Before the Deal: Preparing the Family for the Sale of the Business
Selling the family business is not just a financial transaction.
For many founders, the business is not just an asset – it’s a part of their identity. For many members of the Rising Generation, it’s been a backdrop to their childhood, a symbol of their family’s story, or even a path they once expected to take.
When a business is sold, families often move quickly to finalize tax strategies and hire investment advisors. By doing so, they miss the opportunity to pause and ask: Are we prepared for what this means?
At Wingspan, we’ve worked with families across industries, and we’ve seen that the most successful transitions don’t begin with the deal memo. They begin with a conversation.
This guide outlines the critical considerations both founders and rising generation members should explore ahead of a business sale.
For Founders
Understand Your Own Why
You’ve likely been thinking about this transition for years. But have you fully explored what’s driving it?
Are you selling because you’re ready for retirement? Because your children don’t want to run the business? Because you received an offer that’s too good to ignore? Or because you want to spend your remaining working years doing something else?
Clarity in your motivations will help you communicate honestly with your family and navigate the emotional complexity that often surfaces as a deal nears completion.
Reflect on the following questions:
- What will be most difficult to let go of once the business is sold?
- What do I hope this transition will make possible for me?
Share the Story, Not Just the Strategy
One of the most common pain points we hear from Rising Gen members is: “We found out too late.” Sometimes it’s days before the sale closes. Sometimes it’s years after the decision was made.
Share the story behind the decision. Not just the mechanics, but the meaning. What has this business meant to you? Why now? What do you hope the proceeds will make possible for the family? Let the Rising Generation feel included, not blindsided. And don’t stop there. Thoughtful communication shouldn’t be confined to the family alone. Key members of the management team – and in some cases, customers, vendors, and community partners – may also be affected by the sale. A broader communication strategy can help ensure continuity, reduce speculation, and preserve the values and relationships the family has built over time.
Think Beyond Control: What Role Will You Play Next?
The sale of the business often shifts your identity – from operator to advisor, from owner to steward, from builder to elder.
What role do you want to play going forward? In family investments? In philanthropy? In mentoring the next generation? If you don’t define a new chapter, others may write it for you, or leave you behind entirely.
Plan for Governance, Not Just Growth
A business provides natural structure. It comes with boards, managers, reports, and accountability. When that disappears, the family needs to build a new architecture of decision-making, or risk disconnecting.
You may need to:
- Establish or revamp a Family Council
- Define who gets to make decisions about shared capital
- Clarify how distributions, investments, and philanthropic gifts will be handled
- Create shared values statements or a family constitution
For the Rising Generation
Ask the Questions Now
Many Rising Gen members are afraid to speak up. They worry about sounding entitled, ungrateful, or naïve. But a big transition can affect the whole family, and silence could create future resentment.
You can ask:
- What is being sold, and what is staying?
- How will the proceeds be distributed or allocated?
- What do you expect of me now that we have this wealth?
- How can I be involved meaningfully, even if I’m not an expert?
Courageous questions lay the groundwork for clarity and connection.
Begin Your Learning Journey Early
Most Rising Gen members don’t need immediate access to liquidity. They need access to opportunity and understanding.
Now is the time to begin (or deepen) your education around:
- Financial literacy: understanding investment basics, taxes, trusts, and risk
- Governance: how families make decisions around shared assets
- Emotional intelligence: learning to communicate effectively across generations
- Personal identity: exploring how wealth intersects with meaning, purpose, and contribution
You don’t need to become a CFO overnight, but you do need to understand the landscape you’re inheriting.
Consider Your Role (And Your Boundaries)
Not every Rising Gen member wants to co-invest or sit on a philanthropic board. That’s okay.
Ask yourself:
- What kind of role feels energizing to me?
- Do I want to be hands-on, or simply informed?
- What are my boundaries around privacy, independence, or identity?
Families thrive when members are given space to participate in a way that matches their readiness, temperament, and passions; not when they’re forced into roles they didn’t choose.
Plan for the Relational Side of Wealth
Liquidity changes the temperature of the room. It can affect how friends treat you, how partners view you, and how siblings relate to one another.
Make space for these realities. Build peer support. Find advisors or mentors who’ve been through it. Talk openly about what you’re feeling, even if what you’re feeling is complicated.
The families who navigate liquidity well don’t pretend it’s easy. They build disciplines to manage the complexity.
What You Can Do Together Before the Deal
Host a family meeting or retreat before the sale closes.
Consider a facilitated conversation with an outside advisor to help surface hopes, fears, and assumptions.
Create a “Liquidity Readiness Checklist” that includes governance, communication, education, and relational health (see below).
While advisors will focus on tax strategy and transaction mechanics, families also need to define what a successful transition looks like – for each of them, and for the family as a whole.
Final Thought
The most enduring wealth transitions are not those that maximize financial return, but those that preserve trust, identity, and purpose.
Before the term sheet is signed, take time to ask: What story do we want this transition to tell?
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Preparing the Family for the Sale of the Business – Liquidity Readiness Checklist
This checklist is designed to help families prepare for a major liquidity event; strategically, relationally, and emotionally. Use it as a conversation starter, a planning tool, or part of a facilitated process.
Section 1: Founder Reflection
☐ I have reflected on what the sale means to me personally (identity, legacy, closure).
☐ I can clearly articulate why I am pursuing the sale at this time.
☐ I have considered what role I want to play after the business is sold (e.g. advisor, investor, mentor, retiree).
☐ I have identified any emotional or relational baggage tied to the business or the exit.
☐ I have a plan for how to communicate the sale to family, employees, and key stakeholders with clarity and care.
Section 2: Rising Generation Engagement
☐ Rising Gen family members are aware that a transaction is likely or imminent.
☐ They understand the rationale for the sale and have had an opportunity to ask questions.
☐ We’ve discussed how this transition might affect their identity, career, or sense of connection to the family enterprise.
☐ Each Rising Gen member has access to educational support (e.g. financial literacy, governance, wealth psychology).
☐ We’ve discussed what role(s), if any, they may wish to play post-liquidity.
Section 3: Communication & Narrative
☐ The family has aligned on what we want to say publicly about the sale, if anything.
☐ We’ve considered how to communicate this transition to key non-family stakeholders (e.g. management team, community partners) in a way that reflects our values.
☐ We’ve considered a strategy for managing visibility, press, and privacy (especially for the Rising Gen).
☐ We’ve aligned on what values we want to express through this transition.
☐ We have a shared language to talk about “legacy” that includes multiple generations’ perspectives.
Section 4: Governance & Decision-Making
☐ We have a structure in place (or a plan to build one) for how we will make decisions post-liquidity.
☐ Roles and responsibilities around shared assets are defined or clarified.
☐ There is an identified process for making investment decisions with shared capital (e.g. family investment committee, external CIO)
☐ There is a process for family philanthropy (e.g. pooled foundation, individual DAFs, shared grant making).
☐ There is a mechanism for resolving disagreements (e.g. voting rules, mediation plan, council structure).
Section 5: Technical Planning & Wealth Structuring
☐ We have aligned advisors supporting the transaction (legal, tax, wealth, philanthropic, family strategy).
☐ We’ve reviewed estate planning implications and updated trusts or gifting strategies accordingly.
☐ We understand how liquidity will be distributed or retained (e.g. individual vs. pooled capital).
☐ Asset protection, privacy, and cybersecurity considerations are in place.
☐ Our structures reflect both financial prudence and family values (e.g. mission-aligned trusts, shared values clauses).
Section 6: Relational Health & Family Alignment
☐ We’ve identified the potential emotional impact of the sale, for each person and for the family system.
☐ We’ve planned space (a retreat, a meal, a conversation) to acknowledge this moment as a turning point.
☐ We’ve discussed how we want to stay connected after the business is no longer the family’s anchor.
☐ There is clarity around what success looks like; for the transaction, for the family, and for the future.
☐ We’ve considered how to support non-financial legacy elements (e.g. storytelling, archives, family rituals).
For Families Looking to Go Further
☐ Create a one-page “Family Liquidity Charter” summarizing our shared purpose, hopes, and commitments post-sale.
☐ Design a Rising Gen education arc – over 6–12 months – with coaching, peer learning, and structured exposure to family governance.
☐ Plan a post-transaction family reflection gathering (e.g. 6 months after liquidity) to review how the transition is unfolding.
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How to use this guide:
- Use it as part of a family meeting, advisor planning session, or pre-sale retreat.
- Consider reviewing the checklist quarterly in the lead-up to the transaction.
- Not every box needs to be checked, but each item invites a conversation worth having.
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