How to Enjoy Sales and Do an Effective Discovery Call

One Wednesday a couple of years ago, I closed over $20,000 in new engagements. Yet, the day didn’t feel hectic. My calendar didn’t have the crushing density that characterized my early years of “successful” freelancing.

I attribute the more relaxed pace of my more mature business to implementing a simple, reliable sales process.

Before I take you through the first part of it, let me back up and say that I used to loathe sales or rather what I assumed “sales” was.

We’ve all had encounters with frothing-at-the-mouth sales predator types who use the high-pressure, heavy-handed tactics. We’ve all been on the receiving end of sales pitches that were as rehearsed and mechanical as they were insulting.

In an effort to get as far away from that ick as possible, we can unwittingly commit to the opposite: ignoring good tactics and willfully persisting in being mediocre at selling, which is to say, serving.

Of course, most of the advanced freelancers I coach and those in my Freelance Cake Community have shed their misapprehensions about what sales is and learned some good techniques. Otherwise, they wouldn’t be advanced freelancers. They would have already gone out of business.

That brings me to the first point I need you to accept and believe before you proceed.

No matter what your experiences have been, sales is a part of life. Being “in sales” is part of being a freelancer. Because it’s unavoidable, you must learn how to be good at it.

If you’re like me and you like to pretend you’re a wolf stalking caribou in the Arctic, then I have good news for you. There’s an alternative approach that is enjoyable, effective, and fair.

This approach has 3 phases:

1. Discovery
2. Scoping
3. Closing

The rest of this essay is dedicated to the first phase, Discovery.

Discovery

When a potential client gets in touch through a website contact form, referral, LinkedIn message, or whathaveyou, the first 2 things I do are as follows:

1. Ask the prospect to answer my intake questionnaire.
2. Ask them to book a short discovery call using my scheduling link.

By gaining some insight into their context, goals, challenges, and opportunities before the discovery call, I’m able to show up to those calls with a second set of deeper questions ready.

When we’re facilitating a process of self-discovery for prospects, which we should be doing instead of pitching or “selling,” we’re part archaeologist and part therapist. We’re uncovering what’s hidden, not simply accepting that whatever the client says they need is the project.

That understanding of your role is important for several reasons:

1. Many clients aren’t good at finding the root cause, so they talk about surface-level symptoms.
2. Because that’s true, the client’s initial request may not be the real or most important project.
3. If you accept the initial request as the real project, you’ll likely solve the wrong problem.

You may have been in a situation in the past where you did exactly what you said you’d do for a client. You delivered the scope and fulfilled the contract down to the letter. Even so, the client didn’t get the results they wanted. Though you did nothing wrong and aren’t responsible for their disappointment, that disappointment has a way of ricocheting and hitting you.

What I mean is that it’s hard to get repeat business and referrals from disappointed clients even if you did nothing wrong. And it’s frustrating to have given a client exactly what they asked for and to still be blamed indirectly for the results.

Some of us, based on our personalities, aren’t adept at challenging clients when we believe they’re making the wrong choice and about to waste their money.

Regardless, you can’t keep acting like a short-order cook. You’ve got to act more like a therapist and archaeologist. Create the space where new insights can emerge.

Here’s what effective discovery calls look like:

1. Think of yourself as a listener, collaborator, and expert guide, not a freelancer who needs to pitch something.
2. Use thoughtful, open-ended questions to peel back layers. (You can grab my toolkit of consulting questions below.)
3. When you recognize problems (unpleasant facts of their situation) and pain points (how they feel about those problems), ask follow-up questions. For example, “So you’re saying that your company has never been consistent with your marketing?”
4. When you notice roadblocks (that is, what’s standing between them and what they want) and opportunities, take the time to understand what it is they really want. For example, “If you were to finally achieve consistency with marketing, what would that mean for the company?”
5. Share new ideas and perspectives. Yes, you should let them do most of the talking, but when the opportunity arises, share one or two ideas that they may not have thought of. For example, “Have you considered hiring a marketing coordinator before you hire a fractional CMO? Based on what you’re telling me, you’d be asking an fCMO to do three different jobs.”
6. Use labeling and mirroring. Labeling is putting words or succinct descriptions on what they’re telling you. For example, “What I hear you saying is that marketing inconsistency is the main obstacle between you and your goals. Is that accurate?” Mirroring is what it sounds like. Do your best to reflect back their verbal and nonverbal cues. Smile when they smile. Cross your arms when they do. This builds connection and rapport and makes people feel more comfortable.
7. Take plenty of notes. Capture the language they used to describe their problems and desired outcomes and use their word choice, not your own, in your recap email and proposals.
8. List key outcomes. Clients want to buy a better version of themselves or their companies, not services. No one cares about services; services are simply the delivery mechanism for outcomes. Always put the emphasis on the outcomes.

Imagine uncovering a buried dartboard.

Perhaps the best analogy for understanding the purpose of a discovery call is uncovering a buried dartboard.

Clients will often say, “I want this.” If you accept that at face value, then you’re assuming they’ve correctly identified both the problem and the solution.

That’s been true for maybe 30% of my clients over the years: They come to me already knowing what needs to happen and why.

The other 70%, the majority, fell into three buckets:

• They weren’t aware of the real problem or the solution.
• They were aware of the problem but not of the solution.
• They were aware of the problem and of a solution, which wasn’t the best one.

So my job as a listener, collaborator, and expert guide is to say, “Hey, let’s back up for a second. Tell me how you came to the conclusion that an outdated website was the main problem with your marketing.”

As I ask open-ended, consultative questions and uncover all the edges of the dartboard, the client and I realize together that their initial request (”I want this”) wasn’t the bullseye, not even close. What they really need is not a fancy new website, though that probably wouldn’t hurt. What they really need is consistency in their marketing.

Once you’ve defined the edges of the challenge or opportunity, you and the client can talk through different solutions, and once you land on the best or most feasible solution, you can get into the weeds of scope, price, and timeline.

I’ll add here that slowing the discovery process down can drive the project value up. That is, the dart in the true bullseye often represents a bigger, higher value project than whatever the client originally asked for.

Uncovering the edges of the buried dartboard first will also help you avoid wasting your time on dead ends where the client doesn’t have the budget or where the root problem isn’t one you want to solve.

In Million Dollar Consulting, Alan Weiss calls this process reaching “conceptual agreement.” To paraphrase Weiss, don’t waste time on creating a proposal until you and the client agree on the concept (that is, what the challenge or opportunity is), what the chosen solution is, what the desired outcomes are, what engagement should look like, who is responsible for what, and what the budget is.

Watch this video for a more detailed explanation of the buried dartboard.

So what’s the purpose of a discovery call? Clarity.

When I first started freelancing, I thought the purpose of a discovery call was to make a sale. I felt pressure to perform because I believed the stakes were high.

Now, I know the purpose of a discovery call is clarity—both yours and the client’s.

You’ve probably had that experience where a nice chat with a potential client warmed you right up like hot cocoa and yet afterward you walked away not knowing what specific outcomes the client was after and how you personally could contribute to them.

Better questions yield better insights, so use consultative questions like these to steer the conversation toward clarity:

• Where are we here?
• Tell me about the problem.
• What have you already tried?
• What else have you considered? Is there an easier solution than what we’re picturing?
• Why this? Why not do something else instead?
• What’s the big deal? What’s the benefit? What makes this valuable?
• Why now? Why not postpone the project for 6 months? What changed? Why is this so urgent all of a sudden? Or is it not truly urgent?
• Why me? Why not get an intern or hire your Cousin Vinny? Fiverr?

These questions are purposefully open-ended. Narrow questions produce narrow answers. Wide questions enable you to understand their problems and goals, and at a high level, the transformation they’re after and the value of it.

How to End a Discovery Call

Toward the end of the call, do yourself two favors:

1. Review your notes aloud with your prospect, discuss possible solutions, and quantify the monetary value of the desired outcome—if you can. Otherwise, gather emotional benefits.
2. Ask them to open their calendar and go ahead and book the follow-up then and there. Nobody loves a game of calendar tag.

Once you book that second appointment, you explain that you’ll send a recap email to confirm the project details before you start working on the proposal.

Why do I recommend sending a recap email?

The recap email is a forcing function. You will edit and refine your notes while the conversation is still fresh in your mind.

I alluded to this earlier and it’s worth repeating: Record calls and take meticulous notes so that you can capture the client’s exact word choice and phrasing. If you listen carefully, your prospects will tell you exactly what they want to buy and how they want you to sell it to them.

For example, when a client says he wants his firm’s website to “look good on phones,” a Webflow specialist should not turn around and send him a proposal for “mobile-responsive page designs using a modern, no-code website builder.”

Don’t translate for your clients and revert to your technical jargon or industry slang. Sell to them using their own words. Selling to people in their dialect removes friction.

Recap Email Example

Okay, you might be wondering what a recap email looks like. Here’s one of mine in all of its bullet-pointed splendor:

The result of my discovery call and recap email was a small strategy engagement ($3,675) with a cool machine-learning startup.

In this case, I didn’t even send a formal proposal, but when I do see the benefit of a formal proposal with higher design value and a bit more theatre, I already have a head start. I copy and paste the bullet points from my recap email into my proposal template. I have my notes, too, for filling in gaps.

Yay, I’m nearly finished in 30 minutes.

Remember, what you’re after is trust and clarity, not a sale.

We earn trust and get the insights we need by doing three things during discovery calls: by asking good questions, creating a-ha moments, and bringing clarity.

A splash of technique and the bare-bones tactics I just covered will give you what you need to craft a solid proposal because you took the time to uncover the dartboard. If you ask the specific questions about value and quantify that in terms of monetary value, desirable outcomes, or emotional benefits, then you’ll find it much easier to charge premium prices.

An effective discovery call helps you quantify value so that the client is more focused on the ROI than the initial price.

Don’t let all this blather about effectiveness obscure the real insight. The discovery process I have just covered is so much more enjoyable than trying to convince someone you barely know to buy something you’re not sure they really need.

Why not serve them first by bringing clarity?

If you want the toolkit of open-ended consulting questions I use during discovery calls, put in your email address, and I’ll send you the download link.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign (Group Coaching). Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.