A Question That Comes Too Late
Most people I meet with only ask this once a problem has already landed on their desk: “What would you do here?”
It is a good question. But by the time it gets asked, the options are usually narrower than they should be. Cash is tight, a decision has a deadline attached, or a competitor has already moved. The better version of the question gets asked months earlier, before there is a fire to put out.
The question I think people should be asking is simpler: “What would need to be true for this to go wrong?”
Why the Timing Matters More Than the Answer
I understand why owners avoid this. Running a business takes most of a person’s attention, and sitting down to imagine failure modes feels like a distraction from actual work. There is also a natural instinct to focus on what is going well. Growth is happening, orders are up, so why look for trouble.
But the businesses I see handle a rough patch well are almost never the ones with the fewest problems. They are the ones who thought about the problem before it arrived. A owner who has already asked “what happens if a major customer leaves” has a plan sitting in a drawer somewhere. A owner who has not asked it is improvising in real time, usually with less cash and less patience than the situation needs.
What This Looks Like in Practice
It is not about building a thick contingency binder. It is closer to a habit of asking a small number of specific questions on a regular basis:
- If our biggest customer left tomorrow, what would our cash position look like in ninety days?
- If a key supplier raised prices twenty percent, could we absorb it or would we need to pass it on?
- If revenue dropped for two straight quarters, what would we cut first, and what would we protect no matter what?
None of these require a forecast model or outside help. They require sitting with the discomfort of the question long enough to write down a real answer.
The Pattern I Notice Most Often
The pattern I see repeated is that businesses plan carefully for growth and barely at all for disruption. Owners will map out exactly how they would use a new credit facility, staff a second location, or take on a large order. Ask the same owner what they would do if that same large order got cancelled, and the answer is often a shrug.
Both directions deserve the same amount of thought. Growth and disruption are the same kind of event: a sudden change in conditions that requires a decision under some pressure. Preparing for one and not the other means you are only half ready for your own business.
Why I Keep Coming Back to This
Part of my job is sitting across the table from someone during a hard quarter and asking what they need. The conversations that go well are almost always the ones where the owner has already done some of that thinking. They are not surprised by their own numbers. They know which costs are fixed and which are flexible. They have a rough idea of what they would do next, even if they have not done it yet.
The conversations that are harder are the ones where every question is a new one. Not because the owner is unprepared as a person, but because nobody had asked them to think it through before the pressure showed up.
A Habit Worth Building
If there is one habit I would suggest to any business owner, it is this: pick one uncomfortable “what if” question every quarter and actually answer it in writing. Not a full plan, just an honest paragraph. What would you do. What would it cost. Who would you call first.
It takes less time than most people expect, and it changes the tone of every harder conversation that follows. The businesses that weather a rough stretch well are rarely the luckiest ones. They are the ones who already knew, roughly, what they would do.