The consideration of owner readiness seems like a basic concept, but it can easily be overlooked in the excitement of valuation. In my experience, I’ve seen deals often fail because the owners bypassed exit planning, including the necessary step of assessing the owner’s readiness. The reality is that confirming the owner’s willingness and readiness to sell should be the very first consideration.

If we don’t have full commitment to selling the business, then, as the deal progresses, the likelihood of the owner/seller suddenly having “cold feet” and canceling the transaction increases significantly. The result is a failed transaction, wasted professional fees and loss of time for the buyer in their acquisition search.

Case studies on owner readiness

I have two cases that demonstrate how the lack of leveraging an exit planner and testing owner readiness resulted in failed deals.

A tale of two sisters

In the first case, two sisters were operating a business together. One of the sisters was ready to think about retirement. The conversation between them quickly moved to deal setup, transaction timing and how it might be financed. When the retiring sister was confronted with the reality of leaving the business, she put the brakes on and decided now wasn’t the time.

If the almost-retired sister had a more detailed conversation with an exit planner prior to the escalation of deal structure, we could have confirmed her readiness, and a deal may have still been completed. Skipping the owner-readiness discussion resulted in panic, anxiety, lack of commitment and fear in the exiting sister’s mind, and it was just too much to allow her to move the business transfer forward.

Money isn’t everything

In the second case, a business owner was approached by a buyer to acquire his business. The business owner wasn’t looking to sell, but out of curiosity entertained the conversations with the prospective buyer. The owner had been working in the business—not on the business—for many years and he was running tired of the day-to-day grind. The conversation with the prospective buyer seemed worth exploring.

Very quickly after the initial conversations, the buyer provided a letter of intent with a purchase price that far exceeded what the owner ever thought he could receive for the business. The transaction moved forward until the very final days before closing when the reality of what was happening hit the owner hard. Ultimately, the owner decided that even at that great valuation number, which would have been life changing, it just wasn’t time for him to walk away. It turns out, the owners was more curious than committed to selling, and that spiraled into a deal destined to fail.

Soul-search before sale searching

So, are you ready to sell? Until the owner/seller is committed to selling, the risk of failure is heightened. Here are some questions and considerations exit planners address to assess the owner’s readiness:

  • Have you considered the steps to take to exit such as financial needs, departure timelines, succession plans and value-based goals?
  • Have you considered the current value of your business? If the business valuation does not meet your financial expectations, have you created a plan to increase its value before your departure date or retirement?
  • Identify what is important to you in the transfer of the business: Legacy, protection of your employees, health of the community in which you operate or something else.
  • What is your exit timeline? Have you determined steps to prepare for an effective exit in that timeframe?
  • Who is your successor? Are they a family member, key employee or a third party? Have you considered transitioning to an employee stock ownership plan (ESOP) or employee ownership trust instead of a sole successor?
  • Is the business capable of running without you?
  • Have you considered the tax consequences of the sale and created a tax plan?
  • After the sale of your business, do you have a plan for how to invest the financial resources?
  • Have you considered estate and trust planning as part of your exit planning process?
  • Do you have philanthropic goals like establishing a private foundation or charitable trust?

The above list is not all inclusive, but it does focus on key areas business owners should consider. Something I say to buyers on day one is, “When will you exit and what will the business value be then?”

Exit planning starts early

An exit plan isn’t just for when you are ready to exit, it should be part of the strategic plan from the day you start or acquire your business. Having an exit-ready plan may help convert unexpected solicitations into successful deal transactions. When business owners have a better sense of their goals and have thought through the exit process in advance, they are better able to make mindful decisions related to purchase offers.

Unless you are ready, there will not be a successful sale. Even worse could be selling when you are not ready and experiencing seller’s remorse. Assessing your sale readiness as an owner and understanding how to prepare for a sale are two critical first steps in your business exit journey. If you’re receiving buyer solicitations, or have been thinking about retirement, connect with an experienced exit planner who can help guide you through the process.

Ready to start discussing business value growth advisory and/or plan for your business exit? Learn more about UMB Private Wealth Management’s Business Exit Solutions.

This article is for educational purposes only. You should consult with your professional advisors before making any decisions.


Disclosures

This report is provided by UMB Trust & Investment Services a division of UMB Bank, n.a. for informational purposes only and contains no investment advice or recommendations to buy or sell any specific securities. Statements and projections in this report are based on the information provided by the client or third parties, and available as of the date this report was published. UMB Trust & Investment Services obtained information used in this report from third-party sources it believes to be reliable, but this information is not necessarily comprehensive, and UMB Trust & Investment Services does not guarantee that it is accurate. All investments involve risk, including the uncertainty of dividends, rates of return and yield and the possible loss of principal. Past performance is no guarantee of future results.

The S&P 500 Index is unmanaged, consisting of a market capitalization-weighted index of 500 common stocks. It is not possible to invest directly in an index.

You should not use this report as a substitute for your own judgment, and you should consult with professional advisors before making any tax, legal, financial planning or investment decisions. This report contains no investment recommendations, and you should not interpret the statements in this report as investment, tax, legal, or financial planning advice.

Neither UMB Trust & Investment Services nor its affiliates, directors, officers, employees or agents accepts any liability for any loss or damage arising out of your use of all or any part of this report.

“UMB” — Reg. U.S. Pat. & Tm. Off. Copyright © 2026. UMB Financial Corporation. All Rights Reserved

Securities offered through UMB Private Wealth Management, LLC (UMBPWM), an SEC registered investment adviser, and UMB Trust & Investment Services, a division within UMB Bank, n.a.

Banking services offered through UMB Bank, n.a.

Insurance products offered through UMB Insurance, Inc.

UMBPWM, UMB Bank and UMB Insurance are affiliates and wholly owned subsidiaries of UMB Financial Corporation.

You may not have an account with all of these entities. Contact your UMB representative if you have any questions.

SECURITIES AND INSURANCE PRODUCTS ARE:

NOT FDIC INSURED • NO BANK GUARANTEE • NOT A DEPOSIT

NOT INSURED BY ANY GOVERNMENT AGENCY • MAY LOSE VALUE