In the last post, I talked about how important it is to identify a strong and unique position and getting in front of your prospects frequently and at the right times. If you’re able to successfully do that, you’ll start to see a steady stream of clients inquiring about working with you. What do you do next?

Many service providers would schedule a conversation to learn more about the work. In that conversation, they’ll ask about the requirements of the project. Once they have requirements, they’ll estimate the amount of time the project will take, multiply it by some time-based rate like an hourly or weekly rate, and send the client a contract with the requirements and rates outlined for verification. Hopefully, the client agrees with everything outlined, signs on the dotted line, and you’re off to the races.

Not so fast, tiger.

When projects go south, everyone thinks it’s because of something that happened within the project. Usually, it’s because something didn’t happen during those early conversations.

Shaping work

I appreciate the language that the team at Basecamp use in their book, Shape Up. The way they describe it, all work needs to be “shaped” before it can be worked on effectively.

When shaping, we focus less on estimates and more on our appetite. Instead of asking how much time it will take to do some work, we ask: How much time do we want to spend? How much is this idea worth? This is the task of shaping: narrowing down the problem and designing the outline of a solution that fits within the constraints of our appetite.

If you’ve successfully 7-11-4-ed your prospects, they’ve been hearing from you for a long time. They’re eager to talk back to you. They want to tell you how your ideas fit into their world. The first conversations you have with them is that opportunity. It’s where you can shape the work together.

Signaling a working model

These early conversations are also where the dynamics of the relationship are formed. You’re modeling for each other how you want to be treated. At a fast food restaurant, customers walk up to the counter, declare exactly what they want from a fixed menu of items that’s affordably priced, and receive their order within minutes. At a Michelin-star chef’s tasting menu, you may have no idea what you’re going to be eating before it’s served to you, but you trust that the chefs are going to make you something delicious, and you know you’ll probably pay a pretty penny for it too. Which kind of restaurant is your design business? (There’s a world of options in-between too.)

Many freelancers and agencies act like fast food but try to charge Michelin-star prices. It doesn’t make sense.

So, instead of doing a requirements-gathering session like a fast food counter, how could you act more like a Michelin-star restaurant in these early conversations?

The four conversations

That’s not a typo: I did say conversations… plural. You want a client to pay you 5, 6, or 7 figures and think that can be arranged over one 30-minute phone call? You don’t want your business to be an impulse buy. You want it to be something a client saves up money for and feels like they won the lottery when you finally do start to work together. Get used to doing a little courting, and expect it to take a little time. (For reference, the 7-figure projects I’ve sold in the past had an average sales timeline of 12-18 months.)

Pricing coach Blair Enns calls it The Four Conversations:

1. The probative conversation, in which you prove your expertise to the client or the prospective client, and you move, in their mind, from vendor to expert practitioner.
2. The qualifying conversation, where you vet a lead against some standard sales criteria to determine if an opportunity exists and what the next steps are. This is the typical sales conversation most salespeople have where you're sifting through budget, decision maker, needs, timeframe, etc.
3. The value conversation, where you uncover or determine the amount of value that you might create for the client, and therefore what fair compensation for you would be.
4. The closing conversation, where you transition the prospective client to a client.

The more well-positioned you are, the easier the probative conversation is. You're probably most experienced at the qualifying conversation. So let's focus on the value conversation.

Again, Blair Enns has invaluable resources about this. Here's his framework for a great value conversation:

1. Uncover or commit the client to their desired future state
2. Identify the metrics of success
3. Determine the value of hitting these metrics
4. Set pricing guidance

If you're a novice at these kinds of conversations, try to follow the steps strictly; it’s the easiest way to practice and get better.

Keep ’em dreaming

Once you have more experience, you can riff and improvise. I like to move parts of the value conversation into every conversation, especially the part about identifying the desired future state. The more I can keep the prospect talking about the future they want to see, the more I can show them how I can be an integral part of helping them get there—while also avoiding getting too in the weeds about details that don't matter at this stage, like technical minutiae and logistical details.

The key is to keep them dreaming. Designers are some the best in the world at this. It's a creative exercise. The more you make sales a creative conversation instead of a financial transaction, the more you separate yourself from your competition and the more excited your prospect will be to start working with you.

Here are the types of questions and prompts I use to to talk about the future with my prospects:

• “Does your company have a 3-year, 5-year, or 10-year vision? What is it?”
• “Tell me everything.”
• The Dan Sullivan question: “If we were having this discussion three years from today, and you were to look back over those three years to today, what has to have happened, both personally and professionally, for you to feel happy about your progress?”

In the “Defining Value” section of my Pricing Design book, I share the questions I used to ask prospects in a value conversation. (You can see an earlier draft of those questions here.) I say “used to” because I realized years later that I too was conflating a value conversation and a qualifying conversation.

Stop asking and start telling

At lower-end restaurants—like fast food—the customer tells the service provider what to make. At higher-end restaurants—like Michelin-starred restaurants that have a chef’s tasting menu as the only option—the service provider tells the customer what they’re going to eat.

If your prospects and clients are telling you what to make, it might be that they see you more as fast food than a Michelin-star restaurant. You can’t just raise prices. You have to shift your positioning first so that your new prices feels appropriate.

A good first step there is to stop taking orders. Most service providers think that means saying “no” more or standing your ground when a client demands something. That’s certainly part of it, but that’s the most extreme version. That assumes a toxic relationship between a dictatorial client and a lowly, subservient service provider. It’s the nuances to pay attention to. You may still be politely asking your client what they’d like, and they’re politely answering your question. The problem there is you.

The biggest change in my conversations with prospects over the last few years is that I’ve stopped asking them what their budget is. Real talk: asking about budget often comes from a scarcity mindset; you wanna know how much money they’re willing to spend because you’ll come up with something to do for that cash. Strong positioning is about making clear what you don’t or won’t do, regardless of the money.

I talk to my prospects about their hopes and dreams as much as possible so I understand their desired future state as well as I can. Then, as the expert, I tell them what they should spend in order to achieve it.

This only works if you’re advising from a place of experience, abundance, and humility, not selfishness, scarcity, or arrogance. From the first conversation, I try to act as if I’m on the same side as the prospect and finding ways on their behalf to break even at the very least, if not earn a massive return on investment.

Being well-positioned to help teams with design systems means they already trust that I know more about it than they do before we ever talk. Many of my prospects have worked on 1 or 2 design systems; I’ve worked on hundreds. When you have that much more experience within your positioning than your prospect does, they feel awkward or embarrassed answering questions that you might know the answer to better than they would. I stopped asking my prospects what their budget was because every time, they’d answer something like, “Well, what should we be spending on something like this?”

The key to making this work is knowing what kind of value they’d get better than they do. For example, because I know that establishing a design system that helps a financial organization ship an important dashboard 6 weeks faster with a team of 4 in a way that will save them at least $250k–$450k this year alone, I can honestly advise that it would be worth a $50k investment to get a 5×–9× return. See how specific that is? Most of my prospects don’t know that, or it would take them a long time to figure that out. I’ve already made their job easier before they’ve even hired me. Imagine how much more helpful I could be if they hired me. Which is exactly what you want your prospects to think and feel about you.

Once I’ve identified a few ways to make sure my prospect will be profitable, only then will I explore whether or not I’ll be profitable too. In the next post, I’ll show you exactly how to do that by giving you my never-released-before Project Value Sheet template and breaking it down line-by-line.

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