Are “stupid questions” good?

“Any questions or comments? Don’t be shy! There are no stupid questions.” You’ve probably heard professors, presenters, or leaders say something along these lines.

It’s oftentimes followed by the silence. For presenters or professors, this moment is at best slightly awkward, and at worst mildly depressing.

As a business leader, though, the silence can feel alarming.

Why? Because questions, especially seemingly stupid ones, are the foundation of everything we do as a business and how we progress as a team and as individuals. They’re a key part of filling in knowledge gaps, facilitating communication, and understanding alternative perspectives both from inside and outside the company.

From a customer satisfaction standpoint, questions can often provide valuable internal feedback about new products and features. If your team doesn’t understand or doesn’t like something, chances are your clients won't.

Taking a more positive view, many great discoveries and companies started with a stupid question or idea.

In the early 2000’s the conventional wisdom at auto companies like GM was that mass producing high-performance electronic cars wasn’t feasible and didn’t make economic sense. Elon Musk asked “are we sure though?” and GM CEO Bob Lutz predicted Tesla was headed for the graveyard. Tesla is now one of the world’s most valuable auto companies.

In 2011 it looked like future of video conferencing belonged to Skype, Google, or Cisco Webex. Then Cisco employee Eric Yuan asked “shouldn’t we be trying to improve Webex and move it to the cloud?” His superiors didn’t agree, and when Yuan left Cisco to launch Zoom, neither did the VC community. Today Zoom has ridden the COVID-19 wave to 300 million daily meeting participants.

In the 16th and 17th centuries, Copernicus and later Galileo doubted and eventually rejected the geocentric model of astronomy that was fully endorsed by the Catholic (and Protestant) churches. The writing and teachings of both astronomers were subsequently forbidden, but today we all (I hope…) know that the Earth rotates around the sun and not the other way around.


Assuming that by now we all agree that as businesses we want our team to ask questions and challenge the status quo, if we find ourselves faced with silence, we must ask “why?”

While it’s not exhaustive, your team might not ask questions for three primary reasons:

  1. They don’t care. This is just a job, and they are there to earn a pay check.

  2. They don’t think it will make a difference. Management has its own plans and creative ideas and constructive criticisms never go anywhere.

  3. They are afraid or don’t feel comfortable. Employees who ask too many questions are considered “annoying,” “disruptive,” or even “negative.” Limited interaction means the only chances to ask are during uncomfortable all-hands meeting or under time pressure.

These reasons place us in the employee’s perspective, but the underlying causes and ability to fix them lie with the company leadership.

If your employees don’t care, then you are not doing enough to connect them emotionally, intellectually, or financially with the company trajectory. They need motivation and inspiration and you need to facilitate ideas with helpful suggestions.

If your employees don’t think they will be heard, then you probably aren’t listening and incorporating their ideas into the effort, or at least need to do so more visibly. Do you present new plans and initiatives as finished products or do you involve the team along the way? Why would they ask questions if you already chose the course, laid the plans, and launched it last week? Your team could also potentially benefit from micro-leadership opportunities that show extra-mile thinking being rewarded.

If your employees are afraid, you might need to work on your posture and tone when accepting challenges or criticism, and ensure other leaders are doing the same. Publicly admitting your mistakes could help show openness to challenges, adaptation to feedback, and encouragement of learning through failure. Some employees likely need alternative forums, from coffee chats to #random slack channels and anonymous suggestion boxes to feel comfortable sharing.

So which are we?

If somehow one finds oneself facing the silence, they could look back at the cases of Tesla, Zoom, and Copernicanism, and ask a few more stupid questions:

Is our team GM, with little reason to care about the future when churning out boxy SUVs is easy and profitable in the short term?

Are we Cisco, making people feel unheard when they’ve got a game-changing perspective?

Would Pope Urban VIII be proud of the fear we instill by treating challenges and criticism as punishable crimes?

I hope and believe that Logward won’t ever have anything in common with these cases. We are, after all, a company that started with the stupid question of “can a traditional freight forwarder actually grow and thrive in a digital future?” and said forwarder, Leschaco, responded by funding us.

Yet a culture that encourages stupid questions and bright ideas is not something you install. It’s something you build, adjust, defend, and nurture.

So as we make bold plans for the future at Logward, “ask stupid questions” and “watch out for the silence” need to be on our daily to-do lists.


Logward is a Hamburg & Bangalore based logistics technology company.

We build software, move containers, and change mindsets.

If you have any questions or just want to say hi, reach out to Or you can book time with one of our logistics experts here.