The Heart-to-Heart Guide: 7 Questions Every Business Owner Should Ask Before Selling Their Mid-Sized Company


Deciding to sell your beloved mid-sized company can feel like an emotional rollercoaster. We understand – it’s more than just a business. It’s your passion, your hard work, and your dream realized.

As you embark on this transformative journey, it’s crucial to ask the right questions, not just to potential buyers, but also to yourself. These questions will guide you, tug at your heartstrings, and help you make a decision that aligns with your vision and aspirations. So, let’s dive into the questions every business owner should ask before selling a mid-sized company:

1. Why Am I Selling?

Pause and reflect on your motives. Are you seeking new challenges, or is it time for a well-deserved break? Is it time to retire and enjoy the fruits of your labor, spending time with your family and friends? Understanding your reasons will not only clarify your decision but also prepare you for discussions with potential buyers.

2. What Is My Company’s True Worth?

Beyond the financials, what makes your company valuable? Is it your innovative team, your loyal customer base, or your robust supply chain? Knowing your true worth will empower you during negotiations and attract buyers who appreciate your business’s essence.

3. What Legacy Do I Want to Leave?

Consider the impact your company has on its employees, customers, and the community. What legacy do you want to leave behind? Understanding your legacy goals will help you find a buyer who shares your values and is committed to preserving your company’s culture.

4. Am I Prepared for Life After the Sale?

Imagine your life after the sale. What will you do? Travel the world, start a new venture, or spend quality time with family? Being mentally prepared for the post-sale phase is essential for a smooth transition and a fulfilling future. Do not take this step lightly. Many business owners assume life will pretty much be the same after they sell their business, but they forget how much their psyche is wrapped up in their business.

Their identity is intertwined with their role as the business owner. It’s like losing a family member when you sell your business or your child, and without hopes, dreams, and a plan after your business is sold, you can feel empty inside.

5. How Will the Sale Affect My Team?

Your employees are like family. Consider how the sale will impact them. Will their jobs be secure? Will the new owner uphold the company’s values? Addressing these concerns not only nurtures your company’s spirit but also ensures a harmonious transition for your team.

6. What Are My Deal-Breakers?

Identify your deal-breakers clearly. Is it retaining a certain percentage of your staff or maintaining the company’s name and reputation? Knowing your non-negotiables will help you find a buyer whose vision aligns with yours.

7. Am I Surrounded by the Right Advisors?

Having a trustworthy team of advisors – financial experts, legal consultants, and experienced M&A advisors with experience – is crucial. They will guide you through the complexities of the selling process, ensuring you make informed decisions that safeguard your interests and your company’s legacy.


Remember, selling your mid-sized company is not just a transaction; it’s a transformative moment in your life. By asking these questions every business owner should ask before selling a mid-sized company, and being true to your aspirations, you’ll not only find the right buyer but also embark on a new chapter that aligns with your dreams. 

Here’s to your journey, your legacy, and the exciting adventures that await beyond the sale!