Pricing Course Lesson 5 – How to use Socratic questioning to figure out what your clients need

How to use Socratic questioning to figure out what your clients need

If a new lead reached out to you today with a project request, what would your process be for moving that prospective client through your pipeline?

If you’re like most freelancers, you probably don’t really have one. You’ll probably setup a phone or in-person meeting, and you’ll likely do a bit of research beforehand.

The most important thing you can do early on when talking with new leads is to develop a process around how you learn about who they are and what they way. Don’t leave your conversations open-ended; come armed with an agenda.

Becoming a high-value freelance consultant starts with understanding the why behind each project you work on. Today we’re going to look at the exact process I use to the pains behind each project I work on.

Socratic Questioning

Before I got into computers professionally, I went to college for the classics. During my time as a freshman, I read most of Plato’s dialogues. The dialogues were the transcripts of conversations that occurred between Socrates and other Athenians. What really stuck out was that Socrates always had an agenda; there was some truth or ideal that he wanted the person who was talking with to admit. His method of questioning is still used by trial lawyers, psychologists, and academia — and there’s no reason we, as freelancers, can’t do the same.

When new leads come my way, I lead them through a series of questions that helps me both understand the why behind a particular project, and shows my clients that there’s something a bit different about working with me:

Step 1: Listen

Here the client tells me about what they think they need. They might come to me with a thought out list of requirements, or they might just have a rough idea of what they’re looking for.

“So tell me a bit about this project. What is it, and when are you looking to have it done by?”

This is the step that all of us do — we hear the client out. But most freelancers at this point will move toward discussing the technicals about the project. If it’s a website, the discussion might shift toward how many pages it will be, what theme or template it might use, what the navigation elements should be like, etc.

But I’m not interested in any of that yet…

Step 2: Identify The Trigger

“That sounds fantastic. Tell me a bit about how you came up with this project — what changed, or what happened, that made you realize, ‘I need to do $X’?”

Here we want to know what event occurred to spark this project. Often times, this can be a series of built up events that is ultimately set off by something specific.

Step 3: Highlight The Problem

“OK, so $TRIGGER happened and you decided to seek someone like me out. You wanted something fixed… Could you tell me more about what that something is? What is this project solving?”

Remember: No project exists without a backing problem. Your competitors likely won’t care enough to investigate what that problem is. If we know the problem, we can better tailor the project and what we end up doing toward that end.

Step 4: How Painful Is The Problem?

“That makes total sense. Before we go much further, I want to tell you a bit about how I work that might be a little different than most. I only want work on projects where I can deliver a ROI. We’ll be able to figure out my costs once I know more about exactly what needs to happen to make this project a success and solve this problem, but do you mind sharing about what impact — financial, reputation, or whatever — $PROBLEM is having on your business?”

Most people won’t be willing to open up to you and share the inner workings of their company. At this point, I’ll often present my non-disclosure agreement. I want to show them that I respect their business, and I realize that what they’re about to tell me shouldn’t be public knowledge.

Step 5: What’s The Cost

“Let’s try to figure out what it means for your business to have this problem persist. What’s the opportunity cost or the risk overhead of $PROBLEM?”

You want to understand what it means longterm for this problem to still be a problem. When we eventually go in for the sale, we’re going to anchor the need for this project against the cost of this problem not going away. We want the prospective client to admit the cost to us.

Note that not everyone will have these numbers available — but that’s OK. You’re mostly looking for ballparks or ranges.

Step 6: How Should Tomorrow Look?

“We don’t want that happening. So let’s move to a happier note — when we solve $PROBLEM, describe what tomorrow looks like. What does it mean for your business to have this fixed? What sort of impact will it?”

The question above was pretty painful… we’re talking about how sucky this problem is. Now we want to switch gears and move into happier pastures. Let’s let the client dream about tomorrow. What does it mean if this project succeeds? Try to quantify in hard numbers what sort of impact your project might have on the client’s business.

Step 7: Tie It All Together

“This was really valuable because this is going to help me better understand the why behind this project, which will help us together make sure that what I end up doing aligns perfectly with that end goal. Once we can figure out the total complexity of this project, I’ll be able to provide you a quote, and as long as the net effect of this project on your business heavily outweighs the cost it’ll make sense to talk about moving forward.”

A few key things are happening here. Most importantly, we’re really stressing our focus on their business and their financial well-being. We want them to be successful. We don’t want our portfolio to be a graveyard of failed companies.

The next part of the conversation will be to look at what that tomorrow might mean (financially, reputationally, etc.) for our clients, which will also help us determine how we can make that tomorrow come into being.

What’s really important to understand is that you’re not just looking to collect data. You want your clients to externally vocalize the necessity of this project. You want them to see that something’s different about working with you. You’re just not reacting to a project request — you’re guiding them through understanding what this project means for them and their business.

And this is going to help you tremendously when it comes time send off a proposal. My closing rate is near 100%, and I’m almost always the most expensive quote my clients get (my current rate is $20,000 a week).

Today’s homework is short and sweet. It should only take a minute:

Lesson 5 Worksheet: How do you learn about your clients?

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