The Most Important Questions to Ask Someone Who is Hiring You

You've delivered the perfect pitch, you've wowed the crowd with your experience and credentials, and now you and your new client are talking the nitty gritty fun stuff – scheduling, payment, expectations. When you're going into business for yourself for the first time, it can initially feel daunting approaching prospective clients and finding the reasons why what you offer outshines the rest.


But just because you've landed the contract, it doesn't mean you're out of the woods. While you've done well, poor communication skills – and because of that, it's a wise idea to make sure that you've asked the right questions, and answered in kind, with your new client.


Stuck for ideas? Here are some thoughts to get the ball rolling.


What is this project for?


It may sound bizarre, but there is a surprising wealth of prospective clients out there who operate, without realizing it, in a sort of information silo mode. They pitch you the project, enlist your expertise to produce it, and then you part ways. What was it all about?


Try asking those hiring you what they're hoping to accomplish with what you're working together on here. Is this to convert web traffic? Promote a new product? Is it marketing? Is it more of a success story, or a critique?


Nailing these concepts down helps you in the long run – you know more fully what you're working with, can produce greatness accordingly, and minimise the risk of the dreaded heavy edits.


How long is this for?


Deadlines and schedules are one thing, and something that many freelancers find is that the flexibility on offer in this kind of work is soothing and inspiring. Yet it's more than just a question of delivering A, B and C articles by X, Y and Z deadlines.


Moreover, it's about identifying just how long you'll be working together. Is this a one-off arrangement? Is it for a longer term? If so, great – but for how long? Is it a wait and see thing? Is it a rolling arrangement? Will you touch base with one another from time to time for future collaborations?


If you work well together, chances are much of this will sort itself out in time. Yet if you're planning your schedule, or juggling multiple projects, having a basis of understanding about your client's timetable will help you refine your own.


When will you get paid?


Always a delicate topic to broach, but a vital one. In an ideal world, those hiring you will lay this out plainly for you from the outset. It's crucial, especially if you are juggling lots of opportunities, to understand what is coming in when.


Some companies and individuals dish out the dollars immediately on delivery, some weekly or biweekly, and still others monthly. Some clients will have a 30 day waiting period to sit out before their invoicing cycle picks up your contribution.


There's no hard and fast rule here, but what is definitely wise is simply getting to grips with when you can expect your fees to be settled.


Do they often work with freelancers?


It's no secret that freelancing is a growing market, and because of that many more companies from a whole host of different business sectors are turning their attention to freelancing as a viable way to do business.


Why is this important? Well, as with anything, there can be a learning curve. A company who is only now starting to work with freelancers may have some misconceptions about your chosen vocation. If so, you can help them get up to speed. On the other hand, a company who works with freelancers pretty often is likely experienced, but may add an element of competition – you could well put out some feelers as to how you can stand apart from the pack in that case.


Clarification, clarification, clarification


Painting a broader picture here, if you're not sure on something that those hiring you have put in the brief, ask them to help clarify it for you. Likewise, this can help you from feeling around in the dark if you've been handed a somewhat lacklustre brief to work from.


Pinpoint confusing items now to save you having to rejig them later. Are we using jargon for this project, or easy to read terms? Is this a first person, second person, third person piece? Is it more like a narrative or a white paper?


It's easy to fall into the trap of thinking that if you ask questions like these, you come across as an amateur. Yet you being a creative professional means it's definitely more accomplished to ensure you get it right first time, every time.




Asking the right questions early on in a project does wonders for minimizing hassle, misunderstandings and extraneous edits and reworking. You owe it to yourself to make sure you're going into the forthcoming projects you've earned with eyes wide open – and from precision details to payment deadlines, having a handle on this information is some priceless wisdom. From there, you can deliver projects successfully, build a better portfolio and go into future projects with more confidence.