Have you ever wondered why freelancers have so many problems managing client projects? Endless revision cycles, misaligned expectations, and trouble getting paid are just a few of the issues that can easily plague a freelancer’s career.
👉 Almost every major conflict you’ll face as a freelancer will stem from asking the wrong questions before starting a new project.
Today I not only want to tell you what questions to ask, but offer a short lesson in effective client communication that will help your freelance projects progress more smoothly. These strategic, carefully-written questions have been a fundamental part of my success as a freelancer.
Where to Begin
Every freelance project starts with an initial point of contact. Sometimes it’s you reaching out to the client. Other times the client is reaching out to you (via email or a contact form on your website).
From there, it’s your job to ask the right questions, figure out what the client needs, price the project, collect payment, and start work.
The series of interactions between you and the potential client leading up to the project start date is known as your “onboarding” process — the process of bringing a new client “on board” with your business.
Most freelancers mistakenly ask specific questions about the scope of work right away. For web designers and developers, the pages, features, and functionality are often the center of attention here.
This typically leads you (and the client) down a rabbit hole where you’re estimating hours and pricing the project before discussing what the client is fundamentally trying to achieve.
Why is that problematic? Because it allows the client to be too prescriptive and clients rarely know exactly what they want or need. They’ll tell you what they want and you’ll agree to it. Everything will seem fine until you start delivering work. Then they’ll realize it’s not what they wanted and ask for revisions.
This is where most freelancers lose control of the project and the client — because your expectations were misaligned from the beginning.
If a client asks you to design a new marketing website, you shouldn’t start by asking them how many pages it needs and what features they want. It causes everyone to focus on the scope of work (design, content, features, etc) instead of the goals of the project.
The following are valuable and insightful questions I ask prospective clients via the dynamic contact form on my company website. That form provides all the information I need to evaluate whether or not the client is a good fit for my business before I spend any time talking to them. You can also ask these questions over the phone (in this order).
Tip: If you already have the answer to a question, repeat the answer back to the client and verify it with them. Don’t just skip it!
1. What type of project do you need completed?
If you offer more than one type of service, this is a great place to start learning about the client’s needs. Web designers should understand if the client needs a marketing website, product, or mobile app. Copywriters should understand if the client needs copy written for a website or a blog post for social media.
That’s why having a generic “type-whatever-you-want” message box as a contact form on your website is going to produce low-quality leads and spam. The client has to start from scratch and figure out what to type. Guide the client toward providing better information by asking strategic questions.
2. What services do you need?
At first, this might seem like the same question, but it’s more of a follow-up to the first. If you design and code websites and a client needs a new website design, you should find out if they need it coded as well. Do they only need design services or design + development services?
Even if you can’t code, it’s important to see the entire project from the client’s perspective, not just your part of it. You might even be able to recommend someone you know for another part of the project. This question won’t be relevant in every situation, so skip it if it won’t yield any valuable insight.
3. When do you need this project completed?
This is a highly effective way to get key details about the client’s timeline expectations. It’s also a great way to phrase the question in a way that gets you the information you need as quickly as possible.
Asking, “When do you want to get started?” will always result in the client saying, “as soon as possible”. Asking a vague question such as, “What are your timeline expectations for this project” will leave the client feeling helpless. They can’t answer that question because they don’t know how long it will take you to complete the work.
Instead, meet them where they’re at and ask when they need the work completed. Clients focus on deadlines more than any other timeline details, so this is an easy way to procure valuable insights into their timeline needs.
If you’ve already got some projects scheduled in your calendar, this will instantly tell you if you have availability for the work. You’ll avoid wasting time quoting a project you don’t even have time to complete.
This is one of the most difficult conversations to have as a freelancer. I love phrasing the question exactly this way. Asking, “What’s your budget?” makes it personal. “What’s the budget?” helps keep the conversation objective.
If you’re on the phone, ask this question quickly and confidently just like any other question. Don’t hesitate.
If the client tries to redirect or asks you for a quote first, don’t give in. Say this: “Can you tell me what your max budget is or provide a budget range? This is the quickest way to align expectations. I don’t want to invest time quoting a project you can’t afford and you don’t want to waste time waiting for a proposal that’s way over your budget.”
Here’s the thing: clients need to have a budget in mind for their project. If they don’t have a budget, it’s a sign they aren’t prepared and that’s a red flag. If they won’t share the budget, that means they want to maintain “leverage” over you (also a big red flag).
But sometimes clients new to hiring freelancers and are honestly just price-shopping. In those cases, tell them you’ve done projects between $X and $Y and wait to see how they react. This will at least open the conversation and help you understand their mindset.
The point is, you can’t afford to skip this question. Don’t let clients gain control of the conversation at this critical juncture. Get comfortable talking about money and stand your ground. Know your pricing and be prepared for this part of the discussion. That’s how professionals conduct business and good clients will respect that!
At this point, you should have established that the project is fundamentally a good fit for your business. If the type of project, budget, or timeline doesn’t work for you, there’s no need to proceed. That’s why I don’t start with this question instead!
Now that the client has provided basic information about their project, you can dig deeper into the background and context of what they’re trying to achieve.
What led up to this point? Was there a particular problem they were facing? Is their website, marketing campaign, or copy not getting them the results they wanted? Why are they willing to spend money on this project? Why now and not six months ago or six months from now? What’s making this project important today?
No client wakes up one morning and decides to spend money on a new project.
More than likely, they’ve had a problem brewing in their business for a while — and sometimes they don’t even realize it! It’s in your best interest to uncover that problem with them before quoting the project to make sure you’re solving the right problem.
This information will give you the insight you need to anchor your pricing and “sell” the project in later conversations. It also sets you apart from other freelancers and shows you care about more than providing a quote — you care about the success of their business.
Note: Not every project requires you to ask this question. If the client asks you to design a new website for their company, this is a great question. If they ask you to write a blog post, this question can feel forced and push the client away. They just need the blog post! Put a price on the work and close the deal.
This question will provide valuable insight into what the “end game” is for the client. If they’re asking you to design a new website for their company, what they really want is to drive more leads and sales.
Clients often say their goal is to “establish more trust” with their audience or redesign an “outdated website”. However, this line of questioning will reveal that making more money is ultimately the only reason to invest money into a project.
Businesses don’t spend money just for the sake of spending it.
No matter what, it’s in your best interest to understand the broader context of what the client is trying to accomplish. By asking this question and discussing their business goals, you’re also demonstrating that you’ve got a business mindset. That will help them respect you and your pricing!
I’m always impressed by how a client’s tone will change once I start asking business-oriented questions. If you want to charge premium rates, you have to position yourself as a business and learn how to have business-oriented discussions.
This is my opportunity to let the client speak freely and share any details they feel are relevant. I leave this question for the end so that these are truly additional details that weren’t mentioned in the previous six questions.
It gives the client a sense of control by allowing them to express their needs, concerns, questions, or context in their own words. At the same time, it provides you with more valuable information. This works particularly well as the last question on a contact form.
Why this process is effective
If you ask these questions to every prospective client, you’ll experience fewer problems during the project. You’ll be more likely to close the deal, minimize revision cycles, and get paid on time.
Most importantly, you and the client will be working toward the same business goal, not the client’s prescribed solution. There’s more than one way to solve most business problems.
A client asking for a website redesign might not need a total redesign. They might only need to adjust the copy on their website or make other minor improvements. A client asking for a new blog post might actually need to establish a broader social media campaign strategy.
These questions will help you get to the root of their needs as quickly as possible — and they’ll love you for that!
I’d highly recommend using a dynamic contact form on your website such as GravityForms or an embedded TypeForm to collect these answers from every new client who contacts you.
Having a name-email-message-style form is rarely going to produce quality leads. It also doesn’t help you stand out or encourage the client to provide useful information.
My company website uses Gravity Forms and conditional logic to present a simple form to the client and tailor the follow-up questions as they go.
For example, I show different price ranges in the dropdown menu based on what type of project they need completed. I’ll only ask what service they need if they select a project type that I can offer more than one service for.
Since my project calendar is rarely empty, I even take it a step further. My form shows an inline message if they select “1 Month or Less” for the timeline or “Less than $10,000” for the project budget. That lets them know we may not be a good fit to work together based on their needs.
Time is a precious resource when you’re a freelancer. That’s why I invested in a contact form that dramatically reduces the time and effort it takes me to gather this key information from a prospective client.
If a client emails me with a vague request, I can point them to my contact form and they know what to do. When they ask for a phone call, I ask them to fill out my intake form first so I can make sure we’re not wasting each others time with a meeting.
If they refuse to adhere to my process altogether (won’t fill out the form and demand a phone call instead), then I know we’re not a good fit to work together. Sometimes clients will fill out the form with minimal (aka useless) information just to say they did it. That’s another great way to gauge how that person will behave as a client.
All of these small tactics add up to a powerful pre-qualification system that nearly eliminates the time I spend talking to clients who aren’t a good fit for my business. At the same time, it helps me onboard new clients more easily, quickly aligns expectations, and streamlines early communication.
This onboarding process is a major reason for my success as a freelancer.
Don’t Force These Questions
I want to point out that sometimes the client request is simple. If you’re a copywriter and the client needs a blog post, they probably just need a blog post. There’s no need to dissect things further or force a conversation about “value” and “problem-solving” when there’s no need for one.
This is a common mistake I see freelancers making (and one that I made myself). When I first learned to ask strategic questions and dig deeper with my clients to learn about their needs, I did it with everyone — even if there was no need to.
You won’t be able to force a conversation about the “underlying problem” a client is facing in every situation — and that’s ok. Every project is different and sometimes that means you’ll need to ask different questions to the client.
This key takeaway is this: when you ask specific questions early on, you’ll reduce the risk of miscommunication and misaligned expectations. By asking business-oriented questions with confidence, you’ll earn the trust and respect of that prospective client. That means you can charge more and provide a better client experience, which can lead to repeat work and referrals in the future.
About Matt Olpinski
Matt runs his own web design and development company Matthew’s Design Co. and teaches thousands of freelancers how to succeed through his personal blog, newsletter, and community for freelancers — The Freelance Institute.