If you run a web agency, you have probably felt that tension on a sales call. The client wants a price and a launch date. You know you need questions, access, and time before you can promise anything. That gap between “just give me a quote” and “we actually know what this project needs” is where paid discovery lives.

On a recent episode of The WP Minute’s Agency Action podcast, agency owners Toby Cryns (The Mighty Mo) and Kurt von Ahnen (Manana No Mas) unpacked how they use discovery to close better deals, reduce friction, and be seen as strategists, not just “web people.” This post breaks down their best stories and lessons so you can sharpen your own discovery process and get paid for it.

Shoutout to Simon from Down Under

This whole conversation started with a detailed question from Simon, a small web agency owner in Perth, Australia. He wrote in to say how much he enjoys the Agency Action podcast, then asked for something very specific:

How do you sell paid or unpaid discovery? How do you structure it, what should you cover, and how do you use it to stand out as a business strategist instead of just the “web guy”?

Simon has already run a handful of successful paid discovery sessions and wants to improve his process. Toby and Kurt took that as a chance to talk about:

• Why discovery exists in the first place
• When to charge for it and when to eat the cost
• How naming and pricing affect perceived value
• How to stop giving away free consulting

They closed by inviting more questions from listeners on LinkedIn, YouTube, and podcast platforms, so if you recognize your own struggles in this post, they want to hear from you.

Ditching the “Web Guy” Label: Position Yourself as a Pro

Why “Web Guy” Can Hurt Your Business

Kurt used to lean into the title “web guy.” He even put “Kurt von Ahnen, web guy” in his social bios in the early days. It felt simple and clear.

As his agency grew and he started working with larger organizations, he noticed something. In corporate settings, “web guy” was a kind of downspeak. It sounded like “the person who updates the site,” not a consultant or strategic partner. He compared it to calling someone a “trash man” instead of a “sanitation engineer.” Same job, very different level of respect.

Toby pushed back a bit, and his point is important. For some clients, especially local small businesses, “web guy” is exactly the language they use and trust.

A donut shop or plumber might say, “We just need a web guy.” In that context, it can be helpful to mirror their words and say, “Sure, I can be your web guy.” The key is situational awareness.

Different audiences expect different things from you:

• Corporate and nonprofits with boards and RFPs: They are often comfortable with a clearly defined discovery phase and will pay for it if you explain the value.
• Mom-and-pop shops: They usually want a site yesterday and have little interest in a formal discovery phase. They just want the phone to ring.

Toby and Kurt both treat this as a language issue, not a purity test. You do not have to pick one label forever. You adjust based on who is in front of you.

Discovery as Your Differentiator

Discovery is where you stop being “the web guy” and start showing up as a strategist. Anyone can promise a homepage and a contact form. Fewer people can ask the right questions about sales goals, customer journeys, and content ownership.

Clients often say they want “a simple five-page site.” In discovery, you find out what that really means:

• Who are your best customers?
• What do you want them to do on your site?
• What should be easy, and what should be hard?
• What does success look like one year after launch?

When you talk about things like that, you sound less like a vendor and more like a partner. That is one reason so many successful agencies pitch discovery as a core part of their value. Agencies like Matchstick explain that paid discovery can reduce scope creep and clarify value before a big build even starts. Others, like Holler Digital, stress strategy beyond visual design. (Design is still important though – like not having your sales announcement block your menu)

Discovery is where you earn the right to charge more and to help steer the project.

The Car Shop Analogy: Why Clients Resist Discovery

Kurt has a favorite analogy for discovery, and it lands because it is so familiar.

Imagine your check engine light comes on. You pull into a repair shop and say, “Just turn off the light.” The service writer does not do that. They talk about diagnostic fees, tests, and estimates. To you, this feels like a delay. To them, it is the only honest way to find the real problem.

Many web clients treat their website the same way. The “check engine light” is:

• “My site looks old.”
• “Leads dropped this quarter.”
• “We need a better menu structure.”

They say, “Just fix it,” and get confused when you talk about user journeys, calls to action, or information architecture.

Kurt shared a directory site example from Manana No Mas. The project involved 30 businesses, so he insisted on a single point of contact. For two months, no one sent bios, photos, or social links. The team finally shipped the site with placeholder content and a tutorial.

Once it launched, all 30 stakeholders suddenly had strong opinions.

“Where is my logo?”
“Why is my description so short?”
“Why did you not link my Facebook page?”

The answer, of course, was, “You never sent anything.” This is a classic case where discovery would flag content risks early, and a clear process would make it easier to say, “We cannot move forward until we have your assets.”

Toby shared a similar struggle. His team was working on a redesign for a company owner who was deeply involved, had already paid in full, and still refused to engage in conversations about navigation or user journeys. Both sides felt stuck.

The shared lesson is simple: discovery is not about padding the bill. It is your “diagnostic fee,” so you can be honest about what it will take to get things running.

When And How To Do Discovery

Everyday Micro Discovery

Not every discovery phase needs to be a workshop with Miro boards and stakeholder interviews. Toby’s team does tiny paid discovery tasks every week.

If a client asks for a feature or reports a bug, they do a quick mental test:

• If it takes under 15 minutes to understand, they might handle it as part of support.
• If it looks like more than 15 minutes of digging, they quote one or two hours of research time to scope it.

Almost every client accepts that. It feels fair, and it prepares everyone for a realistic estimate. That is still discovery. It is just scoped very small.

For SEO projects, discovery is not optional. It is most of the work. Toby says 80 percent of an SEO engagement is research and analysis. You cannot “just do SEO” without:

• Keyword research
• Competitor analysis
• Technical review
• Content audits

That is all discovery, and it is baked into the offer.

If you struggle with what to ask during early calls, tools like AgencyAnalytics publish lists of discovery call questions for agencies that can help you build your own script.

Discovery For Larger Projects

For full redesigns or complex builds, discovery has to cover more ground. Toby’s agency sells it as part of the overall process, not as a separate scary thing.

When a client signs up for a redesign, they expect conversations about:

• Site navigation
• Page hierarchy
• Calls to action
• What users are searching for on Google
• Content ownership and production

Kurt goes even further on the planning side. As part of his discovery outcome, he will estimate how many meetings a project will need based on:

• The number of stakeholders
• The complexity of the build
• The expected duration

For example, in an eight-month project with several stakeholders, he might forecast ten meetings. That list goes straight into the proposal. If the client starts asking for extra “quick calls” every week, he can gently point back to the agreed count and either:

• Address whatever is stressing them out
• Or explain that more meetings mean more cost

Toby takes a simpler approach. He does not calculate the exact count in advance. He just prices projects in a way that leaves room for the expected number of meetings. Different styles, same goal: protect your time without being rigid or defensive.

Free vs Paid Discovery

Kurt splits discovery into two buckets.

Free discovery covers:

• A 15–30 minute call
• A quick look in the WordPress admin
• A sanity check on whether a request is even possible

He treats this as “cover your butt” time. Sometimes a request sounds easy until you see a tangle of plugins or a fragile theme. That short look saves him from bad surprises.

Everything beyond that is paid discovery. If he is going to spend hours digging through a codebase, reviewing content, or mapping a user flow, that is billable. Agencies like OGAL Web Design have moved fully to this model, as described in this article on requiring paid discovery. It is not about being greedy. It is about aligning your effort with real money.

What You Call It Shapes Its Value

Not every client loves the word “discovery.” Kurt joked that it sounds like “Dora the Explorer” to some people. Others hear it and say, “What do you need to discover? I thought you were the expert.”

You can often keep the process the same and change the label to match the audience.

Here are some common names and why they work:

Name	Why It Works
Discovery	Clear for marketers and larger organizations.
Diagnostics	Easy to understand, like at the auto shop.
Project consult	Sounds like tailored advice for their situation.
Strategic blueprint	Emphasizes planning and direction.
Website roadmap	Suggests a concrete plan, not just talk.
Planning phase	Fits nicely into waterfall-style corporate processes.

Legal and agency advisors point out that a paid discovery phase can simplify contracts and reduce risk. You can use a lighter agreement for discovery, then a fuller scope of work once you know what you are actually building.

The important part is not the label. It is that the client understands, “We are going to slow down a bit at the start so we do not waste time and money later.”

RFPs, Free Work, And The Paid Discovery Trap

Toby’s agency has been responding to more RFPs lately, and it has been good for growth. They are presenting in person, pitching to boards, and often pulling in an MBA to do real market research. That is serious time and money.

In the past, pre-proposal discovery might have been a 30 minute call. With RFPs, it can easily turn into 10 hours of preparation before a contract is signed.

If you are not careful, you end up doing a full discovery project for free, just to have a shot at the build. That problem is so common that coaches like Agency Mavericks have whole guides on defining paid discovery and how it fits your sales cycle.

Kurt suggests a different path for some situations:

• Sell a paid discovery engagement as its own mini project.
• Deliver a detailed proposal and roadmap at the end.
• Give the client explicit permission to shop that proposal with other agencies.

Now you have been paid for your thinking, even if they decide to hire someone cheaper to execute.

That hurts a lot less than spending 20 unpaid hours scoping an RFP, losing the bid, and having nothing to show for it.

Sell Outcomes, Not The Discovery Line Item

Toby made a strong point that might sting a bit: if you are debating the value of discovery with a prospect, you are probably losing the sale.

When a buyer wants to talk about why they should pay for discovery, that conversation is about your process, not their outcome. It is not exciting for them.

A better approach is to sell the end state:

• “Your new site will be easier to maintain.”
• “Your team will spend less time fielding confused emails.”
• “You will have clearer data about what is working.”

Discovery is how you get there, but it is not the hero of the story.

On the pricing side, a lot of agencies use a credit model:

• Charge for a small paid discovery engagement.
• Apply that fee as a credit toward the larger project if they move forward.

You still raise your final project price to keep margins healthy, of course. Agency coach Karl Sakas shares more about this “mini project first” model in his guide on getting started with paid discovery at your agency.

Kurt’s own discovery pricing has climbed over time. He started at $500, then $1,000, then $1,500, then $2,500. On one group call, he later learned the client had valued the session at $10,000. That was a wakeup call about how much he was leaving on the table.

Price communicates credibility. If a room thinks you cost $200 for a strategy session, they treat your time differently than if they think you cost $10,000.

Make Discovery Mandatory And Protect Your Time

Both Toby and Kurt now treat discovery as non-optional. Every project has some form of it, even if it is not labeled that way in every proposal.

They also tie it tightly to payment.

Kurt’s rule at Manana No Mas is simple: all work is prepaid. Every time he bends that rule because a client is “nice” or “long term,” he ends up chasing invoices. The relationship is good, the behavior is not. Delayed payment hurts cash flow and creates awkward tension.

Toby used to require full payment upfront for all projects. As his client size grew, he had to adapt to formal procurement processes. Some larger clients wanted net-15 terms and milestone-based payments.

They found a middle ground:

• They agreed to net-15 terms, but refused to start work until the first payment landed.
• When a client wanted payments tied to deliverables, they agreed, but defined their own milestones. For example:
  • 20 percent at kickoff
  • 30 percent when initial designs are delivered
  • 40 percent when the staging site is ready
  • 10 percent at launch

One key rule Kurt holds: no money after launch. Once the site is on the client’s URL, and especially if they have admin access, the invoice balance should be zero. That removes the risk of someone changing the site, then arguing about what was delivered.

Kurt’s background in big corporations helps here. He has seen how large firms delay vendor payments with excuses like, “We only cut checks Thursday afternoon.” As a small agency owner now, he is more firm with large companies than he is with small ones. They have more flexibility than they pretend.

How Their Discovery Process Evolved

When Kurt started building sites for other people in 2002, he did not call anything “discovery.” He just thought he was being a good professional. People came to his office, shared their business ideas, and he asked lots of questions.

He later realized he had been doing free business consulting for years.

Some people used his advice to launch successful businesses and never hired him. Others half-applied his suggestions, struggled, and then blamed his “bad advice,” even though there was no formal engagement or payment.

That pain is what pushed him to name and charge for discovery.

Toby went through a similar shift. He now treats early coffees and intro calls as places to share process, not specific advice. He will explain how The Mighty Mo runs projects, but he does not solve a prospect’s unique problem on a free call.

Stop Giving Away Free Consulting

Toby told a story that will feel very familiar if you are naturally helpful.

He got a cold call from someone who found his agency on Google. The caller described a DNS and hosting problem. Toby, trying to be useful, asked smart questions, walked through possible causes, and explained what his team would do.

At the end, the caller said, “Great, I am going to tell my web guy this,” refused to share the site URL, and hung up.

That was 100 percent free consulting handed straight to a different vendor.

Kurt sees this pattern in other industries too. In his powersports training work, he warns service writers never to “diagnose at the counter.” If you guess, “It is probably an oxygen sensor,” the customer buys a part, installs it, and still has a check engine light. Now they blame you.

The same principle applies to discovery. Until there is a paid engagement, you are not there to fix their exact issue. You are there to:

• Listen
• Decide if you are a fit
• Explain how your process works

The fix itself belongs inside paid discovery or the main project.

Turn Discovery Deliverables Into Sales Engines

Toby: Recurring Revenue And SEO Opportunities

Toby treats discovery as a chance to find the right long-term fit, not just upsell for the sake of it.

During discovery, his team looks for:

• Slow or insecure hosting that hurts performance
• Missing security and update processes
• Gaps where SEO could drive meaningful traffic

If a client is on good hosting, he will not push a move, even if he could. If performance is bad or security is poor, he will gather data during discovery and then present a clear case for switching.

That is in line with what many agencies have found. Done well, discovery uncovers real problems and leads into steady revenue like hosting, maintenance, and SEO retainers. It is not a trick. You are getting paid to find and fix things that actually matter. Firms like Matchstick talk openly about these benefits in their writing on why paid discovery is crucial for agencies.

Kurt: Good, Better, Best Proposals

Kurt’s favorite discovery deliverable is a detailed proposal, usually 8–10 pages, with three pricing tiers: good, better, and best. Discovery gives him the data he needs to build those tiers honestly.

A simple version of his model looks like this:

Tier	What It Typically Includes
Good	Meets minimum needs, covers core pages and basic functionality.
Better	Everything in Good, plus hosting, updates, and more support.
Best	Everything in Better, plus premium services such as client support.

Because his agency does a lot of e‑learning, his “best” tier often includes taking over support emails from learners. Instead of the client’s staff resetting passwords or answering “how do I log in” questions, Manana No Mas handles it.

That is a real, ongoing business problem solved, and it comes straight out of what he hears during discovery.

Toby summarized it nicely near the end of the conversation: the output of discovery is a proposal you can sell. If your discovery work does not lead to that, you probably need to adjust what you are doing.

Where To Learn More And Stay Connected

If you want to go deeper on these topics and hear more stories from real agency owners:

• Follow Kurt von Ahnen on LinkedIn and check out his agency, Manana No Mas, for web and e‑learning work.
• Connect with Toby Cryns on LinkedIn and visit The Mighty Mo, his Minneapolis‑based web agency.
• Explore WP Minute for more WordPress news, the Agency Action podcast, and a free course about reselling hosting.

You will find more perspectives on paid discovery from agency owners, lawyers, and consultants who have been where you are.

Conclusion: Treat Paid Discovery As A Service, Not A Freebie

Paid discovery is not a fancy label for “extra meetings.” It is the work that lets you scope projects honestly, avoid messy surprises, and show up as more than a “web person.” When you charge for that thinking, you send a clear signal that your expertise is part of the product, not a free add‑on.

Start small if you need to. Add a couple of research hours to your next feature request or redesign. Rename discovery to fit your clients. The goal is to move your agency to a place where discovery is recognized as real value, for you and for your clients.

And if you are still giving away detailed answers on free calls, take Toby and Kurt’s hard‑earned advice: stop diagnosing at the counter.