The Human Element logo

My big mistake & the 6 questions I now ask everyone I work with.

When I first started dabbling with the idea of starting my own business, I didn’t immediately decide to be a branding strategist. I actually started doing the odd copywriting job as a side hustle.  

One of the first jobs I accepted was to write a public-facing company manifesto for a small family-run company. 

They only had a small budget, like I’m talking $100 small budget, a red flag that, in my eagerness and naivety, I chose to overlook.

Despite the limitations, I dove in. Her response to the first draft? 

“No. It’s really missed the mark. Can you do it more like this one?” 

Cue another red flag. When a client wants something *exactly* like a rival, there’s usually a LOT more to the story than a simple manifesto. 

But did I look for that story? Nope. I dove into the second draft. 

Can you guess the reaction? 

“No, it’s still not what we’re after. Thanks anyway.”

Cue, the owner “writing” one herself.

Now there was a lot to unpack from this experience, but some of the biggest learnings were around VALUE, my own value, and my perceived value, and the importance of asking good questions that could have transformed the outcome. In fact, this incident became a pivotal lesson, prompting me to develop a set of questions that I now consider EVERY TIME before commencing any project.

What legacy do you want to leave for your kids, or the next generation? 

(Aka, what’s your WHY?)

It’s not uncommon to start here, but the question is usually phrased like “What gets you out of bed each day?” Boring!

Phrasing The Why in a way that’s bigger than a daily task, gives it so much more meaning. It also means The Why is underpinned by core values, and not trivialised to something that people feel they should say. 

I’m also acutely conscious of using language like “your kids”. Whilst I work with a lot of other mums, and it can be a common connecting point, I’m very aware that not every female my age is a mum. So I make sure I find this out and approach how they want to leave their legacy with sensitivity and tact. 

Fast forward 3 years from now, what is happening in your business and life?

Because so many people only ask about business, but in real life, what’s going on in your personal life has a *direct* impact on what’s going on in your business life, and vice versa. 

I mean, isn’t the whole point to work to live, not live to work? 

By gaining a holistic view of the client’s aspirations, I can tailor strategies that consider the broader context of their life. Plus, it makes executing a strategy so much more realistic and achievable, when you consider how they’re going to do all the things.

What are you proud of?

This gives me a good sense of their achievements, without asking explicitly. It’s a nuanced approach that helps me evaluate compatibility, and it gives me insight into their personality – we’ve got to vibe, right?!

I also like to flip this one and ask what they’re not so proud of too. The answer is important, but their approach to the answer is even more so. 

Tell me how your brand would dress to impress. 

Here I go deep – what labels? What styles? How long would they spend getting ready? What impression do they want to make?  

Taking a creative turn, this question taps into the client’s visual, stylistic and personality preferences. By understanding how they envision their brand’s appearance, I can tailor strategies that align with their desired impression.

How do your clients feel after working with you? 

This question unravels the transformative impact the client has on their customers. Going beyond surface-level results, I explore the ‘result of the result’, or the ‘so that…’ factor. For example, they may have processes now that have made their work day more structured, so that they can then spend more time with their family. 

Why you?

This is a good way of finding out their unique selling proposition (USP). The thing that separates them from their rivals and tells me why clients choose them. 

Asking these questions has been a game changer in the way I approach client relationships. These six questions have become my compass, guiding me towards a deeper understanding of those I work with and ensuring a better end result, for everyone. 

Got any to add? 

Like this article?

Share on Linkdin

you may also like...

8 signs you need a rebrand

I see excellent brands stand the test of time for decades, and I see not-so-excellent brands crumble at the slightest whiff of change. But one of the toughest jobs you have as a business owner is knowing when it’s time to refresh your brand.

Scroll to Top