Questions that Move a Sale Forward

Well cha-cha-cha! You were able to resurrect a pre-COVID conversation you were having with a potentially good prospect and not for anything, you need to consummate this sale. Selling a prospect is like a dance and s/he who is selling must learn to lead with style and grace.

Step 1 is to understand what the prospect needs and the job specs, the specific work that must be done. Step 2 is to confirm that you’re able to do the work within the requested timeframe and allotted budget. Step 3 is to convince the prospect that you have mastered Step 1 and can achieve Step 2.

Since the shutdown, the ground has been quaking beneath our feet. Business owners and leaders are in various shades of panic, searching for answers and in need of reliability and support from their Freelancer colleagues. The need to establish trust cannot be overestimated. Your prospect must believe that you will not disappoint.

If you have not worked with the prospect before and the discussion will take place over Skype or other video platform, establishing the familiarity and comfort level that are the ingredients of trust will be more of a challenge. Turn up your listening skills and empathy because you’ll need those qualities more than usual. See my post

The 12 questions below are designed to 1. Display your empathy and ability to become a trusted resource; 2. Confirm the prospect’s intentions; 3. Specify the work you would perform; 4. Learn if your prospect is the decision-maker; and 5. Get an estimated starting date. At the conclusion of the conversation, the prospect should invite you to submit a proposal. If that does not occur, I would follow-up with a thank you email and then put this company on the back burner.

“In light of the new business environment, how has your process changed?”

“What are you doing that’s working well right now?”

“What’s hardest for you now?”

“What can you still do that you were doing before the shutdown?”

“Do you see what seem like good opportunities on the horizon?”

“Are there plans or intended projects that have been cancelled or put on hold?”

“Confucius said that a journey of 10,000 miles begins with the first step. What first step can I help your organization take?”

“Is the project we’re about discuss today something you planned to do before the shutdown, or is this a new initiative?”

“Is there something that is blocking you from taking the next step forward, or causing you to hesitate ?”

“What is the solution that would give the most impactful long-term benefits to the company?”

“How can I be a good resource to you and help you move forward?”

“If you were the only decision-maker, what would be your preferred start and completion dates?”

Thanks for reading,


Photograph: Kim Clark. Dancing to the music at the 2019 Tito Puente Latin Music Series at Villa Victoria in Boston’s South End neighborhood.