What challenging part of this job are you most experienced in? (Upwork)

What challenging part of this job are you most experienced in? (Upwork)

This is another entry in the Upwork proposal-series, where you and I will dive into how to answer often asked questions, so we can land more clients. 

Today, we’ll look at the question “what challenging part of this job are you most experienced in?” and how to answer it.

Similar to many other template-questions asked by clients on Upwork, this one can feel redundant but clients often ask them because they are desperate for in-depth proposals that are actually insightful. Most freelancers don’t write those.

What the client is really asking

If we put ourselves in the client’s shoes and brainstorm what we would want to hear if we were the ones posing this question, we will notice a few things:

  • What makes this project challenging?
  • What experience do freelancers have that are relevant to the project and those particularly challenging tasks?
  • What can the freelancer do to make sure the project goes smoothly and without me (the client) being deeply involved?
  • Will the freelancer need access to my team and if so, will that delay other projects?

That’s a lot to take in at once.. and all that from a simple question. But the key thing to remember is that this is just a way for the client to try to understand if we are a good fit. 

Ultimately, they want to hand the project over to someone capable that can get it done within the time frame and smoothly.

Looking at past similar projects is just one indicator that we might be a good fit. Overall, we can break the question up into two parts:

The client wants to understand how much experience we have with this type of project and if we judge the same parts to be challenging as they do.

If you know a great little trick that most people don’t know, this is a good time to point it out. For example by saying “X task has been a challenge for a long time and recently there was a new update to XYZ tool that allows me a new way to implement XYZ. It is much easier in the past.”

The other part of the question is what we have the most experience with within this project.

It will be tempting to just say that we have experience with similar projects or specific tasks but that is too easy and doesn’t really help the client better get to know us. Remember, it is easy to say so expect everyone to do it. 

Instead, let’s share some specific examples of how we solved a similar task in another project (or if not, how we will go about solving it for the client).

For example, for an email automation project where we set up email flows, we might share an example of a popular funnel that tends to work well (e.g. the five-day launch funnel for an online course) and describe a situation where we used it.

What challenging part of this job are you most experienced in - upwork answer example

First, let’s look at an example script to do just that:

Examples scripts for “what challenging part of this job are you most experienced in?”


“I worked on a similar project for another client launching an online course and we had great success with a 5-day email sequence. We used ConvertKit to run the email sequence and Zapier to automatically push the new leads from the Facebook ads into a spreadsheet and directly through to ConvertKit and into the funnel. The campaign gave 57% ROI after my fees.

The most challenging part was that at first, the automation of transferring the leads from Facebook to the email sequence was flawed, and overnight we would notice a chunk of leads not being transferred correctly. 

They would be stuck via the direct transfer but by experimenting we discovered that if we ran them through an arbitrary spreadsheet before sending them to the email sequence the number of leads that didn’t get transferred dropped from 20% to 3%.”

In order to do business with us, they need to trust us. In order to trust us, they need to like us… and finally, in order for them to like us, they need to get to know us. By showing what we did in detail, it gives the client an opportunity to get to know us better.

It doesn’t have to be something long for the sake of just being long. Busy clients don’t have time for long essays about our life story but they do have time to see how their problem will be solved, so worry about how relevant it is for the client, first, and the length of it, second. You can always trim it down once you have the right points you want to share with the client.

The length of your answer to this question also depends on how long the cover letter is and the rest of the proposal altogether.

Here is a shorter version. 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.”

A note about your answers

It is tempting to complete the proposal fast and focus on sending out lots of proposals to get a chance of landing more freelance projects. 

In reality, we tend to land more projects, and earn more for each project, by sender fewer and writing better proposals for each project.

It is easy for clients to spot bad/lazy copy-paste answers and proposals because there are so many of them next to each other.

The client might accept the proposal but instead of it being because they are excited to work with us — someone awesome — it might be because they are desperate to complete the project and because we seemed like an ok choice in a bad bunch.

That is totally different from a freelancer that shows a great first impression and give the clients a white-glove service throughout their experience, from the first message, through discussing the project and until the project is delivered.

Not only have I gotten tips/bonuses with this approach but it is much easier to charge good rates because the client feels the difference. We don’t have to tell them, they can see and feel it.

Similar to when we buy an iPhone, we might not know anything about the software or the technical specifications… but it’s an iPhone! When we touch it, it feels good. When we use it, it is smooth and rarely crashes. It just feels good to use one.

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