September 21, 2026

The Why Conversation

Today I realized that my core piece on The Why Conversation is a podcast episode, and I have never really shared an equivalent text version. Here’s my adaptation of the original audio.

Imagine you’re a web developer and a prospective client gets in touch. Maybe someone referred them to you. Maybe they found you through a Google search. Either way, they have a list of things they’d like you to build, and they want to set up a call.

You schedule the call, get on Zoom, and start chatting.

How should you NOT handle this conversation?

You should NOT handle it by thinking through their punch list and figuring out how much to charge.

What you SHOULD do is spend the time together understanding why they want any of this stuff in the first place.

That’s the purpose of what I call The Why Conversation.

Let them get it all out

When the client gets on the call, they probably have a lot on their mind. They’ve been thinking about this project, and they’re going to want to tell you about it.

Let them brain dump.

Have a paper and pen ready. Take notes as they describe what they want. Capture their language and anything that stands out.

Some of what they say might not make sense yet. They might launch into detailed, tactical requests without giving you enough context to understand what they’re talking about.

That’s okay. Listen. Take notes. Ask a question here and there as you start to get a grip on the situation. Give them room to exhaust everything they came prepared to say.

By the time they run out of things to add - and you run out of clarifying questions - twenty or thirty minutes might have passed.

Now you can step back.

Get the bigger picture

Thank them for sharing the information, then ask something like:

“Could we step back for a second? I’d like to understand the bigger context.”

They might not immediately understand what you’re asking. After all, they just told you what they need.

You can explain it this way:

“There are different ways to approach this. If it’s supposed to be a long-term solution, I’ll make different decisions than I would if it’s a temporary solution to help you get funding or bridge the gap until a bigger system is installed.

“There are hundreds of little decisions I’ll make while doing the work. I’m not going to bother you with every one of them. But I need to understand the bigger goal so those decisions don’t paint you into a corner.”

At this point, they’ll usually back up and explain the situation.

Maybe a competitor is moving into their space.

Maybe an existing competitor released a feature their customers are going to love.

Maybe something changed in their industry, and they see an opportunity to capitalize on it.

Now you’re learning where they are, where they want to go, and how important this project is to the business.

That’s very different from accepting a punch list of things to do on their behalf.

Try to talk them out of hiring you

Once you understand the bigger picture, The Why Conversation really begins.

This is the part where you try to talk them out of hiring you to do the project.

Yes, seriously.

It sounds counterintuitive, but it builds trust. It also helps you understand what would actually make the client satisfied with the engagement.

Because completing a punch list doesn’t guarantee a happy client.

You could build every feature they requested. But if those features don’t accomplish anything meaningful, the client won’t be happy they spent the money.

They might not blame you. You did what they asked, after all.

But that’s not the same as being happy with the result.

To get beyond the punch list, you need to explore three categories of questions:

Why this? Why now? Why me?

Why this?

The first question is whether this project makes sense at all.

Why not NOT do it? Why not leave things the way they are? Why not approach the problem differently? Why not use an off-the-shelf solution?

A project is a costly, risky commitment. It can go over budget. It can take longer than expected. It can blow up in your face.

Without a good reason to do it, you shouldn’t do it.

So part of your diagnosis is to ask:

“Why not just leave things the way they are?”

They might say:

“We couldn’t possibly do that.”

Your next question is:

“Okay. Why?”

Now you’re getting somewhere.

They’ll explain what prompted them to start looking for someone like you. You’ll learn why the current situation is unacceptable and why they believe this project is the right way to address it.

You’re not making the case for the project.

They are.

Why now?

The second category is about urgency.

Why does this need to happen now?

The way you explore this depends on whether they just discovered the problem or have known about it for a while.

For a newly discovered problem or opportunity, you might ask:

“Why not keep an eye on this for six months or a year? You could see whether it turns into a big deal before committing to a project.”

They might respond:

“No, we can’t wait. We need to do this now.”

Great. Why?

Whatever reasons they give you, write them down.

For a problem they’ve known about for a while, the questions are different:

“What changed? You’ve known about this for some time. Why address it now?”

Maybe it wasn’t a big deal before, but something happened that made it urgent.

Write that down, too.

Of course, they might agree with you:

“Actually, waiting six months is probably a good idea.”

That’s a useful outcome. Now you don’t have to write a proposal for a project that doesn’t need to happen yet.

You can agree to check back in six months and see how things are going.

But when there is a reason to act now, you want to understand it. By the end of this part of the conversation, you should have a clear sense of the project’s urgency - not just its importance.

Why me?

The third category is about why they should hire you instead of someone less expensive.

You’ve established that the project makes sense. You’ve established that it needs to happen now.

But why hire an expensive resource like you?

Ask about the alternatives:

“You mentioned you have an internal development team. Why not have them do it?”

Or:

“Why not outsource this to an overseas team? That could be much less expensive.”

Or:

“Could junior contractors or interns handle this?”

Again, they might say:

“Good idea!”

But they’ve probably considered at least some of these options and have reasons for ruling them out.

Maybe their internal team is already maxed out on another project.

Maybe they tried an overseas team, and the time-zone difference caused major problems.

Maybe they have junior contractors, but this project is beyond what those people can handle. They want someone more experienced to take responsibility for it.

Whatever their reasons, write them down.

You’re learning why the cheaper options aren’t suitable for their situation. And the client is articulating why hiring you could make sense.

Two good outcomes

By the end of a thorough Why Conversation, one of two things will have happened.

You might have talked the client out of doing the project, doing it now, or doing it with you. You’ve helped them avoid a commitment that didn’t make sense.

Or you’ll have convinced yourself that there’s a mutually beneficial project here, AND the client will have talked themselves into hiring you.

You’ll both understand why the project is worth doing, why it needs to happen now, and why you’re a good choice to help.

The key is to explore all three categories. Not just why this. Not just why now. Not just why me.

All three.

Then you’re no longer working from a punch list and hoping it adds up to a satisfied client.

You understand the situation, the goal, the urgency, and the reasons the alternatives won’t do.

Now you have what you need to write a killer proposal.