5 Extreme Brainstorming Questions to Help Imagine a Better Future for Your Association

The pandemic knocked many of us out of our comfort zones, however, it also sparked growth in ways we couldn’t have foreseen. Today, we’re proposing a gentler way to stretch those comfort zones and remove the invisible cloak of familiarity we wear despite our best intentions. This exercise will help you imagine different new futures and perhaps take your education programs and associations to places not thought possible.

Jason Cohen, founder of WP Engine, published 14 extreme brainstorming questions he uses to trigger new better ideas—we’re sharing five of them here. These prompts are intended to “jostle you out of tiny thinking.” Some of them might seem outright crazy, but they get you to drop conventional wisdom and adopt new perspectives. He believes “dramatically different perspectives can reveal distinctly new ideas.”

This exercise reminds me of jootsing, which we’ve written about before. Jootsing means Jumping Out Of The System. Not just thinking out of the box but abandoning any conception of a box.

The world is changing unimaginably quickly. Just think how suddenly ChatGPT became a hot topic of conversation in the association community. A year ago, that type of AI tool would have seemed like a crazy proposition. Now, it’s working its way into our workplaces. It’s time to leave the box behind.

extreme brainstorming questions

5 extreme brainstorming questions for stretching the realm of possibilities

The new rules of the game: nothing is too crazy to be off the table. Gather a group of colleagues to work through these extreme brainstorming questions. Invite a group of recent graduates and early-career professionals too—their lack of inhibiting knowledge might be just what you need to stretch the limits of possibilities.

#1: 10x your prices

Imagine you had to multiply your program registration fee by 10. What kind of experience would you design and deliver to justify that new price—a price perhaps ten times higher than any competitor’s? Assume the learner is eagerly paying ten times the price. Budget is not an issue for them. They’ve got money to burn. What are they getting and experiencing?

How do you make the learning experience look and feel more expensive? Perhaps more exclusive, personalized, or immersive—something you don’t do now?

What expensive services would you provide? Coaching? Post-program support? Let your imagination go wild.

How do you position this program in the marketplace? How is your website and marketing done differently?

Which subset of your market (or new market) do you target? Are you solving different problems or meeting different needs?

What would this high price signify or mean for your target audience—exclusivity, marker of success, or marker of program quality? What kind of relationship do you want to cultivate with each learner? How is this different from what you provide now?

Okay, imagine instead you are only doubling or tripling the price. What would you offer? What can you offer for real, right now?

#2: No customers

Imagine all your customers vanished, and you had to start all over from scratch. You have a blank slate. Scary but freeing.

No member expectations, no legacy programs, no sacred cows, no board or committees.

It might help to know what you’d definitely not do again—and whom you are no longer going to please. Who and what isn’t worth your time and effort? Who’s blocking progress? You no longer have to cater to their bullheadedness.

What would you do if you got to design your educational curriculum (or membership experience) from scratch, without worrying about other departments, people, traditions, and conventions?

What do you want your association to become known for? How do you differentiate yourself from the competition? Who is your new competition? What do you brag about on your home page?

Would you use a new business and pricing model to better compete or dominate the market? How would your association’s brand change? What’s your unique selling (or value) proposition now?

#3: Complete rip-off

What if your biggest competitor copied every program and feature you offer—how would you still win?

What if they offer the same content and award the same number of credits? Now it sounds like they’re simply ripping off a commodity, which is already happening to many associations.

Commodities are a race to the bottom. How do you make an emotional distinction between your products and your competitors’ products? Your programs must resonate beyond someone’s wallet or budget. How do you distinguish your programs emotionally?

How do you differentiate yourself from a copy-cat? How do you make your programs more convenient, effective, memorable, and satisfying? What adjectives am I leaving out? Which ones do you want to claim?

What can you offer to stay ahead of the competition? You’ll have to anticipate your audience’s needs and desires, especially the ones they haven’t yet acknowledged, like Apple did with the iPhone.

What do you have that competitors can’t rip off? Remember, you have the association advantage. You’re not a for-profit merely making money off the industry. You are the industry. Everything you set out to do is to benefit the industry. How can you capitalize on that? How do you combine this mission with your educational programs in a way that benefits learners?
Are you communicating how you make your industry and world a better place? How can you connect that with what you’re selling? How is your culture special? How is your brand distinctive? Why do members and customers trust you?

extreme brainstorming questions

#4: No time—or permission

In Cohen’s article, this question focused on time, but given the constriction of association governance, let’s expand the question.

Imagine you need to deliver a new program in just two weeks that would delight and surprise some fraction of your customers, but you don’t have to seek anyone’s permission to do it. You don’t have to deliver a final polished product, only enough to test the waters.

Or, within two weeks, you could add a new feature to an existing program? Remember, you don’t have to ask anyone—your boss, the C-suite or any committee or board—for the permission, time, or budget to do it. Magically, you can proceed without worrying about any of these mundane issues. What do you create?

#5: No website

Imagine your association couldn’t have a website. Or, to make this more interesting, imagine you couldn’t have email marketing either. How would you grow your learning business? How would you grow by word-of-mouth?

What kind of experience or results would get learners talking enthusiastically about you? Think about the experience that would cause fervent fandom in different market segments, both members and non-members.

How could you use industry influencers, channel partners, or ambassadors to spread the word about your amazing programs? What programs and experiences would cause them to rally on your behalf and promote what you’re doing to their audiences?

How else could you give your target audience a taste of the learning experience at your association? Could you lure them in with individual or organizational self-assessments? What would a free sample look like?

How could you entice customers (program alumni) to keep coming back? How do you keep them in the fold?

The more you brainstorm, the looser your brain becomes. It loses its inhibitions as you give it permission to think boldly and wildly. Many of your ideas will be crazy, that’s okay. The exercise helps you think more creatively, which is necessary in a world changing so quickly.

Do this exercise in a group together or asynchronously. Many people think better when left to themselves—there’s no pressure to confirm and conform. Give people permission to be preposterous and watch nuggets of possibility emerge.

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