The One Most Important Question

If you are approached to help an entrepreneur in some role, be sure to ask one question.

Case 1: A colleague was approached by an entrepreneur who wanted to discuss his being on the company advisory board. After several conversations that consumed several uncompensated hours, he said he wanted to move forward and started to outline benchmarks, expectations, and deadlines. A week later, he informed the candidate that, after discussing the compensation arrangement with his wife, that the deal was off.

Case 2: I referred a friend to someone who told me he was looking for sales people for his emerging company. The friend spent several hours in due diligence and the entrepreneur gave him the distinct impression he was interested in hiring him. A week later, he told my friend, that after a conversation with his wife, the deal was off.

Case 3: I mentor an entrepreneur who was having doubts about her career pathway. She expressed interest in building, scaling, and exiting a company and has been successful so far in moving in that direction; so successful, in fact, that someone approached her to be part of another company. She asked for my advice. You know what I said: “What does your spouse think?”

Entrepreneurs have their own dreams, and some admit, their own psychopathologies and personality disorders. Some don't honestly have "the conversation" with their spouse before going down an entrepreneurial road that will have considerable impact on their families, relationship and finances and unsuspecting prospective participants wind up being disappointed, cynical, or frustrated with the interaction.

If you are approached to help an entrepreneur in some role, be sure to ask one question: What does your spouse think of this idea? It's better to find out that the person you are dating is married sooner than later.