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Wanna Play 20 Questions?

Question everything. Learn something. Answer nothing.”


Euripides, a playwright from ancient Athens, knew all about asking questions. Questions spark discussion and lead to understanding, whether it be between two people or within oneself.

Here are some questions you can ask yourself (or a trusted partner!) to inspire deeper understanding and creativity in your professional life.


  • How do I want people to describe my brand to their friends?

  • What are my brand colors?

  • What is my brand “voice”?

  • Who are my competitors? How are our brands similar, and how are they different?


  • Who is my target audience? Age, occupation, geographic location?

  • What are the engagement habits of my audience?

  • What am I doing to reach my audience? Where do they find me?

  • What are the pain points my audience is facing? How do I solve those problems for them?

  • What is my audience “searching” for? Materially, and more generally, in terms of lifestyle?


  • What is it about a post/ad/product that stops my scroll?

  • What am I trying to say in the simplest language? How can I say that same thing in a casual tone, a professional tone, a friendly tone, an expert tone?

  • What’s my “hook”? How can I catch someone’s eye and then lead them to my information?

  • Can I condense my selling point into 5 words or less? Can I stretch it to 10 words? What looks better, what resonates more?


  • What brands resonate with me?

  • What are my 5 favorite ads I’ve seen this month?

  • How would I describe my “professional mood board”?

  • If I could describe my brand…


  • What is my goal for my company in 1 year? In 5 years?

  • What are 5 things I can get done this week to get me closer to my goal?

  • What’s my favorite part of my job? How can I do more of that for myself?

And as a bonus, what questions did we miss? Let us know.

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Written by Jordan McAndrew

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