The decisions that still find you on holiday

Imagine taking two weeks away from your company. Orders leave on time. Customers pay. Your team tells you everything is fine.

On your first morning back, three people are waiting. A customer wants unusual payment terms. A supervisor needs permission to hire. Someone has held a disputed invoice until you can speak with the supplier.

The business kept moving while you were away. The difficult decisions stayed on your desk.

For an owner approaching retirement, that distinction deserves attention. A company can look well managed in its weekly reports while relying on the founder to resolve anything outside the routine. A buyer will want to understand that reliance. So should the owner who hopes selling will finally make the phone stop ringing.

The pattern can develop for sound reasons. Making quick decisions may have been an advantage when the business was smaller. Employees learned which issues you handled well and brought you more of them. Over time, your availability became part of the operating model without anyone expressly deciding that it should.

Retirement asks the business to operate under a different arrangement. The useful question is which decisions need your judgment, which need information only you possess, and which return to you because nobody else has been given permission to make them.

Those are different problems. Hiring a manager does not automatically solve all three.

Listen to the question behind the interruption

Consider an illustrative service company where the owner approves every exception to standard pricing. The sales manager understands the customer and knows the cost of providing the work. What the manager lacks is authority to accept a lower margin in exchange for a longer commitment.

Another company may have the opposite problem. Its manager has permission to negotiate but cannot obtain reliable job-cost information. Giving that person a larger signing limit would increase responsibility without improving the decision.

For a few weeks, pay attention to the issues that reach you. Ask what would have allowed the employee to resolve each one: a financial limit, access to records, experience with a similar situation, or an explicit instruction that the decision belongs to them.

Keep the exercise proportionate. A smaller company may need a capable second person and a few clear boundaries. A larger business may need several managers with defined responsibilities. Creating a complicated management structure simply to impress a future buyer can add cost without transferring judgment.

Start with one recurring decision that has a manageable consequence. Agree what the employee can decide, the information they should use and the circumstances that require escalation. Safety, regulatory requirements and financial controls still apply. Employees should know the arrangement; this should never be an undisclosed test of whether they can cope without you.

The owner’s behaviour then matters. If a reasonable decision is reversed because you would have handled it differently, people learn to wait for you again. They may continue to use the new job titles while operating under the old permission system.

What would let the buyer stop calling?

A promise to remain for six months after a sale is easy to make. It becomes more useful when those months have a purpose.

One customer relationship might need an introduction followed by a successful renewal. A purchasing responsibility might require the new manager to complete a full seasonal ordering cycle. A technical role might need supervised training and an assessment of competence. The right duration follows from the work; an arbitrary calendar period does not establish that it will be finished.

Discuss how progress would be recognized. Who takes over the relationship? Who makes the next decision? What records, explanations or access will that person need? A handover becomes easier to evaluate when everyone can see what remains incomplete.

The same exercise helps you assess a buyer’s request that you stay involved. A short, defined transition may be compatible with retirement. An open-ended expectation that you remain available whenever something difficult happens is a different commitment, even if it comes with the title of consultant.

Be honest about dependencies that cannot be removed quickly. A specialist qualification, a longstanding relationship or an unusual technical skill may require more time. Identifying it early gives the parties room to consider recruitment, training, a different buyer or a different timetable. Hiding it leaves fewer choices when diligence exposes it.

BDC’s Canadian exit-readiness guidance includes reducing day-to-day owner dependence as part of preparation for an external sale. The practical evidence is in how decisions are made, not merely in the organization chart.

If you want my position on the transition period, it is this. Six months is the number everyone writes down and almost nobody tests. Write the handover from the work that actually has to move, not from the calendar, and be willing to tell a buyer that one relationship needs a full renewal cycle before it will transfer. A seller who agrees to a short transition and then cannot leave has given away the thing they sold the company to get.

You do not need to announce a sale to begin this work. Nor do you need to remove yourself from everything the business does. Choose one decision you should not still be making a year from now and help someone else take responsibility for it.

After your next absence, look at the queue on your desk. Which issues disappeared because another person handled them well? Which were simply postponed? That answer tells you something useful about how close the business is to being able to let you retire.