Hiring a Marketing Agency — Are You Asking the Right Questions? — Jesse Olive
JESSE OLIVE
Brushed steel pyramid on a writer’s desk
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June 2026  ·  15 min read

Why most businesses ask the wrong questions when hiring a marketing agency.

One of the questions I get asked most often is whether a business should hire a marketing agency. It’s usually framed as though there’s a definitive right or wrong answer, but after 28 years working with agencies—competing against them, hiring them, managing them, and returning to them later in my career—my answer has always been exactly the same: it depends.

It depends because most business owners are asking the wrong question. They aren’t trying to figure out whether an agency is right for their business, but are instead trying to evaluate a highly specialized service they are rarely equipped to judge. When you are looking into hiring a marketing agency, that lack of structural evaluation becomes a very different, and very expensive, problem. If you decide an agency is the direction you want to go, let me vet your prospects before you sign anything, because I know agencies from angles most people never see.

Sitting in every seat at the table.

My career started as a web design intern, which I turned into a lead position before graduating. By the time I left, I was being brought into sales meetings to represent the creative and development side of the business because the traditional sales team had been phased out and I had become the person who could speak to both the work and the client. It wasn’t a full-service agency by today’s standards, but it was my first education in how agencies operate, how they sell, and how they think about clients.

This early foundation proved invaluable when, after college, I became Director of Internet Services before making the decision that shaped everything after it: I started my own company. The timing was right, as the dot-com crash had exposed something I couldn’t ignore. Companies had been paying well over $100,000 for websites that small businesses didn’t need and couldn’t afford. I knew I could build better work at a fraction of the cost, and I went straight after the Charlotte market—and won—against agencies that had been there for years.

I didn’t win because I had more people, but because I understood what those businesses actually needed and built systems around delivering it. I ran that company for years, building custom content management systems before WordPress, Joomla, or Drupal existed—not because I was ahead of my time, but because I watched a broken pattern repeat itself everywhere. Agencies would finish a design, hand it off, and wait, sometimes for months, while clients had to stop running their businesses long enough to produce content. The website just sat there generating nothing, and a custom system solved that bottleneck by naming the problem and the solution in the same breath.

Seeing how these systems transformed client outcomes ultimately shifted my trajectory into executive roles, where I became the person responsible for hiring and managing agencies rather than competing against them. That is where I learned the other side of the gap—not just what agencies were selling, but what business owners and stakeholders actually needed that agencies rarely delivered.

Armed with that dual perspective, I eventually returned to agency environments, where I helped build digital marketing departments, introduced programmatic advertising, got certified in campaign management platforms, and overhauled operations. The unique perspective that comes from having sat in every seat at that table is exactly what most businesses are missing when they begin the process of hiring a marketing agency.

Understanding the alignment gap.

When you sit across from an agency, you’re usually talking to someone who is very good at their job—and their job is to close you. That is worth understanding clearly. An agency salesperson isn’t just representing their company; they are representing their own livelihood. The pitch is polished because the stakes are real for them. That doesn’t make them dishonest, but it does mean their incentives and yours aren’t perfectly aligned from the first conversation, and that dynamic doesn’t disappear after you sign the contract.

Contrast that with a strong internal marketing hire, a contractor, or a consultant. They aren’t there to sell you on anything; they are there to do the work. If they are genuinely good, their first instinct isn’t to impress you with a deck or sell you into a campaign, but to establish structure and build visibility into what is actually working and what isn’t.

That distinction matters. It doesn’t mean hiring a marketing agency is wrong for every business, but it means you should walk into that sales meeting understanding exactly what kind of conversation you are in. It doesn’t pay to lie to yourself or bloat your own ego to the point of thinking you know what you don’t know, just as your marketing person might not know everything you know.

The leadership vacuum and the systems thinker.

Admitting what you don’t know is crucial, because looking at an agency requires balancing what you are actually buying versus what you are capable of managing. On one hand, a good agency removes real operational burden because you don’t have to hire specialists or manage multiple disciplines yourself. For a business owner who isn’t ready to bring marketing leadership in-house, that convenience has real value.

The problem, however, is that most business owners don’t understand marketing well enough to provide the leadership that needs to exist before an agency is ever hired. If that leadership isn’t there going in, the agency fills the vacuum on their terms, not yours.

This problem is compounded by the fact that agencies vary enormously. Some are exceptional, some specialize in one discipline while selling ten, some produce beautiful creative but can’t connect it to strategy, and others know the advertising platforms cold but can’t explain how any of it connects to your bottom line. Furthermore, almost none of them have visibility into what happens inside your business after their marketing works.

That is exactly why you need a marketing systems thinker managing the relationship. A systems thinker knows how to extract real value from an agency and turn their deliverables into permanent business assets. They understand how to integrate marketing data with actual sales operations, maximize the value of every strategy conversation, and manage the agency to ensure they provide reporting in a format that actually drives decisions.

Most importantly, a systems thinker builds a foundational system that stays within your company, slowly wrapping its arms around more and more of your marketing operations over time. This setup ensures that if the relationship should ever sever, the agency’s “stinger is still left in the skin”—meaning your business retains the infrastructure, the data history, and the assets rather than being left with nothing.

Because your company owns the system, you gain the agility to easily pivot to another agency, hire internal resources, or seamlessly move the entire operation in-house when the time is right. They know how to quantify real performance, dictate exactly what data the agency must provide, and look far beyond surface-level fluff like a daily click count on a social post.

Without that internal filter, general business savvy simply won’t qualify you to protect yourself when hiring a marketing agency. To be fair, most business owners aren’t completely oblivious to marketing; they built their business, know their industry, and many came up through sales.

But the digital age has added a thick layer on top of all of that over the past two decades. It doesn’t equip someone to evaluate whether an agency is genuinely strong in a particular discipline, whether they are offering what you need first versus what they’d rather sell you, or whether the strategy they are pitching is even the right starting point for where your business is right now. It also doesn’t put you in a position to roll up your sleeves and work alongside, in tandem with, or instead of that agency when the situation calls for it. That is a different skill set entirely—one most business owners don’t have and shouldn’t be expected to have.

I watched this play out firsthand when an agency was working its way into a business over me, brought in by a supervisor who lacked the digital background to evaluate what he was actually considering buying. I never hired them, but I watched them try to get hired. From what I could see, they were mildly competent at SEO and not much else, yet they were positioning themselves to own everything.

I saw where it was heading, had better opportunities waiting, and took one that offered more money to work with people I’d worked with before and trusted. I only learned what ultimately happened through relationships I maintained inside the organization. That is why you need someone in that seat who knows what they are doing before any agency ever walks in the door, because unfortunately, that lack of internal oversight is also where many businesses lose visibility into whether their agency is actually producing results.

Auditing the fluff: revenue tracking over report formatting.

This exact lack of visibility explains why I’ve reviewed agency reports that looked impressive until I examined what was actually in them, such as keyword rankings built entirely on variations of the company’s own name. If you type your own name into Google and you come up first, that’s not an achievement—that’s just having an indexed website. Those aren’t growth keywords; they are brand searches from people who already know you exist.

I’ve also seen reports loaded with keywords that technically ranked but had only five or ten searches a month, which is technically true but practically meaningless. Business owners often don’t know enough about how this works to ask the right questions, and some agencies count on that.

Here’s what separates the businesses that get this right: they’ve invested in tracking systems that tie marketing and advertising directly to revenue. They don’t just look at traffic trends or ranking movement, but actual revenue traced back to the medium, the campaign, and for paid platforms, often the specific keyword that drove it. That’s not a luxury; it’s the baseline for any intelligent conversation with an agency, and without it, you’re not managing an agency relationship—you’re funding one.

Modern tracking does something even more important by capturing first-click attribution, which identifies the tactic that started a prospect’s journey, rather than the last thing they touched before converting. Last-click attribution gets the default credit, but first-click tells you what actually moved someone from unaware to interested. That distinction matters because of what it reveals about how people actually find businesses.

SEO is still the single biggest lead converter in digital marketing by a wide margin. When someone finds you through a non-branded keyword phrase, they didn’t know you existed; they were searching for a solution, you appeared in the top results, and they clicked. That’s not a supporting touchpoint—that’s the exact moment your relationship began. First-click attribution captures that, while last-click buries it, and if your agency isn’t tracking first-click, they may be taking credit for a journey they didn’t start.

Some tracking platforms are pushing toward Multi-Touch Attribution to map the entire customer journey across what research shows averages 27 interactions in a B2B sale, tracking the role that calls, SEO, emails, and paid ads each play before a deal closes. For enterprise companies running coordinated campaigns across SEO, paid search, display, social, TV, and radio, that kind of full-funnel visibility has real value.

But most small businesses aren’t running that; they are investing in two or three channels—usually digital—and the question isn’t how all these touchpoints contributed, but rather which of these few things is actually starting conversations. For that question, first-click is cleaner, more actionable, and a lot harder to spin.

If you’re not tracking any of this, you have a problem. Agencies don’t typically build that infrastructure for you, and without it, you can’t prove or disprove what’s actually driving your revenue, leaving most agencies happy to take credit for results you have no way to verify. The businesses investing in proper revenue tracking can speak intelligently to their agency, ask sharper questions, and spot the difference between real performance and a well-formatted report.

The reality of the retainer model.

Beyond navigating these complex data reports, you also have to brace yourself for the financial reality of how these firms operate. Agencies that are genuinely excellent at everything are expensive, and there is a clear reason why. Building teams with real depth across strategy, creative, paid media, development, analytics, SEO, branding, and account management isn’t cheap.

When you’re paying for all of that expertise, you’re also paying for the infrastructure that holds it together: office space, management, sales, operations, software, and profit margin. Industry data and my own experience suggest that only about 35 to 50 percent on average of what you pay an agency actually funds the direct work going toward your account, while the rest covers what it costs them to stay in business.

That’s not a condemnation, as that is simply how agencies work, but it is why businesses that compare an agency retainer against an internal hire and wonder where the volume of work and communication went are comparing two completely different business models. Neither is automatically better, but you need to know what you’re actually buying.

Demanding partnership over procurement.

Because of these steep overhead dynamics, agencies often get evaluated on the wrong things—like portfolios, logos, awards, and misleading case studies—to justify their price tags. All of that matters on the surface, but none of it answers the question that actually counts: can this agency consistently produce measurable business results, explain how, and show you the proof?

Can they tell you what changes inside your business once their marketing succeeds? Because if they can’t speak to that, they’re selling you a service, not a partnership.

The real problem isn’t that bad agencies exist, but that most business owners don’t know what questions to ask, don’t have the marketing depth to evaluate the answers, and don’t have anyone in their corner who does. An agency will fill whatever vacuum you leave them, meaning the businesses that get real value out of agency relationships are the ones that show up with leadership, structure, clear expectations, and the tracking infrastructure to hold everyone accountable—including themselves.

You don’t necessarily need a bigger agency or a more expensive one.

You need someone who knows how to evaluate both, and who is more invested in your growth than in keeping the engagement alive. Hiring a marketing agency shouldn’t feel like a roll of the dice. That’s a very different conversation than the one most business owners walk into, and it’s the one worth having before you sign anything.

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