What Questions Should I Ask Before Selling My Company?

Questions About Pre-Sale Tax Structure

• What is the current tax basis of the ownership interest being sold — and what tax strategies are available given that basis and the anticipated transaction structure?
• Has the entity structure been reviewed by transaction tax counsel for its implications on the deal structure and tax treatment?
• Are there charitable vehicles — donor-advised funds, charitable remainder trusts — that could be established before the transaction to address both tax and philanthropic goals?
• Is an installment sale structure a viable option for this transaction — and has the tax impact of that structure been modeled relative to a cash close?
• What is the interaction between the transaction structure (asset sale vs. equity sale) and the tax treatment of proceeds?

Questions About Advisor Coordination

• Are the transaction attorneys and deal-side tax advisors coordinating with personal estate attorneys and financial planners — or are these teams working in separate tracks?
• Who is responsible for the view across all professional disciplines involved in this transaction?
• When were estate documents, beneficiary designations, and trust structures last reviewed — and have they been updated to reflect the expected post-transaction financial picture?

Questions About Post-Sale Wealth Management

• What is the income replacement plan after the transaction closes — including how business income will be replaced with investment income?
• Is there a framework for managing the transition from illiquid business wealth to liquid investment capital?
• Has an investment policy for post-close proceeds been established, or will that decision be made reactively after close?
• If the transaction includes deferred consideration — earnout, seller note, escrow — what is the plan for managing that deferred cash flow and its tax implications?

Questions About Planning Timeline

• What is the realistic planning timeline, and have the most time-sensitive structural activities been identified and initiated?
• Are there pre-sale strategies that require establishment before a letter of intent is signed — and have they been evaluated?
• If the transaction happens earlier than the current timeline suggests, is the personal planning sufficiently developed to accommodate that compression?

Questions About Life After the Transaction

• What is the plan for the period immediately after close — the weeks and months when major decisions will arrive and emotional bandwidth may be reduced?
• Has consideration been given to what personal role, if any, continues with the business post-transaction?
• Are there family communication considerations — a spouse, adult children, key employees — that would benefit from advance planning?