Questions to ask the seller: the 50 essential ones

BlogBuyingNovember 6th, 2025
Questions to ask the seller: the 50 essential ones

Introduction

You have identified an interesting business on Leez. Initial contact has been established. Now comes the crucial stage: questioning the seller to understand what you are actually buying.

Too many acquirers focus solely on financial figures. They forget the operational, legal or human questions that can transform an opportunity into a trap. The right questions asked at the right time reveal the hidden strengths and masked weaknesses of a business.

This questionnaire of 50 questions covers 8 essential dimensions of a business acquisition. From history to strategic opportunities, including financial and legal aspects, each category helps you build a complete and realistic vision of your potential acquisition.

These questions do not replace formal due diligence. They structure your initial discussions with the seller and allow you to quickly assess the opportunity before committing significant resources. Use them as a basis for discussion, adapt them to your sector, and supplement them according to your specific needs.

📌 Summary (TL;DR)

This guide presents 50 essential questions divided into 8 categories to effectively question a business seller. It covers history, finances, customers, team, operations, legal aspects, transition and strategic opportunities. These questions structure your initial discussions and reveal the strengths and weaknesses of an opportunity before undertaking complete due diligence.

Questions about history and general situation

Start by understanding the overall context of the business. These questions lay the foundations for your analysis and reveal the seller's real motivations.

  • How long has the business existed? Longevity demonstrates stability and the ability to weather different economic cycles.
  • Why are you selling now? The answer often reveals more than expected: planned retirement, hidden difficulties, or personal opportunity.
  • How has turnover evolved over the last 5 years? Identify trends: stable growth, stagnation or decline.
  • What major changes have occurred recently? New products, relocation, loss of a key client, restructuring.
  • Have there been difficult periods? How did the business overcome them?
  • What is your vision for the future of the business? This reveals perceived opportunities and challenges.

These questions allow you to quickly detect warning signs and guide your evaluation grid.

Essential financial questions

Financial questions are at the heart of your due diligence. They reveal the real economic health of the business.

  • What is the net profitability over the last 3 years? Request certified accounts, not just tax returns.
  • What is the cost structure? Breakdown between fixed and variable costs, margins by product or service.
  • What is the state of cash flow? Operating cash flows, working capital requirements, available reserves.
  • Are there any debts or financial commitments? Bank loans, leasing, guarantees given, supplier debts.
  • What is the state of customer receivables? Average payment terms, doubtful debts, provisions.
  • What investments have been made recently? And which ones are necessary in the short term?
  • Are there any exceptional charges to anticipate? Repairs, equipment renewal, compliance upgrades.

Use the Leez valuation tool to cross-reference this data with an objective valuation.

Questions about customers and the market

Turnover stability depends on the quality and diversity of the customer base. These questions examine the seller about commercial solidity.

  • Who are your main customers? What proportion of turnover do the 5 largest customers represent?
  • What is customer loyalty like? Retention rate, average longevity, order recurrence.
  • Are there any ongoing contracts? Duration, termination conditions, change of ownership clauses.
  • How do you acquire new customers? Acquisition channels, acquisition cost, effectiveness of marketing actions.
  • What is your positioning against the competition? Competitive advantages, market shares, identified threats.
  • What are the trends in your sector? Growth, digitalisation, regulations, technological developments.

Excessive customer concentration or dependence on a single channel are major risks to identify quickly.

Questions about the team and human resources

The team is often the most valuable asset of an SME. These questions allow you to assess human risks post-acquisition.

  • How many employees does the business have? Breakdown by function, full-time vs part-time, seniority.
  • Who holds the key skills? Is there process documentation or does everything rest on a few people?
  • What is the staff turnover rate? Recent departures, reasons, general social climate.
  • What is the salary structure? Salaries aligned with the market, bonuses, benefits, social charges.
  • Is the current manager indispensable? Customer relations, technical know-how, operational decisions.
  • Are there any HR conflicts or disputes in progress? Employment tribunal disputes, internal tensions, identified risks.

Excessive dependence on the seller can complicate the transition and justify prolonged support.

Operational and systems questions

Operational robustness guarantees business continuity after the acquisition. Question the seller about critical systems and processes.

  • Who are your main suppliers? Dependence, contractual conditions, available alternatives.
  • What IT systems do you use? Business software, CRM, accounting, licences, data ownership.
  • Are processes documented? Written procedures, manuals, training available for a buyer.
  • What is the state of equipment and infrastructure? Age, maintenance, short-term replacement needs.
  • Do you own or rent the premises? Lease conditions, remaining duration, possibility of renewal.
  • What intellectual property does the business own? Patents, trademarks, licences, copyrights, trade secrets.

Obsolete systems or dependence on a single supplier may require post-acquisition investments.

Hidden legal liabilities can transform a good deal into a nightmare. These questions identify legal and regulatory risks.

  • Are there any ongoing or potential disputes? Disputes with customers, suppliers, competitors, administrations.
  • Is the business in regulatory compliance? Sector standards, environment, safety, data protection.
  • What insurance covers the business? Professional liability, business interruption, cyber risks, amounts and excesses.
  • Are there any guarantees given to third parties? Personal guarantees, bank guarantees, contractual commitments.
  • What authorisations and licences are necessary? Validity, transferability, renewal conditions.

To secure these aspects, the Leez expert network includes lawyers specialising in business transfers who can support you.

Questions about transition and support

A well-planned transition maximises your chances of success. These questions clarify the handover arrangements with the seller.

  • Are you available to support the transition? Desired duration, availability, remuneration arrangements.
  • How do you plan to announce the sale? Communication to customers, suppliers, team, planned schedule.
  • What relationships do you maintain with stakeholders? Key customers, strategic partners, critical suppliers.
  • What information do you share before signing? Access to documents, visits, meetings with the team.
  • What are your departure conditions? Post-sale role, non-compete clauses, availability for advice.

Prepare these discussions in advance with our guide on how to prepare for your first meeting with a seller.

Strategic questions and opportunities

Beyond what exists, identify development potential. These questions reveal opportunities not exploited by the seller.

  • What growth opportunities do you see? New markets, products, services, distribution channels.
  • Why have you not exploited these opportunities? Lack of time, resources, skills, or other reason.
  • Are there any abandoned or pending projects? Why were they put aside? What was their potential?
  • What synergies do you identify with other activities? Sector, geographical, technological complementarities.
  • What would be your first priorities if you kept the business? Strategic priorities according to the seller.

These answers help you build your development plan and justify your offer during price negotiation.

How to use these questions effectively

Asking 50 questions all at once is neither realistic nor productive. Here is how to use this questionnaire strategically.

Adapt according to context. Not all sectors have the same issues. Prioritise questions relevant to the activity concerned.

Plan several discussions. A first meeting covers general and financial questions. Operational and legal aspects come afterwards.

Take structured notes. Organise your answers by theme to facilitate comparative analysis and decision-making.

Request evidence. Do not settle for verbal answers. Demand documents: accounts, contracts, certificates, reports.

Cross-reference with due diligence. These questions complement but do not replace in-depth analysis of legal and financial documents.

Explore businesses for sale on Leez and use this questionnaire to structure your initial discussions with sellers.

Asking the right questions to the seller transforms a simple visit into in-depth analysis. The 50 questions presented cover all critical aspects: finances, customers, team, operations, compliance and transition. They allow you to identify real opportunities and avoid unpleasant surprises.

The essential thing is not to ask everything at once, but to adapt your questions to the context and listen carefully to the answers. Hesitations, vague answers or contradictions are often as revealing as the figures themselves.

Good preparation makes the difference between a successful purchase and a risky investment. Take the time to document each answer, verify key information and seek expert support if necessary. Explore businesses available on Leez and apply this method to identify the opportunity that truly matches your objectives.

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