6 Questions to Ask a Prospect

Woo-hoo, you’ve got a live one here! You’ve stumbled upon a prospect and you do not want to screw up and lose what might be an opportunity to get paid. You want to keep this fish on the line and figure out 1.) if s/he is serious about hiring a Freelance consultant to work with and 2.) if the project is something you can handle. A series of easy-to-remember questions that help you to encourage the prospect to open up and tell you what s/he needs and also move the process toward a commitment for further discussion are essential. Your goal, of course, is to obtain a project that will both enhance your revenue and if possible, enhance your CV as well.

Picture this—you and the prospect have each given the meet’n’greet (short) versions of your elevator pitch and the prospect is showing an interest in your offerings and would like some details. You’re asked if you’ve ever worked on a particular sort of project, or provided a solution for a certain kind of challenge or problem. Presented below are questions designed to make it easy for your prospect to share information and allow you to position yourself as a good candidate for hire if a project actually becomes available.

  1. How can I help you?

“A customer’s time is valuable, so that first question must be impactful while still respecting their time,” advises Eng Tan, Founder and CEO of Simplr, a customer service and customer experience start-up. ‘How can I help?’ is open-ended enough to invite feedback, but also show that the customer comes first.”

2. What is the problem or pain point?

You cannot jump into a sales pitch until and unless you hear the prospect describe the matter that must be resolved or challenge that must be overcome. Only then can you determine if you have the expertise and resources to provide the desired solution. Allow your prospect to tell you what s/he would like you to do.

3. What is your goal?

Get the prospect to articulate the purpose of the proposed project and what the resulting deliverable means to the organization. Determine if this is a mission-critical goal and the date that the deliverable must be received. It is to your benefit to understand why the prospect feels it’s worth paying outside help to get the project done. The proposal you write and your pricing structure, if negotiations get that far, will be impacted by this information.

You must also understand what will happen if the client does nothing (and nothing is precisely what most of them do anyway, am I right?). So do your best to find out what it all means to the prospect and the company and how the proposed project fits into important goals.

BTW, not every project that gets funded is tied to a meaningful goal. I know someone who probably makes 3x what I make in a year by producing an ultimately ridiculous vanity-driven deliverable for well-known for-profit and not-for-profit organizations. Enhancing reputations can be big money, it seems.

4. Have you done anything about it so far?

With this question, you’ll learn if the prospect has worked with a competitor. You can follow-up and ask if there was dissatisfaction with the competitor’s deliverable, price, or customer service. If the matter has so far been handled in-house, you can follow-up and ask why outsourcing looks like a good option now. In short, you’ll learn why your decision-maker or stakeholder/ decision-influencer prospect is motivated to talk to you about the problem and inquire about how you might resolve the problem or produce the deliverable.

5. Is it you who decides how this matter gets resolved?

At this point in the conversation, it is both prudent and politic to ask who makes the decision to bring in someone from the outside, i.e., a Freelancer. You will have earned the right to know if the individual with whom you are speaking has the authority to green-light a project on his/her own, or in concert with a select group of stakeholders. You need to get a sense of how superiors, colleagues, or stakeholders feel about bringing in a Freelancer and I recommend that you get an answer before proceeding with the conversation.

It is possible that your prospect is alone in thinking that an outsider should be brought in to manage the project and his/her opinion may or may not prevail. Now is the time to get a sense of whether outsourcing this project is wishful thinking or a possibility.

6. What would you like to see happen next?

With this question, you invite the prospect to commit to follow-up, be it a face-to-face meeting, an email, or a telephone call. The prospect will be able to reconfirm his/her confidence in your capabilities as s/he shares more information about the proposed project and digs deeper into the how and why your product or service can address pain points and facilitate realization of the company’s goal.

This conversation will determine whether you are considered a serious candidate for managing the project and if the company is serious about hiring a Freelancer. You could very well be invited to submit a proposal and if that is the case, it is a big vote of confidence (but alas, still no guarantee).

If asked upfront about pricing, you might like to respond “What’s your budget?” If it’s smaller than you hoped, work with the prospect to provide the project must-haves, minus the too-expensive extras, at a price the organization can afford. Then again, they could surprise you and appropriate more money. You just never know!

Thanks for reading,


Photograph: The Fuller Brush man visits a prospective customer (circa 1950)


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