Key Questions Every Prospect Is Asking Before They Say “Yes” (And How to Address Them in Advance)

Our featured expert today is Abby Wood. She has spent years helping agencies refine their messaging, attract the right clients, and streamline their sales processes.

Starting her journey in copywriting, she went on to launch a white-label copywriting and content marketing agency helping agencies craft content that truly connects with their audiences.

As a UGURUS mentor, she has worked closely with agency owners, guiding them through the challenges of growth and positioning.

In this session, she breaks down the key questions prospects ask before committing and how agencies can address them early to build trust, improve conversions, and stand out in a competitive market.

Let’s get started.

Q1. Can you start by telling us about your background and how you became involved in helping digital agencies scale?

I got my start in the wonderful world of copywriting during the recession of 2010. There were absolutely no jobs available, so I decided to bite the bullet and try my hand at something that had always been a pipedream.

I co-founded an eCommerce agency with my now-husband and joined the UGURUS community to help scale it. Getting to know so many agency owners, I realized there was a huge issue with getting copy from clients to a high standard. So, I launched a white label copywriting and content marketing agency called The Content Lab in 2019.

Working with so many inspiring web designers, entrepreneurs, and agency owners, I really enjoyed getting to know their businesses and helping them achieve their goals. I was honored to be asked to be a UGURUS mentor a few years ago.

I know it’s a steep (sometimes very steep!) learning curve to set up, run, and scale your own company. With the insights I’ve gained in my time in the industry so far, I’ve been proud to run many training sessions, webinars, and workshops for agency owners, as well as working closely with mentoring other digital agencies through the UGURUS agency training program.

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Q2. Can you share an example of an agency you’ve worked with that struggled to convert prospects into clients? What challenges did they face, and how did you help them overcome these obstacles?

One of the agencies we’ve worked with for many years is a strategic marketing agency working with SaaS software founders.

The founders came to us with an ambitious goal: to double their number of clients. The problem was they were busy building marketing assets and designing innovative websites for the clients they already had.

They needed extra copywriting and content strategy support to help them deliver captivating, SEO-friendly website and blog content on time and free them up to focus on scaling, but it didn’t make sense to hire a full-time copywriter in-house.

Whenever we have an agency that is struggling to turn prospects into clients, we always check on their brand positioning and brand messaging before we do anything else:

• Are they using language that accurately reflects their business?

If they appear very formal and super professional on their marketing materials but turn up to sales calls in a t-shirt and shorts, there’s a really big disconnect between what the prospect has been attracted to and what’s going to be delivered.

We want to attract good-fit clients who want to work with us, not with a false front that makes us look like something we’re not.

• Are they talking to their audience about pain points and solutions they actually care about?
• Do they speak directly to their reader in their marketing materials and website, or are they just talking about themselves?

With positioning better aligned with their target audience, we focused on educational pieces of content, answering the most common questions their prospects had during the sales process.

By addressing those repetitive queries before leads even reach out to the agency, the sales process is a lot shorter, and the prospects the agency was getting were much better fits to work with them.

We’re effectively the agency’s outsourced content department, delivering content strategy support, blog writing, website copywriting, and more. With our help, they were able to reach—and surpass—their goal of doubling their client base in the first 8 months of working together.

Q3. In your experience, what are the key questions prospects ask before making a decision to work with an agency?  

I find the key questions prospects ask before hiring an agency tend to be the same, with a few more niche questions based on industry/experience with the web:

1. Services and experience questions:

• “What does your team look like? Do you outsource?”
• “What are the services you offer?”
• “I’m aiming to raise my brand’s visibility and get more conversions—do you offer content strategy and SEO services?”
• “How much experience have you had working with my industry?”
• “Do you work with any of my competitors? If you do, how will that work?”
• “Can you show me a portfolio with real-world examples of work you’ve done within my industry?”
• “Can I speak to a couple of your clients to hear their experience working with you?”
• “Are you insured?”
• “Do you work with *software/CMS/programme name*?”

2. Process questions:

• “How does your team get things done?”
• “Who will be my point of contact, and how will we communicate?”
• “What tools do you use to optimize the content?”
• “How do you (or don’t you) use AI throughout your process?”
• “How involved do I have to (or get to) be from start to finish?”
• “How soon can you typically deliver a project like this?”
• “What if something goes wrong? How is a problem addressed?”

3. Pricing questions:

• “How much does *service name* cost?”
• “Can I see a pricing breakdown for the services I need?”
• “Is there any room for flexibility if things change down the line?”
• “What’s included in the monthly service charge?”

Questions like these give prospective clients a clearer idea of how a digital agency can meet their needs, make their jobs easier, and keep their clients happy.

Q4. How can agencies address these questions in advance to make the sales process smoother? Can you share a real example of a strategy that worked for an agency?

The more a prospective client knows before the sales call, the better. Instead of waiting for them to ask, it’s best to make it easy to find as much of this information as possible.

For instance, laying out the services you offer—and the goals that each service can help a prospect reach—clearly on your website brings them one step closer to making a confident decision to work with your agency, especially if you offer something unique.

Service pages are a great place to spell out your process, too, showing how simple it is to go from a discovery call and strategy to content delivery and ongoing support when they choose to partner with you.

Make it clear which industries you specialize in, and publish content optimized for prospects in those niches. Gather social proof like reviews and case studies from clients you’ve worked with before, and place them where prospects can easily find them, building trust before they even get to your contact form.

And if you don’t lay out your pricing structure on your website, have a pricing ballpark conversation on your first call with them. By the time you sit down for the sales call, most of these general questions will have been answered, and you’ll be free to get to know each other better, gain a better understanding of their goals, and discuss how you can help.

Q5. Trust is a major factor in client decisions. How can an agency build credibility early on in the client relationship? Do you have any examples of agencies successfully building trust from the start?

Prioritizing your own branding and marketing efforts—a high-quality, well-optimized website, a value-packed blog, and an engaging social media presence—is a strong start. Addressing their needs, their pain points, and their goals upfront helps position your agency as the go-to expert and builds client trust from day one.

And again, social proof can go a long way. Shining a spotlight on your specialized experience, how long you’ve been in business, how many clients you’ve served, and the positive reviews and successful case studies you’ve collected can reassure a prospect of your expertise.

Knowing that you’ve made a tangible difference for clients like them can strengthen their trust before they even book a call.

And when they do reach out, being transparent about your services, your processes, and your pricing can give clients the confidence they need to start a partnership. From there, it’s all about keeping communication clear and open and delivering on your promises.

Q6. What role does pricing play in the decision-making process, and how can agencies structure their pricing to make prospects feel confident?

In my experience, compared to proven processes, quality, reliability, and trust, pricing isn’t often THE deciding factor when clients choose an agency, but it’s an important factor, nonetheless. A website and effective digital marketing is a significant investment for many companies, and prospects need to know they’ll see real results in terms of ROI when they partner with you.

There are so many different ways to structure pricing, from monthly fees to date-based invoicing – whatever works for you and your clients. I would recommend avoiding deliverable-based invoicing to keep your payments on time and not hanging on their sign-off on project deliverables.

My main advice is to be clear, be honest, and be upfront. Don’t drag someone through 7 meetings just to be told you’re completely out of their budget. Get their ballpark figure on the first intro call and see if you’re a good fit. If you are, continue.

If not, recommend someone else who can help them. Make them feel confident that you know how much your services cost and that you’re not just plucking a figure out of thin air because you think they’ll pay it.

Q7. Agencies often face competition. How can they differentiate themselves effectively to show prospects why they’re the best choice? Can you provide an example of an agency that successfully stood out?

My best advice for differentiating yourself from your competitors is to really lean into what makes you uniquely you. Generic, boring clichés make people move on really quickly.

• Do you have 10 years of experience?

So do 4 other web developers, all competing for the same work. Don’t be afraid to show who you are and what you actually care about (within reason!).

We’re not built to serve everyone, so stop trying to appeal to anyone and everyone. Focus on your favorite client:

• What are they like?
• How do they speak?
• What makes them work with you?

Write your website and marketing materials as if talking to someone just like them.

Become known as the go-to agency for what you do. Expand your ideas and reach in authority content and leadership articles. Guest post on well-respected industry publications, appear on podcasts, lead webinars, and speak at industry events.

I have worked with so many agencies who are knocking it out of the park with this: Squeak Media, engage5w, OGAL Web, LearnRight, Wunderstars, and Branding and Beyond, to name a few!

Q8. How can agencies reassure prospects who may have had negative experiences with other agencies?

Whether it’s over-promising and under-delivering or great one minute and ghosting the next, negative experiences like these can kill client trust and damage your reputation with prospects. Address those pain points head-on, either on your website, social media channels, or in an open conversation with your prospect.

Get clear on what they didn’t love about the last agency they worked with, and show them how your team works differently. A consistent brand presence, strong portfolio, and glowing testimonials will go a long way toward establishing a baseline of trust with your agency’s prospects.

But beyond those?

It’s simple: don’t make promises you can’t keep!

Whether it’s a 2-day turnaround or 1 million quarterly conversions guaranteed, it’s never a good move to promise something you just can’t deliver.

Q9. Could you share any strategies that help agencies refine their communication with prospects to ensure they feel informed and confident?

Establish clear expectations upfront, from which channels you’ll use to check in, answer questions, deliver updates, and field feedback to how frequently they can expect to hear from you.

This keeps them in the loop, reassures them that you won’t just disappear, and gives them a clear, consistent way to collaborate on every project moving forward.

And make sure scope, timelines, and details are all discussed before you start a project, especially with new clients. Using a project management tool Monday.com, Teamwork, ClickUp, or Asana can help keep everyone on the same page, and some clients have unique needs that require a little bit of flexibility on your end.

When in doubt, it’s always wise to gather some feedback to see how communication could flow a little more smoothly for all involved.

Q10. Looking at long-term relationships, how can agencies ensure they continue addressing prospects’ and clients’ concerns throughout their journey with the agency?

As always, the key to a successful, long-lasting relationship is communication. Keep it timely, clear, and respectful, and if problems arise, acknowledge them gracefully and offer solutions to resolve them quickly.

If a client’s gone quiet for a while, check in between projects and see how they’re getting on—they may realize they could use your help on a project they’re working on.

It’s wise to take a look at your internal processes from time to time, too.

• Are there areas where you could smooth out your workflow to deliver better value?

Gathering feedback is a great way to find out—and acting on that feedback in real, tangible ways is a great way to show your prospects and clients how much you care about their concerns.

And a little appreciation goes a long way. Rewarding client loyalty shows them how much you value their partnership. Consider implementing a referral reward program, offering exclusive access to resources, or simply sending a personal thank-you message or gift on National Customer Service Day (April 18th!).

I’m a big fan of sending long-standing clients birthday or Christmas gifts.

Q11. Can you share an example of a particularly successful client win and explain why you think it worked so well?

Addictivity is a UK-based digital agency known as the go-to for recruitment businesses. But when it came to their web design projects, they kept encountering the same issue: copywriting bottlenecks.

Waiting on their clients to write the copy themselves was seriously delaying projects, payments, and client satisfaction. They desperately needed copywriting support—but didn’t want to hire a full-time in-house copywriter that they’d have to keep busy in between projects.

The solution?

A flexible, trusted partnership with my agency The Content Lab!

For the past few years, we’ve been helping Addictivity with all of their copywriting needs. From website copy and lead magnets to video scripts and blogs, we’ve done it all for Addictivity—so they (and their clients) can focus time and energy where they’re needed most and leave the copywriting to the pros!

They no longer hit web copy roadblocks, and their clients enjoy a smooth copywriting experience that perfectly encapsulates their brand.

Why does this partnership work so well? It’s built on trust and strengthened by a deep understanding of Addictivity’s needs, values and goals as an agency—and the audiences they serve.

Q12. Partnerships can play a significant role in helping agencies scale. What are some of the most valuable partnerships or programs agencies should look into to grow effectively?

And as a mentor in the UGURUS agency training program, I’ve been proud to offer that guidance and support to fellow agency owners, giving them the insights, tools, and frameworks they need to lead their agencies with confidence—and see real growth and lasting success as a result.

I’m also proud to be part of The Admin Bar—a community where agency owners and WordPress professionals are welcome to learn, connect, and collaborate. It’s all about sharing experiences, swapping insights, offering support, and pushing each other to grow in effective, sustainable ways.

Q13. Cloudways offers an Agency Partnership Program designed to provide agencies with dedicated support, co-marketing opportunities, and growth incentives. How do you see such programs helping agencies build better relationships with prospects and address client concerns effectively?

As a digital agency mentor, I know firsthand how much it can help to be part of a network of industry experts who get it. In an industry that changes as fast and as often as digital marketing, it’s all but impossible to keep up on your own—let alone get ahead of the game.

With a support system like UGURUS or the Cloudways Agency Partnership Program, agency owners can connect, keep each other up to speed, and open doors to opportunities they might never have found on their own.

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