Six questions I ask a founder in the first thirty minutes.

One · Where the company is going

If I asked your three most senior leaders, separately and in writing, where this company will be in three years, how many different answers would I get?

You will guess one. Your leaders will write three. The gap between your guess and the count is the size of the hole in the frame, and it explains the thing you came to talk about, which is why you sit in every decision. You are the only person who knows the destination, so every real choice has to pass through you to be checked against it. Two more senior hires do not fix that. They add two more people who have to ask.

I have scored companies with excellent meetings and documented processes, sevens out of ten on both, sitting on a frame that scored a three. The machine was superb. Nobody agreed where it was going.

Two · Where the founder actually belongs

Of the decisions that reached your desk last month, how many could only you have made?

List what came to you. Then mark the ones that needed your judgment rather than your signature. At scale the second list is usually a fifth of the first. The ratio measures how much of the company's attention is spent getting yours, and the items on the long list that are missing from the short one are the ones the structure is failing to catch.

The usual advice is to get out of the business, and it is half right. The question is not how far you are from the work. It is where you are concentrated.

Three · Whether anyone else can carry weight

Name the last decision a leader made without you that turned out wrong, and tell me what happened to that leader afterward.

If you cannot produce the first, nobody is deciding. If the answer to the second is anything other than nothing, nobody is allowed to. Those are the same condition seen from two sides. Being wrong in front of you costs more than waiting for you, so a rational leader waits.

No hire fixes this, because the next leader will do the same arithmetic the current ones already did. A leadership spine is measured by what happens after the miss.

Four · Whether the business has a heartbeat

Open the notes from your last monthly review. How many decisions left the room with an owner and a date, and how many left as take it offline?

A cadence built to decide has a long first count and a short second. A cadence built to brief you has the reverse, and it is usually the better run meeting, because a room designed to inform is easier to run than a room designed to commit. The second count is the business routing back through you once a month, with everyone's agreement.

A strong cadence on a weak frame does not cause the mistake. It distributes it, weekly.

Five · Whether the work survives the person

Pull last month's exceptions on anything that touches cash, the discounts, credit holds, rush orders and refunds, and write the name of whoever resolved each one.

If one name covers most of them, the company does not have a process. It has a person. At this size the steps are written down. Follow any of them exactly for a week and the business slows down, because the documents describe the steps and the steps were never the hard part. The hard part is the exceptions, and the rules for those live in one head until the day that person leaves.

Six · Whether the company knows what is working in time

On a Wednesday morning, which three numbers tell you whether this week is working, and who puts them in front of you without being asked?

A founder who can only answer for the month cannot correct inside it. The first half of the question tests whether you know what the business runs on. The second half tests whether anyone else does. A company where the founder has to ask for the numbers is a company where the founder is the measurement system.