Your company should survive your vacation.

Unlimited permission can still feel like no permission

Consider an employee with unlimited PTO who reports to someone who never takes a day off, answers messages at midnight, and praises colleagues for being available during family trips.

The handbook offers freedom. The examples suggest consequences.

That employee does not need a formal rule prohibiting vacation. They can read the room. If advancement appears to depend on constant availability, taking leave becomes a private negotiation between exhaustion and ambition.

Unlimited PTO can work. A fixed allocation can also go unused. The practical question is whether people have enough clarity, coverage, and confidence to use the benefit they were offered.

A minimum expectation can help make leave ordinary. But announcing that everyone must take time off will accomplish very little if the same workload is simply compressed into the week before departure and the week after return. You have given someone a vacation with two emotional handling charges.

I would want to know how many days people actually take, how often approved leave gets interrupted, and which managers repeatedly have teams that cannot get away. An average across the company can hide an entire department living on postponed plans.

The executive sets the real policy

Senior leaders have an unusual problem: their behavior becomes instruction even when they did not intend to teach anything.

A CEO sends a harmless question from vacation. Someone replies immediately. A department head sees the exchange and decides to stay available during their own trip. By the time the habit reaches the rest of the organization, being offline feels like a small act of career sabotage.

“I don’t expect you to respond” has limited value when the company consistently rewards the people who do.

This is one reason I see disconnection as an executive strategy issue. Leaders decide what receives attention, which decisions require approval, and what the organization interprets as commitment. A policy becomes credible when those decisions support it.

An executive who names an acting decision-maker, defines that person’s authority, and honors reasonable decisions made during the absence is demonstrating something useful. The organization can continue. Other people can lead. Responsibility can move without everything falling apart.

That also requires some restraint on return. If the first Monday becomes a courtroom examination of every decision made while the boss was away, next year’s backup will wait for the boss.

Some roles deserve particular attention

Everyone deserves a workable opportunity to take leave. Certain roles also create concentrated business risk when knowledge, access, authority, or relationships sit with one person.

These are different coverage problems. A cybersecurity lead cannot be replaced by forwarding email to whoever happens to be available. A hotel does not stop receiving guests because its general manager is away. Clinical responsibilities require qualified coverage and the appropriate professional safeguards.

“Everyone should unplug” needs an operating plan beneath it.

Distance is part of executive judgment

There is another reason I like this idea for people paid to think. An executive can become very fluent in the company’s internal conversation while losing contact with the people outside it.

Spend enough time discussing a customer segment and you can forget that it consists of people buying groceries, looking after parents, worrying about money, and trying to get through Tuesday. A dashboard can show abandonment. It cannot tell you everything about the human circumstances surrounding the decision.

For marketing leaders, product teams, strategists, writers, and founders, time away creates room to notice ordinary life again. How does a hotel handle a mistake? What makes a small shop easy to buy from? What does your family find confusing about a product your industry considers obvious?

I am not suggesting that employees turn their vacation into an unpaid research assignment. They should be free to do absolutely nothing useful to the company. I am saying that executive judgment benefits from having a world outside the organization. A leader whose entire experience is filtered through meetings and internal reporting has a narrow sample from which to draw conclusions.

The scientist in me cares about the quality of the evidence. The writer in me cares about the people the evidence describes. Both have reasons to occasionally close the laptop.

Banking understood part of this long before we called it touching grass

Mandatory absence has a separate history as an internal control. Banking guidance has long used consecutive time away from sensitive duties to help expose irregularities that could remain concealed when the same person continually controls a process.^[2]

That does not mean every employee in every financial role faces an identical legal requirement. New York’s Department of Financial Services, for example, revised its guidance in 2022 to require covered banking organizations to use written, risk-based absence policies tailored to sensitive roles and their controls.^[3]

The distinction matters. Recovery time and fraud controls have different purposes, even when the same absence supports both. Logging out does not guarantee that misconduct will be discovered, and leave does not replace independent review or separation of duties.

The wider management lesson is useful: allow someone else to perform the work, with appropriate authority and oversight, and you may learn things the procedure manual never told you.

Perhaps the documentation is outdated. Perhaps an approval exists only because nobody remembers who created it. Perhaps your most dependable employee has spent years quietly repairing a broken process.

Do not turn that discovery into punishment for the person who finally took a vacation. Fix the process they have been carrying.

“We need another person” may be correct. Find out which person.

An inability to cover leave can reveal a staffing shortage. It can also reveal unclear authority, poor documentation, a skills gap, or a leader who keeps pulling delegated work back onto their own desk.

Those problems require different responses.

Additional capacity helps when the team cannot reasonably absorb the workload. Cross-training helps when the capacity exists but the knowledge does not. A clear approval limit helps when people know what to do but are afraid to act. Better records help when every account history lives inside a private inbox.

Hiring before making those distinctions can produce an expensive new employee who also has to ask the same overloaded person for permission.

For firms in the staffing and recruiting business, this is a useful client conversation. What must continue during the absence? Which qualifications are necessary? How long will preparation take? Is the need temporary coverage, a permanent addition, or a role that has become too large for one person?

At the leadership level, executive staffing and advisory conversations should examine what authority a new leader will actually receive. Recruiting an impressive executive into a role where the founder retains every meaningful decision does very little to reduce dependence on the founder.

What I would put in place

I would begin with one practical exercise: choose a critical role and walk through what would happen if that person were genuinely unavailable for a planned period.

List the decisions, deadlines, relationships, and systems that would need attention. Name the people who would handle them. Ask those people to explain how they would do the work. A name in a backup column is not evidence of readiness.

Then build the leave arrangement around a few concrete commitments.

Set an understandable minimum and preserve reasonable choice. Define the paid time people are expected to use, how scheduling works, and whether a continuous block is appropriate. Give people room to plan around their families, circumstances, and preferences. An employer can protect time away without deciding what someone should do with it.

Fund the coverage. Make time for training and handovers. Reduce or postpone lower-priority work when necessary. Do not quietly transfer two jobs to the colleague least likely to complain.

Give the backup authority. Explain what they can approve, spend, promise, or change. Specify decisions that should wait and decisions that require another authorized leader. Keep access individual and appropriate; coverage is no excuse for sharing passwords.

Define a real emergency. A serious safety incident and a client asking for a routine update are different events. Identify an escalation owner and a narrow route for exceptional contact. In regulated roles, design that route around the applicable absence controls rather than creating an informal workaround.

Make disconnection operationally possible. Redirect requests, assign account ownership, remove routine meeting expectations, and establish whether any system restrictions are appropriate. A person should not need to monitor everything to determine whether they are needed.

Protect the return. Leave room for a useful handover back. Review interruptions, delayed decisions, and coverage strain. If the employee returns to every task they left plus a fresh week of work, the coverage arrangement needs another look.

I would start with a manageable pilot, including a senior leader, and improve it before announcing a companywide success story.

A founder leaves for a week. What actually happens?

Here is an illustrative example. A founder plans five working days away. The sales director has a renewal negotiation, a campaign needs final approval, and a supplier invoice comes due. None of this is a surprise.

Without preparation, each item generates a message to the founder. The founder replies quickly, feels useful, and concludes that taking time off is impossible. The team concludes that the correct procedure is still to ask the founder.

Before the next absence, the company changes three things. The sales director receives a documented negotiating range. The marketing lead receives the agreed brief, budget, and authority to approve work that meets both. Finance follows its existing payment controls with a properly authorized alternate approver.

A genuinely exceptional decision can still go through the designated escalation route. The rest moves without the founder’s phone being involved.

Five days is an illustration, not a recommended annual leave allowance or a substitute for any required absence period. The point is to distinguish work that requires a specific person from work that merely requires permission nobody else has been given.

When the founder returns, the useful questions are what delayed, what lacked context, and what needs a better handover. “Did you miss me?” provides less actionable information.

Do not build the policy around forfeiting benefits

The phrase “mandatory vacation” can mean a company requirement; it does not automatically mean the law requires employees to take two to four weeks off. In the United States, the Fair Labor Standards Act generally does not require payment for vacation time.^[4]

Accrual, scheduling, carryover, payout, and forfeiture also need jurisdiction-specific review. California, for example, does not allow employers to erase earned vacation through a use-it-or-lose-it policy.^[5]

Where unused accrued leave creates a liability, taking leave may reduce that balance. The financial treatment depends on the plan and applicable rules. It is not a universal savings claim, and it is a poor centerpiece for explaining the policy to employees.

Have HR, payroll, and appropriate counsel translate the operating intent into a lawful policy. Keep the leadership message straightforward: people should be able to use their paid leave, and the organization should prepare to support it.

Measure whether the business learned anything

I would pay attention to actual leave taken, interrupted leave, canceled leave, the backup team’s workload, and work that stopped unnecessarily. I would also ask employees whether they felt able to disconnect without damaging their standing.

For executives, I would examine the decisions that came back to them. Which genuinely required their involvement? Which needed clearer limits? Which could have been handled by someone already on the team?

Use those findings to improve the business. Avoid turning vacation into another competition with a dashboard and a suspiciously cheerful trophy.

A successful absence can show that a leader has developed capable people and a business with some durability. It should not become evidence that the leader was unnecessary. If people believe making their work transferable threatens their employment, they have a strong reason to keep knowledge to themselves.

You should be able to matter without being permanently available

I understand the satisfaction of being needed. Owners and executives often have years of sacrifice tied up in the business. Letting go of the phone can feel strangely similar to letting go of responsibility.

But responsibility includes preparing the organization for the moments when you are unavailable. Some of those moments will be planned. Others will arrive without asking about your calendar.

If your business struggles whenever one person steps away, I would want to understand why. It may be a leadership issue, a staffing issue, a growth problem, or several things tangled together.

You do not need to know exactly what needs to be solved to talk with me. Tell me what happens when you try to get away, who gets called, and what stops moving. We can start there.

Then, ideally, you can go somewhere without having to ask for the Wi-Fi password.