We did some work for a tutoring company around 2017 or 2018. Then they left us. In their words, they needed a 50-person agency with the full service. (It is just my twin brother Alan and me, and we still do all the work, so yeah, that one got me.)

Eighteen months later, I got a call from someone on their team: “I really don’t know why we left you.” Business wasn’t going well, the graph didn’t look good, and they didn’t like the experience with the big agency. Not only did they want to come back, they asked, “Do you do the type of work we thought you didn’t do?”

Yes! Of course we did. But honestly, that question was on me.

The Why Conversation Can’t Stop at the Proposal

Back then we built them a website and we weren’t doing any strategy for them. I wasn’t doing a great job of showing clients how we help solve problems across a lot of disciplines. If a client has to ask whether you do something, you haven’t been asking them enough questions while you work together.

Jonathan Stark calls it the why conversation. Before a project, you keep peeling back layers, you ask the questions you are actually curious about, and you sit there in the silence until the client reveals the thing they didn’t want to reveal. Reading his work (and talking with him) totally changed how we sell. What took me longer to learn is that the why conversation can’t end when the proposal gets signed.

In other words, take everything you learned about the proposal phase and bring it into the relationship.

Why Hourly Billing Makes Curiosity Expensive

When you bill by the hour, every extra question you ask about a client’s business lands on their invoice. So you ask fewer, they share less, and pretty soon you’re taking orders. When Jonathan and I talked about it on his show, I said hourly billing creates toxic relationships, and it does it immediately. It sets you and the client up as adversaries when you should be on the same team, looking at the problem from the same side.

When the price is tied to what the client gets out of the work, I can afford to be curious. Here is what that looked like with one client.

30 Hours of Sales Calls

We were in a client’s CallRail account (call tracking, it swaps the phone number on the website so you can see where leads come from, and it can record the incoming calls). I am super fascinated by the sales process, so I started listening to their calls. And I kept thinking, “Oh man, they are leaving so much money on the table because of little things their team is doing that they don’t even realize.”

So I listened to probably 30 hours of calls. Nobody asked me to, and they were never going to pay me for those hours anyway. It was still worth it to me. I found six places where their reps were consistently falling short.

A human going through that many calls was going to be a waste of time, but CallRail has an API that pulls in the transcripts. So I built a custom GPT that graded every call against those six criteria, created a doc, and emailed the results to me and their marketing director. Now we could see how things were trending, plus anything that came up on a call the sales team wasn’t surfacing. (This was a couple years ago, I might build it differently today.)

They loved it, and it became part of our engagement. None of that happens if I only think of myself as the website guy. One word of caution: if your client would not like you listening to their calls, please don’t do this (and don’t say I told you to).

I talked through all of this (and a lot more) with Jonathan, nine years after I first came on his show to talk about pulling the trigger on value pricing. Hear the full conversation with Jonathan Stark on Ditching Hourly:

How to Keep Asking Why With Clients You Already Have

Now, you don’t have to listen to 30 hours of anybody’s phone calls. Here is what I would do with the clients you have right now:

• Don’t let their cows become sacred to you. The things they have always done are the first places to ask why.
• Watch out for the status quo meeting. If your monthly call has turned into “we have this meeting, we say the things,” use it to check in on what is really going on.
• Ask what they expect from you. You don’t always have to meet those expectations, but you can’t guide them if you never ask.
• Be honest when something goes wrong. Tell them, and say “I did that.”
• Bring up the gaps you see, even when you don’t know how to fix them yet. It is okay to say, “I don’t actually know exactly how to do that yet, but I’ll either help you find out or figure it out myself.”

That tutoring company is one of my favorite clients now. We have a value-priced monthly agreement where we are in calls constantly, looking for problems they might not even see, and that work keeps spawning separate projects with their own proposals. Alan and I have been doing this for 18 years, our average client has been with us for 8 of them, and our longest for 12. At the end of the day it comes down to trust, and you build it by asking a question and listening.

Not Every Long Relationship Is Worth Keeping

One quick aside. Long relationships only work when they are real partnerships. Since we aren’t hungry for leads, we get to vet people and make sure we are going to be partners and not just a client-vendor relationship. If a client popped into your head while you were reading this, and not in a good way, run them through the Capacity Tax. It is a quick bit of math that shows what a wrong-fit client is really costing you, including the better client who can’t get a seat because they are sitting in it.

So this is my call to action: pick one client this week and ask them a why question about their business as a whole, then be quiet long enough for them to really answer.

Takeaway: Don’t stop asking why once the proposal is signed. Value pricing gives you room to stay curious about your clients’ businesses, and that curiosity is what keeps them around for years.