For many business owners, deciding when to sell is one of the toughest calls they’ll ever make. But preparing your business for sale starts long before you sign an agreement. It begins with building operational discipline, leadership alignment, and sustainable systems that make your company attractive to potential buyers — and ready to thrive without you.
According to Kiplinger[i], if you are a baby boomer business owner, and as you edge closer to retirement age, you need to ask yourself, “is my business ready to sell?”
Patrick Ungashick, celebrated author of “Dance in the End Zone”, an exit planning playbook, would suggest that if you’re planning to sell, commence 3-5 years in advance if you can.
Most business owners are uncertain of how best to proceed after a lifetime of hard work building a business.
Why Preparation Matters Before You Sell
If this fits you and your prevailing situation, consider the following:
There are two (2) components to selling:
- Making sure the business is ready for sale. That includes legal, financial, managerial.
- Making sure that you are ready; more internal, emotion-driven, depends on the owner’s individual situation and priorities. Often, sellers are surprised at how important the business is to their sense of identity, legacy, even self-worth.
Key areas to Focus When Preparing Your Business for Sale
In re: to making sure the business is ready for sale, consider these key elements:
- Tracking and boosting financial performance; in particular, bolstering recurring revenue streams. Acquirers and those funding acquisitions are enamored with recurring revenue streams.
- Strengthening the management team.
- Differentiators from the competition.
- Diversifying your customer base.
When prospective buyers begin “kicking the tires” during due diligence a premium can be extracted based on how well the seller has done with the key elements described above.
What You’ll Need
If selling, you’ll need a good:
- Business broker.
- Business lawyer.
- Tax lawyer.
- CPA and/or valuation consultancy
- Certified financial planner (CFP)
Trimming certain liabilities well ahead of the planned sale (as above, typically 3-5 years in advance is best); for example, trading out pension obligations with an annuity.
Try to time a sale in the most interest rate friendly environment that you can. Naturally, sometimes that is just not possible.
4 possible exit strategies
If you believe that you’re ready, consider what Patrick Ungashick[ii] refers to as the four possible exit strategies:
- Innie (oftentimes, owner financed; sell to the management team)
- Outie (sell the business to an outsider)
- Passer (pass to family)
- Squeezer (Planned liquidation; squeeze the business dry)
In conclusion
Selling a business isn’t just a transaction — it’s a transition. Whether your goal is retirement, reinvention, or reinvestment, the right preparation determines your outcome. If you’re considering an exit, start by ensuring your business runs as smoothly without you as it does with you.
[i] The Kiplinger Letter, July 17, 2025
[ii] Patrick Ungashick, NAVIX, 4 Key Questions to Determine Your Best Exit Strategy
