Image credit: Freigeist67
“How can we do that?”
Five words. Two completely different meanings. One choice that determines whether your organization thrives or dies.
After 20+ years as the World’s Only Motivational Improviser (Yes, I made that up. No, no one has ever contested it…yet.) teaching thousands of leaders how improv principles can transform organizations, I’ve discovered this pattern plays out everywhere - and it explains why some teams innovate while others get stuck.
Let me show you what I mean.
The Tale of Two Emphases
Listen carefully the next time someone on your team says “How can we do that?” Where’s the emphasis?
Version 1: “How can we do THAT?!”
Translation: “That’s impossible. We’re screwed. Why are you even suggesting this?” (Usually followed by a sudden “bathroom break exit.”)
Version 2: “HOW can we do that?”
Translation: “Interesting challenge. Let’s figure this out. What are our options?”
Same words. Completely different futures.
The first is defeat dressed up as a question. The second is curiosity disguised as uncertainty.
This is pure “Yes, And” thinking - the foundation of all improv. When we say “HOW can we?” we’re saying “Yes” to the reality AND exploring what’s possible.
The “Strip Club Moment” That Changed Everything
(Don’t worry, no actual strip club here…)
I was keynoting for a real estate management company, and had everyone from executives to frontline workers all in one room. I was closing with my signature “Blind Line” game where I weave audience-supplied movie quotes into an improvised story.
“Give me an activity to start the story,” I said.
Someone yelled: “STRIP CLUBS!”
The HR person who hired me? Her face went from professional smile to genuine consternation in 0.3 seconds.
Now, I had two options:
“How can I do THAT?!” (Panic. Deflect. Play it safe.)
“HOW can I do that?” (Get curious. Find the angle. Make it work.)
My brain chose door #2.
I made the story about an accountant who worked at a strip club trying to leave for a better life - to become a financial advisor helping other performers invest their earnings wisely. The strip club was just the starting point, not the destination.
The room erupted. It became the highlight of the keynote.
Afterwards, the HR person pulled me aside: “When you said ‘strip clubs,’ I thought my career was over. But that was brilliant.”
That’s the power of emphasis. (Though I don’t recommend testing it with strip clubs at your next all-hands meeting. But if you do, record it. You know, for science…)
Why This Matters More Than You Think
Over my 30+ years of teaching and performing improv, I could break performers up into two camps:
The “THAT?!” improvisers:
- Only took “safe” suggestions
- Avoided anything unfamiliar
- Placed an artificial ceiling on their true improv performing potential
- Became Dallas Cowboys fans (Kidding! But as an Eagles fan during football season, I needed at least one dig in here, right? Lighten up Cowboys fans, I still love ya!)
The “HOW” improvisers:
- Lit up at weird suggestions
- Turned challenges into opportunities
- Constantly evolved and grew into stellar performers
But here’s what kills me - this same pattern plays out in every organization.
The Corporate “Crazy Improv Suggestion” Moments
Your team faces similar moments every day, where a change or setback raises a lot of questions and concerns:
- “We need to cut the budget by 30%.”
- “New regulations just changed everything.”
- “AI is disrupting our entire industry.”
- “Our biggest client just left.”
- “We need to modernize our 20-year-old system… with no downtime.”
Watch what happens next. Do your people say:
“How can we do THAT?!” (We’re doomed!)
Or…“HOW can we do that?” (Let’s solve this.)
One question. Two futures.
The Pixar Principle
Nine months before Toy Story 2’s release, Pixar realized they had a disaster. The movie was terrible. They had two choices:
Option 1: “How can we redo the ENTIRE MOVIE?!” (Impossible. Release the bad version.)
Option 2: “HOW can we redo the entire movie?” (Let’s figure this out.)
They chose option 2. Threw everything away. Slept at the office. Worked insane hours.
Result? Toy Story 2 got a theatrical release instead of going direct-to-video. Many consider it better than the original. It cemented Pixar as an animation powerhouse.
All because they asked the right version of the question.
The Innovation Killer Hidden in Plain Sight
Here’s what I’ve learned from training thousands of people: Innovation doesn’t die from lack of resources. It dies from the wrong emphasis.
When you say “How can we do THAT?!” your brain immediately lists obstacles:
- Not enough time
- Not enough money
- Not enough people
- Not enough experience
- “We’ve never done it that way before” (my personal favorite)
But when you say “HOW can we do that?” your brain starts solving:
- What resources DO we have?
- Who could help?
- What’s the smallest first step?
- What if we tried…?
Mindset before mechanics. Always.
Building a "HOW" Culture (Without the Overwhelm)
You can't flip this switch overnight. I learned this teaching improv - throw someone into the deep end with a "strip club" suggestion on day one, and they'll quit. Or worse, they’ll stay and become “that person” who brings everyone down with their complaining about how terrible everything is.
Instead, use the YES AND Framework:
Yield to What Is: Accept that the challenge exists. Don't waste time or energy denying reality.
Explore and Express Your Core: Get clear on what truly matters - your mission, values, and non-negotiables. When you know your "why," the "how" becomes clearer.
Start Small: Ask: "If we COULD do this, what would the first tiny step be?" Lower the stakes.
Access Your Creative Genius: Shift from "THAT?!" to "HOW." This opens up possibility thinking.
Notice and Nurture Emotions: Fear kills innovation. Acknowledge the discomfort, then ask "What would we try if we knew we couldn't fail?" Create psychological safety for wild ideas.
Dig Deeper: When someone offers an idea (especially a "bad" one), respond with "Yes, and what else?" Keep building. The fifth idea is usually better than the first.
Make it safe to explore wild ideas. Not every weird suggestion becomes a great story, but you'll never find the great ones if you don't explore.
Your Monday Morning Test
Next Monday you’ll face your first “How can we do that?” moment. Probably before lunch. Definitely before your second coffee. It will start with the dreaded, “hey, you got a few minutes?” opener…
Listen for your emphasis. Catch yourself.
If you hear “THAT?!” creeping in, pause. Take a breath. Shift to “HOW.”
Then watch what happens.
The Choice That Changes Everything
Every disruption, every change, every “impossible” request is a strip club suggestion in disguise.
You can panic about the suggestion.Or you can get curious about the possibility.
You can list why it won’t work.Or you can explore how it might.
You can protect what is.Or you can create what could be.
Same five words. Two different futures.
Which emphasis will you choose?
Ready to transform your team’s “How can we do THAT?!” into “HOW can we do that?” Let’s explore how the YES AND Framework can help your organization turn impossible challenges into breakthrough innovations. Click here to discuss bringing this approach to your team.