Five Questions

The best advisers I ever sat with were not the ones with answers. Answers were abundant even before the internet made them infinite; every seat I held came with corridors full of people who had answers. The advisers I remember, the ones whose influence outlived the engagement by decades, were rarer and quieter. They were the ones whose questions rearranged the room.

A question of that kind does something no answer can. It stays. An answer is consumed at the moment of delivery and depreciates from there, but a real question keeps working long after the conversation, surfacing in the shower and on the drive, reorganising what you thought you knew each time you pass it. So rather than end this series with answers, here are five of the questions I work through with entrepreneurs. They are not tricks, and there is no scoring. Each one is a door into the same house.

First: which decisions in your business can genuinely only you make? Write the list. Most people expect ten and find three, and the gap between the expected list and the real one is a map of everything being held that could be given.

Second: when did a number last change a decision before the event, rather than explain it after? This is the question that reveals whether your business has instruments or merely records, and most have records.

Third: which hat should have been handed over a year ago? Note the tense. The question is not whether to hand things over, which invites a committee of internal objections, but which handover is already late, which your instinct answers before the objections convene.

Fourth: what does the business need that you are currently the wrong person to give it? This is the uncomfortable one, because it requires saying that love and fitness are different things, and that a business can be starved by a devoted owner of exactly the thing an indifferent stranger could supply.

Fifth: what would the next stage cost you, the person, not the P&L? Every growth plan prices the money and almost none price the operator: the hours, the identity, the way of working that the next stage will demand or destroy. It is the only question on the list that treats you as a stakeholder rather than a resource, and it is the one most worth an honest evening.

Notice what the five have in common. Not one of them can be answered by a framework, a module, or anyone else's blueprint, because every one of them is about you and the business at the same time, which is precisely the territory the pre-recorded industry cannot enter. A curriculum can hold answers. It cannot hold your answers, and this whole series has really been about that single distinction.

The questions are yours now; take them somewhere quiet. And if you want the structured version, the one that asks its questions across all eight roles a business runs on and hands you the findings in about ten minutes, the Entrepreneur Gap scan is free and built for businesses past £15k a month. Start with question one either way. Which decisions can genuinely only you make? Most people expect ten. Write the list.

Continue reading: Decks Persuade, Documents Commit →

Or take the structured version: Take the free 10-minute Entrepreneur Gap scan →