The out-of-office reply said she’d be back on August 3rd, and to contact Karen with anything urgent. Karen’s auto-reply said she’d be back on the 10th.
I wish I were making that up. It came from a company of about forty people, and for nine days in July, every urgent question had exactly nowhere to go. Nothing catastrophic happened. A customer waited longer than they should have, a vendor payment slipped, and one employee made a judgment call well above her pay grade that happened to turn out fine. But every one of those outcomes was luck, because nobody had decided any of it on purpose.
That’s the thing about summer in a growing company. It runs a test you never studied for, and then it hands you the results.
Vacation season is a free diagnostic
Most owners treat summer as the time when things slow down and get a little sloppy, and they plan to tighten everything back up in September. I’d offer a different way to look at it. When you step away for a week or two, your company runs on whatever you’ve actually built.
If approvals sat in your inbox while you were gone, you’ve found a decision bottleneck. If a client issue waited ten days because you’re the only one who could handle that conversation, you’ve found a single point of failure. If your phone lit up every afternoon at the beach, your team is telling you exactly where the gaps are. You didn’t have to hire a consultant to find any of this. You just had to leave.
The problems were there in March. Summer is simply when they introduce themselves.
The summer hire deserves its own conversation
There’s a version of this that costs a lot more than a slipped vendor payment, and it happens every summer. You finally land the hire you’ve been chasing since spring. He starts on a Monday. You leave that Thursday, because the vacation was booked in January and you’ve earned it.
Nobody builds him an onboarding plan. The team isn’t sure what he’s allowed to decide, so they work around him. He spends his first month guessing, and by the time you get back, he’s stopped guessing and started keeping his head down. Six months from now you’ll be telling someone he just never got traction, and you’ll be wrong about why.
A new hire’s first thirty days are when he decides whether he made the right choice. He’s watching how the place actually works and whether anyone is invested in his success. If you disappear in week one and there’s no plan in place, the message lands loud and clear. And you’ll pay for it months later, when he underperforms or quietly starts returning recruiter calls.
If you’re hiring this summer and you have time off on the calendar, you have two good options. Build a first month that runs without you, meaning a written plan with a named owner who isn’t you, and check-ins that happen whether you’re in the office or not. Or push the start date until you’re back. A later start beats a lonely one every time.
Run the diagnostic before the tan fades
When you get back from your time away this summer, sit down for twenty minutes before you dive into the pile and answer these honestly:
- What broke, or almost broke, while I was gone?
- What sat untouched because I’m the only one who can do it?
- Who covered for me, and what does that tell me about who’s already stretched thin?
- Which processes exist only in someone’s head?
- Whose vacation makes everyone else nervous?
That last one matters more than people think. If the answer is “Karen in the office, because she’s the only one who knows how billing works,” you’ve got a risk sitting on your books that no financial statement will ever show you.
Take the vacation anyway
None of this is an argument against time off. Take the vacation. Your business needs you rested more than it needs you available.
But treat what happens while you’re gone as data, because that’s exactly what it is. A company that can’t run without you for two weeks is going to have a hard time growing past you at all. The gap between those two things is org design work: roles that are actually defined, decisions that live below you, and processes that survive contact with someone’s absence.
If you need help with that org design work, let’s talk.
