The data point that should stop every family business owner cold is this one. Of the executives surveyed by Deloitte who admit their succession planning is behind schedule, 62 percent gave the same reason. Succession was not a critical priority for the business right now. They knew it was coming. They knew it mattered. They simply had not gotten to it.

Deloitte released findings in February 2026 from a survey conducted in September 2025 of 300 family business executives at U.S. companies with annual revenues ranging from 100 million dollars to over one billion dollars. Respondents included C-level executives, board members, and partners and owners. The findings were summarized by the ABA Banking Journal and other industry outlets.

The headline numbers tell a familiar story. According to the Deloitte data, 78 percent of executives expect a CEO transition within the next decade. 42 percent expect a transition within three to five years. 85 percent agree that strategic CEO succession planning is critical to long term success. 57 percent have established a plan. 23 percent are actively implementing one. 30 percent admit they are behind schedule.

There is a gap of 28 percentage points between executives who agree planning is critical and executives who have actually done it.

In The Business Sale Paradox I describe what I call the 98 Percent Trap. Most sellers spend 98 percent of their focus on the transaction itself and roughly 1 percent each on preparing for the sale and planning for what comes after. The Deloitte data is the family business version of the same problem. Respondents agree the transition matters. Respondents are intellectually convinced it should be planned. The implementation is not catching up.

The reasons are not hard to understand. Day to day operations crowd out the long term work. Family dynamics make the conversations uncomfortable. Tax and liquidity issues complicate the transition. And founders who spent a lifetime building the business often struggle to imagine stepping away.

There is a more uncomfortable finding buried in the data. According to the Deloitte report, 61 percent of family businesses report at least one family member interested in becoming the next CEO. Only 23 percent believe that family member is ready in the near term. The interest exists. The readiness does not. And in companies above one billion dollars in revenue, only 32 percent expect a family member to become the CEO at all. The larger the business gets, the less likely the next CEO role is expected to stay within the family.

This is where what I call the Why Letter in The Business Sale Paradox becomes a forcing function rather than an exercise. The Why Letter is the single most important document I encourage every owner to write before contemplating any kind of transition, sale or succession. It forces you to clarify your motivation. Your vision for the business. Your non negotiables. What you actually want for your family beyond what is convenient or expected.

For a family business owner facing succession the Why Letter answers questions the survey suggests most owners are avoiding. Why does it matter to me that the business stays in the family. Is that for the family or is that for me. Are my children genuinely interested or are they performing interest because they think it is what I want. If they are interested, are they ready. If they are not ready, what does ready look like and how long does it take to get there. If readiness is years away, what bridge do I put in place between today and that day.

These are not financial questions. They are not strategic questions. They are not tax questions. They are family questions and identity questions. And until those questions are answered honestly the rest of the planning has nowhere to land.

The Four Pillars of Sale Readiness in The Business Sale Paradox apply equally to succession readiness. The four are personal and emotional readiness, financial strength, transferable value, and diligence readiness. Weakness in any pillar creates risk.

For a family transition each pillar takes a slightly different shape. Personal and emotional readiness asks whether the founder is genuinely able to let go. Most are not. The Deloitte data is consistent with what experienced advisors have observed for decades. Founders who built the business are reluctant to relinquish control. Successors feel disempowered. Those tensions do not resolve themselves. They have to be addressed directly through structured conversations and clear timelines.

Financial strength asks whether the business has the resources to fund the transition itself. Pulling cash out for the founder while still capitalizing the next generation is harder than it sounds. Transferable value asks whether the business can run without the founder. If the founder is the customer relationship, the technical expert, the deal closer, and the strategic mind, the business is not transferable. It is a job. A job cannot be inherited the way a business can. Diligence readiness in a family context means having the systems, controls, and documentation that any next CEO would need to take the reins. Many family businesses are weaker here than they admit. They often run on trust, history, and the founder’s memory. None of those transfer cleanly.

The 30 percent of executives in the Deloitte survey who admit they are behind on succession planning are not outliers. They are the visible part of a much larger readiness problem. The 23 percent who have a plan and are actively implementing it are the unusual ones. If you are reading this and your business is closer to the first group than the second, the question is not whether you can afford to start. The question is whether you can afford not to.

More on this in The Business Sale Paradox.

Sources: Deloitte Private, “Survey Reveals Family Businesses are Facing a ‘Succession Paradox,’” February 10, 2026 (https://www.deloitte.com/us/en/about/press-room/deloitte-private-survey-reveals-family-businesses-are-facing-a-succession-paradox.html); ABA Banking Journal summary, February 17, 2026 (https://bankingjournal.aba.com/2026/02/survey-family-businesses-facing-a-succession-paradox/).

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