We’ve all had one of those projects. You dive in with excitement, only to realise three weeks later that you’re working off assumptions. The deadline feels fuzzy, the scope keeps shifting, and you’re not even sure if what you’re creating is what the client actually wants.
If that sounds familiar, you’re not alone. According to Upwork, freelancers say unclear expectations are one of the biggest challenges when working with new clients. One of the most important things we’ve learned, often the hard way, is that when you ask clients the right questions upfront it can make or break a freelance project.
Whether you’re a new freelancer still finding your feet or you’ve been running your freelance business for years, a solid list of questions to ask new clients is essential for building a successful working relationship.
When a potential client reaches out, especially if they’re new to hiring freelancers, they might not know what information you need. That’s where your questions come in. Not just to get clarity, but to set the tone for your working relationship.
Asking specific questions during onboarding shows that you’re thoughtful, professional, and proactive. It helps you understand the client’s goals, manage expectations, and prevent costly revisions later down the line. In short, asking the right questions saves time, avoids misunderstandings, and leads to happier clients.
GoCardless highlights that one of the most common challenges freelancers face is “setting clear expectations with clients”, something that, when skipped, can lead to late payments, scope creep, and confusion throughout the project. Starting with a thoughtful list of questions can nip those issues in the bud before they start.
Whether it’s a short-term job or a long-term retainer, these are the essential questions freelancers should ask clients before diving in. You don’t have to ask all of them at once, but weaving them into your discovery call or onboarding process will help create a smoother path forward.
This open-ended question gives you insight into the client’s business goal. Do they want more sign-ups, stronger brand messaging, or a faster website? Understanding the client’s vision early on helps you align your work with what actually matters.
You need to know exactly when the project starts and when the deliverables are due. Ask follow-up questions about any key milestones, review stages, or stakeholder sign-offs the client may need throughout the project.
It might feel awkward, but asking this question upfront avoids surprises later. It helps you decide if the project is worth your time and allows you to suggest a realistic scope. Some freelancers prefer to ask this after they’ve scoped the work, others ask during the discovery call, either way, it needs to be addressed.
One of the things you need to know to avoid confusion is who you’re actually communicating with. Is it the founder, the marketing manager, or someone else entirely? Understanding the client’s preferred communication style and who signs off your work will save a lot of back-and-forth.
This question encourages the client to share inspiration or benchmarks, helping you avoid vague feedback like “this just isn’t quite right.” It also gives you insight into their aesthetic or strategic preferences.
If you’re a freelance writer or designer, you’ll want to ask this before you even start concepting. Every client has their quirks. Some love exclamation marks, others ban them entirely. Asking this question early makes sure your deliverables hit the mark.
This is a subtle but important question to gauge how much hand-holding or explanation might be needed. Clients often assume freelancers are mind readers, but this gives you a chance to outline your onboarding process and any project management tools you’ll use.
Some clients like to jump on a call. Others prefer bullet points in an email. Knowing this helps you manage expectations and avoid misunderstandings during revision rounds.
While this doesn’t guarantee future projects, it opens the door for ongoing conversations. If they’re looking for long-term support or a monthly retainer, you can plant that seed early on.
Sometimes the most important detail isn’t in the brief. Maybe the client’s CEO is picky about language. Or they’ve just been burned by a previous freelancer. Giving them a chance to share any extras helps you build trust and show you care about the full picture.
These questions will help you not only understand the scope of the project but also build confidence in your ability to deliver. Clients want to feel like they’re in safe hands. When you show that you’ve thought through the details, they’re far more likely to give you space to do what you do best.
It also means you’re less likely to face scope creep or unrealistic expectations. You’ve laid the groundwork, clarified everything up front, and shown that you’re invested in a smooth onboarding process.
Keeping track of every client conversation can be tough, especially if you’re juggling multiple projects. That’s where a CRM like Capsule can really help. It lets you log calls, track tasks, and manage your freelance clients without letting anything slip through the cracks.
You can also head over to our Toolbox for more resources we’ve tried and tested to help manage client projects like a pro.
The questions you ask at the beginning of a new client relationship are just as important as the work itself. They’re your best defence against last-minute surprises and the key to creating confident, happy clients.
So next time you land a new project, pause before diving in. Ask the questions. Get the clarity. And give yourself the best chance of success.
Want a done-for-you checklist of questions to ask clients? Download our Starter Kit and feel confident from your next discovery call onwards.
