The Question Small Business Owners Avoid

One of the first things I ask every small business owner I work with is this:

“What’s your disaster recovery plan?”

The room gets quiet. Not because they’re thinking. Because they’re not sure what I mean — or worse, they know exactly what I mean and they’ve been hoping nobody would ask.

That look — the deer-in-headlights look — tells me everything.

Here’s what I’ve come to understand about human psychology: we are wired to protect ourselves from emotional discomfort, not from actual risk. There’s a name for it — it’s called optimism bias, and it’s one of the most dangerous features of the human mind when you’re running a business.

We don’t plan for the quake because we don’t want to imagine the quake. And the brain is very good at justifying that avoidance. It sounds like: “We’re doing well right now.” Or: “That’s not something I want to put energy into.” Or the classic — “I’ll think about it when things slow down.”

Things never slow down. That’s the point.

There’s also something else at play, something more primal. A business, for most owners, isn’t just a business. It’s identity. It’s proof of something. When you’ve poured years into building it, being asked to plan for its potential collapse feels like being asked to plan your own funeral. Nobody wants to sit with that.

So they don’t. And nobody around them pushes them to.

That’s the first problem: no one asked the question.

Let me tell you what I mean when I say “disaster.”

I’m not talking about a flood or a fire — though those count too. I’m talking about the scenarios that are far more likely, far less dramatic, and somehow even harder to prepare for.

The owner gets sick. Not a cold. Something that takes them out of the business for three months, or permanently. Is there a plan? Is there someone who can make decisions? Does anyone even have the passwords?

Your biggest customer — the one who accounts for 55% of your revenue — calls on a Tuesday and tells you they’re going in a different direction. You hang up the phone. Now what?

Your top salesperson, the one who built half your client relationships, gets a call from your competitor. Better offer. They take it. They leave on a Friday. Monday morning, their clients start getting calls.

A competitor enters your market with something you don’t have — a price point you can’t match, a service you haven’t built, a value proposition that makes yours look ordinary.

These aren’t hypotheticals. They happen constantly. I’ve watched them happen. And in almost every case, the business that suffered most was the one that never asked “what if.”

There’s an analogy I keep coming back to.

Commercial pilots — regardless of how many years they’ve flown, regardless of how clean their record is — are required to go into a simulator regularly for recurrent training. In each session, they are presented with a malfunction. An engine failure. Hydraulic loss. Something going wrong at the worst possible moment.

They don’t get to skip this because they haven’t had an emergency lately. They don’t get to opt out because emergencies make them uncomfortable. They train so that when something real happens, their response isn’t panic — it’s protocol.

That’s disaster recovery.

Not fear. Not pessimism. Protocol.

The best pilots in the world are not the ones who’ve never faced an emergency. They’re the ones who’ve already lived through it in a simulator — calmly, methodically, without crashing the plane.

So where do you start?

You start with the question. You sit down — with your business partner, your key people, maybe a coach or advisor — and you ask it plainly:

“If this specific thing happened tomorrow, what would we do?”

You don’t need to solve everything at once. You need to break the silence. Because the silence is the problem. Most businesses don’t have a disaster recovery plan not because they couldn’t build one — it’s because nobody created the space to think about it clearly, without anxiety shutting the conversation down.

This is exactly the kind of thinking I do with clients. Not to frighten them. Not to spiral into worst-case paralysis. But to get clear, get grounded, and make sure that if something shifts — and something always shifts — they’re not starting from zero.

A business that can only survive when everything is going well isn’t really a business.

It’s a good streak.

The question is whether you want to keep hoping the streak holds, or whether you’re ready to build something that can absorb a hit and keep going.

Most owners, when I ask them that question directly, already know the answer.

They just needed someone to ask.

Action Points:

• Ask the question, with your top team members around the table

• Prioritize: The owner incapacitated is #1. Develop a one-page roadmap with steps and who is responsible for each one

• List the next 3-4 and repeat.

For many small businesses where one customer represents a significant portion of sales, “our top customer left us” constitutes a disaster. Can you plan for that? Yes you can. Loyal customers don’t just bail out! It happens over time and there are usually signals that will warn you - if you ensure that your customer success team stays in touch with your top customers.

But the question must be asked and the outcome planned for.

How?

Adopting a strategy of managed growth without allowing one or two customers to control your future. And, having a vibrant marketing program that generates ongoing healthy inquiries and leads.

What’s next? Sort your revenue by customers and look at the list, even if intuitively you know what you’ll find. Sometimes staring at a list and seeing Company X represents 30% of top line revenue will get your attention.

• How are we doing with X? (With the sales rep and in-house account executive present).

• When was the last time we spoke to them? Visited them?

• What do we know about their growth plans or challenges?

• Who’s our main contact there? When was the last time we heard form him/her?

You get the idea. The worst time to plan for a disaster is after it happened.