Selling Your Business Is No Walk in the Park—But It Can Be Smoother with the Right Prep

selling your business is not a walk in the park

Selling Your Business Is No Walk in the Park—But It Can Be Smoother with the Right Prep

Successful business owners are no strangers to adversity. If you’ve owned your company for 25+ years, you’ve likely weathered 9/11, the Great Recession, and a global pandemic. You’ve earned that “bring it on” attitude.

But selling a business? That’s a whole different mountain to climb—especially if it’s your first time.

Without the right preparation and support, many owners find the process overwhelming. Here are some of the top challenges to expect—and how to handle them:

1. Confidentiality Is Critical

One of the hardest parts of selling a business is keeping it quiet. This is a big life decision, and it’s natural to want to talk about it. But leaks can be costly. If word gets out to customers, vendors, or competitors, it could shake confidence and impact your bottom line.

Of course, your spouse should be in the loop. Beyond that, be selective. Even well-meaning family members can inadvertently breach confidentiality, especially children.

Employees? Be extremely cautious. While it may feel like you’re going behind their backs (because, in a way, you are), informing staff too early can create anxiety or lead to resignations. If you do need help with buyer meetings or due diligence, limit disclosure to key team members—and have them sign a simple NDA.

2. Due Diligence Can Be a Grind

Ask anyone who’s sold a business, and they’ll probably agree: the due diligence phase is the most stressful. Buyers (and their lenders) will request dozens—sometimes over a hundred—documents: financials, tax returns, legal agreements, employee data, and more.

And yes, this all happens while you’re still trying to run your company.

The best way to manage this? Start early. Begin assembling a secure data room with the most commonly requested documents before you even list your business. It’ll save you time—and sanity—later.

3. Prepare for an Emotional Rollercoaster

Even when you know it’s time, second-guessing is normal. I felt it myself when I sold my business. Many sellers do—especially when the business is still profitable.

Sometimes owners wait too long, only to find their business is no longer “sellable.” If you’re financially stable, burned out, and thinking more about retirement or your next chapter, it might be the perfect time to exit.

Remind yourself why you’re selling, and focus on finding the right buyer to take your business to the next level.

4. Choose the Right Advisors

Having the right team makes all the difference.

  • Start with your CPA. Let them know your timeline so they can strategize on minimizing taxes.
  • Hire a financial planner at least 2–3 years in advance to prepare for your post-sale life.
  • Work with an exit planning advisor or coach who can help optimize your business and increase its value before going to market.
  • Bring in a proven M&A advisor or business broker to manage the sale process, market the business, vet buyers, and negotiate the best price and terms.
  • Use an experienced M&A attorney. This is not the time for your family lawyer or a generalist. Make sure they’ve handled deals like yours before.

In Conclusion

Selling a business typically takes 6–12 months. It’s not something to jump into lightly—but with the right planning and guidance, it doesn’t have to be a nightmare.

You’ve spent years building your business. Make sure you invest the same care and intention into your exit. Done right, it might not be a walk in the park—but it won’t feel like climbing Everest either.