Exiting a business, whether through a sale, succession, or restructuring, is about more than financial planning. It’s an emotional and personal journey that affects not just the business itself but the relationships, shared history, and futures tied to it.
For family enterprises, the decision is often uniquely challenging. These businesses are intertwined with generational legacies, personal connections, and a shared sense of identity. And for privately owned businesses, while formal family ties might be absent, owners still feel a responsibility for their people, clients, and the legacy of what they’ve built.
The path forward is rarely straightforward. Successful changes in leadership or ownership require not just strategy and logistics, but also empathy, open conversations, and respect for everyone involved. Navigating these dynamics is just as important as the business strategy itself. That’s why it’s critical to choose the right M&A advisor (like STS Capital Partners) who not only brings strategic and logistical expertise but also prioritizes empathy, open communication, and respect. The right advisor will guide you through delicate conversations and pivotal decisions from the very beginning, ensuring a human-centered process that protects both the value of the business and the relationships that define it.
This article is designed for private business owners contemplating what comes next. It offers practical guidance on balancing business goals with the human aspects that make selling a privately owned or family-run enterprise so personal.
Table of Contents
1. Start with Clarity: Define Your Preferred and Required Outcomes
2. Have the Hard Conversations Early
3. Structure for Success: Financial, Legal, and Legacy Planning
4. Plan for the People Who Matter
1. Start with Clarity: Define Your Preferred and Required Outcomes
Before any conversations happen with leadership teams, family, or external advisors, you need to be clear on what you want to achieve with the outcome of the sale of your business. Not just financially, but personally, emotionally, and operationally.
One of the most effective ways to achieve this is through a structured exercise like the Owners Outcomes Exercise used by STS Capital Partners.
This exercise is designed to help business owners and stakeholders articulate what success looks like from multiple perspectives: personal, business, financial, and people-centered outcomes. It uncovers assumptions, reveals conflicting priorities, and ensures every future decision is made with those priorities in mind.
Every exit involves multiple, sometimes competing, priorities. Financial outcomes, employee well-being, preserving company culture, family harmony, and personal freedom don’t always align. Left unspoken, they can lead to misunderstandings or decisions you’ll later regret.
This exercise typically uncovers things like:
- A founder wishes to protect the workforce while a buyer intends to restructure.
- One sibling wants to keep the business while another is ready to move on.
- Differing views on how much influence family should retain after a sale.
- Personal fears about what life will look like post-sale.
It’s better to surface these early when goodwill is intact and there’s still time to work through difficult conversations.
The outcomes of this exercise guide how you approach timing, how you evaluate potential buyers or successors, what financial structures you’ll need, and how you’ll care for your employees and leadership team.
A few questions to consider as you begin:
- What are each family member’s or stakeholder’s long-term goals for the business and themselves?
- Are there buyers or successors who share your values and vision for the business?
- How can your business’s culture and workforce be protected during a transition?
- What do you want life to look like after you step away?
Clarity comes first. And it rarely happens in a single conversation, but it can happen through structured, thoughtful exercises like this one.
2. Have the Hard Conversations Early
Once you’ve gained clarity on your preferred and required outcomes, the next step is opening meaningful, honest conversations with the people involved.
Among business owners, emotional ties, differing visions, and personal ambitions can easily derail transitions when left unspoken. By starting these conversations early, you give yourself the chance to surface concerns, align expectations, and build understanding long before a sale or succession decision is imminent.
A few tips for making these conversations productive:
- Set the tone with empathy and transparency. Acknowledge that this process affects everyone differently and that no perspective is wrong.
- Create a safe space for difficult topics. Be prepared to hear things you may not have expected. Encourage honesty, even if it’s uncomfortable.
- Decide when to bring in mediators or trusted advisors. An impartial third party can help facilitate sensitive discussions, especially where emotions run high or interests diverge.
3. Structure for Success: Financial, Legal, and Legacy Planning
Once you have clarity and alignment, it’s time to set up your financials and legal affairs so you’re protected and in control of when and how you exit. Good structuring means you make the decision on your terms, at the right time, without pressure. It ensures your financial future is secure, the people you care about are looked after, and your legacy is preserved.
The smartest move you can make early is to bring in trusted experts. People who know you well, understand what you’re trying to achieve, and can navigate both the technical and human sides of the process, including tax implications, estate planning, and protecting key relationships. The sooner you start planning, the more options you’ll have when it counts.
Key priorities:
- Clarify ownership and roles to avoid disputes later.
- Structure for tax efficiency and to preserve value.
- Balance fairness and legacy, remembering that fairness doesn’t always mean equality.
- Make the business buyer-friendly with clean, clear structures that reduce risk.
4. Plan for the People Who Matter
Building on your structured exit plan, it’s equally important to plan for the people your decisions will affect most. How you manage those relationships can define your personal and professional legacy.
Consider:
- When and how you communicate plans to employees. Transparency, handled with care, builds trust.
- How do you honor longstanding commitments and relationships? This might include retention packages, transition bonuses, or guarantees about employment terms.
- What cultural values and traditions do you want preserved post-sale? Buyers appreciate businesses with strong, stable cultures as it adds value.
Conclusion
“Exiting a business is one of the most personal, emotional, and consequential
decisions an owner will ever make. It’s about more than a financial transaction… It’s about protecting relationships, honoring history, and shaping futures. In my experience, the most successful transitions don’t happen by chance. They begin with clarity, are guided by open conversations, grounded in thoughtful planning, and centered on people.” – Brenda Jacobsen, STS Managing Director.
STS offers entrepreneurial business owners the opportunity to create a legacy through their financial success and philanthropic initiatives, helping them achieve an Extraordinary Exit. By helping clients sell their businesses and realize maximum financial value, we provide limitless opportunities to reinvest their proceeds for good, channeling incremental sale assets into foundations, trusts, and other philanthropic activities that can make a meaningful and lasting difference. This approach to philanthropy is core to our foundation and sets us apart as a unique M&A firm.
