Pricing your services

How To Socratically Question New Project Leads

By Brennan Dunn

The other day, a designer friend and I were chatting over coffee.

“I have no idea what I should be saying when I meet with a new potential client.”

She’d read my case study that laid out exactly how I closed a recent client, but was a bit unsure about how she could translate my success into something she could emulate in her web design business.

With her permission, I’d like to do my best to recreate our discussion. If you’ve ever been in the dark about how you should approach talking with a new client for the first time, I think you’ll really get a lot out of what’s below.


Startup Stock Photos

Her: “I have some questions about what I should say and ask when talking to a new potential client.”

Me: “Let’s hear ’em.”

Her: “Well, I know I’m supposed to Socratically question new clients. I learned that in Double Your Freelancing Rate, but I’m not really sure about how I could do this in practice. I’m not too confident when it comes to asking business questions to people, especially on the phone. And I don’t really know how I can help people figure out the value of design.”

Me, channeling Socrates: “OK, so there are two issues: first, you aren’t sure of your ability to ask business-y questions. Second, you can’t seem to figure out how to position the design work you do as an investment. Right?”

Her: “That’s right.”

Me: “Let’s start with the second issue, because I think it’ll help with the first. We agree that your clients aren’t in the business of handing over large 5-figure checks to designers like you for no reason, but have a goal in mind?”

Her: “Yep.”

Me: “And the majority of your clients run for-profit businesses?”

Her: “Yeah, but most of the work I do is branding or identity type work. There’s no easy way to figure out how much money or whatever I’ve done has made my clients.”

Me: “If a client comes to you for a branding project, what are they typically asking for?”

Her: “A new logo.”

Me: “Why?”

Her: “Well, on a recent project, the client said that he was looking to refresh his company’s branding. He showed me a few of his competitors and said that he wants his website to look more like theirs.”

Me: “Why would he want to look more like his competitors?”

Her: “I imagine he thinks they’re doing really well?”

Me: “OK, so maybe he’s thinking that his competitors are doing really well—conceivably better than he is—because they have a nice looking site and branding?

Her: “Probably.”

Me: “So somewhere lodged in the back of your client’s mind, he’s thinking: ‘If I could be more like X, I might be able to tap into some of the success that I’ve heard they’re enjoying’?”

Her: “Yeah, I mean he didn’t say that. But he’s probably thinking that.”

Me: “Then your client has assumed that looking like one of his seemingly more successful clients will result in him becoming more successful.”

Her: “Yeah.”

Me: “You’ve been following DYF for a while and you recently enrolled in The Blueprint. Do you think redesigning his site to look like one of his competitors is going to do that?”

Her: “Truthfully, no. I mean, a new design will help them look more professional—their site is dated. But just redesigning the website isn’t going to be enough. I think they have some issues with how they turn visitors into customers… their flow was just really weird, and I was really confused by the language on their website.”

Me: “You know that, but it doesn’t sound like he does. Otherwise, he’d have asked for more than just a new design—right?”

Her: “I guess you’re right.”

Me: “OK, so let’s sum a few things up… Your client is looking to hire someone to redo his branding. He’s referenced a few competitors that, in his mind, are doing things right. In his mind, redoing his brand to emulate his competitors means he’ll be more successful. You agree—to an extent. But you also think there’s a few other pieces missing that might hinder his success.”

Her: “Yep.”

Me: “Can we agree that he really wants to be more successful, and that he’s told himself branding himself like his competitors is the way to do that?”

Her: “Yep.”

Me: “The value of design, in his mind, is whatever it does to help make more sales. Let’s talk about a few ways of how a new design could do that. How does he make money?”

Her: “His company sells software online. People go to his website and sign up for a trial, and some of them turn into paid customers.”

Me: “That’s his funnel. So design and branding influence the step from ‘people go to his website’ to ‘sign up for a trial’. Poor design means fewer people will end up signing up for a trial, right?”

Her: “Yes. And poor copy will do the same thing—like I said, I’m a bit put off by how the trial flow works. It’s confusing, and the messaging on the website doesn’t do a great job at telling somebody why they should sign up.”

Me: “And that’s something you can help with, even if you don’t think you’re the best copywriter. Because you know what your role is with this project (getting more visitors to sign up for a trial), you’ll make sure the work you do—design or otherwise—is optimized to get more trial sign-ups, right?”

Her: “Right, but I’m still not sure if I can get him more trials.”

Me: “Fair enough. Imagine that I wanted to build a new house. I reach out to two builders and tell them that I’m looking to build my dream house. I want this house to be everything I’ve always wanted in a house. I want a sauna. A hot tub. A giant bathroom. I want it to look a little rustic, but without looking cheesy. This is what, to me, a dream house has to have. However, only one of the builders bothers asking me about what I want in my house… the other just goes and does his house-building thing.”

Her: “Where are you going with this?”

Me: “Who has a better chance of building the house I want?”

Her: “The one who tried to figure out what your dream house is.”

Me: “Your client’s dream is to have more trials, because he knows that each new trial means another shot at a paid customer. And paid customers are what pays the bills. If you’re just creating an asset—a website—you could end up stumbling upon the dream of new trials. Sometimes a really good looking site is enough to just lift confidence enough to measurably increase trials. But imagine you go into the project with the intent of creating more trials. This is going to affect what you design, how you structure the site, and everything else.”

Her: “Sure, and that’s what I told him: I’m going to focus on getting more trials.”

Me: “Forget track record and case studies and all of that… who’s more likely to succeed at getting more trials: the designer who just redesigns the site to be pretty, or you?”

Her: “I guess what I do would be more successful.”

Me: “So even if you didn’t have a huge amount of experience yet in actually doing this sort of stuff, because you know what your client needs and what’s lacking in his business, the design and whatever else you end up doing would by definition be better than the design that was created without increasing trials in mind, right?”

Her: “I think you’ve convinced me. OK.”

Me: “We’re not done yet, though. What’s at stake?”

Her: “What?”

Me: “If you can get more trials, what would that mean? And if trials stay the same, what would that mean?”

Her: “I don’t know. I guess the project would be a failure if he doesn’t get more trials.”

Me: “…and his business would stagnate, which would mean he spent money on nothing. But that’s not going to be happen, because your single objective is to focus on getting more trials, and you’ll do everything in your power to figure out how to do just that. You’ll study what you need to, read case studies from conversion optimization experts who have helped their clients get more trials for their software, and so on. You’ll be a designer hell-bent on lifting trial sign-ups for this client, and you’ll do that by focusing your design on that end.”

Her: “Exactly!”

Me: “So what’s that worth?”

Her: “I have no idea.”

Me: “Let’s walk backwards. How does money end up his account?”

Her: “Well, his customers are billed monthly. So when they pay for a month of service.”

Me: “And he’s not engaging with you to help him increase his pricing, right? So that’s not something you can control. You can’t help change how much each customer puts monthly into his bank account. Walk backwards still, why does someone end up putting money in his company’s account?”

Her: “Because they decide to pay. They’re given a 14-day free trial, and if they want to use it afterward they need to enter in their billing info and pay.”

Me: “Is he hiring you to get more of those people to pay?”

Her: “I don’t think so, though I guess the branding work I’m doing will change the way the app looks which might help with that. But I’m not sure. It’s not something he explicitly said he wants help with.”

Me: “So a percentage of people going through the two week trial will turn into paid users, who put money monthly into his account. Let’s ignore this for a second, since he isn’t explicitly asking for this. You don’t control how many trials end up paying. The next step backward is the amount of people who visit who end up signing up for a trial, right?”

Her: “Yep. And that’s where I come in.”

Me: “Do you have any idea what the value of his average customer is? Meaning, people sign up and pay monthly. After a while, they’ll end up quitting. Like, maybe the average person ends up paying 12 months and then cancels. And if the average person is paying $50 a month for his software, the average value of a customer is $600 (12 x $50).”

Her: “I don’t, but I think I could find that out.”

Me: “Good, because once you figure out what the average customer value is, you can figure out what the value is per trial. If a customer is worth $600 and 1 new paid account comes out of every 10 trials, a trial is $60.”

Her: “Simple math, sure.”


Me: “Now you’re basically selling him something that makes him $60 every time someone fills out the trial sign-up form on his site, right?”

Her: “…Yes.”

Me: “Which means that you’ve now unlocked the value of the ‘design’ you’re doing… because you’re not really selling him design. You’re not selling him new branding or whatever else. This project has you working to sell more $60-a-piece form submissions. And as a designer, your job is to get more people to put their information into that form and click submit.”

Her: “You’re absolutely right about that.”

Me: “So what are you going to sell him: a redesigned brand and website, or more $60-a-piece form submissions through some branding and design work that you’ll be doing?”

Her: “The latter.”

Me: “And what’s the value of that?”

Her: “$60 per trial.”

Me: “How many visitors does he get a month? And how many trials does he average a month?”

Her: “I don’t know, but I can ask.”

Me: “Find out. Because if he’s getting 10,000 visitors a month and 100 trials a month, his business makes $6,000 a month by getting 1% of visitors to fill out the $60-a-pop signup form. You aren’t talking to him about helping him get more traffic, so you’re just affecting ONE part of his funnel: visitors to trial sign-ups.”

Her: “Right.”

Me: “What would happen to his business (assuming the numbers above are correct) if you could get 2% of visitors to become trials? How much more revenue would he make a month?”

Her: “Er… $6,000 more a month.”

Me: “I assume the work you do for him will stick around for a while. Give it 2 years, how much more revenue have you made his business?”

Her: “$144,000… assuming nothing changes.”

Me: “Is the work you’re proposing for him valuable?”

Her: “Absolutely.”

Me: “What’s the value of someone who just comes along and throws a new design on his site?”

Her: “I guess… nothing. I mean, there’s no way to tell what that design is worth, since like you said it doesn’t really fit anywhere into this visitor -> trial -> paid customer flow thing you described.”

Me: “Every business has a funnel. It doesn’t matter what that organization does, it has a funnel. It’s up to you, as a consultant, to figure out your place in that funnel—what can you influence? ‘A new site design’ is contextless; it’s floating around in a vacuum. It has no value because it’s not tied to anything of value… it’s just pixels on a screen.”

Her: “I hate hearing this, but I love it all the same.”

Me: “Here’s the thing: We owe it to our clients to learn as much about their funnel as possible. We want to be investments, because if we’re investments… guess what’s going to happen?”

Her: “What?”

Me: “Our clients will be more successful as a result of the solution we delivered to them. Who’s more willing to refer or hire you again: a client who has grown because of you, or one who received a great looking design that was a total dud?”

Her: “That’s easy. The successful client.”

Me: “And you want more clients to refer or hire you again, right?”

Her: “That’s a ridiculous question.”

Me: “Good! So how are you going to close this client? What are you going to pitch?”

Her: “I’m going to use my skills as a designer to get more trial sign-ups. From what you’ve told me before, I’m going to project what’s possible by taking actual raw numbers and running simulations on them. ‘What if we could get 2% of visitors to sign up for a trial?'”

Me: “And now you see how you can create even more value for your clients by offering them more. What if you could setup marketing automation campaigns on top of the design work you’re already doing? What if you subcontracted out to a great copywriter who could help get the copy figured out?”

Her: “There’s so much more I could do, and I’m starting to really get how I could help holistically, rather than just being the hired designer.”

Me: “That’s the thing… I think a lot of us just think our job is to take orders. A client needs a new site design, so we go about designing it. But the best way to truly serve our clients is to reverse engineer their funnel and figure out where we fit into it. What levers can we pull to increase each stage of the funnel? Think about it this way… in our little fake example above, the business is making $6,000 a month by getting 100 trials a month from 10,000 visitors. 10 of these trials turn into paid accounts, and paid accounts are worth $600. Still with me?”

Her: “Yes!”

Me: “Let’s play with a few levers. Let’s say you help get 2% of all unique visitors a month to become trials, rather than 1%. Maybe that means setting up lead magnets on their blog and having really good and compelling call-to-actions in the company newsletter. Let’s also say that you can help the client with content marketing, and you’re able to get the client to 15,000 visitors a month (a 50% increase). And let’s go a step further and have you help them with their new trial onboarding and lifecycle email campaigns, and you’re about to get 20 out of 100 trials to become paid. What would that mean?”

Her: “Er… 2% of 15,000 is 300 trials, a 3x increase in monthly trials. And now we’re getting 20% of trials to pay, which means 60 new paid accounts, each valued at $600. So… wow, $36,000 in revenue a month.”

Me: “Or six-times more than their current revenue?”

Her: “Yeah.”

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Me: “Can you do that?”

Her: “I honestly have no idea.”

Me: “Would your client appreciate you focusing on this sort of stuff? Could you imagine your client pushing back with, ‘Why are you trying to figure out ways to 6x my business?’ Of course they wouldn’t. Do you see how business-y you’ve become throughout the course of this conversation? Do you see how you’re able to combine your own talent, your ability to learn (for example, from people who have written case studies or training material on conversion-focused design), and the stated wants and needs of your clients to put together the right plan of action?”

Her: “Yeah, this is all coming together so clearly now. Before I was a little intimidated because I figured I had to have a ton of business experience and know-how to do this sort of stuff. But I see it’s really just me taking an interest in the overall business of my clients, and seeing where and how I can serve.”

Me: “When we started talking, you told me that you doubted your ability to ask the right business questions to prospective clients, and you doubted the value of the work you do. How are you feeling now?”

Her: “Honestly, this is all making so much sense. I thought I had to have some script worked out before going into any sales meeting, but now I see it’s just about getting the client to lay out their funnel and the weaknesses they’re looking to improve upon. And the work I do—the design—is just a lever I’m pulling to increase a steps (or a few steps) of the funnel.”

Me: “Awesome. Here’s what I’d recommend you do in the future. When you get a new lead, immediately qualify them and give them an abridged version of what I recommend for collecting information pre-Roadmapping. You can’t expect people to have all these funnel stats when they jump on a call with you, so get them to share these figures with you prior to meeting. Then once you meet, your job is to identify how you can better their funnel. How can you get them from here to there? How can you leverage your skills and talents to help meaningfully grow their business? This should only take 20 minutes or so. From there, Roadmapping. And then pitching them on having you do the implementation work to carry them over to the promised land.”

Her: “That was very, very useful. Thank you!”

It’s pretty obvious that I had a goal in mind going in to this conversation.

I knew what I wanted her to walk away thinking.

This is the Socratic Method in practice.

It’s not about jumping on top of your soapbox and telling people what they need to think and why they need to think it.

Rather, it’s entering into a conversation with someone and meeting them on their level. Listen to what’s being said, and use their response to prompt the next question.

You’ll notice I tend to say “we agree that…” often, or I’ll make a statement that sums up the last few volleys of our discussion and ask my conversation partner to affirm what I just said. This is intentional, because no one wants to be told what to think. Persuasion—or getting someone to see something the way you do—isn’t done by decree, but instead through self-realization.

The above is an example of how you should talk with prospective clients. I wrote it as a dialogue because seeing an example Socratic questioning session is the single best way for everything to make sense.

If you’re looking to dive even further into Socratic questioning and really optimizing the way you sell, I encourage you to join thousands of others who have enrolled in Double Your Freelancing Rate.

Otherwise, I hope you’ve taken a lot from today’s dialogue and will make it a goal to start Socratically questioning your new clients.