February 18, 2022

The Four Questions Pt 2

A few people responded to yesterday’s message asking for examples of how I might deploy the four questions in an actual conversation.

Here’s a quick example:


Me: What do you want?

Client: I want a custom software system to automate our invoicing process.

Me: Why?

Client: Because our current manual process is inefficient.

Me: So what?

Client: Our accounts receivable people are working nights and weekends and just can’t keep up. Sometimes we get so far behind that clients can refuse to pay because the invoices are so old. We had to write off $40,000 of uncollectible invoices last month alone.

Me: Why don’t you just hire more accounts receivable people?

Client: Because our business is growing like crazy right now and I already can’t hire A/R people fast enough to keep up with the volume of new business.


As I said yesterday, I would phrase these questions more politely, and depending on how the conversation unfolds, I might not ask them in this order.

But I would make sure to keep asking them until I was satisfied with the answers.

If the answers gave me confidence that I could help improve the client’s condition, I’d move to the proposal stage.



P.S. Of the four questions, I think “So what?” is the one that people are the worst at asking. They get a statement of fact in reply to “Why?” and then leave it at that without finding out the business impact in the client’s own words.

Here’s an old Ditcherville Comic that provides a few variations on the “So what?” question: https://jonathanstark.com/ditcherville#7