The Questions Nobody Asks the Owner

By Craig Meddin — strategic advisor to established business owners.

Established business owners are surrounded by people with opinions: advisors on the specifics of their specialty, employees with a partial view, peers offering what worked in their own company. What owners rarely get is a question they cannot answer immediately.

Six questions worth sitting with

• If you could only fix one thing this year, what would it be — and why isn't it already being fixed? The second half of that question is where the real answer lives.
• What are you tolerating that you would never accept in a business you were buying? Owners forgive their own company things they would flag immediately in due diligence.
• Which part of the business still depends entirely on you, and what would break first if you were out for a month? This is a structural question, not a vacation question.
• What did you decide to stop doing this year? A strategy with no subtractions is usually a wish list.
• Who on the team would you enthusiastically rehire today? Hesitation is information, and it is usually old information you have been carrying.
• What are you avoiding because the conversation would be uncomfortable? Almost every stuck business has one of these, and it is usually the shortest path to movement.

Why questions outperform advice

Advice imports someone else's context. A good question uses yours. Most owners already know more about their situation than any outside party will — what they lack is an hour of undistracted thinking with someone who will not accept the first, tidiest answer.

How to use these

Take one question, not all six, and write for fifteen minutes without editing. Then read it as if it were written by an owner you were advising. The advice you would give that person is usually the advice you have been avoiding giving yourself.