As a freelancer, you may find yourself in a situation where the stakeholder doesn't know what questions to ask. This can be frustrating and make you feel like you are not doing your job well enough. However, there are ways to deal with this situation so that you can get through it successfully.


  1. First, try thinking about what questions would be helpful for you as a freelancer. For example, if they are asking for more details about your background or experience, then it might help them to know what skills and experience are necessary for the project at hand.
  2. Consider asking questions yourself. One thing that's important to remember is that you're working for the stakeholder—not the other way around. Asking questions about their expectations and needs will help you better understand what you need to do for them, and it can also help them articulate those expectations clearly.
  3. Ask open-ended questions that give them space to tell you what’s important to them. For example, instead of asking “How many hours do you want me to work each week?” ask “What kind of schedule works best for you?”
  4. Another strategy is to make sure that your stakeholder knows how much information they need to provide in order to get what they want from you. If possible, give some examples of what kind of information would be helpful (for example: "I'd like to know what kinds of posts you'd like me to write.") This will give them a better idea of what kind of answers they should be looking for when they ask questions themselves.

Dialogue Examples

Example 1

Stakeholder: I don't really know what questions to ask.

Freelancer: That's okay! I'll help you out. What are some things that you're curious about?

Stakeholder: Well, one thing is how much this will cost.

Freelancer: Great question! Let's figure out how much it will cost and then we can go from there.

Stakeholder: Okay, so what does that mean?

Freelancer: To figure out how much it will cost, we need to know what the work entails and how long it will take. Can you tell me more about what you want us to do for you?

Example 2

Stakeholder: I'm looking for a freelancer to help me with a project. Can you help?

Freelancer: Sure! What kind of project are you working on?

Stakeholder: I'd like someone to write a press release for my company.

Freelancer: That sounds like it could be challenging. Are you looking to get a lot of attention from the press, or is this more of an internal document?

Stakeholder: A little bit of both. We're hoping that we can get some coverage in some local papers, but also want to make sure our employees understand what we're trying to accomplish.

Freelancer: Okay! Why don't we talk about your goals for this piece before we get started? That way we can make sure that we're on the same page and make sure that I'm providing the right services for your needs!