By asking questions, the CEOs for whom I worked always seem to figure out if I was doing the best thing for the organization even without knowing the details of the project I proposed. They had a knack for figuring out when I had not done my homework to maximize the benefits to the organization and minimize the risks.

I noticed that they just asked a series of really good questions. Their job was not to know how I did my job. Their job was to make sure that I really knew how to do my job to the extent that they could trust me to carry it out successfully.

The sort of questions that they would ask to determine if I know my job included:

• What does the customer want?
• Why does the customer want this?
• What are the alternatives for the customer?
• Why would the customer want our product rather than alternatives (e.g. from our competitors)?
• How is our organization going to meet its objectives through this project?
• How could those benefits be increased?
• What are the alternatives to implementing this project?
• Which alternative provides the greatest benefit for our organization?
• What implementation process are you going to use?
• What is the next phase for implementation?
• What are the costs of this next phase of implementation?
• What are the technical risks to the project?
• What is the impact if the project takes longer than we expect?
• What is the impact if the project costs more than we expect?
• What is the impact if the customer buys fewer products than we expect?
• How can each of these risks be mitigated?

Obviously, in a commercial organization the objectives for the organization were financial, and the benefits, costs and risks would all need to have their answered in economic terms. However, in a not-for-profit organization, the objectives, costs and risks can all be stated relative to the Mission of the organization, or in progress towards achieving the Vision.

If I could not answer these questions then I clearly did not know my job, and I would not get approval for the project.

If I could answer all of these questions there was a much better chance that the project would be approved.

Having said all of this, I have concluded that the hardest question that a CEO could ask me would be: “Show me how you will make the most effective progress toward achieving the Vision of the organization.”