Asking the Right Qualifying Questions to Get Way Better Projects

Sooner or later, you reach the point in your freelancing career where you can’t take on every new project that comes your way because you’re pretty booked up. And that’s a whole new problem because it means you need to get good at figuring out which ones to take and which ones to let go.

Unless you’re psychic, you’ll need a powerful batch of qualifying questions to help with this. What can you ask a potential client to get a glimpse into the future of the project? And how can you give yourself the strongest start in terms of understanding the project’s real requirements?

Now, I am a beginner at qualifying questions. Last year was the first year in my freelancing career where I needed to turn work down. So I’m putting this list together to help myself, and I’m publishing it just in case it can help someone else who’s in the same place.

Also, I thought it’d be nice to acknowledge some of the amazing freelancers, consultants and entrepreneurs here in London that I’ve learned from over the years. Thank you, guys!

Without further ado:

1. “How will this project change things for you and your business?” is Alex Magill’s current favourite starting point, even though in his experience it “rarely gets a direct answer — but it does start a good conversation”. In his reply to my email, this digital designer & branding strategist mentioned a case where asking this question lead him to realise that a potential client shouldn’t yet be spending any money on web development— but, thanks to his ability to provide this insight, their business benefited and they later hired him (at the right time!) for several projects.
2. “Why did you choose to call me?” In her answer to my question, Julie Stevens (creative director of Younique Designs) spoke about the importance of ‘speaking the same language’ as her clients. If they answer this qualifying question by mentioning that her website’s words and images resonated with them, she knows the project will have a strong foundation of shared perspective.
3. “What’s the time-frame for this project?” If you compare the client’s idea of how long a project should take with the work involved in completing it, do they match up? If not, as Jamie MacLean (independent PR & digital strategy expert) noted in her response to my email, that could be a red flag. It’s certainly a reason to dig deeper into what is required — and to see how the client responds to the suggestion of a more realistic time-frame.
4. “Is the client a kind person?” This is the question Lia Choi, an independent property manager here in London, mentioned as vital. If a landlord doesn’t prioritise their tenants’ happiness, then she can’t provide the best service to all parties. And I agree that, for any self-employed person working directly with their clients, making sure that you are working with people whose motives fit well with yours is so important. It’s amazing how demoralising it is to work with someone who doesn’t prioritise their clients’/customers’ happiness, for example, when you strive to prioritise it at all times.
5. “What’s your budget?” This is a well-known question but always deserves a mention (even if, as the next point covers, you might want to steer away from budget talk quickly afterwards). Adam Messer, a conversation rate optimisation consultant, points out that there’s just no point discussing the details of a project if your idea of the cost involved differs from theirs by one or more zeroes.
6. “What does success look like for this project?” Guy Routledge, web developer & author of AtoZ CSS, gave me several answers but I picked this one as the most helpful for understanding the client’s vision. It’s also a useful example of how to move the conversation away from budget (once you’ve established that there is a reasonable budget, as noted above) so that you can price on value. Because if success looks like a million extra pounds for the client’s company, then an investment in top-quality work from you (rather than corner-cutting due to quibbles over hourly rates) makes much more sense.
7. “If money was no object, and you could do anything to achieve this project’s goal, what would you do?” Lucky question #7 comes from creative copywriter & idea machine Rebecca Magnus, who enjoys prompting her clients to get out of the ‘freelancer as a commodity’ mindset. Since she provides value by using her unique perspective and free-thinking skills to spot new opportunities for her clients, she does her best work on projects where the client is happy to break out of their established way of thinking. As she reminded me, “Naivety and curiosity really help in opening up new possibilities.”