I understand the confidence an experienced founder brings to a business, particularly when a customer threatens to leave and that person knows which promise will matter. The founder makes the call, settles the dispute, and gets everyone back to work before the damage spreads. The problem gets solved.
From my position as a CEO, it’s easy to see why people would want that person involved the next time. There’s less uncertainty, the customer feels heard, and the team can return to the work it already knows how to do. But the next time carries a question that the relief of this time can obscure: how much more capable has anyone else become? A successful rescue can leave the business exactly as dependent as it was before.
That possibility should trouble those of us responsible for developing other leaders. A company can accumulate years of profitable operation while its ability to handle the hardest decisions remains concentrated in the person who started it. A business can grow old without learning how to survive its leader.
A Change of Owner Tests the Whole Business
In a Gallup survey conducted in fall 2024, 22 percent of employer-business owners said they planned to sell or transfer ownership within five years. The findings, published in March 2025, covered people who spent most of their working hours in businesses they owned. Those answers describe intentions, and tell us nothing by themselves about whether the businesses are ready. They do place the work of preparing another owner within a horizon that should concern anyone still handling every consequential decision. Gallup’s report
A transfer puts the distinction between personal ability and organizational ability under pressure. The customer list can change hands while the customers continue to trust the departing owner, leaving a buyer with relationships that still depend on someone else’s presence. A complete set of procedures may offer little help if the most important decisions have always happened outside them, especially when the departing founder supplied the explanation that made contradictory instructions work together.
The calendar won’t teach anyone. If the business needs someone else to exercise that judgment after a sale, it needs to give that person opportunities to develop it beforehand. The same obligation exists when the founder plans to stay but wants to open another location or give a manager responsibility for an important customer. Each expansion asks the business to carry its standards farther from the person who first supplied them.
From the lending side, the distinction matters because the cash flow being reviewed was produced by a particular arrangement of people and relationships, which a transfer may change. A founder may have been limiting price concessions, renegotiating promises the operations team couldn’t fulfill, or repairing a customer relationship before the customer took its business elsewhere. A new owner’s ability to continue those interventions belongs in the assessment of whether past results can support future expectations. An operating history deserves respect, along with a careful account of who made it possible. Otherwise, we risk treating the departure of a central decision-maker as an administrative detail in a business whose success depended on that person’s daily presence.
An owner can deliberately build a business around personal work and plan to close it when that work ends. The obligation changes when the owner intends to sell a continuing enterprise, or asks employees to build their futures around its survival. That intention creates a responsibility to prepare other people while there is still time.
Time Tests Whatever Meets It
Nassim Nicholas Taleb’s discussion of the Lindy effect offers a useful starting point: for certain things without an intrinsic biological lifespan, including ideas and practices, longer survival can imply a longer expected remaining life. Taleb develops the idea in Antifragile and returns to it in his essay “An Expert Called Lindy,” where exposure to consequences is essential to the test. Something that persists while protected from those consequences can give us misleading evidence about its strength. Taleb’s explanation
That is a valuable discipline in business, where novelty can attract more attention than the reasons an older practice works. A rule that has survived changing customers and difficult markets may contain knowledge its current users would struggle to reconstruct. The age of the rule gives us a reason to investigate before replacing it. It deserves a hearing.
However, applying that idea to a company requires deciding what the company’s years have actually tested. A business is an arrangement of capabilities, some held by individuals and others spread through the organization, and its name can remain unchanged while the arrangement beneath that name changes substantially. The evidence supplied by its history has to be connected to the capabilities it will need next, particularly when the people carrying those capabilities are preparing to leave.
Consider the difference between a team that has learned how to handle customer disputes and a team whose founder has handled every difficult dispute. Both can belong to businesses with long records of satisfied customers, yet those records support different conclusions about what will happen when a new manager answers the phone. The second team’s experience has taken place largely within reach of someone else’s judgment.
The founder’s contribution is real in both cases, and the years may have tested that person’s judgment severely. Yet a record earned with the founder present leaves the business’s ability to operate without that person partly untested. My application of Lindy begins with that distinction: identify the capacity responsible for survival, then determine whether it will remain available when the person responsible for it leaves.
The same examination applies to the practices a founder leaves behind. A longstanding approval rule may encode a painful lesson about promises the business couldn’t afford to keep, or persist because changing it creates an argument with the owner. Time can pass around either arrangement, leaving the next generation with the work of discovering which explanation fits.
For a standard to survive succession with its purpose intact, people need to understand why it exists and practice applying it. They also need permission to correct it when circumstances expose a weakness that the person who created it couldn’t have anticipated. Each repetition gives someone an opportunity to acquire judgment that previously belonged to someone else. Experience becomes transferable when another person can use it to make a sound decision.
A procedure stored in a folder is only part of that acquisition: the person applying it needs to recognize the situation it was designed for. They also need to notice when the present case differs in a consequential way. Without that understanding, a successor can preserve every instruction while losing the purpose those instructions once served. Continuity requires people who can think with the inheritance they receive.
There’s also the matter of who pays for the business’s apparent resilience. If continuity requires the founder to remain available during every vacation or quietly work the hours a missing manager would have supplied, the cost is being carried somewhere. A buyer needs to understand the work behind those earnings and whether someone else can realistically take it on. The founder’s family may already have a clear account of how much uninterrupted service has cost, even when the business records give that contribution no separate name.
A Rescue Can Become a Ceiling
From the CEO’s chair, there are sound reasons to intervene. A manager’s hesitation can carry a cost the business has little room to absorb, while the founder may understand details that genuinely change the decision. Telling that person to step aside in the name of development would be irresponsible when the immediate consequences exceed what the team can safely manage.
The responsibility being transferred should match the person’s readiness and the business’s capacity to absorb error, with enough room for the person to acquire experience before the next transition. Some decisions require close supervision, while others can become useful practice with clear limits and a timely review. What matters is whether intervention leads to a more capable team or simply establishes another reason to intervene next time.
The distinction applies at my own desk, where I have to examine what the arrangement is teaching if every difficult question ends with my answer. A manager who learns that uncertainty should immediately travel upward may become very good at identifying the moment to stop thinking. Calling that person dependent would leave my part in the arrangement conveniently unexamined.
This was a systemic issue at B:Side in the years prior to my joining as CEO in 2020. B:Side, or Colorado Lending Source as it was then known, was an incredibly strong organization staffed by equally strong individuals. The level of technical expertise, particularly at the top of the organization, was staggering. It was also oppressive. All decisions ran through the top office, and that had two unintended effects. First, it robbed the team of agency. Second, and more importantly, it never allowed confidence to take hold in the staff. That lack of confidence led to a lack of agency, and that led to an underutilization of our team’s immense talent. Building that confidence and establishing a culture of agency is an ongoing process.
Being needed can be gratifying, particularly when the need appears to confirm the very competence that earned someone the right to lead. We can become attached to a role that gives us immediate evidence of our usefulness, while helping another person acquire the same judgment makes our contribution harder to see. That’s an awkward incentive.
From the professor’s chair, the problem becomes one of formation. Watching someone produce the right answer gives a learner access to the result, with only partial access to the work that produced it. A student can follow an explanation and still struggle to recognize the same problem when its surface details change. A manager can understand the founder’s decision after the fact and still lack the practice needed to make the next one.
That practice includes choosing which information deserves attention, deciding what remains uncertain, and committing to an action whose consequences the learner will have to examine. When the teacher resolves every ambiguity first, the student receives a cleaner problem than the one independent judgment requires. Business can repeat that pattern without anyone intending to teach it. The founder removes the difficult part, and then wonders why nobody else has learned to handle difficulty.
Our response to mistakes completes the lesson, especially when a manager makes a reasonable decision within agreed limits and the owner publicly replaces it with a personal preference. People pay attention to those moments because their standing depends on understanding the actual rules. A title that promises ownership will carry less weight than the last visible consequence of using it. Eventually, the manager may learn to seek permission before making even ordinary decisions, because the stated boundaries no longer predict what the owner will allow.
This places a real obligation on the leader who wants the business to endure. The opportunity to practice judgment has to survive the leader’s preference for a faster answer. There will be times when intervention is necessary, and those decisions should carry an explanation that helps the next person improve. Over time, the evidence of progress should include fewer problems that require the founder’s particular presence to resolve.
Pass Along the Reason
For the owner, the first useful distinction is between a standard and a preference. A standard protects something the business owes its customers or its people. A preference describes how the current leader likes work to happen. The two can become so closely associated that a successor has to copy the founder’s habits simply to demonstrate loyalty.
The difference matters. A commitment to telling customers the truth must survive a change in leadership, even when the next leader finds a better way to communicate it. The founder’s preferred meeting time carries a different kind of authority, which is why I should be especially suspicious when my principles happen to require everybody to do things my way (a remarkable coincidence).
Passing along the reason means preserving the circumstances around an important decision, including what was uncertain and what would have changed the answer. Someone learning from it also needs to understand which risk the decision-maker considered most serious. Those details allow a future manager to adapt the lesson when circumstances change, while a record containing only the final instruction offers little help in understanding.
A late-payment decision gives this work a concrete shape: the useful record would explain what the customer’s payment history suggested, how much room the business had to wait, and why further credit was allowed or refused. The next manager could compare those reasons with the next customer’s circumstances and reach a decision they could defend. That is much more to inherit than a record that the founder approved an exception.
For someone buying a business, this suggests looking closely at where explanations live. Customer relationships deserve attention alongside the records describing them, and the people handling exceptions deserve attention alongside the written procedures. The seller’s continued availability can help a transition, provided that availability is used to build the next team’s capability. Every question permanently reserved for the former owner extends the dependence the transaction needs to address.
For a manager preparing to assume more responsibility, the work can begin with a recommendation that gives an experienced leader something to examine: a proposed decision, the reasons behind it, and a clear account of uncertainty. That exchange makes the differences in judgment visible enough to discuss. Eventually, the manager also needs permission to act on what has been learned.
Practice Leaving Before You Leave
Choose a decision that can move. Identify a recurring decision currently reaching the founder that another person could handle with preparation. Start where mistakes can be detected and repaired before they cause serious harm, with enough substance in the task for the person to learn something consequential. Name the decision owner.
Explain what deserves protection. Work through a real past case together, including the evidence that mattered and the uncertainty that remained. State the boundaries the new owner must respect, the information they can use, and the conditions requiring escalation. Ask them to explain how those boundaries would apply if the facts changed.
Make the authority real. Tell the people affected who now owns the decision and what that person is authorized to do. Allow decisions within those boundaries to stand, including choices you would have made differently. If intervention becomes necessary, explain the specific risk or limit that required it so the team can understand what remains theirs to decide.
Review the reasoning after the result. Set a time to compare the decision-maker’s expectations with what happened, examining an unfortunate result from a sound process differently from a lucky result produced by carelessness. Use that conversation to improve the next decision, and record any change in the standard or the person’s authority.
Repeat the test with more distance. Let the new owner handle the next case before supplying an answer, and observe where the work still returns to you. Bring that person into the customer relationships their authority will depend on, then give them room to earn trust through their own conduct. As their judgment develops, expand the responsibility and ask them to begin teaching someone else.
The Next Call Belongs to Someone Else
There is no clean formula for how much error a business should accept while another person learns to lead it. Customers bear real consequences, and the tension remains even after the boundaries are clear and the preparation is careful, because another person’s learning can still cost them something. Responsibility includes making those choices without pretending the costs disappear.
But the difficult customer will eventually call when the founder is unavailable, and by then another person needs to have practiced hearing the complaint, judging what the business owes, and making a promise the team can keep. The quality of that response will reflect what the founder helped others learn while there was still time to teach it. The customer may never know how much work made that conversation possible.
For a leader accustomed to receiving the call, that can be an unfamiliar kind of success. The business keeps its word, someone else carries the responsibility, and the day continues without a rescue. Its history has become something another person can carry forward.
Let someone else make the call.
Building a team that can lead without you takes daily practice. I explore that work in my book, The B:Side Way, including how to earn trust, develop people, and give them real ownership.