There's an old Chinese proverb I take to heart: He who asks a question is a fool for five minutes; he who does not ask a question remains a fool forever.

I can't tell you how often I present to groups of people - or just sit through meetings - and hear crickets when the call for questions comes at the end.

When I'm the one at the front of the room, I know the silence isn't because I have some unerring ability to anticipate every query. And I doubt it's because the audience is so disinterested that it couldn't summon a single synapse.

Here's what I've observed: people are more afraid of the prospect of looking dumb, than inspired by the opportunity to look - and be - smart.

After decades of leading teams in the tech industry, the one thing I know is that smart people never accept answers without question. They are critical, thoughtful and analytical. Most importantly, they're willing to put themselves out there - and even risk vulnerability - by asking questions that can challenge, shift and elevate a conversation.

But sometimes it's difficult to come up with questions on the spot that make you sound as smart as you are. So here are five to get you started.

1. Why? Why? Why?

Always ask why. Even if it makes you feel naïve. People who ask why look at circumstances with a fresh perspective and challenge the status quo. Henry Ford revolutionized transportation when he asked why. Steve Jobs transformed personal computing when he asked why. A few years back, author Simon Sinek gave a TED talk called "Start With Why."  He outlined a theory that most businesses can say what they do and how they do it, but few can articulate why. Asking why at the beginning of a project enables you to tease out the purpose of a task to better construct a how and a what. Digging into the whys tests strategy and helps link the purpose, big picture and specific elements together.

2. Why not...?

In her book InGenius, Tina Seelig, executive director of Stanford University's Technology Ventures Program, writes about the importance of reframing a problem to unlock innovation. She reminds us that getting outside ourselves and looking at a situation through different lenses can spark new ideas and unleash imagination. So, why not offer a new service for free? Why not team up with a competitor? The next time you're in meeting, imagine yourself in a different set of shoes and ask the questions that test boundaries and create new realities.

3. How could this fail?

The point of this question isn't to be a doomsday-monger or naysayer; it's to make sure you start stress-testing a project before the stakes get too high. Just like defense and intelligence organizations sometimes appoint so-called "red teams" to identify problem spots before an enemy can pounce, play the devil's advocate to help improve your outcomes.

4. How do you measure success?

The old adage of "if you can't measure it, you can't manage it" stands true here. This question shows you're goal-orientated and that you're looking for signposts showing that you and your team are heading in the right direction. It's also a way to uncover - and prioritize - the outcomes that are really important to your business, as well as make sure everyone on the team is aligned around those goals.  

5. Where's the evolution?

No matter what you're doing, something came before it and something will come after. Probe how similar projects fared in the past and anticipate how parallel efforts could play out. Inquire about the pivotal moments in comparable plans. This kind of questioning shows that you can link big trends to specific actions and that you're looking for patterns of success. It also signals that you're interested in building the future, not just reacting to it.