Five Ways to Improve Your Brainstorming and Problem Solving Skills

According to most of the brainstorming teams I’ve seen, it’s apparently useful to sit in a circle and write down words that everyone likes. I have no idea why it’s productive, but it has to be useful for someone, right? That’s why you see people doing it all the time?

I’m writing this because of my second-biggest pet peeve: My biggest is the sound of people whispering in my ear, but my second is having to watch awful brainstorm sessions.

I firmly believe bad brainstorming is an active detriment to the workplace. It devours time and energy, it forces context-switching, it makes quiet people feel unheard, it makes loud people feel self-conscious. It’s a shame because brainstorming can actually be awesome when done right - it just seems like most groups go through the motions without producing anything genuinely useful.

So, ask yourself these questions to see where you or your team stands:

  • Do you brainstorm alone or in a group?

  • Do you feel like you’re intelligent?

  • Do you feel like you’re supposed to be intelligent?

Okay, let’s review the answers.

  • Do you brainstorm in a group? If yes, you are probably wasting time.

  • Are you intelligent? If you said “yes” or “I don’t know but I hope so”, you might run into trouble brainstorming.

  • Are you supposed to be intelligent? If you said anything along the lines of “yes”, then you can definitely improve your brainstorming. While it’s not your fault that others place this expectation on you, you are most in need of a brainstorming guide to keep your sanity.

It’s okay if you have trouble brainstorming. It takes lots of practice, an honest understanding of your emotions, and a good environment. But it doesn’t take natural-born talent. You can learn this.

Brainstorming is tough, but I actually love it. I work several different contracts, and my role in three of them is specifically to brainstorm ideas for teams (generally prototypes and user solutions). And, within Cloudfall Studios, my dynamic is also primarily based in idea-generation. So after a few months of consistent brainstorming as a living, I’ve noticed some patterns emerging, and now I’d like to share what I’ve learned.

Let’s start with my #1 tip:

You must let yourself have incomplete and bad ideas.

They are better than you think. They will lead you to better things soon.

Okay, let’s go!


#1: Do It Alone

First: if you haven’t had the pleasure of sitting through too many brainstorm sessions yourself, here’s a study that explains how ineffective group brainstorms are.

There’s a good chance you know how unproductive and uninspired brainstorm sessions will be when everyone is in the same room or call. In my experience, group brainstorms are a few seconds of awkward silence before the person with the strong personality says something. Then, you see a cascade of people playing gentle word-association while the person up front happily writes down anything that makes the word web look less depressing.

The main reasons everyone should brainstorm alone are 1) to prevent your ideas from cross-contaminating each other into boring middle-grounds, and 2) to prevent you from feeling like people will judge you (even lightly) for what you’re about to think of.

1-BrainstormBlog.png

So get out of there! Do your brainstorming alone! You can prune and review later. And for the next tips to properly land, you’ll have to keep in mind that there is plenty of opportunity to handpick your ideas for presentation or sharing once the brainstorm is over.


#2: Play With Your Goals

Any motivational speaker will tell you that one of the best ways to ensure that you can actually follow through with something is to have very tangible, specific goals. Well, when you’re thinking of ideas, you actually want to do the exact opposite. Shift your goals around. Try different angles. Get more abstract. Get more specific.

For the sake of simplifcation, we humans love to latch onto our first impression of what we think we want. But what you think your goal is, at first, can very easily change with one word: “why?”

Instead of having your goal be “brainstorm a good icebreaker game for the new staff members”, asking “why” can give you a better goal, like “brainstorm a way for the new staff members to get comfortable with the workplace”.

Maybe you’ll end up with a neat icebreaker game anyway. But alternatively, maybe your work dynamic is as such that asking the new staff to place their pizza orders and have lunch while you work in the corner for an hour is way more appropriate than “two truths and a lie”. Maybe immediately pairing off new and veteran staff members in a low-stakes workshop is actually best. But you wouldn’t think of it if you were stuck only thinking of icebreakers.

Rosalind.png

For an example in Captain’s Gambit, we’re in the process of revamping Rosalind. After countless internal and several external iterations on how she could appropriately “be a healer”, we realized that the broader goal wasn’t to make Rosalind actually heal, necessarily: it was to make her somebody who cared about the well-being of other players more than normal. Which means she doesn’t have to have a heal ability, nor does she need to prevent all deaths. She just has to care. And that’s what brought us to our newest form for her.

In between your idea-generation frenzies, make sure you periodically asking yourself why you are generating ideas. Don’t question the ideas you’ve written - just keep checking in on your goals. See if your latest ideas helped you recognize what you’ve been looking for this whole time. Sometimes you’ll realize you’ve been constraining yourself for no good reason.


#3: Let Nice Things Die

This is more relevant if you’re brainstorming changes rather than creating something from scratch. But there’s a really important life lesson here too, no matter who you are.

The idea is this: often, the best overall thing you can do will involve losing one genuinely nice benefit of something you currently have. Let’s start with a lighthearted example: if you order ergonomic sandals to replace your crocs, you might lose the actual upside of your crocs being waterproof.

It’s sometimes daunting to think about letting go of something you enjoy, and for a simple reason: it’s just sad to say goodbye to a nice thing. And sadness is bad, right?

It’s very easy to fall into a loss-aversion trap. If a certain choice will cause you to lose access to something nice - and you might feel sad about losing it - it’s easy to feel like it should therefore be avoided. This trap is particularly easy to fall into if you don’t feel confident about how much happiness you’ll feel with this new choice, but you do feel confident about the amount of sadness or yearning you’ll feel.

2-BrainstormBlog.png

Unfortunately, this mindset can cause a lot of harm in the long run, especially when paired with the sunk cost fallacy, which is when you stick with something just because you think you’ll have “wasted” your time otherwise.

When you’re brainstorming ideas for any reason, don’t stop yourself from writing out options that you think you’ll hate (provided they won’t literally cause you harm to consider). Be ready to write down options that may involve saying goodbye to something you like.

And try to pay attention to your own internal voice: you’ll be surprised at how many times you almost think of an idea, but then turn it away by saying “but it’ll mean I can’t ___”. Who cares what you can’t do! Who cares how bad of an option it is! Assuming you’re following tip #1, writing it down doesn’t have any bearing on what you’ll actually end up doing. And provided you’re not brainstorming for a harmful goal, you won’t actually be hurt just by writing down the option.

Often, once you’ve let the idea sit for a period of time, you’ll come back and realize that you actually have a way to preserve that one nice thing. Or, even better, you might realize that you’re actually okay with leaving something you previously thought you couldn’t go without. By being open to the idea of tradeoffs, you’ll have an easier time refining your idea generation to move towards whatever your core goal is.

It can sometimes take time and practice to become okay with options that involve letting go of something nice. But it’s very important to develop this skill if you want to truly unlock your creative and problem-solving potential.

(And on a side note: if you know anyone with an unhealthy friendship or relationship, and they justify it by saying “but sometimes they’re nice”, it’s time to read this.)


#4: Delay your Inner Critic

You’ve probably read this one before. And depending on your mental health, you know that silencing your inner critic isn’t a magical switch you can flip - it’s really not that simple to just “go easy on yourself”, even if you want to. But regardless of how loud your personal critic is, there’s a few things you can do to help your thoughts make it to the paper. You don’t have to succeed at silencing your critic every time in order to get practice doing it, and it will take practice no matter who you are.

First, a brief explanation of why you want to avoid self-critique during brainstorms: the act of critique itself is to restrain ideas and chop off the parts that go into unwanted territory. In my mind, critique is strictly reductive. It can definitely be a catalyst for growth, for the next brainstorm session. But when you’re currently designing or thinking of solutions or ideas, it will 100% stifle the brainstorm itself. Self-critique tends to snuff out any ideas that are not immediately perfect, and it especially seems to prevent us from even coming up with certain realms of ideas if it sounds embarassing, silly, random or “stupid” at first.

When brainstorming, I try to remove every possible source of shame I can think of. I write down awful ideas. I write down ideas that don’t solve even 1% of the problem, ideas that solve totally unrelated problems, ideas that specifically make the problem worse without resolving anything. I write down every single thing that enters my mind, that at least tangentially match some part of the goal I’m seeking. You should too.

I let my ideas have typos, misspellings, words I don’t 100% understand, bad grammar, imperfect knowledge of how related mechanisms work. Yes, you should too!

This is important: you must write down incomplete and bad ideas. They are either better than you think, or they will lead you to better ideas as something to contrast or copy from.

Forgive yourself if you start to accidentally ‘edit’ or snip down your ideas, because self-critique is normal in our little panopticon world. But keep trying your best to make sure you don’t critique even unrelated parts of your idea-writing, like your handwriting or how much space you’re taking up on the paper, etc.

4-BrainstormBlog.png

Okay, you get it. Stop critiquing yourself. So, then, part two: how the heck do you make your inner critic shut up?

It’s mostly a few small techniques, plus a lot of practice. Your inner critic might have a hilarious time critiquing your difficulty in getting rid of itself, so be ready for that too. It can help if you think of your critic as a character with a punchable face who doesn’t feel pain - this is because personifying them can make them feel easier to ignore and less of an inextricable part of you. You’re not defined by your unwanted thoughts, and having them be a clearly different entity than yourself can make that fact easier to remember.

Additionally, inspired by a mix of personal experience and a good tumblr post, here are some useful thoughts you can tell yourself before, during or after brainstorming:

  • These ideas will not be complete.

  • It is not useful to criticize these ideas right now. I will criticize them later.

  • I don’t need to justify the ideas I come up with in brainstorming.

  • My thoughts don’t need to be perfect to be OK.

  • I don’t have to figure out this question.

  • I don’t have to fully explore this idea.

  • This idea doesn’t have to go anywhere.

  • I can handle being wrong.

  • Finishing this idea is not my responsibility.

  • If this idea isn’t useful, it’s not my problem.

  • I am making ideas right now, not choosing them.

Step number five kind of wraps things up, but this is probably the most difficult and important hurdle. Pretty much everyone starts out with one of these buggers in the back of their head, and while some people have it easier than others, it will always be useful to develop your ability to let yourself think without concepts of perfection slowing you down.


#5: Make Jokes

I am (ironically enough) being absolutely serious about this being the final step to improve your brainstorming and idea generation skills. In order to do this properly, you will have to already be practicing the other 4 steps, especially #4.

When I design captains and game concepts, the main I have to look out for is to avoid taking myself too seriously. I have to make jokes, even outside of the brainstorm sessions themselves.

Your jokes don’t necessarily have to be said out loud, and they don’t really have to be funny. But you have to keep your mind open to humor, to keeping some kind of silliness, some form of irreverence if you want to be agile. Your best ideas will arise when you let yourself play.

Let yourself notice when you get sudden cravings for dorito-based loaded nachos or sangria. Make silly references to pop culture, make fun of relatable topics, write down parody ideas, think about the weirdness of your situation, lean on situational humor, sarcasm, dry humor. Don’t force yourself to necessarily look for jokes like it’s your job - rather, let yourself maintain a wholesome lightness and sense of humor about things as you work.

5-BrainstormBlog.png

Here is why: the same mindset that allows you to make a joke is the mindset that is able to rapidly make connections and spontaneously produce a synthesis of ideas. Usually humor is an unexpected comment or reference that slams two things together - for example, a pop culture reference when someone’s behaviour is similar to a character, or the astute observation of a relatable feeling that you didn’t realize you shared with others.

This style of design is something I like to call “whimsical design”. This process involves rapidly generating a mountain of ideas, choosing a few concepts to take forward (rather than consciously cutting away ‘inadequate’ ones) and then then generating more with the handful of ideas that really resonated.

To increase your creative energy, remember that you don’t have to stay utterly focused on the problems and the mechanics of something. Remember that there is still a world outside of the current task at hand, and that you’re still a person who has instincts and emotions. It’s all important for ensuring a healthy stream of new ideas, and a zippy hand that can grasp them as they flow by.

Assuming you’re a responsible person who knows the obvious lines of what’s appropriate, I believe it is absolutely crucial that you avoid the trap of thinking you’re ever “above” the concepts of having fun or going easy on yourself.

For me, where four of my weekly tasks are specifically about creativity, living with irreverence has to be a kind of lifestyle default. But even if you only let yourself loose when you’re brainstorming by yourself, you absolutely still have to let it happen.

Once you do, you’ll find that over time it somehow gets almost effortless to think of at least a handful of responses to any given situation. Humor hones your ability to make connections, zoom out, think about the greater context of things and understand the underlying experiences that we share. You don’t even have to be funny, you just have to appreciate it. You’ll be amused at your own snappiness when it comes to improvising responses to even completely unexpected needs.

Let yourself doodle, stack your cards, play with your utensils, wander around. Do whatever it takes to stay comfortable with subverting your own thoughts and your own work. This is how you brainstorm! This is how you grow.


Want to play this cool Captain’s Gambit game? Join our Discord here if you’d like to play with us on Tabletop Simulator, or sign up for our newsletter to get good ad-free content every few weeks. We’ve also got a Facebook and a Twitter if you’re into that, and an Instagram too.

Stay lofty!