The old adage that there's no such thing as a stupid question is 100 percent true. Still, some questions do you more good than others when it comes to opening your eyes and helping you grow--questions like what your blind spots are, for instance. And unfortunately, it's often the case that those questions typically don't find their way out of people's mouths until the opportunity to truly apply and get full use of the answer has passed. There are some pretty basic reasons for this.

1. Inexperience gets in the way.

There's another saying that you don't know what you don't know. Asking the right question that really is necessary at the right time requires you to have enough pieces of the big picture to think critically about the situation you're in or problem at hand. But when you're still just starting out in your business or career, you're still unintentionally ignorant to a large degree from simple lack of life experience. You haven't had time to get all the information that will let you come to a solid conclusion about what's really relevant and what's not, so although you might not ask bad questions, it doesn't occur to you that you need to ask others that are deeper and have more potential for effect.

2. You don't want to lose ground you've gained.

As people rise to the top, they know the competition is fierce. They can be desperately afraid that, if they admit what they're not good at or what they don't know, they'll look unprepared and unqualified to continue forward. Rather than seek guidance, they stay mum and try to figure out how to navigate on their own.

3. Access to the right people is locked.

In many regions around the world, business is built on a strict hierarchal structure where it's incredibly difficult for lower-level workers to communicate directly with higher-level employees and those in the C-suite. At the same time, even where more direct communication is accepted as a matter of philosophy, time with higher-ups can be ridiculously limited. Subsequently, people who are just starting out can find it nearly impossible to rub elbows with the individuals who actually have the insight and expertise to answer inquiries in the most helpful way.

4. You don't know what problem you're trying to solve.

Young leaders are often anxious to make their mark and offer up solutions for the sake of asserting personal value. So they spend time doing something, anything to come up with some kind of answer, rather than thinking about whether they're moving themselves and others in the direction that actually is right.

5. You've been trained to give responses.

Especially in recent years with the adoption of standardized testing, the educational emphasis (at least in the United States) has been on rewarding people for the right answers, rather than for thinking critically and coming up with thoughtful additional inquiry. Because we never get much practice formulating important questions on our own, we don't know how to ask for the specific information we sense we need.

You can't magically make yourself more experienced. But you can


  • look at the reflections/memoirs of people who have gone ahead to see what questions they regret not asking or didn't realize were necessary,
  • practice all kinds of confidence-boosting exercises so you feel more secure and aren't afraid to admit you're a little lost,
  • be politely persistent in reaching out to those you admire,
  • lobby and be an advocate for tools and protocols that help dissolve silos,
  • focus on vision, purpose and values instead of mere participation or quantity,
  • take classes in philosophy or critical thinking and explore educational practices in other areas of the world, and
  • pause before speaking to resist the initial urge to give advice or a response.

So go do. Ask. The worst that can happen is you learn something new about yourself along the way.