Value uncovering questions to ask your client

As a freelancer, nothing is more exciting than a promising client enquiry in your inbox. As we know, each client and project is different — different challenges, scope and constraints. Perhaps the client is operating in an extremely niche market, or is on the brink of losing everything due to competition.

I’ve seen a fair few client enquiries in my inbox over the years, and there’s one recurring question they want to know the answer to:

"How much will this cost?"

Without much information, this becomes a really difficult question to answer. I’ve seen freelancers rush to answer this question in fear they might lose the client if they don’t act quickly. Almost every time this leads to them under-charging and huge headaches along the way.

As the smart freelancer that you are, you know that the best way to answer the client’s question is to first uncover the value and scope of the project. To do so, you’re going to need to ask a few questions so you can price accordingly and create a proposal tailored to their needs.

While we know we need to ask questions, the real question is what questions do we ask?

In the past I’ve spent quite some time going back and forth with clients constantly asking questions. Then as I start drafting the proposal I uncover questions I don’t know the answer to, that can have a massive influence on the price of the project. “What did they say success looked like again? Oh wait, I forgot to ask.”

Sound familiar?

I know I’m not the only one that’s fallen into this, because I recently received this email from a fellow solopreneur:

"I was wondering, what are the first questions you ask to get to know more about the project, to be able to make a proposal that fits their needs? I have my questionnaire, but maybe I’m not asking some questions that can give me a better scene of the project. I always end up missing something!"

A questionnaire is a great way to collect ideas and responses from your client. But how do you discover the things you need to know and condense that into just a few questions? You want to find that perfect balance of asking just enough vs asking too much. Have too many questions and the client will give up. No one wants to feel like they have to write a novel.

So that you can truly uncover and understand the project and write the best proposal ever, there’s a few key things it’s worth discovering:


1. Uncover their struggles and weaknesses

Without uncovering the struggles your client is facing, it’s impossible to provide them with a solution to fix it. Knowing your clients problems gives you insight into the potential value you can deliver and the problem you can solve. There’s bound to be areas in their business that can be improved upon or where they’re lacking resources or momentum. Identifying these areas can help uncover opportunities where you can help.

Clients are good at assuming they know the information you need as the freelancer — but usually they’re wrong. While your project may just focus on one area of their business, how can you do an effective job if you don’t understand the impact it will have on the business as a whole?

Ask your client for the broader picture and biggest pain points so you can get a sense for where your project fits on the spectrum.

Identifying areas that are existing hurdles lets you keep an eye out for them throughout the project. Knowing where the challenges lie allows you to prepare to approach them with momentum and perseverance.

Lastly — working with a freelancer can be scary for a client! Shock I know. Talk to them and listen to their worries so that you can guide and comfort them throughout the project.


2. Establish the goal & needs

Without defining the project goals how will you know if it was a success?

Ask your client to explain what success looks to them. At the end of the day, what are they hoping to achieve?

It’s good to approach this question with a holistic view in mind. While success of your project is vital to define, it can help to paint a picture of what success looks like for the business too. From there, you can always refer back to the success definition throughout the project, especially when you need to make difficult decisions.

The success definition of a project is important to know, but so is uncovering how important it is that they reach that level of success.

Once they achieve that success, what does that mean for their business?

Will they be able to raise more investment? Open that new office in Berlin? Understanding their future goals and the impact of your project lets you work with these goals in mind.


3. What does their business actually do?

This is an important one. To provide your client with the best results you’ll need to understand three things:

  1. What they do
  2. The market the operate in
  3. Who their customers are

Working without a solid understanding of the context of what and who you’re creating for means you’re creating in the dark.

You need to uncover their unique value proposition and service offering. What is it they actually do? Who do they serve? What do their customers want?

Understanding your client’s customers lets you create with the end user/customer in mind. Remember — you’re not creating for your client. You’re creating for your clients customers.

Once you’ve got some information on their market or industry, scope the competitive landscape. It’s worth evaluating how others are achieving success (or failure!). This helps you to learn about the challenges and constraints of the industry so you can work with those in mind.


4. Why now?

Did your client just receive a huge round of investment or is this their last chance to prove their idea? There could a lot a stake for your client. Perhaps they have an upcoming event or product launch.

Maybe your client is throwing everything on the line and this is their last chance. Or, perhaps they’re trying something new for fun and seeing if it will stick.

There could be many reasons for the client to want the problem solved now. Is the problem new or old? Have they tried to solve it before? If so, what failed? Learning about their past can provide you with better judgement on whether you want to take on the project, or work with the client.

Establish what they have to lose by not doing this project now.


5. Why me?

This is an important question that’s often overlooked. Learning how the client found you and why they want to work with you can help reveal some critical insights.

Their answer to this question will help you understand their expectations and why they chose you over someone else. Knowing this helps you form a trusting relationship with them.

If at this point you’re feeling nervous about the amount or weight of questions you’re asking them, this is a nice one to throw in half way or at the end of your questionnaire.


Every project and client is unique. Unfortunately there’s no one-size fits all set of questions to ask every client.

However, there are key aspects you want to uncover so that you can work towards making both you and the client more successful.

Remember, if you and the client are going to work together, it’s up to you to set the expectations of your working relationship.