I’ve watched companies waste millions on innovation initiatives that produce nothing. Not because they lack creativity or resources, but because they’re asking optimization questions disguised as innovation questions.
You know the type: “How can we improve our product by 10%?” “What features should we add?” “What are competitors doing that we’re not?” These questions keep you trapped in incremental thinking. They’re maintenance masquerading as innovation.
Real innovation questions make people uncomfortable. They challenge sacred cows. They expose the gap between what you’re building and what people actually need.
The problem is that most teams don’t know which questions unlock real value versus which ones generate activity. So here’s what actually works, organized by what you’re trying to uncover.
Diagnostic Questions: What’s Actually Broken?
These expose the friction your customers tolerate but won’t tell you about directly.
What do your customers complain about to each other but never tell you?
This reveals the real pain points, the ones people have accepted as unchangeable. When Stripe asked this about payment processing, they discovered developers hated existing solutions but assumed payment complexity was unavoidable.
What workaround have people invented because your official solution sucks?
Workarounds are innovation signals. They show where your solution fails and where people care enough to fix it themselves. Dropbox emerged because people were emailing files to themselves, a workaround that revealed a broken file-sharing system.
What makes people feel stupid when they use this?
Shame and frustration are gold mines. When people feel incompetent using your product, that’s not a user problem; that’s your design exposing unnecessary complexity.
Where do people waste time, energy, or money every single day?
Daily friction compounds. A 5-minute annoyance happening 250 workdays a year is 20+ hours of wasted life. Find those, and you’ve found your opportunity.
What part of this experience do people accept as “normal” but actually hate?
Normal doesn’t mean acceptable. Banking fees were “normal” until fintech companies asked why. Two-week shipping was “normal” until Amazon made it absurd.
What breaks when usage increases by 10×?
Systems designed for current scale often collapse under growth. This question reveals structural weaknesses before they become crises, and opportunities to build for scale from the start.
What these unlock: Process innovations, user experience breakthroughs, and service design improvements. These questions typically reveal opportunities worth $1M-$10M in efficiency gains or customer satisfaction improvements.
Generative Questions: What’s Actually Possible?
These break you out of the current frame and reveal latent demand.
What would make customers feel stupid for not switching immediately?
Not “what would make them switch”, what would make staying feel like a bad decision? Slack hit this mark. Once teams tried it, going back to email felt prehistoric.
What do people wish was possible, even if it sounds unrealistic?
People self-censor their desires based on what exists today. When you ask this, you hear their actual needs, not their constrained requests. “I wish I could just talk to my computer” sounded unrealistic until it wasn’t.
What would surprise and delight users, not just satisfy them?
Satisfaction is table stakes. Delight creates evangelists. Zappos didn’t just deliver shoes, they surprised people with overnight shipping when they promised 5-7 days. That surprise generated more marketing value than any ad campaign.
What emotional job is being underserved?
People don’t just hire products for functional jobs. They hire them to feel competent, connected, or in control. Peloton sells fitness equipment, but people buy it to feel part of a community and accountable to something bigger.
What becomes possible now that wasn’t possible 6 months ago?
Technology shifts faster than market awareness. AI, sensor costs, regulatory changes—these create windows of opportunity that close quickly. Ask this quarterly.
What requires expert knowledge that AI can now democratize?
Expertise used to be a moat. Now it’s increasingly a feature. Legal research, medical diagnosis, code review—what was once protected by years of training is becoming accessible. Where’s your industry’s expertise being democratized?
What these unlock: New product categories, business model innovations, and market-defining opportunities. These questions surface opportunities worth $10M-$100M+ if you move fast.
Strategic Questions: What Actually Matters?
These separate real opportunities from distractions.
What rule in this industry is treated as gospel, but shouldn’t be?
Every industry has sacred cows. Hotels required front desks until Airbnb didn’t. Taxis required dispatch until Uber didn’t. Cars required dealerships until Tesla didn’t. What’s your industry’s unquestioned assumption?
What do incumbents assume that’s absolutely false?
Incumbents optimize for yesterday’s constraints. Blockbuster assumed people wanted selection. Netflix realized people wanted convenience. What false assumption is your industry built on?
What would an outsider with no history in this space do?
Industry experience is both an asset and a liability. It gives you knowledge but blinds you to possibilities. This question forces you to see your space with fresh eyes.
What would competitors be unable to copy, even if they wanted to?
Network effects, proprietary data, and cultural elements create real moats. Everything else is temporary advantage. If your innovation can be copied in 6 months, it’s not strategic.
What is everyone optimizing for, and what if we optimize for something else entirely?
Most companies in an industry optimize for the same thing. Hotels optimize for occupancy rates. Airbnb optimized for belonging. Restaurants optimize for table turns. Sweetgreen optimized for ingredient quality. Find the unoptimized dimension.
If this industry were invented today, what would it not include?
Legacy infrastructure creates drag. Banks wouldn’t build branch networks today. Retailers wouldn’t build massive inventory systems. Universities wouldn’t require physical attendance. What would you eliminate if you started fresh?
What shifts (AI, regulation, demographics) will make today’s solution obsolete?
The best innovations anticipate change rather than react to it. Remote work tools won before COVID forced adoption. What’s the forcing function coming to your industry?
What these unlock: Category-defining innovations, competitive moats, and long-term strategic positioning. These questions reveal opportunities worth $100M+ and potential market leadership.
The Questions You Should Stop Asking
These generate activity without value:
“How can we improve X by 10%?” – That’s optimization, not innovation. It keeps you trapped in the current paradigm.
“What features should we add?” – Feature bloat kills more products than feature gaps. Subtraction is usually the answer.
“What do competitors have that we don’t?” – Following competitors makes you a follower. You’ll always be late and always be worse.
“What do customers say they want?” – Customers are terrible at articulating latent needs. They’ll ask for a faster horse, not a car.
“What can we do with this new technology?” – Technology-first thinking produces solutions looking for problems. Start with the problem.
How to Actually Use These Questions
Here’s what doesn’t work: Running a brainstorming session where you ask all these questions and collect 100 ideas that go nowhere.
Here’s what does:
1. Pick ONE question based on your context:
- Early stage/exploring? Start with diagnostic questions
- Have product-market fit? Focus on generative questions
- Facing competition? Go straight to strategic questions
2. Ask it to 10 people this week: Not your team. Not internal stakeholders. Customers, users, people in the trenches. Record the conversations. Listen for the things that make people emotional—anger, excitement, frustration.
3. Look for the pattern that breaks your assumptions: You’re not looking for feature requests. You’re looking for the insight that makes you say, “Oh shit, we’ve been thinking about this completely wrong.”
4. Validate it with behavior, not words: Would people pay for this? Would they switch for this? Would they tell others about this? If the answer isn’t an immediate yes, keep asking questions.
5. Move fast or move on: Innovation opportunities have windows. If you’re not prototyping within two weeks and testing with real users within a month, you’re doing innovation theater.
The Real Test
An innovation question only matters if it produces an uncomfortable answer.
If your team responds with “that’s interesting” or “we should look into that,” you asked the wrong question.
If they respond with “that would completely change how we operate” or “we can’t do that because…” followed by a reason that’s actually just fear, you’re onto something.
Most innovation fails not because companies ask the wrong questions, but because they ask questions they’re not prepared to act on. Don’t ask questions you’re not ready to have answered.
Now pick one question. Ask it to 10 people this week. Report what broke your assumptions.
The worst case? You learn something valuable. The best case? You spot the opportunity everyone else is missing.
