When you conduct a Why Conversation you are like a doctor looking to diagnose the problem your patient has before you decide to prescribe medication.

Let’s start with Why This? questions:

“Why not leave things the way they are?“

“Why embark on such a costly and risky endeavor?“

“Why not do something cheaper?“

“Why not do [other alternative]?“

“What would a home run look like?”

We tried having the intern work around the problem and it blew up in our face.

We tried to create a tool internally, but it crashes all the time.

If we don’t get something that works, we’ll lose a lot of business.

We need a tool that can handle at least 500 requests at a time, so 1000 without crashing would probably be a home run. If it crashes once, it’ll cost us thousands.

Whatever the answer is, put it in the proposal.

You want to do this project because you tried having the intern work around the problem and it blew up in your face, you tried to build a tool internally, and it crashes all the time, and if you don’t get something that works, you’ll lose a lot of business.

A home run would be a tool that can take 1000 requests at a time without crashing even once.

When they answer your questions they convince themselves (and you) that it’s necessary to do the project (if they’re a good fit). It also tends to reveal bad fits early.

If they have not yet convinced you the project is necessary, ask more questions until you are convinced.

Look for the business outcome they want to achieve. In this example, it’s not losing business due to crashes.

Sometimes it’s personal.

“I want to do this so I can afford to take the summer off to spend with my family.” can be a valid “business outcome “.

Josh