10 Questions to Ask When Choosing a Digital Agency

Asking questions is the first step to determining whether you can trust anybody with anything. And the same can be said when choosing a digital agency partner. A competent and aboveboard agency will welcome your questions. Here's a list of ten critical ones you should feel free to ask.

by Drew Barton

Inbound Marketing

Reading Time | 8 min

Asking questions is the first step in determining whether you can trust a digital agency with your digital assets. An agency that is competent and aboveboard is going to welcome your questions and will have clear answers to them. An agency that is dishonest or doesn’t have their act together won’t have clear answers or will employ diversion tactics to avoid answering. That being said, vetting an agency isn’t just about asking questions in general but also asking the right questions. Think of this stage as a job interview for the agency. If you’re about to hire this person or company to work on your behalf, asking the right questions will give you a clear indication of whether or not the agency is worth hiring.

What are the “right” questions?

Question mark on a chalkboardThe “right” questions differ from project to project, and not every good digital agency practices the exact same workflow. The important guiding principle here is for you to gain confidence in a prospective digital agency, so the right question is any question that helps you gain that confidence. Likewise, there might be no single right answer to the question — you just need to be satisfied with the answer before moving forward. In this blog post, we’re going to hone in on a few key questions you should ask during the vetting process to help you determine whether to entrust an agency with your project. The answers you receive should tell you whether to move ahead with the company or walk away.

Q: Have you done work for companies similar to mine? If so, may I see it?

Asking this question helps you determine if the digital agency has any experience working with a business like yours. Do their solutions represent a good fit for your type of business? It’s not necessarily a deal-breaker if they haven’t worked with companies similar to yours, but it’s something you’ll have to take into account. If you’re a law firm, for example, and the agency’s experience consists mostly of drop-ship eCommerce sites and retail stores, you may need to be prepared to navigate a pretty steep learning curve with the agency as they adapt to your business needs. If you’re willing to walk that path, fine. If not, you might want to keep looking.

Q: Is all the work being done in-house, or will you be subcontracting work to freelancers or overseas?

Some digital agencies handle all the aspects of development with full-time employees, while some may hire subcontractors to carry out certain elements of the project. For example, if you need web copy written for your site and the agency doesn’t have a staff copywriter, they may hire a freelance writer to compose the copy for you. It’s not “right” or “wrong” if an agency hires subcontractors — many excellent websites are created with the work of highly experienced freelancers. This question is more about knowing who will have a hand in representing your business online. Ultimately, it’s the agency’s responsibility to make sure everything is correct with your site, whether they subcontract certain parts of it or not. That said, it’s completely appropriate for you to ask them to identify which elements of the site will be handled by freelance labor and who will perform the work. If you’re uncomfortable with the proposed arrangement, you’re free to look elsewhere. Likewise, if you feel their answer to this question is vague, it may be a warning sign.

Q: What are the terms of payment?

Logistics and details about payments will be mapped out more concretely during the contract process, but it’s important to bring this up during the vetting process, too. Why? Not only will it prepare you financially, but it will also help you to further vet the agency’s professionalism. Does the agency expect payment installments by certain calendar dates, for example, or by the completion of certain project milestones? Or perhaps they tell you something vague, like, “Oh, don’t worry about that right now — we’ll get to that later.” If an agency can explain their payment expectations clearly, they’ve obviously put some effort into developing a payment policy that is fair to both parties, however, they choose to be paid. Incidentally, you should never pay in full upfront because it instantly makes you vulnerable by assuming all the risk, while the agency assumes none. If a digital agency asks for up-front payment in full without a convincing reason, this is a huge red flag.

Q: Is this a fixed-price project? If not, what could make the price increase or decrease?

Bear in mind that you’re not necessarily demanding that the digital agency give you a firm quote here — that can come later. What you’re asking is whether the agency can give you a firm estimate once they understand the full scope of your project, and if not, what the variables might be. Your goal in asking this question is to determine whether the agency actually has developed consistent, fair pricing for its services and whether you could be blindsided with unanticipated expenses further down the road.

Q: What is the estimated time frame for a project like mine?

Once a good agency understands the scope of your project, they should be able to provide an estimate of how long the project will take. There’s no litmus test for how long a project should take — it depends on how much work must be done on your website, the agency’s current schedule, etc. — but the key is that they should be able to provide some sort of specific answer, even if the timeline needs to be adjusted along the way. If they can’t give you an estimate for completion, it’s a signal that they might not have thought it through, or worse, that they don’t have a good grasp of their own project management process. If you work with the agency, under those circumstances, be prepared for delays.

Q: When my website goes down, who do I call or email? How long before I can expect a response?

Statistically speaking, your website will go down at some point. By asking your digital agency what their procedure is in such cases, you’re really asking whether they have a procedure in place. As long as they provide an answer you’re okay with, you should be good to go. But if they balk at this question, expect long periods of downtime with slow response times because they’re obviously not prepared for the inevitable.

Remember: It’s not just what they answer, but HOW they answer.

The answers to all these questions aren’t as important as how the digital agency answers them. The most important thing is that the agency can answer the question, clearly and succinctly. From there, you decide whether you can live with the specifics. If the answers are too vague and you can’t get the agency to be more specific, that could be a red flag. Likewise, agency representatives acting annoyed or frustrated by your questions is another potential warning sign. A good agency wants to make the working relationship as clear as possible, so they will welcome as many questions as you need to ask.

Ask yourself some questions, too

So the digital agency has survived all your questions and answered at least most of them. Now it’s time to ask yourself a few questions before moving forward.

Q: Do you like their work?

When you look through the agency’s portfolio or client list, do you like what you see? It’s not enough that you have a friend who strongly recommends them, or even that they conducted themselves in a professional manner. If you can’t honestly say that you personally like at least 75 percent of their work,  chances are you’re not going to be happy with the work they do for you. This is highly subjective, of course, but it matters. They might be entirely trustworthy, but that doesn’t mean they’re the right fit for your business.

Q: Do you respect the company?

In addition to liking their work, do you feel you can respect the people on the team, the agency’s process, and the product? This is important to ask yourself, because you may be working with this digital agency for some time to come, especially if they will be hosting and maintaining your website after building it.

Q: Can you accept the estimated time frame the agency gave you?

Most clients ask one question: “How long do you think this project will take?” It’s a valid question, but not the right one. Most projects have multiple milestones. Heck, even washing your clothes has multiple milestones. The question you need to ask is “How long will each phase take?” This will give you a much clearer idea of the microphases of your project — and if one phase runs long, you should expect the final deadline to do the same. Only airplanes are able to make up time in the air.

Q: Are you satisfied with the digital agency’s answers?

During the vetting process, were you in agreement with the agency’s responses? If not, are there any deal breakers in the mix? Is there room to negotiate with the agency? If you have misgivings about the payment schedule, for example, can you suggest an alternative approach? In many cases, the agency might be flexible with certain policies in order to make the client comfortable. In others, they might stand firm. If you feel comfortable with most of the answers they give you, it might be worth it to ask about one or two sticking points. If you find yourself having trouble with most of their policies, however, it’s probably best to walk away rather than press a list of issues. Once you’ve answered these questions, you can determine whether you want to move forward with an agency.


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Drew Barton | President and Founder

Drew Barton is the President and Founder of SiteCare, LLC. For over two decades, Drew has helped thousands of businesses grow online. He is the author of the book, Buyer’s Guide to Websites, an Eagle Scout, and he is active in the Entrepreneurs' Organization.