How to answer prospects’ questions to land the sale

tweet share share pin email

Earlier today my partner, Louisa, called a CRM company to ask some questions.

We’re outgrowing what we’re using now, so she wanted to see if they could help.

“[Blank] CRM,” a man answered.

“Hi, yeah, I had some questions about your CRM,” Lou said.

☘ Bad luck with clients? Trade your worst clients for some of the best companies in the world. Real clients with real budgets are hiring freelancers like you. Click here to learn more.

There was silence on the other end of the phone.

“Hello?” she asked.


You'll also enjoy this episode of our new podcast...

“I have some questions, is that alright?”


“I don’t really know much about CRMs and what they do. What’s the main difference between what you guys do and a help desk like Helpscout?”

“Uh, we’re a sales platform.”

More silence.


The conversation went on like that for a few minutes and finally she got off the line, frustrated, unable to pry more than one-word answers from the guy.

Lou expressed so many things that made her an EASY target for a sale, for example: “I don’t know anything about CRMs” – the guy could’ve told her anything. But this frustrating experience made her swear off the company for life. (And she sent them an email letting them know it.)

The thing is… I know that lots of agencies and freelancers don’t do much better.

How do I know? A while ago, I went “undercover” and reached out to a couple dozen or so freelancers and agencies, posing as a prospect with questions, and the responses I got weren’t much better. Only 1 or 2 of the bunch did a good job. Only 1 did a great job. And the rest made me cringe, like the conversation above.

So let’s talk about how to answer customer questions in a way that actually lands the sale, alright?

This applies to both email and phone interactions as well.

Step 1: Set your intentions about customer service long before your prospects reach out.

The guy above, while he really… sucked… wasn’t actually the problem.

The problem is that their company so systemically neglected good customer service that a guy like him could end up answering the phones. 

See the difference?

So before you interact with another prospect, decide right now on the experience you want them to have.

How do you want them to feel during the email / call? What do you want them to think about you? If they were to tell someone else about the interaction, what would you want them to say?

At Reliable PSD, we take time every couple months to re-evaluate these questions. Here are our most recent answers:

  1. We want people who reach out to feel like they’ve encountered old friends. Like a homecoming, almost. We want it to be more about building a relationship than making a sale.
  2. We want them to think that we’re extremely kind, helpful, knowledgeable, and maybe a little funny.
  3. If they were to tell someone else, I’d want them to say they were super happy with the interaction and that we’re simply awesome.

This doesn’t fit every company’s culture. Some people like to be more “professional” and not turn clients into friends. Just depends on your culture.

There are no right or wrong answers. Think about what fits your personality and business.

Step 2: Listen for the “questions behind the questions”

Prospects usually don’t know what to ask you at first, so they lead with the question, “What are your prices?”

Think about what this question really means though. Think about what you mean when you ask someone that question.

I hear a few concerns and questions wrapped into that one, but they all pretty much are variations of this:

“What kind of value can you offer me? Is it worth my money? If I pay you, will you deliver what I’m really looking for?”

Look at the price question now and see if you can “hear” these other questions hiding inside of it.

“What are your prices?”

This is important because people rarely ask what’s really on their minds. That’s not because they’re deceitful or anything. It’s because most people don’t know how to, or don’t realize they’re even thinking / feeling these things.

It’s up to you, the professional, to know these underlying concerns and questions are there, and to address them head on.

So when answering the price question, which is really a value question, make sure you respond by listing out all of the value you deliver for your price. Make them realize they really get a lot for what they pay.

If someone asks for references, they’re expressing concern about trust and reliability. Make sure you address that head on.

If someone asks for payments to be broken up a certain way, they’re afraid of being ripped off, so they want to control the payments to ensure you won’t bail or bait and switch them or anything.

Step 3: Respond to the “question behind the question” head on, then move the conversation forward to taking action.

For example, someone recently reached out to us requesting alternate payment terms that included partial refunds for missed deadlines and some other conditions. These terms protected him from being ripped off essentially, and that was crystal clear to us. Without “telling” us, he’d just told us he’s worried about that.

So we responded to the concern he didn’t express “out loud”, but that we inferred.

We told him with a request like that, he’s likely been burned in the past, and we can totally relate to that and understand. With that said, our contract already protects him from missed deadlines and such because we have a penalty system worked out in it already.

Since we addressed his concern, we then shifted gears, and asked if he’d like to get a quote on his project.

His response was very positive. He felt re-assured, and was willing to use our current payment terms from that point forward. You could almost feel the sigh of relief in the response.

That’s what happens when you break through the ice, and make people realize you really care about them.

The simplest way to address these concerns is to tell people you understand them. The man above didn’t tell us he’s concerned about that. We could tell from his requests.

If someone asks for references, we tell them that’s a wise decision and we completely understand why they’d want to be so sure. We applaud their due diligence.

Respond to what people are really saying, not just what’s on the surface.

Step 4: 2 simple tests to see if you’re getting it right.

The first test I came up with myself. If emails take a lot longer to write than you think they “should”… and you find yourself obsessing over every word… you’re probably getting it right.

This next test Lou came up with: If what you’re writing is making you smile — like genuinely smile — you’re probably getting it right.

What do you think? How do you respond when potential customers ask questions and express objections?

I’d love to hear your thoughts. Leave me a comment below, will ya? 😉

tweet share share pin email

Say Goodbye to Roller Coaster Income

Your income doesn't have to be a guessing game every month. Let 4 thriving solopreneurs show you how in our free guide.

Related video:
About David Tendrich

David Tendrich is the co-head of creative agency Unexpected Ways, as well as the co-founder of Reliable PSD: the first-ever PSD to HTML & PSD to Wordpress service run by designers, for designers. He co-runs his companies from Portland, Oregon with his lovely wife and biz partner, Lou Levit.


More about David’s business: David is co-founder of Reliable PSD – what happened when a group of designers got fed up with PSD to Code companies… and created their own. Check them out, and see why freelancers & agencies are head over heels for this amazing new service.

Leave a Comment



  1. I don’t even understand the initials PSD and CRM but the content still applied to freelance business if you’re you follow all the directions you lay out here. Good job! PS: I don’t even run a business yet, I just manage a blog, still, for someone even thinking about when they do put it all together, it makes perfect sense.

  2. Very well written @David. As a designer when I am approached by prospective clients and they start with their conversation with questions like “what are you charges” OR “How much time you take to get done so and so designs”. I take a deep breath and revert them with a convincing mail telling my work process, turn around and with a questionnaire that helps them knowing better what exactly they want out of this project & that really helps me further.

  3. I love this article. My entire life has been about great customer service, and you addressed a few situations that I find myself getting stuck on. Also, thank you for adding your two tests at the end, it’s always good to have something you can measure your performance by.

  4. Customer service has so many hats. As a freelancer, you’re providing a service and the key is to ask the right questions and prompt for the ones that are not getting asked. Listening generously can help you land the sale!

  5. Loved this article – would make for a fabulous customer service workshop! Keep up the good work David & Millo, I look forward to checking my inbox with my morning coffee every day 🙂

  6. This is one of the hardest things to do! Discerning the questions behind the questions and responding to THOSE instead 🙂 What an awesome article, thanks so much for this. I always read your posts as they are released, as I KNOW I’m going to find great content to help me run my business!

  7. This was such a valuable read! Bad customer service could bring a company to it’s knees if they aren’t careful. Especially these days when it’s all about the “experience.” Definitely referencing this in one of my upcoming posts…

  8. I’m so relieved to read “Step 4: If emails take a lot longer to write than you think they “should”… and you find yourself obsessing over every word… you’re probably getting it right.” I’ve been told I get the tone of my emails just right, but that I take forever. It’s nice to think of it in the reverse, which is that I take a long time to email because I get the message just right. Thanks!


Need more clients?

Download our free guide:
25 Top Freelance Job Sites for Real Clients with Big Budgets