keep solving a useful problem.
Private ambition
A Big Hairy
Audacious Goal.
There is another objective behind this work. That one stays off the public board.
Room for ambition. Room for privacy.
We used the OKR framework described in John Doerr’s Measure What Matters as a reference for the discussion. OKR means Objectives and Key Results.
Objective
Where are we trying to go?
A meaningful change worth pursuing. It gives the work a direction.
Key result
What would demonstrate progress?
A specific, measurable result we can verify within a defined review period.
Monthly commitment
What will we actually do?
The work we choose to carry out, with an owner and room for it in real life.
The monthly commitments are our way of organizing the work toward the key results. Completing an activity still leaves the question of whether it produced the intended result.
The dialogue did
the sharpening.
We worked back and forth on the language, the evidence and what could realistically fit. dot helped make the draft explicit; I kept responsibility for the choices.
The point was to leave the conversation with objectives we could explain, key results we could evaluate and monthly commitments we could carry.
A useful planning partner gives you something concrete to question.
Name the change.
Start with what should become true. Tighten the objective until its purpose is clear.
Agree on the evidence.
Ask what an observer could check. Replace vague confidence with a measurable, verifiable key result.
Test the realism.
Look at the capacity and dependencies. Refine the result until it is challenging and credible.
Choose the work, then return.
Make monthly commitments that support the result. Come back with evidence, discuss what happened and adjust the work.
Keep the ambition.
Make progress checkable.
This is a firm being designed and tested. Reliable delegation and a working business still have to be demonstrated.
Try it with a goal you care about
What evidence would let someone else tell whether you made progress?
Write that down before adding more tasks.