“What hurdles are you facing right now that are getting in the way of your progress in X area of your business?”
“What is the single most difficult thing in your business right now?”
“What will happen to your business if nothing changes?”
“Why now? Why haven’t you made this change yet?”
Expectations/Dreams based questions
“How did you find out about me?"
“How do you think I might be able to help you?“
“How do you perceive success with this project and what does that look like?”
“Where do you really want to take your business?”
If they’ve come to you with a particular deliverable in mind (let’s say a website redesign), try to talk about the “why” behind the “what”.
Why do they want/need a redesign? Do they need more customers? Do they need their site to convert better? Maybe changing the copy is a better solution than redesigning the entire website.
Your job is to find out if what they are asking for is actually going to solve their problems. They’ve self-prescribed themselves as needing a redesign, and you need to find out if that is the correct prescription for the diagnosis.
There might be a better way to get the results they are seeking instead of jumping into a massive web redesign project.
It’s not widely talked about, but you can charge more for providing a more professional process and experience to a client.
This entire onboarding sequence of getting the prospect to jump over these barriers is designed to weed out prospects who are a bad fit by asking them questions that gauge whether or not they align with you.
But the additional upside to you is that prospects that do jump over these hurdles are set up to trust you and be more engaged clients (and pay higher prices).
Just the experience of walking the client through the onboarding/intake process and asking good questions that get them thinking about their business is a valuable service—a service that you could even charge a fee for.
Many agencies do just that, by offering paid discovery. But even if you don’t charge for it, you can still get benefits from it. \
I’ll give you a recent example in my business:
A prospect came to me after working with a cheap logo design service. The fact that they didn’t get what they were looking for and needed to find someone else to do the design work over again should tell you all you need to know about the level of service they were provided.
After taking the client through my onboarding process and before this prospect signed on with me, he told me, “Ian, you are bringing a level of professionalism to this project that is through the roof compared to what we experienced before.”
He said this before the project even started.
When you hear something like that, you know the client is ready to work with you and already seeing you as a freelancer that delivers high value. And when the value goes up, the price goes up with it.
This level of service, of behaving in a professional way and walking a client through a process, builds trust and really gets you on the same page with your client to set you up as a trusted partner instead of a low-priced commodity vendor.