Start with a diagnostic session

The Magical First Question I Ask All My Clients

clients vision setting

There's one question I start every single one of my clients on. It starts us off on the right foot, focusing on the right things.

The question I ask first is: Why do you really want to start (or run) this business?

I then just let them talk. I note down everything they say as just one big list of bullet points. And when they're done I ask, "why else?"

And I keep adding to the list. The list can be really, really long. It can include everything from wanting to help a target market to wanting to make a lot of money to being able to pick up the kids from school to being able to work from their laptop on a Tahitian beach.

The first reason I ask this question is because it forces them to articulate something they've probably never needed to before.

Think about it – if someone asked you this question, do you have a nice clean mission statement to respond with? Because in all my years of doing this, I've never heard anything even remotely like:

"I want to help 20,000 high school girls become entreprenuers by 2028 because when girls are empowered with self-employment at a young age, it improves their chances of entrepreneurship, which improves entire communities".

They're more likely to give me the usual "to have more flexibility".

So my follow-up is "what is flexibility to you?"

Now most people haven't actually thought that far ahead!

They know they want more flexibility and freedom, but they have no idea what they'd do with it!

In I Will Teach You To Be Rich, Ramit Sethi writes that people always say they want more money, they want to be rich, but can't tell you what they'd do once they had the money. Sticking with just this really high-level answer is easy – it's actually much harder to decide what you want to do with your time or money or flexibility once you have it.

But without it, you don't really have a compelling reason to do the hard work. To save money to increase your wealth. To work on improving the mechanics of your business to increase your flexibility.

In Simon Sinek's famous book Start With Why, he writes:

"We don’t want to come to work to build a wall, we want to come to work to build a cathedral."

If you can't articulate why you're doing all of this, the hard times in business are really hard because there's no compelling reason to keep working.

Another reason I love this question is because it helps show me the gap between where they are and where they want to be

When their imagination starts up, and they're able to list lots of reasons why they want to run this business, that list starts to paint a picture of where they want to go. I can then measure their current finances, current strategies and current lifestyle against this.

If someone tells me they want to be able to take days off whenever it suits them, but they currently have a week full of 1:1 recurring meetings... well that's something we can start to design around.

If someone says they want unlimited earning capacity but they're currently charging by the hour, that's something we can design for.

The roadmap may be 5-10 years long – or it may be a year! – but at least we know what A and B are so we can chart the journey.

And finally, this question brings them back down to basics, so that we can focus on building the right business

We first start by getting clear on your lifestyle goals – where you want to work from, how much you want to work, how much you want to earn, what sort of work you enjoy doing...

And then we spend just as much time thinking about who you want to serve through this business.

Only then do we think about designing your offerings. Most people jump straight to offerings – they think "I'm a photographer, I'll offer three packages with varying numbers of photos delivered".

But I find time and time again this leads to people spending a lot of money, blood, sweat and tears on building the wrong business. A business that doesn't align to their lifestyle goals, or doesn't properly serve an ideal client.

And that's what I love about this question – it starts to paint a picture of lifestyle goals, and who may be best served by this entrepreneur.

This is an example of what we talk about in my course, Build The Right Business. If this sounds like something you want to dive into deeper, you can join the wait list at



Prefer to listen and watch instead of read? 

Ready to build that profitable, flexible business you thought you'd signed up for?

I work with freelancers, consultants and coaches (basically: one-person service-based businesses) to move away from the hustle and create a business that gives them freedom.

Explore the Blog
Work With Me