Each freelancing job is unique in some respects and we are constantly dancing with new partners. It’s one of the reasons we like freelancing; the variety keeps it fresh and interesting. A consequence of the variety is the initial back and forth we do for each job while we are coming to grips with this buyer- their particular expectations and requirements.
Getting a handle on a new project quickly is important. Relevant questions help, and they accomplish two goals. They frame the job as clearly as possible and they show buyers that you are a focused professional.
If you don’t ask meaningful questions and get good answers, you and your client are left without concrete milestones and objectives. We are writers; we are communicators; soliciting key information from your buyer is the first chance you have to show off your skills.
There’s one other side to consider- the buyer’s perspective. They are as much in the dark about you as you are about them. When you ask good questions they can see you are taking the project seriously. This instills confidence. It’s happened to me more than once: I asked questions on the message board to narrow down a job’s scope and landed the job before placing a formal bid. The buyer could tell I was interested and focused on the problems and specific needs of his project.
Buyers appreciate that you need some essential information to bid accurately and unless they are experienced at posting jobs on oDesk, they’ve probably left something out of the description. Here’s the top five questions I need answers to before I start work:
Who am I writing for?
I don’t mean the buyer, I mean the reader. Who is going to be reading this and why? Are they already well versed in the subject or are they lay readers? What are their interests? This is what makes a press release a different animal altogether than an ‘About Us’ page. The same basic article would be unrecognizable when written for an editor who just needs the facts, a lay reader looking for engaging narrative, or a search engine picking out key words for ranking (yes, sometimes our readers are machines).
The more I know about who I am writing for, the better. Are they educated readers who won’t put up with hype or fluff? Are they less serious readers just looking for an entertaining piece? The questions vary depending on the project, but the information I want to extract is the same: I want to know who the expected audience is.
What is my writing supposed to accomplish?
Buyers should have a clear objective in mind for their project. Sometimes you have to remind them of this and get them to think it through. You want to know if your piece is meant to sell a product, inform naive readers, push an agenda, establish authority, connect on an emotional level… the list is long and the objectives often mixed. The clearer your buyer is on the purpose of the piece, the easier it will be for you to mold it to fit. And when the time comes to submit your work, the same standards will be in play. There won’t be any mystery about whether or not your piece has the right spin.
What are the firm deadlines?
Every buyer wants it today, or maybe tomorrow morning. If you pay attention though (and especially for integrated projects where your writing is only one brick in a large wall) you will notice that while you are sweating to meet some deadline, your material doesn’t appear for weeks or even months after submission. I’ve adopted a rule many subcontractors use: Good, Fast, Cheap- pick two. The idea is to allow for rush jobs, but charge for them.
You should have two things in mind when you are talking deadlines with a buyer. The first is your own private estimate of how long the project is actually going to take you. This is your, bottom-line-do-it-as-fast-as-possible date. Keep this private.
The second is your, ‘how much time I’d like to do it in with my other jobs and the level of stress I’m comfortable with and knowing life in general will intrude’. This second estimate is what you predicate your regular bid on. Anything quicker than this is a rush job. Add at least 10% to your bid for short-deadlined work.
What are the format restrictions?
The catch-all term ‘format’ refers to the final form your work will take. Here’s some examples from recent projects I’ve completed:
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MS Word. The most common way (along with Rich Text Format) we submit our written gems.
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PDF. If you don’t have the ability to produce .pdf files, you are going to be shut out (or at least ranked lower) when a buyer expects deliverables in this, or any other specific file type.
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Email. Yes, emails have their own style. You are limited in length, tone, and maybe fonts.
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Dialog. I did a script for an animated cartoon that limited sentence and word length, couldn’t have bold or italic script, and had to meet ‘run time’ parameters.
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Graphic. Pictures, graphs and other visual add-ons mean you have to address file size, pixel density, color and readability issues for different browsers. My graph looked great on my screen, but the labeled points were impossible to make out in the final version. Graphic arts is a field all by itself for a reason.
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Word count. There are situations where word count mismatches occur between what a buyer has in mind to cover in a piece and the amount of room necessary to do it justice. Generally, buyers think they are getting more for their money when word count goes up. But at about 450 words per average website page (when font and formatting is taken into account) they can overshoot if they ask for a thousand words where only 500 will fit.
How and when will I be paid?
I suppose it’s human nature to ignore uncomfortable subjects. And for some reason, money issues can fall into the category of ‘unpleasant’. I used to avoid talking money upfront with clients because it made me uneasy. That changed when a fundamental misunderstanding about pay rate ruined an otherwise ideal job.
Freelancing is a business. Buyers are usually in business too, and they understand that ‘how much’ and ‘how soon’ impacts your ability to continue doing business. By clarifying payment amounts and methods, you demonstrate to your buyer that you are a serious business person. Don’t think that you are insulting anyone by asking money questions. They will appreciate knowing where things stand as much as you do.
The right questions help you in other ways too.
Simply by asking and evaluating the answers to these 5 questions, you will get a better appreciation for what the actual job is (as opposed to what they posted). But there’s a hidden bonus. The interaction with your client will tip you off to what it is going to be like working with them. Quick, informative answers tell you as much about their business style as a history of completed jobs on oDesk. Difficulties in communication, whether because of personality conflicts or language barriers, will become evident before you’ve taken the plunge and started work.
So ask away. It’s only going to help smooth the road and mark you as a mature professional freelancer.
- Get Your Freelance and Sub-Contracting Questions Answered
- How to Close a Deal
- You’re Ready, but are you oDesk Ready?
- Interview Mistakes I Have Seen
- Creating a Professional Profile at oDesk

Good post Bill
Those are all really important things to know. There’s nothing worse than being hit by a sudden ugly surprise because you didn’t ask the right questions to be able to understand the job.