How do you get the right answers when starting on a new project? Make sure you’re asking the questions your clients didn’t know to ask themselves.
You might have noticed a pattern recently, of professionals and thought leaders talking about questions. What questions should you ask yourself in your business? What questions should you ask to motivate and plan for the future? To stimulate ideas and creativity?
Wherever I look right now, people are talking about asking the ‘right’ questions.
Kira Hug and Rob March at The Copywriter Club recently discussed in an email the right questions to ask to get the information you need to grow your business and get better at what you do. (Tip: it’s about being clear on your goals, but knowing you need help with getting there.)
Michael Hyatt in his ‘Lead To Win’ podcast of 5 Feb 2019 talked about the four questions that will transform your leadership. (Spoiler: they’re very basic, but worth re-visiting.)
Sam Ovens (think what you like about him) says the best question ask your clients is: “If you could wave a magic wand and have our product do anything (doesn’t matter if it’s possible or not), what would it do?” This identifies quickly the problem you need to solve better in your business, and you can work to create something people dream of.
AND… people always love a Q&A at the end of a webinar, or a list of FAQs on a web page. People are naturally curious, and being a great marketer is about answering the right questions.
‘So, what are these questions you’re talking about?’

Irony-free stock image of a client discovery session, or perhaps simply mansplaining
I’ll cut to the chase. Here are 7 key questions (disclaimer: there may be one or two more I could add at a future date!) to ask clients at the start of a project:
What was going on in your life that brought you to me or my website?
This is a favourite question among many copywriters, and likely originated with the great Joanna Wiebe of Copy Hackers (she is a constant source of great guidance and tips for all things copy-related – I recommend going through the archive and dipping into their Tutorial Tuesday videos). This question establishes the primary causes and motivations for the prospect getting in touch, the immediate problem they need to be solved, and will be a guide as to the type of project they actually need.
Note how this question doesn’t say “Why did you visit my website?”. Using ‘why’ is accusatory, and implies a personal choice or feeling that should be justified. Saying “What brought you here?” instead implies an external stimulus, not of the questioner’s own making, but that they had to react to. This makes them seem proactive; handling a situation like a pro. Psychologically, this is far more comfortable – it puts them at ease, and not under the spotlight.
What are you specifically expecting from this project, and from me?
The original source for this question was the book ‘Copywriting: Successful Writing For Design, Advertising & Marketing’ by Mark Shaw – worth dipping into for some great insight. This question allows you to learn what exactly the client needs, what their desired outcome is, and also how they want to deal with you. If they say something unreasonable, now is a great time to nip it in the bud and manage expectations.
What problem do you solve?
The nuts and bolts of any promotion campaign. A deceptively simple question, and one some clients might need a little time to answer properly (often because they have never needed to frame it in this way). But once they have, you and they will be able to focus your efforts and messages towards this mission. What are the target market’s pain points? Asking this question allows you to start to understand what direction your copy can take.
What bothers your target market about your industry?
It’s all very well knowing who the target market are, but what problems do they keep running up against when dealing with someone in your line of business? What annoys them about other people offering your kind of service? This will give you clues on what objections you will need to address in your copy, and how to position yourself, make your business stand out or actually make improvements to your service.
What do your customers/clients/visitors always ask about?
Thinking about this will be invaluable when it comes to considering what needs to be up-front in all your (or your client’s) messaging. The question highlights what information is lacking on the current website, brochure or promo material, meaning you can take steps to address what people need to see and place it front and centre. They’ll feel like you knew they were coming (because you did!).
What is your timeline?
There’s nothing more likely to kill motivation and creativity than leaving things open-ended, and saying things like: ‘there’s no rush at all’ or ‘take your time’ (or, similarly: ‘you have carte blanche’). Set some parameters. Consider what else is happening around this project, establish a deadline, and stick to it. This way, you’ll have a focus for your work, and be more disciplined about getting it done.
If you were a car or high street brand, what would you be?
A light-hearted way to tie up a meeting, but also gives you a window onto how the client really sees themselves. More often than not, their answer will surprise you, and you’ll have gained a new insight into their character. This will give you clues about tone of voice and positioning in your copy.
Is that it? Probably not…
There must be one or two more key questions out there that I haven’t covered here. One or two incisive enquiries to reveal the golden nuggets of info that will turn a bland message into a compelling statement. I’m always looking 🙂
Sometimes, these things only emerge out of further conversation – and this crucial to understand: these questions are just starting points. Every answer you get should lead to further enquiry, digging deeper to understand a business, a client, and their motivations. Keep asking questions!
Now I’m just off to update my onboarding questionnaire…
Looking for new copy for your website, or just want to talk over how you can change your messaging? Drop me a line via the contact page.