July 29, 2026
How to uncover value without making things weird
On today’s Ditcherville LIVE session, I was asked:
What are some good questions to ask to uncover the value to the client without being too overt? Like, “How much is this costing the business?” can make people shut down.
My approach is counter-intuitive, but here it is:
Try to talk the person out of hiring you.
WAT?!
Let me explain...
You want to walk them through a series of questions that will convince you that you can improve their condition.
If you think about it, why would you even want the gig if you weren’t reasonably sure the client would be better off after you were done?
Makes sense, right?
Right.
Okay, but exactly how do you try to talk them out of hiring you?
With The Why Conversation
- Why this?
- Why now?
- Why me?
On the call, I described it this way. From the call transcript:
Going through The Why Conversation uncovers the value. And if you can’t find the value, there’s no reason to write a proposal. So if you approach with genuine curiosity, like, “Why would you write me a giant check to do this list of things that you just told me about?” or, “Okay, great. You just spent 15 minutes telling me about this list of things you want me to do. But why these things? I can make a guess, but I don’t want to paint us into a corner. Can you share your actual goal so I can make sure my work is aligned with it?” Because they almost never talk about the goal, the thing that they believe will happen after you’re done. They don’t usually bring that up so you need to uncover it by asking the Why questions.
You don’t need to interrogate them about money because they will usually bring it up naturally in an effort to convince you that they would benefit from your assistance.
Anniversary Deal
If you’ve been thinking about joining Ditcherville to get your burning business questions answered, now’s the perfect time!
To celebrate the 10th anniversary of Hourly Billing Is Nuts, I’m offering a 50%-off deal for new members.
Use coupon code HBIN10BDAY at checkout to get half off your first year, whether you choose the monthly or annual.
But don’t wait! Your coupon expires at midnight.
Hope to see you inside :-)
Yours,
—J