Business of Web Development
·12 min read

12 Discovery Questions to Ask Freelance Web Development Clients

As a freelance web developer, being able to complete your work from a technical perspective is only half of the job. To be a successful freelancer, you also need to take a client’s vision and turn it into a tangible product that achieves the business outcomes they desire.

This is why asking the right discovery questions when starting a project is vital. The right questions not only ensure you understand the project’s scope and deliverables but also allow you to deliver a higher quality product that is better suited to your client’s needs.

A higher-quality product is more likely to yield a happy client who will recommend your services to other potential clients. So, in short, by asking the right questions at the start of a project you’re setting the stage to grow your business in the long run.

So with all of this in mind, we will look at 12 questions you can ask in your next web development project. Let’s get started.

Business Questions

In this section, we will focus on questions that you can ask a client to get a better understanding of their business, how it functions, their clientele, and how these factors can influence your decisions on the project.

Q1 - How do you envision this project helping your business, both in the short- and long-term? Are there particular objectives you’re looking to achieve?

This question draws out the underlying motives behind a project from the business’ point of view. Businesses don’t spend money for no reason; they need a tangible return on their investment, and we want to understand what they’re looking to gain.

For example, clients may want to increase sales on their eCommerce platform, increase traffic to their blog posts, or improve their site's SEO rankings. These are all valid goals for a business, and we need to understand them upfront so we deliver a product best-suited to achieving them.

Another key part of this question is the time-boxing we ask them to do by thinking about their short and long-term goals. This time-boxing allows us to implement solutions that achieve both types of goals and prompts the client to think about them if they haven’t already.

A good example is the short-term goal of increasing traffic to a blog. That’s a good goal but we need to understand why we are increasing the traffic. Is it brand reputation? Is it monetization of the traffic? Or, something else entirely? By helping the client think about their goals and the timeframes they want to achieve them in, we can collectively implement a solution now that can be extended easily in the future to support their long-term goals, rather than coding ourselves into a corner.

Essentially by understanding our client’s goals and timeframes, we can collectively build a better picture of the solution that needs to be implemented and then work on building that together.

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Q2 - Who will be leading the project from the business side?

As a freelancer, you need a single point of contact in the business to whom you can direct any queries, have catchups with, and ultimately receive approvals from. By asking the client up front who will be leading the project before starting work, you can build a rapport with them and start a collaborative relationship from the beginning.

Another outcome of this question is getting the business to decide on a project lead and assigning accountability and authority to that person if they haven’t already. As a freelancer, this might be something you think you don’t need to worry about, but if there isn’t a single person with authority to take direction from, it can be easy for a project’s requirements to change and shift as multiple people from the business give their opinions.

Often inside a business, different people will have different visions of how a project should work, look, or function. Ultimately, if this isn’t managed or addressed early on by the business this leads to scope creep for you. If we’re not careful a project can swell in size and end up a lot larger than originally intended, which comes with its own set of problems.

This is why it’s key to establish who the project owner will be and ensure that all new feature requests and scope changes are signed off by them. This ensures the scope stays manageable and a cohesive view of the final product is overseen by one stakeholder.

Q3 - Who would they consider to be their biggest competitor(s) in their industry right now?

This seems an unusual question to ask at first but understanding who the client is competing against for business can help you deliver a better project. Once you have the competitors’ names, you’re able to scope out their websites. What do they well? What could they improve on? What are they missing? Things to note about them?

You can then take the best ideas from their competitors for your project, add in the things they missed, and avoid the mistakes they made. Why is this important? Because, your client and their competition are fighting for the same consumers, which means if you can create a website that the consumers will enjoy using more, you increase your client’s chances of taking the competition's market share.

An image of a team meeting around a table that is scattered with company reports, notebooks, a laptop, and an iPad.

Q4 - Describe your typical/average user?

The most important part of a business is its customers. Without the customer, there is no business to run. This is why it is important for us to help the client build a project that emphasizes their users.

We want to work with the business to get as much information on the people who will be using the website as possible; we then need to use this information to inform our design and development decisions.

For example, if the target audience of the website is more prominent on mobile than on desktop then you would want to invest in making the mobile version of the website as full-featured as possible while also being a seamless experience for users. Also, think about the UI layout; does it need to appeal to a less tech-savvy audience with a simpler design? Or, can it be more elaborate? Thinking about the target audience gives us these answers.

Understanding who you are making the project for and why and then using this information to drive the design and development of the project is more likely to create a successful project that will achieve your client’s goals. By putting a large emphasis on the user experience, we can ensure we optimize journeys and features to increase the likelihood that users will complete a purchase or another action.

If we think about some of the most successful websites in the world like Amazon and Google, they both put the user experience first. Google makes it quick and easy to search for things, Amazon lets you buy things in seconds and gives you recommendations on your past purchases. They’re designed to make your life as easy as possible and that’s why people keep going back to them.

This isn’t exclusive to the largest companies in the world — any business can and should put their users first. Don’t let a bad user experience on a website be the reason a customer goes to a competitor.

Project Questions

In this section, we focus on questions more aimed at the project specifically and how they can help inform your choices.

Q5 - How are you currently tackling the problems that you want this project to solve?

With this question, we are looking to gain deeper insight into how the client is currently approaching the problem they are asking you to solve. Is this a new or old problem? Have they dealt with it at all? The aim here is to help us identify other potential problems they could be having outside the scope of this project that might influence their expectations for your work.

For example, let’s say a client wants to increase the sales of a product via their website, and they want you to redesign their online shop to achieve this. That is a valid project to undertake but we want to also check that the other portions of the sales pipeline are in place and working, how is their social media strategy? What about marketing? How about existing SEO?

If these other portions of the pipeline aren’t in place, how is the business handling them? Are they currently investigating potential solutions? Or, are these things they haven’t considered before?

It’s important for us as freelancers to ensure that the project we are working on can be judged by metrics that our project influences. By identifying these extra requirements/problems early on we can adjust and agree upon metrics with the business that are relevant to the project.

To carry on with our shop example, redesigning the shop page might help increase the conversion rates of existing traffic, but if they’re looking to increase sales, other factors could influence this metric. In this example, we could agree with the business that our project for redesigning the shop page will be measured on the shop page conversion rate rather than the raw quantity of sales. This way the metric judging our success is directly related to our project and not influenced by other issues outside of our project scope.

Q6 - Will the business provide designs, copy, and assets? Will there be resources available to answer queries on these?

When it comes to building a website regardless if it’s for a client or not, there is a lot more to a successful website than its code. For a successful website, you need effective copy, a design that enforces the desired user journeys, and assets that show off the business or its products.

When scoping out the work required in a project, you should take this content into account. Will you need to provide these services? If so, do you have the skills and experience to provide them to a standard that will achieve your client's goals? Or, will you need to outsource this work?

Or, is the client providing these assets themselves? If so, who is the person to go to for queries? Are they available to discuss changes or problems during the process?

All of this should be taken into account when pricing a project and planning your timelines.

Q7 - What type of content will be displayed on the website? Does the website need to interface with existing systems/processes?

In the modern world we live, very few websites are purely text; the majority now have multiple forms of media and content on them, from images and videos to live streams and embed posts from social media. All of these content types are valid requirements from a client, and we need to know about them upfront.

While images are mostly trivial to handle these days in modern web frameworks, videos can be a bit trickier. Do they need a custom solution built for this? Or, will they be embedding public videos from existing platforms? Building a custom solution will take more time and require specific knowledge and expertise, so we need to account for this in the project.

But, it’s not just the type of content we need to investigate and be aware of. A lot of businesses, have existing processes and systems in place that need to interface with their website. For example, imagine a clothing retailer who needs their website to communicate with their warehouse and store inventory systems; if the website can’t do that then it will never fulfill the business's requirements.

Understanding a client’s requirements for content as well as the systems/processes that run their business before a project begins is vital to a project's success. We need this information to inform our choice of technology, services, and solutions for the project. It’s better to spend more time upfront researching the right service(s) for the project than it is to rush into it and find out halfway through the wrong service was used and it all needs to be changed; incurring more cost and delays.

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Q8 - Who will be maintaining the website going forward? Who will be editing, uploading, and managing the content on it?

Another key question is who is going to be looking after the website? Who will be uploading and creating new content in the future? The answer to these questions will heavily impact the route you take for handling content on the website.

If it’s non-technical users you’ll want to use a CMS like Prismic, which gives them a GUI to use for editing, uploading, and managing their existing content so they don’t need to worry about the technical details of doing it. Alternatively, if it’s developers or more technical users, then you might explore other services and products to use on the project.

But, either way, the important thing is building a solution that meets the business’ needs and the people who will ultimately use the project you build. At all costs, we want to avoid building a project that fits all of the client’s requirements but that they can’t use in the long run.

Q9 - Is this a completely new project or is it an adaptation of an existing one?

This question is designed to help you understand the scope of work required and the technical experience/knowledge you might need to have. If the client informs you they have an existing codebase and they want to keep it for some reason, you need to evaluate whether you currently have the skills required to work on it. What if it’s coded in a language you don’t know? Or, using a technology you’re not familiar with?

Of course, a valid approach to this situation is pitching a migration to a new solution, but you will need to factor this extra work into your timelines and pricing to ensure they cover everything your client needs and wants from the existing solution in the new one.

The optimal outcome of this project for many developers is the client informing them they want a new project built from scratch. This means you have the freedom to make your own choices about the tech stack and services, but the importance of this decision shouldn’t be understated.

The decision you make now will likely be with this client for some time so you want to avoid experimental technologies that might disappear overnight. Plan for the long term when you choose the tech for a new project, not just what you want to use right now.

Person shaking hands with another person.

Q10 - What is the single most important part of this project for you and the business? What concerns you the most?

With this question we want the client to identify what is important for both them, the project, and the business. Most project managers, want the project to be a success for themselves and the business overall, and this question helps you understand what is most important to all parties and cater to that.

For example, the goal for the business might be to drive traffic to their shop pages, but the project manager’s goal might be to bring this project in on time. Knowing this information upfront lets you account for these needs in your estimates of work and as the project progresses.

In this example, as the project progresses, you know the project manager is focused on timelines, so you want to keep them up-to-date with progress and estimated completion dates, as well as any potential setbacks which could influence delivery. By helping the project manager achieve their own goals, as well as the overall business’s goals, you’ll build a good rapport with the project manager who will in turn be more supportive of you.

Q11 - What is the budget for this project? What are your upfront and ongoing allowances?

Budgets are one of the most important parts of a project’s success. Before starting the project and designing a solution for the problem the business is facing, we need to know both their upfront and ongoing budgets.

Both budgets are important. When setting up the technology, products, and services for the project, there will likely be higher costs that the business will need to absorb as an upfront fee, but just as important is the ongoing budget.

If we find a solution that fits the client’s needs but is way out of their budget, it’s pointless because the client won’t be able to afford the solution over time. With many services and products transitioning to a pay-monthly format, we need to ensure the solutions we use for the project are affordable in the long term to ensure client success.

Q12 - What is the desired deadline for the project? When do they want to start seeing results?

This is as much about the business as it is about you. The client should know the results they want to see from the project but, just as important, is when they want to see them.

We need to make sure that the timelines are feasible for us to complete the project. But, we also need to set the right expectations for when the client will see results from the project.

As an example, if the goal was to redesign a marketing website to increase traffic via SEO, it’s not reasonable to expect a sharp increase in traffic from SEO after just three months. Instead, it’s more reasonable to set the expectation of 6 - 12 months since SEO is a long game of consistent effort and not a one-time piece of work.

Ensuring the client is well aware of these timelines and being fully transparent with them is important to prevent potential issues later in the project.

Managing a project’s timelines and deadlines is as much about when we can deliver the project as it is about giving the client realistic and feasible expectations for seeing results.


Throughout this article, we have looked at 12 different questions, why they’re important to ask, and ultimately how they help us deliver higher quality, finished products for clients.

Instead of viewing a freelance web development project as just another website to build, we should be viewing it as an opportunity to help a business grow and achieve its goals, which ultimately will be infinitely more rewarding to us. Asking the right questions allows you to choose products like Prismic that enable your end-users to thrive.

Finally, if you’re ever in doubt if you have asked enough questions about a project, ask more. There is no such thing as knowing too much about a project. The more information we know about the business, the project, and its consumers, the better the product we can create.

Article written by

Coner Murphy

Fullstack web developer, freelancer, content creator, and indie hacker. Building SaaS products to profitability and creating content about tech & SaaS.

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