Stuck, frustrated, discouraged? Ask a better question

Updated to Habits, Productivity on January 3, 2023.

Working at home, late at night, after putting in a full day at his job at DuPont, Earl Tupper was about to have a breakthrough that would change his world forever and launch an international company. Modeled after an over-turned paint can lid, Tupper used early forms of Polyethylene to create a simple, re-sealable lid that could be used for hundreds of shapes of containers.

His invention?


The original Tupperware parties

Not only did that simple invention launch a thriving company that now reaches over 100 countries, it introduced multi-level marketing to the world of selling.

And it started by asking a better question.

When Tupper asked himself how he could adapt the sealing properties of a can of paint to other containers he unlocked a whole new world of thinking.

Just like it did for George de Mestral (Velro), Spencer Silver (post-it notes), and Jacques Brandenberger (cellophane).

Let’s look at why questions are so critical to good thinking.

Our brain loves questions

The average adult brain weights in at about 1.3 kg (3 lbs), or about 2% of your body weight – not much. On the other hand, it chews through about 20% of your body’s energy – it’s a voracious engine that needs to be fed.

To save fuel it takes short-cuts.

Not sure what to make for dinner? Cook up stir fry, again.

Thinking about going to the gym? Put it off till tomorrow, again.

Need to make that sales call? Check your email, instead.

Still feeling the bruise from last night’s argument? Assume it’s his/her fault, like always.

Need I go on?

We all do it – take the path of least resistance. It’s easier, it’s faster, and, heck even more rewarding – in the short term.

And as you know, dear reader, once you think something is true, you can’t help notice evidence that proves you’re right.

The trick is to trick the brain.

Ask a better question

When you ask a better question you trick your thinking into exploring a new path. Instead of “Why is she is always….”, you venture down “What can I learn from this about me?”, or “What does she need right now from me?”

Usually it’s not that important if your question is the right one – as long as it prompts new thinking and new behaviour.

That’s what I did when I envisioned BOSS.

Why I created the Business Of Speaking School

Over past six years I’ve experimented with hosting conferences, bootcamps, one-day retreats, webinars, podcasts and other ways of teaching people the business of speaking. All methods worked – some were riskier (unless you’ve rented a hotel conference room and paid for catering, you’ll never know) and more work than others.

I wanted an anchor program – one I could be proud to offer every year – that wouldn’t be a huge risk to launch.

So I asked a better question.

Rather that asking how I could host a bigger conference, or how could I enrol more people in my bootcamps I asked this question:

“What could I invent that was good for both me and the students?”

You see, all the previous program designs were convenient for the students (just come to the conference, just sign up for the webinar, just listen to the podcast), but they left me exhausted.

The answer that emerged was a hybrid model combining recorded and live lessons with a community forum. That’s BOSS (the Business Of Speaking School). Every week, for 8 weeks, students learn from pre-recorded curriculum, we have a live 90 minute call with me and visiting expert faculty, plus we use a private Facebook group for daily conversation and answering questions.


It’s super convenient for the students (this year we have students from 8 countries) and convenient for me: no hotel room to rent, no catering, transportation, or crazy logistics. The profit is more predictable and I can put more energy and time into curriculum and helping the students.

What about you? Have you got an itch that needs scratching?

Start with an itch

To challenge your assumptions with a better question, start with an itch – what frustrates you over and over?

Maybe you’re putting in too many hours at work, procrastinating about speaking up to your boss, or skipping the gym. The trick is to recognize the frustration as being worthy of improving and then to narrow the question to one point.

If you want to enjoy better health, it might not help to tackle long work hours, children in hockey, and your spotty history of commitments. Instead, choose one area to improve (like how you spend the first hour after waking) and then form the better question you need to break through your story.

When I wanted more exercise when traveling I asked what can I do in just 15 minutes. The result (which I’ve used consistently for over 5 years) was my 15 minute hotel room workout.

Got an itch? Ask a better question – you might be surprised at what you invent.