10 Essential Questions to Ask During a Discovery Call with Your Client

March 24, 2017

Image credit — Pavan Trikutam via Unsplash

How do you feel about talking to clients on the phone (Skype / Zoom / whatever)?

In my experience, freelancers tend to fall in one of two camps on this issue:

1. “I do client calls all the time, no big deal. They’re very helpful, and sometimes I even enjoy them. Is that weird?”

2. “Nope. Nope nope nope. I became a freelancer literally SO I DON’T HAVE TO TALK TO PEOPLE!”

I breathed awkwardly into the speaker — surely, that’s enough social interaction for the week

I used to be in camp #2, my precious introverted heart aching at the very idea of calling someone. Now, I’m firmly in camp #1 and I believe that client calls are essential for doing a great job. Especially if you don’t have enough experience yet.

Specifically, I’m talking about discovery calls — the kind you do when you’re preparing for a freelance project, and set out to learn as much as possible about the client’s needs and goals.

“What’s so great about discovery calls, Oleg?”

If I had to sum up the answer in one sentence, it would go something like this…

Before you do ANY amount of work on ANY project, you want to gather as much information as you can in the shortest time possible; this is the best way.

(I cheated by using a semicolon there, but I hope you’ll forgive me.)

Discovery calls will help you:

1. Complete projects faster. If you do an effective discovery call, you’ll save a ton of time and energy down the line. There will be fewer misunderstandings, less email and phone back-and-forth, and general headless-chicken-like running around.

2. Raise your value in the client’s eyes. Like, a lot. Remember how 2 weeks back we talked about asking smart questions, and how competent it makes you look? Well, asking them live is even more impressive.

3. Fuck up less often. As soon as I started doing discovery calls with clients, my rate of shitty first drafts that missed the mark by 100 light-years has declined dramatically. In hindsight, I should have figured this out way sooner, and saved myself, and my clients, many hours — and billions of brain cells.

4. Price your services better. Both freelancers and clients constantly underestimate the scope of projects. To a client, much of your work process is unknown or hidden, so they are terrible at judging how long something will take. To you, this means that any (supposedly) easy-peasy job can morph into a terrifying rollercoaster from hell once you dig in and learn all the details. In-depth discovery calls help to dispel that dewy-eyed naivete, on both sides.

This week, I’m sharing the most important questions you want to ask during client discovery calls, divided into 3 categories. I did my best to adapt everything in this post for any type of freelance work, not just copywriting. Hopefully, I succeeded — but you be the judge.

Questions about the audience

Readers, viewers, listeners, website visitors, customers, employees, business partners, investors… The people who are going to see your work will ultimately define what it’s going to look like. Learning about that in as much detail as possible is your #1 priority during a discovery call, regardless of what you do: copywriting, design, coding, voice work, or nude modeling.

1. “What’s the ONE group of people you’d like to see this the most? In other words, if you could have an endless line of them queuing up for this, who would they be?”

In my experience, most clients want to please everyone. They want to appeal to the greatest number of people. It’s your job to explain to them: that way lies madness. Or at least, that way lies the creation of eye-rollingly dull, instantly forgettable work nobody will look twice at.

This question forces them to think in terms of what they really want to achieve with every project they do. And it makes your job as a freelancer ten times easier.

2. “If we look at everyone who could possibly be your customer… what’s the #1 pain or problem they all share?”

In a way, this question is the opposite of #1. Exposing shared pains and problems will help your work connect with other groups of people your client wants to attract — even if you’re still focusing on that one “ideal” group. It’s a really useful thing to know.

You can also flip this question and ask about the target market’s motivations or goals instead. Talking about pains and problems doesn’t resonate with all clients.

3. “Does your audience have any likes or dislikes I need to be aware of? Anything they love or hate that could affect how they perceive this?”

Fun fact: I used to get in trouble for using curse words in client copy. One time, I used the word “hell” in a blog post for a client and caused a shit storm in their inbox. It never occurred to me that some people won’t buy from businesses that have a potty mouth. Go figure.

I just wanted to craft an emotionally charged message, and honestly I feel so attacked right now

Most clients (the good ones, anyway) know what their audiences love — and they know what makes them lose their shit. If you can make your job easier by appealing to those likes and avoiding the dislikes… why shouldn’t you? For this reason alone, #3 is a useful question to ask.

Questions about the client

Talking about the client is the second most important objective of your discovery call. Ask about them as a person — to learn about their background, previous experiences and preferences. And learn more about their business — the company, its products, services, its unique advantages and weaknesses.

4. “When you ask your customers why they chose you over all other options, what do they say? Can you tell me about a recent example?”

This is a very revealing question, for many reasons.

For starters, it will let you know how seriously your client takes their customer research… and if they do it at all. Also, it will expose the difference between what the client thinks their target market wants — and what customers themselves say they want.

That’s why it’s important to get the client to name a specific example. Ideally, they will tell you a story, and quote a customer’s words directly.

5. “Help me understand what makes your product / service / content / business etc. great. What is it that you can offer to people that nobody else can?”

Last year, I wrote some copy for a wine producer in Australia. They were just one out of dozens of similar wineries. They were producing the same vintages as everybody else. They were marketing to similar customers.

When I asked this question during a discovery call, it felt like I inadvertently shattered the client’s heart into dust. It worked out after all (we found what made the winery unique) — but I want to warn you:

Sometimes, your client will not have a good answer to this one. And that’s OK. Not every business has a unique offer that will inform how you approach the project.

The point is, if they do, you want to know about it.

6. “On a scale of one to ten, how would you rate your previous experience with a freelancer? What can I do for you to make this one a 10? How about 11?”

This question is pretty self-explanatory. It’s just one of those things that signals your competence. And depending on your client’s previous experience with freelancers, it also reveals if you have some big shoes to fill or not.

Questions about the project

This is the final piece of the puzzle — to discuss your client’s needs and goals with the project you’re going to be doing. We started with the big picture, and we have worked our way inward.

Like eating pizza crust first, only not disgusting (seriously, Pizza Hut, what’s wrong with you?)

7. “What’s your ultimate goal for this project? How does it fit into the big picture of your business / career / [whatever it is you’re helping them with]?”

This is sort of like that job interview question everybody hates: “What’s your biggest weakness?”

The important thing is not what the client says, but the fact that:

– They have an answer.

– The answer is not vague.

– You now know what the answer is.

8. “How are you currently doing on this goal? It would help if you could share specific numbers, stats, or quotes — later, once we’ve wrapped up this call.”

Again, it’s important that the client has a specific answer. Because if they are not aware of how they are doing right now, it’s a big red flag. It shows you that the client has no frame of reference to measure the success of your freelance project.

But once you know about the client’s current situation, and you know why the client believes what they believe, it will make your job a lot easier. You will know what the “before” picture is, and what the “after” picture is supposed to look like.

9. “Can you think of any examples of similar work you absolutely loved? How about any examples you hated?”

Freelancers don’t ask this question enough — and for the life of me, I can’t understand why.

It’s so much better than just working from a creative brief, or your client’s words alone. If the client can show you what exactly they like and don’t like about other people’s work, it eliminates like 90% of any guesswork involved! It’s like a custom sample in reverse.

If I could only ask one question in all of my client interactions for the rest of my freelance career, it would probably be this one. Because even if I don’t have all the other information, I can infer what I need just by looking at the client’s examples.

10. “How do you want your audience to remember this? What do you want them to do about it?”

Your client doesn’t just want people to see the work you did, shrug, and move on with their lives.

They want to elicit some type of emotional response. Some type of action. Maybe they want to sell something. Maybe they would like to communicate an air of expertise and authority. Maybe they want people to laugh their asses off.

It’s your job to find out. And if the client isn’t 100% sure about their answer, it’s your job to help them figure out what they want. And as with question #1, you want to focus on one thing at a time. One thought. One emotion. One action.

What questions do YOU ask your clients?

I’d love to hear from you — especially if you’re not a copywriter, because I’d love to know more about how other freelancers approach discovery calls.

Leave a comment and let me know! I’ll respond to every single one.


  • Reply Rocky Kev March 24, 2017 at 6:50 pm

    This is great Oleg!
    #7 is important for me. I remember I had a friend look over my list of questions and said, “if you look at their website, you’d know what they’re looking for.”

    When I asked the client… they fumbled and gave me a whole different response, as well as thinking I was somebody else.

    Its a great question and important to make sure everyone is on the same page!

    • Reply Oleg Starko March 29, 2017 at 4:33 pm

      Thanks for the insight, Rocky! I actually got burned on a recent project precisely because I *didn’t* ask that question. That’s why I included it. 🙂

  • Reply Nadine Mandjoli Yaya March 25, 2017 at 8:34 pm

    This is a masterpiece and I have been slowly consuming it, because, all the questions are great, though, I like this particular one: “What’s your ultimate goal for this project? How does it fit into the big picture of your business / career / [whatever it is you’re helping them with?”

    I will love to ask my client, about their communication style/work personality. In this sentence, you will want to know which communication medium your client is more responsive and if they will like to approve any decision, you will take as per their project, or they trust you to take the best decision. I had a client’s call this evening and have been discussing with this client for days now. I thought, he wanted to oversee everything, but he told me, he trusts my choices and anything I come up with. I might have come across like a poor services provider to him, if he didn’t see my earlier inputs.

    • Reply Oleg Starko March 29, 2017 at 4:35 pm

      Thank you, Nadine! I agree, asking the client about how they like to work is really useful. If only to weed out the ones whose work style / communication style doesn’t agree with your own. 🙂 E.g. I try to avoid clients who micromanage everything, because I like to have some autonomy when I work.

  • Reply Nikki March 31, 2017 at 2:18 pm

    Do you usually charge for client calls? I never know if I should make them free or actually bill for them. If you bill, how do you go about telling the client that non-awkwardly?

    • Reply Oleg Starko March 31, 2017 at 10:42 pm

      Great question, Nikki! 🙂 And my answer is, it depends. For example:

      1. When I’m jumping on a super-fast call — like, around 5-15 minutes — I usually waive the fee. Even if I’m already working with the client, and billing for my time. It’s just a little extra thing that I can do to make them feel special, and my relatively premium hourly rate lets me not worry about it much. I usually get the client to say yes to a longer call down the line, which is going to be billable.

      2. For longer discovery calls, I only bill for them if it’s a new project with an existing client. Otherwise I try to limit the time as much as possible and it’s the same as situation #1.

      3. Sometimes I also do strategy calls, or short consults. They are different from discovery calls, in the sense that I’m using my expertise to help the client — not just trying to find out what they want. In that case, I charge based on a percentage of my hourly rate. I.e. if we talk for 30 minutes, and my hourly rate is $150, I bill for $75. I’m going into these calls having warned the client beforehand that those are paid.

      As far as saying it non-awkwardly — I just say matter-of-factly that I will bill them for the call. They are either working with me already and are fine with it, or I’ve explained the value of the call beforehand, so they are also fine with it.

      Let’s workshop it, if you’d like some advice? Let me know how you would ask this, and I’ll critique your response. 🙂

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