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What Socrates Taught Me About Uncovering Client Pain Points


Trent asked a great question last week that outlined his fears on digging too deep for the pain behind a project:

I can’t just keep asking, “Why?” Eventually I’ll reach the issue they don’t want to talk about – their point of shame – and the prospect will get uncomfortable and the conversation is over.

How does one get the prospect to say (and this isn’t my space, it’s just an example), “I went on a diet because I got out of the shower and saw myself in the mirror and it was gross.  My kids want to go to the beach, but I don’t want to take them because I don’t want to take my shirt off. I feel like I’m letting them down”

That’s the real conversation, not “I wanted to lose weight.” Nobody cares about losing weight; there’s a REASON they want to lose that weight. How to get there without just digging at the wound?

I’ve talked about “proxy pains” quite a bit over the last few months. The idea is that projects are never commissioned in a vacuum… behind each website, app, or whatever you might be hired for, there’s a business problem that needs to be solved.

Obvious, right? It is — after you think it over. But for years, I was convinced people were hiring me to build websites or apps. And that the list of requirements I were brought to the table weren’t up for discussion, but rather the result of a lot of deliberate and calculated study by my client.

After I started coming out of my shell a bit and started asking why instead of just focusing on the hows, my business improved on all fronts. My clients got better results. I was treated with more respect. And I made more money.

But like Trent brought up, digging out pains behind a project might bring to light more than a few open wounds. I know that when I ran my consulting firm, I was convinced that a smart business owner should act like everything is always peachy and never expose their problems (especially to their employees.)

However, there is a method that you can use to reliably get to the core of a problem. And it’s something that’s been in use for over 2,000 years — Socratic questioning.

(Bear with me here, the former liberal arts major in me is about to rear its head.)

The idea behind Socratic questioning (sometimes known as the Socratic method) is that good dialogue can open itself up to critical inquiry. And while Socrates helped people understand what they really thought about Truth or Justice, our purposes will be much more mundane.

So let’s say we’re approached to build a website for a real estate company. We might make the assumption that, “They need a new website because they aren’t getting enough business.” But an assumption is just a guess. The client needs to admit their own problem.

We need to peel away the website through active conversation to find out why this project’s on the table, and — like Trent mentioned — we don’t want to outright proclaim, “you’re suffering — aren’t ya?” In Trent’s example, we want the dieter to admit that they are unhappy with how they look. That’s not our job.

  • Expose the issue. What prompted this project? Are they just unhappy with their current website? Is it ugly? Do they maybe think it’s unprofessional?
  • Uncover consequences. Dig further… If the “current website is ugly”, ask them if their ugly website is somehow affecting their business.
  • Evaluate the consequences. If the ugly website is negatively affecting their business, how does it do that? Can we be certain that the aesthetic of the website is responsible for this issue, or could something else be to blame? Would the inverse — a non ugly website — remove the issue? Or should we keep looking…?
  • The big question. If the website was suddenly non-ugly, which we assume is the goal with this redesign, can we be positive that the issue they’re facing will go away? And is this issue costing money, or keeping them from making more money? How can we — with our technical skills and business acumen — help conquer this problem? …And is the website redesign project they brought us the sword that’s going to do that?

And this, my friends, is how you simultaneously gain a client’s trust, better understand their business, and prove that you’re the right guy or gal to make their problems go away.

This is consulting, plain and simple — the art of taking a problem, understanding it, and forming a solution. And this sort of inquiry is what separates low-rate freelancers from high-value consultants.

Do you know what likely comes right after the above hypothetical website discussion? “OK, let’s talk about how I can help you out…”

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