Here are 42 questions every contractor should ask their clients…
Company Background Questions
- What kind of business is your company in?
- How long has your company been in business?
- What is the size of your company?
- What is the company’s reputation?
- What is your typical customer like?
- Who are your competitors?
- What is your address?
- What is your phone number?
- What is your e-mail address?
- What is the best way to contact you?
Questions About Work Philosophy
- What is most important to you, quality or speed?
- How often do you want updates on my progress?
- Do you hire freelancers very often?
- Is your preferred work process structured, or unstructured?
- If necessary, would it be okay if I used subcontractors or outsourced parts of the project?
Project Specific Questions
- What is the purpose of this project?
- What sort of background do you expect a freelancer working on this project to have?
- How technical is this project?
- Describe how you envision the finished project?
- How many (words/pages/screens) are needed? (Modify this question for your own specific field.)
- What are the specific project instructions?
- Do your customers have any special requirements or needs to be met by this project?
- Can you show me an example something like what you have in mind?
- Who will be my contact for this project?
- How available are you (or the contact) to answer questions during the course of the project?
- If necessary, will I have access to (your website/company-specific information/etc.)? (Choose one.)
- Is it necessary to have any special (equipment/software) to complete this project? (Choose one.)
- Do you envision any potential problems with this project?
Work Agreement Questions
- What is the budget for this project?
- Who will own the intellectual rights to the finished project?
- What is the deadline for this project?
- How will you be making your payment?
- When will you pay?
Follow Up Questions (After a Project)
- How do you think the project went?
- Do you have any suggestions?
- Do you anticipate having any other projects based on this one?
- Will this project need to be updated or revised at some point?
- If the project needs updating, do you consider the updating or revisions to be a separate project?
- Are there any other projects that I can do for you?
- How often do you need the services of a (writer/web designer/programmer/consultant)? (Choose one.)
- Can I use this project as an example on my portfolio? (If the project has gone well.)
- Would you be willing to give a testimonial on my work for my web page? (If the client is pleased.)
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Jason Bass is a marketing strategist, community builder, and founder who turns bold ideas into real momentum. At the helm of Jason Hunter Design, Pixel Partner Digital, and The Citizen, he brings clarity to chaos, structure to startups, and firepower to brands ready to scale. Known for his visionary thinking and down-to-earth leadership, Jason helps businesses grow — not just in revenue, but in purpose and impact.