What questions do you have about the project? (Upwork proposal series)

What questions do you have about the project? (Upwork proposal series)

In this Upwork proposal series, we’ll be looking at the question “what questions do you have about the project?” and how to best answer it.

How other freelancers are answering “what questions do you have about the project?”

Before we dive into the answer with a word-for-word example script and the questions to ask, let’s first look at what other sites tell us to do — that’ll give us an idea about how other freelancers are answering this question.

When searching around for answers we’ll get a generic list of questions we can copy-paste into our Upwork proposal without any explanation of what and why. That is great news for us because we now know what we’ll be competing with.

Since this blog focuses on doing a bit more work in exchange for better results, you and I are taking a different approach. We’ll impress the client right off the bat, so they immediately put us in a different “bucket” than other freelancers. 

Instead of the standard, flaky, freelancer, we’ll show them how we are a serious asset to their business — an asset that deserves to be paid well.

That starts right from the first impression, which on Upwork, is the cover letter and any additional questions the client has added like “what questions do you have about the project?”

Client’s are usually busy and the challenge I’ve noticed is that it is tough to ask a busy person multiple questions via email or Upwork chat messages and actually get a response to all of them. 

If you have multiple questions about the project, you’ll want to start just with one so as to not overwhelm them.

I know it seems ridiculous since they would want to know and answer our questions but the reality is different. Busy people (all of us?) tend to get overwhelmed by large walls of text online and many questions since we need a lot of time to think and formulate a response.

Instead, we are going to end the proposal with one question, mention that we have more questions but didn’t want to bombard them, and then suggest a call to dive deeper to make it more convenient for them.

Here’s an example script you can use to base your answer on:

“I have several questions that would help make sure that your project goes well and to ensure that you get the project done exactly how you want it. 

I’m sure you are busy so I don’t want to make this overwhelming by bombarding you with questions all at once. 

If you’d be up for a quick call, I can ask them there and take notes so it’s easier for you than having to write everything down. Do you prefer a call or that I share them in writing?”

Good vs bad questions to ask

A question isn’t just a question. Some make us look like a fool while others show that we are competent. I’m not talking about asking questions that make us feel stupid like when we didn’t understand a math problem at school.

Instead, I’m talking about asking questions that show how well we understand the type of project or even better, those that show we understand the client.

Questions showing that we understand the problem well will be project-specific and based on your expertise. For example, if it’s about Facebook ads not giving the return the client was expecting, I might ask about the click rate and conversion rate to troubleshoot.

The thing that most beginning freelancers underestimate is how much they focus on the problem they are solving for the client. Most jump directly to the solution.

Since most do the same, we often win by doing the opposite. In this case that is diving deeper in the first part of the pitch to ensure, no only that we understand the problem, but that we make the client feel we understand it by asking in-depth questions.

We as the expert might have solved the problem many times before and know exactly what’s going on. But the client might not and so we need to help them go from their current frustration to our level of understanding before moving forward.

There is immense value in being able to communicate well and being able to explain what’s going on in a simple and easy manner to the clients. Often they don’t want to know what we know, they just want the problem solved and an explanation that they can understand.

Just take a look at this job description:

what questions do you have about the project - Upwork job description example

With that out of the way, let’s dive into the questions. 

It should be obvious but in case it isn’t: don’t talk about questions like holidays, payment, or things like time off just yet, since it can come across as if we have no interest in the work and just care about the money. Even if that’s true, there’s no reason to make the client feel that way about us.

I know that payment can be tempting to throw out there at first to clarify if the client is even able to pay what we charge, since there is no point in talking for both of you if they can’t.

In some cases, a number can sound a lot at first but once you get talking the feeling about that number might change – it shouldn’t be like that but it is the reality we live in (feelings vs logical thinking).

Instead, at this stage, focus on showing your value and the impact we can make on the project.

Examples of good questions

Categories of questions:

  • More info about their products, pricing, business
  • The timeline for the project
  • The goals and what the project would look like day to day
  • Other experiences they’ve had with freelancers and what to avoid
  • Who we’ll work with the most in the project
  • What they’ve tried in the past and what worked/what didn’t

More info about their products, pricing, business

This will likely be the most common category to start out with since Upwork clients are notorious for not adding details to their projects. 

We might ask them what the price of their product is, which one is more popular, if they have a type of customer that is better or buys more often than others, etc.

These questions can help us understand the size of the client and if it’s worth it for us to help out with their project and it can help with specifics in terms of how to solve the problem. For example, approach to take or product to sell.

The timeline for the project

This is especially interesting if we are looking at urgent projects. The timeline is key since we never want to deliver something late and we might even ask if they have buffer days before their deadline.

Besides asking for the specific deadline or timeline for the project, we might also ask if it affects other projects or team members.

The goals and what the project would look like day to day

It’s always good to ask about the client’s goals or targets and then use the same phrases when describing the success of the project later since that tends to make them feel that we are aligned.

That can be as simple as “do you have any specific targets or goals you are looking to reach?”

Other experiences they’ve had with freelancers and what to avoid

This is a more advanced tactic to understand if they worked with other freelancers and perhaps had a bad experience. By asking about it we show that we are aware of it and it allows us to show how we can give them a different experience since clients that have been burned before often are vary about the next freelancer they work with.

The question can be as simple as “have you worked with any freelancer on similar projects before? How was your experience?”

Who we’ll work with the most in the project

This type of question is to better understand how many team members will be involved in the problem and who we’ll be working with. It can also help us understand if there are any invisible stakeholders.

The question can simply be phrased “besides you, who else will I be working with to complete this project?”

What they’ve tried in the past and what worked/what didn’t

This type of question tends to be used to understand what the client has done to solve the problem before and what they tried that worked or didn’t work. This helps to understand the client’s way of thinking and avoid offering a solution they have already tried.

We can simply ask “what have you tried in the past? What worked and what didn’t?”

Relevant articles

Here are other articles in the series you might find interesting:


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