Kickass Upwork questions and answers that win clients

As part of the Upwork-series, let’s look at Upwork questions and answers that often come up in proposals.

Throughout this short guide for ambitious freelancers, you and I will dive into two techniques you can use to answer the questions. 

We’ll also look at specific word-for-word example scripts for each question and how to create your own templates, so you can answer the proposal questions fast.

Let’s start with the underlying techniques to answering the questions.

Two techniques to answer Upwork proposal questions

The challenge many of us have with common Upwork questions like “do you have suggestions to make this project run successfully?” or “what part of this project most appeals to you?” is that they are awfully generic and it is tempting to respond with “I want to earn money!”

We see the same questions over and over again on different projects and it feels discouraging to answer the same thing again after having just prepared the cover letter. 

The questions might be displaying that the client is not experienced in hiring since the questions are vague and not project-specific. As soon as you have hired on Upwork a few times, you’ll notice the useless and time-wasting answers given to these questions and hopefully, change direction.

Either way, they want as relevant project details as possible and are looking for clues to trust us, the freelancer.

Before we dive into specific examples of each of the Upwork questions and answers we can give, let’s go through techniques that we can use to answer them.

The hidden question and what the client is really asking

An effective approach is to find the hidden question behind the question. What is the client really asking for?

We can do it by asking ourselves why the client wants to talk about the topic a few times. For example, why does the client ask how to make the project run smoothly?

It might be because they have had freelancers that disappeared or slowed the team or a project down in the past, and so they are concerned that it might happen in the future. Why?

Perhaps the freelancer was unprofessional and now the client is concerned about hiring outside help. Why? Because they are concerned that it might happen again and they don’t want to waste their time and money, and feel cheated.

Assuming that it is accurate, we need to show the client that we are professional and reliable.

We might do that by highlighting examples from previous projects (e.g. freelance, work or hobby) where we delivered on time despite complications.

We can figure out if it is accurate by looking for clues in our conversations with them e.g. if they mention negative experiences or assumptions related to freelancing. 

I prefer to simply ask about their past experience with other freelancers and if there is anything they wish would be improved, so that, together, we can avoid it in the future.

It shows the client that we are aware of potential implications and that we are working to be proactive. 

“Play the client”

By acting as the client, putting ourselves in their shoes, we can predict what they might be looking for.

Imagine you are the client writing the job description and work to visualize what will happen step by step throughout the project. Which steps will the freelancer take and how might the client respond?

Is a major holiday coming up? Is it likely that there might be something unforeseen that could delay the project from the client’s side?

As the client, what kind of concerns do you have? List them down and prepare an answer for each.

Examples might be:

• Will the freelancer disappear?
• What happens if I have changes/revisions? Will it cost extra? When will it get done and will the freelancer complain?

I will be sharing example scripts with you below and I do NOT recommend that you copy-paste any of them or use a template until you’ve mastered turning Upwork client proposals into clients. 

We’ll dive into how to answer the questions quickly in the second following the answers.

Upwork questions and answers for your proposals

Next, let’s look at some specific examples for each of the common Upwork proposal questions. 

Several of the questions contain example answers that describe specific stages, tasks, or parts of the project. 

If you see multiple questions with that on the job you are applying for, I suggest not repeating the stages, tasks, or parts for each question like if done in the examples below. 

Instead, give the examples once and refer to them in the other answers to save the client time instead of having to read almost the same phrases several times. And if you are smart, you might even point this out to the client.

1. What past project or job have you had that is most like this one and why?

Example script: 

“I’ve worked on many projects that are similar to this one and I’d like to highly three examples below.

In project A, I worked on KEY TASKS and achieved SPECIFIC RESULTS. I’m highlighting it because TASK/GOAL/OTHER appears to be similar to what you are looking for help with in your project. X appears similar across both projects [e.g. that the audience or customer base the project is targeting is the same and so there are likely similarities in their needs]. 

In project B, I worked on KEY TASKS and achieved SPECIFIC RESULTS. I’m highlighting it because TASK/GOAL/OTHER appears to be similar to what you are looking for help with in your project. X appears similar across both projects [e.g. that the audience or customer base the project is targeting is the same and so there are likely similarities in their needs]. 

In project C, I worked on KEY TASKS and achieved SPECIFIC RESULTS. I’m highlighting it because TASK/GOAL/OTHER appears to be similar to what you are looking for help with in your project. X appears similar across both projects [e.g. that the audience or customer base the project is targeting is the same and so there are likely similarities in their needs].“

2. Do you have suggestions to make this project run successfully?

Example script:

“Could you help me understand what it might look like to you when this project is running smoothly and successfully? 

That way I can adjust to help you the best.”

This script might not make sense as is since it is taken out of content. Read the full background and details here.

3. Which part of this project do you think will take the most time?

Example script:

“Based on the project description, it appears as if we can divide the project up into three stages: [stage 1, stage 2, stage 3]

As a basic overview, we can divide stages up into these overarching tasks:

[Stage 1: task 1, task 2, etc…]

[Stage 2: task 1, task 2, etc…]

[Stage 3: task 1, task 2, etc…]

We’ll need to talk further to clarify the specifics but based on that assumption stage 2 will likely take the most time because of ABC.

To avoid it sucking up time, I can mitigate it by doing XYZ.”

4. What part of this project most appeals to you?

Example script: 

“The most appealing part of this project is that I know I can help you because I worked on very similar projects before. 

I helped another client in the bathroom utility industry generate leads with online marketing. We tested out three different channels: SEO, Linked ads, and Google search ads. LinkedIn was decent yet expensive. We built a great combo between different channels that I think you’ll find attractive.

Even though the items sold were slightly different, they were in a similar industry so there is likely overlap with the buying decision between their customers and yours.

With another client that sells portable gear for events, I’ve helped build a short term funnel with ads to get client leads quickly and a long-term approach with organic search traffic.

I figure your business is likely selling to event owners and in the second example my client was doing the same yet selling different gear.”

Read this article for instructions on how to tweak the example script to fit your own situation.

5. Why do you think you are a good fit for this particular project?

Example script:

“I’ve attached a case study running Facebook ads for an online furniture business that yielded X result. While furniture and lamps aren’t exactly the same, both are upscale products and the customers are similar. 

They are not looking for the cheapest solution but rather something that shows off their personality and interests. Something that they can show to friends and family when they visit and perhaps even bring back memories from a trip or experience abroad.

Throughout the project, I noticed that images with highly contrasting colors and with the product placed in a real-life setting (e.g. a living room) worked well. I figure it might work well for your project too.”

Read this article for the specifics.

6. Do you have any questions about the job description?

Example script:

“Yes, I have a few questions that I’d like to go over with you to make sure that the project goes smoothly.

A few of them are:

*Question about their business e.g. “which product is your most popular?

*Question about their project logistics e.g. “what does the project look like when it is successful and do we have a specific deadline we need to work towards?“

*Question about their project goal e.g. “What is the most important to you? Project speed, cost, sales? Something else?”

7. Which of the required job skills do you feel you are strongest at?

Example script:

“Within this project, we have several tasks: TASK 1, TASK 2, TASK 3, etc.

I have worked on projects involving all those tasks, and I feel the strongest specifically around TASK 2 where I delivered RESULT in a project I worked on. I like to think that I can deliver a similarly great result because of XYZ [e.g. the similarities between the projects]”

8. What challenging part of this job are you most experienced in?

Example script:

“This project contains challenging parts such as PART 1, PART 2, PART 3, and I’m the most experienced in PART 3 because I’ve worked on very similar tasks in other projects. 

For example in PROJECT for CLIENT TYPE where I delivered RESULT. It was challenging because of PROBLEM and I solved it by doing Y.”

How to answer the Upwork proposal questions FAST

The best approach to creating templates for things like Upwork proposal questions is to first learn what works and then figure out how to create an effective template out of it second.

Templates that are quick to fire off have less value, if they don’t work, than spending a lot of time answering the question in a way that works, since we are guaranteed to not get a response at all.

Only when we are confident that the responses work, can we figure out how to deliver them faster.

A good approach is to compile the winning proposals and copy all the answers you have used for each of the questions into a doc.

Then mix and match sections of the answers to create something that fits the specific Upwork proposal you are working on.