How to Use Creative Questioning for a Better Brainstorming Session

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How to Use Creative Questioning for a Better Brainstorming Session

Updated: Aug 2, 2019

A good brainstorm is so underrated. No matter what problem you’re trying to solve—what’s for dinner or what career move to make next—start it with a brainstorming session. When done correctly, brainstorming leaves you with a giant pool of ideas. Some will be terrible, sure, but a few of them are going to be great. Starting a project without brainstorming means you’ve left most of your creative potential behind before you’ve even started.


Why Brainstorm?


One of the best parts of brainstorming is that it allows you to fail fast, early, and often, but painlessly. Failure is one of the best ways to figure out what does and does not work. By knocking lots of terrible ideas out of the running early in the process, you give yourself a good picture of what doesn’t work, which in turn paints a better picture of what kinds of things will work.


Brainstorming gives you a bigger pool of ideas to pick from. The bigger your pool of ideas, the more likely it is that one of them is good. If you’re thorough in your brainstorming, you may even flesh out some of the details for the better ideas, giving you a more detailed map of what directions may end up working out.


Brainstorming gets you started! Getting started is difficult. So often, we leave great plans and ideas on the table because we never find a way to actually start executing them. If you’ve spent the last five years saying you want to redo the kitchen but still haven’t actually touched a can of paint, a brainstorming session might just be the perfect thing to finally get you started.


Brainstorming Techniques


Ask Creative Questions


This is my absolute favorite tactic for solving pretty much any problem. When I’m trying to figure out what to write about, rather than asking myself the obvious, “What should I write about?” I ask myself related questions that could still give me the answer: What advice did I need when I was in college? What have I seen someone struggle with recently? What problem have I recently solved in my own life that others may also have? These questions force me to think both more broadly and with more depth than, “What should I write about?”


Revisiting the kitchen makeover scenario, rather than asking myself what I want my new kitchen to look like, I may ask questions more like, “What functionalities do I need in the kitchen that don’t currently exist?”, or, “What is and is not working about my current kitchen?” or, “What do I like most about other rooms in my house, and how could I incorporate those things into the kitchen?”


Reframe The Situation


Most often, reframing the situation means removing any preconceived notions about what the answer should look like.


“If I had asked people what they wanted, they would have said faster horses.” -Henry Ford

Make sure you haven’t already limited the scope of what the answer could be. Get rid of any preconceived notions about how to solve the problem. Just because most people do something a certain way doesn’t mean you need to.


Back to the kitchen redesign problem, rather than asking what you want your kitchen to look like, ask what purpose a kitchen serves in your life. Maybe you rarely cook, aside from making yourself nice coffee every morning. Perhaps you do lots of entertaining. Maybe everyone who comes into the house enters through the kitchen, so you need a place to hang coats and take off dirty shoes. Think beyond the obvious.


Set Arbitrary Limitations


Arbitrary limitations are one of the best ways to force creativity. They push you outside of the box, whether you want to be there or not. “Green Eggs and Ham” by Dr. Seuss contains only 50 different words and was written after Seuss’s editor bet that he couldn’t write a book with fewer words than “The Cat In The Hat” at 225 words (source).


How would you redo the kitchen if it had to be finished in a week? In a day? Using only things from a garden store? What if you specifically wanted to impress your best friend? Your worst enemy? What if your budget was $100? What if it was $50?


Set limits to push yourself to be more creative and remember that the goal of brainstorming isn’t to have perfect, fully formed ideas, it’s just to have lots of ideas.


Find Inspiration


No matter what is it that I’m creating, I find other people who have done the same thing. Pottery? Find other potters. Want to write? Read. What are the experts doing? What are they not doing? Why aren’t they doing it? What works about what they did? What didn’t work? What do you like about what they did? What do you hate?


It isn’t enough to just seek out and surround yourself with the kind of thing you’re brainstorming about, you also need to analyze it. Ask yourself as many questions about it as you can think of. It’s easy to make a Pinterest board of all the kitchen ideas that you love, but why do you love them? Is it the color scheme? The functionality? The overall aesthetic? Maybe they all just have lots of windows? What isn’t making it on to your Pinterest board? Why not?


Think From a Different Perspective


It’s easy to get stuck inside our own minds, but often the problems we’re trying to solve effect other people or other people may be better able to solve the problem. Get out of your own mind and into someone else’s.


Who would do a phenomenal job solving this problem? How would they approach it? Why would they be the best for the job? Can you ask them for advice?


How would your mom solve this problem? Would your mom even have this problem in the first place? Why or why not?


If you have an audience, how does your audience think? What would they want? What problem do they want you to solve?


If you can, bring in other people to help you brainstorm. They’ll be able to offer perspectives and ideas that you would never have been able to think of. This is one of the many reasons that diversity is so important.


Don’t Hold Back


It’s easy to avoid saying or writing down ideas that don’t seem reasonable at first because we fear embarrassment. Especially if we’re brainstorming with other people, we don’t want them to think our ideas are terrible. Make it clear from the beginning that unnecessary judgment and shaming aren't allowed in your brainstorming session, including judging yourself. Really, these shouldn’t be allowed in any areas of your life, but especially not in a brainstorming session.


By sharing even the ideas that you might think are bad, you give people more to work with. Maybe that idea isn’t great, but it could inspire a phenomenal idea from someone else, or be tweaked slightly to become great.


Getting all of your ideas out of your head and on to paper—and yes, you better be writing everything down—gives them a life that they didn’t have when they were still living in your brain. Once they’re out, they can begin to grow and change, so it’s crucial that even the ones you aren’t proud of make their way into the world.


Stop Trying to Think on The Spot


Ever freeze up when someone asks you a question that you don’t have an answer to yet? Of course you have. Thinking on the spot is difficult. So why would you try to force yourself to think on the spot? Our best ideas often come while we’re busy doing other things. Give yourself some time.


The vast majority of my blog post ideas come to me while I’m at the gym. I’m not sure if it’s the fact that more blood is flowing, or that I’m typically listening to a self-help audiobook or motivational podcast, but that’s where the best ideas happen—not while I’m sitting at my laptop with my fingers waiting impatiently on the keys.


Don’t get me wrong; you can’t always just sit around and wait for inspiration. Most days, you aren’t going to feel that lightning bolt of creative energy that forces you to get moving immediately. Most days, creating is going to be a grind. That’s the reality of creative life. I made 1000 pots (sorry if you’re tired of hearing about them). That’s ten a day for one hundred days. Do you know how many of those days I was feeling inspired? Like, six.


Brainstorming is one of the few times where it’s alright to step back for a bit and let the ideas come to you. After that, don’t wait for the lightning bolt. It doesn’t come often.


Don’t Worry About It Too Much


This is closely tied to not holding back. Don’t immediately knock out every idea that comes up because you’re able to find a downside. Every idea is going to have its pros and cons. You aren’t going to find any perfect ideas because perfect ideas don’t exist. Perfection isn’t real.


Keep in mind that you’re still at the very beginning of the process. No matter what idea you end up going with, it’s eventually going to be refined, likely several times. Just keep going.


Don’t overthink it. Unless the ideas are truly terrible or unfeasible, give yourself a bit of time to process them. Sleep on it. Aim to amplify the good areas of each idea and minimize the not-so-good areas, but don’t eliminate any possibilities too soon.

Good brainstorming requires good questioning. You’re looking for answers, and the best solutions come from asking the right questions. Throughout this post, I asked almost forty questions designed to help you think outside of the box.


Creative questioning is one of the most valuable and underrated skills out there, and practicing creative questioning will improve your ability to think outside of your comfort zone and come up with new and useful solutions.


In the end, brainstorming needs to end with a decision and lead into action. Once all of the ideas are out there on the table, don’t get up from the table until a decision is made. If you need to, give yourself a time limit, or use any of the other strategies that exist to facilitate decision making. Then, get started. Don’t let that great idea go to waste.


Recommended Reading:

Why Mindfulness Matters and How You Can Bring More of It Into Your Life

Six Surprising Life Lessons About Happiness That Were Difficult for Me to Accept

7 Signs that Your Life Is Lacking Balance and What You Can Do About It



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