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)

Presentation Checklist: Audience Matters

Next week, I will make two 15 minute presentations and in four weeks, I will make a 30 minute presentation and also preside at a big meeting. The latter engagement is an annual event and I knew well in advance of my obligation, but requests for the first two talks came up unexpectedly. Fortunately, I have time to prepare for all. Here’s how I’ll get ready to stand and deliver:

Who’s in the house and what do they want to know?

All presentations are ruled by the audience and the information that is desired. That information is the purpose of your talk and it determines what you’ll present. Find out also if any stakeholders whom you must persuade will be unable to attend and arrange to follow-up with them personally, if possible.

Hecklers and haters

While researching your talk, ask the organizer if anyone in the audience might have a reason to undermine your objective and why that would be so. To neutralize expected opposition, acknowledge somewhere in the solutions section of your talk that some in the audience may have considered another recipe for resolution and state how your approach will likely be more effective, sustainable over the long term, easier or less expensive to implement, or whatever. Handle the matter like a sales objection, because that’s what it is.

Audience size

The size of the audience guides your method of presentation. An audience of five is intimate and calls for a different approach —most likely more relaxed and personal— than an audience of 50. A larger audience often requires that the speaker use visuals, along with a speaking style and pacing that engages a bigger room.

Does the audience know you?

Friends in the house will make your job easier because you will feel more comfortable standing in front of them. If you are mostly an unknown quantity, it’s important to establish rapport with the audience early in the talk. A statement about how you understand or empathize with a priority or concern is a good ice-breaker and gives you credibility, since you agree with them.

What do you want audience members to do post-presentation?

Design your presentation to frame your call to action as logical, effective, beneficial and inevitable. Describe what you would like audience members, in particular the thought-leaders and decision-makers, to do on your behalf. Do you want them to donate money or time? Approve your proposal? Vote in a certain way? If you are able to make fulfilling your call to action easier for them, then do so.

Thanks for reading,