We humans tend to perceive the world as a series of yes/no answers. Limited questions nurture limiting beliefs. Our questions yield black and white answers.

It used to be ok to think in simple terms. If you were alone in the forest 12,000 years ago and heard a cracking sound of wood breaking, you should decide quickly whether to run or not. It could be a leopard. There was no gain in anything other than yes/no. You better run 100% of the time.

In today’s world, though, thinking through yes/no is far from ideal. Civilization got here by sieving through nuances. In the last 150 years, science and engineering shaped our new reality through the discovery of penicillin, relativity, telecommunications and the internet, mobile phones and AI. Consider the development of weather forecasting, a field that relies heavily on probabilistic models. Meteorologists don’t simply ask, “Will it rain tomorrow?” but rather, “What is the probability of rain given the current atmospheric conditions, wind patterns, and temperature?”

The world is a space of random possibilities with different degrees of probabilities. There’s a 50-50 chance a coin will fall on either side. There’s a 75% chance that I will have ice cream this week because there’s also a chance that I will get sick or it’ll be cold. There’s a 98% chance we will see a revolutionary new technology announced this year, and there’s a 1% chance we will see civil unrest.

These probabilities change constantly, and are chained to other probable and improbable events. There’s a 20% chance it will rain, and if it does, there’s a 95% chance I will have to drive to my destination instead of cycling.

Yes/no questions box us in, they limit us. Let’s consider two questions you can ask yourself to assess a situation at work:

- Will this project be delivered in 30 days?
- From 0 to 100%, what is the probability that this project will be delivered in 30 days?

The second question is a lot richer than the first one. You might feel like you’re 90% confident, which could mean “yes” for a lot of people, but 90% is still not a “yes”, 90% is still uncertain. “90%” *begs* the question, “what 10% of it is undermining our confidence?” It also gives us space to attribute different probabilities for different dates, you can feel 20% confident that it’ll be delivered in 20 days, 40% in 25 days, 60% in 30 days, and 95% in 40 days. 100% sure it won’t go over day 50.

That is how I communicate with my clients/bosses or whoever I do business with. “When will it be delivered?” is replied with three estimates, an optimistic (e.g 25 days), a pessimist (50 days) and a realist (40 days). This shares the risk and transfers the conversation from a mere contract negotiation to collaboration.

I was once approached by a company that wanted me to move close to their office, and a friend asked me, “Would you move to that city?”, and I pondered, “would I”? This got me thinking on both, “Yes but I feel uncomfortable” and “No, but I’d be shutting down opportunities”.

And then it hit me that a much better question would have been, “What are the probabilities of moving to that city given the various aspects of the offer?” Every benefit adds a higher probability of moving. Under the offer? 0% chance. Maybe if they paid a premium we could get it to 30%, but would still be bad. Maybe if the role was specific and the offer included better equity or compensation it could move chances to 80%. But maybe including the family variable it could be lower.

I’m fairly confident you got the point (maybe something around 85%). It’s not that we won’t have yes/no answers, but it’s that questions are what fuel our creativity and we rather start well, with good questions.