You're reading the blog of

Adii Pienaar

Now working on Receiptful. Co-Founder & ex-CEO of WooThemes. Author of Brandiing. New Dad. Ex-Rockstar.

Asking Better Questions

You are facing an issue or challenge in your business.

What's the first thing you do? You fire up Google to search for answers. Perfect. Google is great, because it likely gives you thousands of resources to work through.

You start following all this advice in solving your issue or overcoming your challenge, but nothing seems to really work.

Eventually you give up and move onto the next thing. This time it's growth hacking, just because you've heard that this is the way to solve ALL THE THINGS.

You rinse and repeat the above process, including the eventuality of quitting, because it turned out not to be the silver bullet.

Now you have a bigger problem though... After months of facing these issues and challenges, you've not solved any and you kinda don't know which issue or challenge to Google next.

We've all been there.


It's a great characteristic to be willing to ask questions, seek advice and learn from that. Especially if you are asking the right people.

I'd define "the right people" as someone with very relevant experience (to your specific situation) that is willing to not hold back the punches when giving you advice. Any other advice is of the bullshit variety anyway.

The trick with asking questions though, is asking good questions. Not the right questions, because there's probably not something like an absolute right or wrong when asking questions. But there is most definitely good and bad questions.

Yesterday I sent out another e-mail like this one and this time I sent it to almost 1000 people. I've received questions from hundreds of people and there's a recurring theme: they're not asking good questions.

Why aren't the questions good?

Well, the questions are being influenced primarily by these two things:

  1. Bad assumptions; and
  2. A perception about what the real issue or challenge is.

This combination is such a clusterfuck, because it turns out there's automatic symbiosis between the two that creates the kind of rabbit hole that not even Alice wants to go down (even by accident).

This clusterfucked combination almost always sees the individual asking a question that is only treating the symptom. This means that even the best of answers to that question will only touch the surface of the real issue. So whilst you'll be able to possibly solve that, you won't really move the needle within your business.

It's like thinking you'll strike it rich with some oil, but you are only drilling inches below the surface.


The key to asking better questions is to figure out what the core issue or challenge is. Core meaning the bit that lies slightly deeper below the surface.

And the way you do that is to simply ask "Why?" enough times. In fact, you should ask "Why?" until the answers you are getting becomes child-like in their answers.

Let me explain with this example:

  • Entrepreneur builds a new platform / marketplace that connects designers with startups, specifically to design logo's / branding with a minimal budget.
  • The entrepreneur asks: "What's the best way to market this platform? Google Ads? Or through content marketing?" So judging by the question, the challenge is marketing / generating initial revenue.
  • Ask why the first time and figure out why this is a challenge.
  • I asked the entrepreneur for whom they have built this. Entrepreneur says "startups that want a logo design with a low budget". I ask whether he has spoken to these startups and whether they want this thing he has built. He says he has been speaking to many of them and they definitely want it. I challenge him and ask why he's not just selling to them at the moment.
  • Entrepreneur says it's because he doesn't know how to market to the startups or what words / pitch to use. This seems like a very different challenge than the one they started out with.

By poking holes at every fact or assumption that you have, you can eventually figure out what the underlying cause is. Solve the root issue and it kinda bubbles up to solve many of the symptom issues too. Maybe not all of them, but if some are left unresolved, you'll definitely have greater clarity about how to figure out solutions for those.


There's a bucketload of advice out there from various sources; some better than others.

Taking a kinda blanket or generic approach to using this advice in your business is dangerous. If you look at the proposed solution long enough, you will start to think that this is your problem too. Which might not always be the case.

I made this mistake in the past when I started listening to everyone else about measuring all the things. Whilst this was a possible solution to some of the issues I was facing, I wasn't addressing the real cause and everything I tried ended up in vein.

Ask "Why" often and you'll eventually ask better questions.

Better questions means better answers. That bit is obvious.

Join 3,000+ rockstars who get my best content directly in their inbox: