Ask Better Questions

Creative Hustlers are curious creatures. It’s one of the things that set us apart from everyone else.

We ask the tough questions that make all the difference.

Your questions have a direct correlation with how you create and hustle. They also influence the amount of money people will pay you.

Don’t believe me?

Then try doing this

Think about a person in your line of creative hustling who is extremely good at what they do. This person may have even influenced some of your work.

If you’re motivated by money, then think about a creative hustler you suspect makes way more money than you.

Got it? Okay.

What kind of questions do you think they ask? Do they ask the same questions you do?

Are their questions standard or are they different for every project?

How do they frame their questions? How and when do they ask them?

Who do they ask them to? Most importantly, why do they ask them?

Don’t just skim the questions above. Really think about them. Stop reading this email if you have to.

Now that you’ve pondered a bit, let’s dig a bit deeper.

5 types of questions for your creative hustling

I won’t get into the technicalities or science of questions. Instead, I’ll focus on 5 types of questions that will make all the difference in your creative hustling.

1. Factual

Ask these questions to know the facts. The answer to factual questions paints an accurate picture of what the problem is and how things work.

These questions help you understand the parameters and limits of a project. The answers establish the boundaries and space in which you can create.

Use these questions as the base of your project. All future questions are based on answers to these factual questions.

When you ask these questions right, clients easily see that you know your stuff.

Some examples:

  • What kind of x does this use?
  • What does your current x look like?
  • What is this x for?
  • What’s the deadline for this project?

2. Preferential

These questions reveal someone’s preferences and tastes.

Ask these questions to understand what makes someone happy (or at least what they think makes them happy).

Use these questions for design and influence. The answers can be used as guidelines only if it makes sense.

Sometimes what a client prefers isn’t necesarily what’s best – especially if it doesn’t align with what they’re aiming to accomplish.

Some examples:

  • What type of x do you like?
  • What do you not like about x?
  • What would be ideal in this area?
  • What x do your customers prefer?

3. Exploratory

You probe and discover with exploratory questions.

Ask these questions to brainstorm and experiment.

These questions enable your magic. You literally create when answering these questions.

Ask as many of these questions as you can. Let your mind wander and chase ideas that are born from these questions.

Exploratory questions make you different. The questions and answers are the reasons you create differently from anyone else. Train your mind to dig as deep as you can with these questions. Your creativity depends on it.

Some examples:

  • What if we approach x with y?
  • If we implement this, then what will happen?
  • Can we accomplish x and y in one piece or do they have to be separate?
  • If we move this here, does it look better?

4. Leading

Leading questions can be controversial.

Many believe these questions are evil. Mostly because they picture a smug lawyer leading a witness into saying what he/she wants them to say. While leading questions can be used for manipulation, that’s not what us creative hustlers use them for.

We use leading questions to educate our client. We lead them into understanding a solution.

You’ll most likely know / suspect the right answer but sometimes it’s important to hear it from someone else’s mouth (or even yours just to make sense of things). You may ask a leading question to confirm your suspicion. Other times it will help someone see what you see or provide context for your next question.

Lastly, don’t confuse leading questions with rhetorical questions. They’re not the same.

Some examples:

  • Would x work if we did y?
  • When x happens, does y happen?
  • What if we did x, would y react this way?
  • When we spoke about x, you said y, right?

5. Decision

These questions force a person (sometimes, that’s you) to make a decision.

Decisions will consistently be made within your project. Learn how to narrow down the best options and ask questions in a way that make decisions happen.

Never leave a decision question open-ended. Always ask by giving clear choices.

Use decision questions to move your project forward. The answers help mold your work of art and finish a project.

When you ask questions like these, you invite your client to be a part of the creative process and solution. It also helps you understand how they make decisions, their logic, and priorities.

Some examples:

  • Does x or y work best for you?
  • Do you like x or y better?
  • Will x or y solve your problem?
  • Would you like to pay me using a credit card or cash?

The better you get, the better questions you ask

As you grow in your craft of creative hustling, you’ll ask better questions. You’ll develop your own style of asking and understand what to do with the answers.

Remember this:

When you ask questions your clients have thought of, you prove to be proficient.

When you ask questions your clients have never thought of, you prove to be an expert.

Ask better questions.

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