So there I was, standing in my dad’s office at 6 a.m., holding a mug that said “World’s Okayest Boss” (his joke, not mine), staring at a filing cabinet that hadn’t been opened since the Clinton administration. The keys to the whole operation had just been handed to me. Not metaphorically. Literally. A ring of about forty keys, half of them unlabeled, jangling like a set of wind chimes from hell.
If you’ve inherited a business, you know this feeling. It’s equal parts honor, terror, and “wait, where’s the bathroom key?” I’ve been there. And because I made plenty of mistakes early on, I want to save you some of that pain with a first 90-day roadmap that actually works.
Week 1: Do Not Change a Thing (Seriously)
Your instinct will scream “improve everything!” Ignore it. Your first week is about observation, not revolution.
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Meet every single employee, even the part-timers. Ask one question: “What’s one thing you’d fix if you could?” Write it down. Don’t promise anything yet.
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Sit in on normal operations. Watch how orders get filled, how customers get greeted, how the money actually moves.
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Find the person who really runs the place. Every business has one. Usually it’s someone who’s been there 22 years and knows where the bodies are buried (metaphorically, hopefully). Befriend them immediately.
One more thing: resist the urge to redecorate. My cousin inherited a bakery and repainted the whole front counter in week two. Loyal customers lost their minds. The counter wasn’t the problem. It never is.
Weeks 2 to 4: Learn the Money Like Your Life Depends On It
Here’s the uncomfortable truth. You probably don’t know what this business actually earns. Inherited businesses come with inherited financial habits, and some of those habits are creative in ways the IRS would not appreciate.
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Pull 24 months of bank statements and actually read them. All of them. It’s boring. Do it anyway.
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List every subscription, lease, and recurring payment. You will find at least three things nobody remembers signing up for. Cancel the obvious junk.
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Meet the accountant and the lawyer separately. Ask each one: “What keeps you up at night about this place?”
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Figure out your cash conversion cycle. In plain English: how long does money leave before it comes back?
I once found a standing order for a fax line. A fax line. In the year 2023. Small stuff like that adds up to real money over time.
Weeks 5 to 8: Talk to the People Who Pay You
Customers will tell you things employees won’t. Make time for real conversations.
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Call or visit your ten biggest customers. Not a sales pitch. Just: “Hey, I’m new at the wheel. What do you need from us?”
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Read six months of complaint emails and reviews. Patterns will jump out fast.
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Ask your team which customers are the biggest headache relative to what they pay. Some clients cost more than they’re worth. That’s a lesson nobody teaches in business school.
Meanwhile, start a simple list: things that are clearly broken, things that are fine, and things you don’t understand yet. The third list will be long. That’s normal.
Weeks 9 to 12: Make Small Moves, Not Big Ones
By now you’ve earned the right to touch a few things. Keep it small and reversible.
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Fix one operational bottleneck your team flagged in week one. Then tell them you did it. Credit goes to them, not you.
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Set a weekly one-on-one with your key managers. Fifteen minutes each. Keep it casual but consistent.
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Write down your 12-month priorities on a single page. If it needs two pages, it’s not a priority list, it’s a wish list.
And please, keep your predecessor’s phone number on speed dial. I called my dad roughly eleven times a week in those first months. Some calls were business. Some were just “how do I turn off the alarm system?” No shame in it.
The Honest Truth About Inheriting
Nobody hands you a manual. You’ll feel like an impostor for a while. That’s fine. The people who inherit well aren’t the smartest ones in the room. They’re the ones who listen first, spend carefully, and respect what’s already working before they start fixing things.
Ninety days won’t make you an expert. It will make you dangerous in the best way. You’ll know where the money goes, who really runs things, and which fires are real versus smoke. From there, the rest is just showing up, asking questions, and occasionally laughing at your own mistakes.
Now if you’ll excuse me, I have forty keys to label.