Exit Planning
Exit Planning Prompts
Structured prompts for owners planning a business exit. Covers readiness assessment, buyer type selection, deal structure, tax optimization, and post-exit financial planning — decisions most owners make only once and get wrong.
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7 prompts
Exit Readiness AssessmentFREE
The "business or a job" framing in dimension 1 is the most useful provocation for owner-operators who have not yet se...
I am considering exiting my business within the next [1 to 5 years].
[Describe: revenue, EBITDA, number of employees, your role in day-to-day
operations, whether you have a management team that could run without you,
and what exit path you are currently assuming -- sale, succession, MBO,
or winding down.]
Assess my exit readiness across four dimensions:
1. Business readiness -- would a sophisticated buyer see a business or
a job? What specifically needs to change before this business is
transferable?
2. Financial readiness -- are the books clean, are revenues recurring or
repeatable, are margins at or above industry benchmarks?
3. Personal readiness -- do I have a clear picture of what I am exiting
to, not just exiting from? What financial outcome do I actually need?
4. Market readiness -- is this the right time in the cycle to sell this
type of business, or should I wait?
For each dimension: score 1 to 5, identify the specific gap, and tell me
the one action that would most improve my position.
Then tell me: if I went to market today, what would kill the deal?
When to use: The "business or a job" framing in dimension 1 is the most useful provocation for owner-operators who have not yet separated their identity from the business. The final question -- what would kill the deal -- forces the conversation past optimism into actionable preparation. Strong entry point for any owner in the 3-5 year exit window.
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