Always Ask Questions

If you know me, you know I ask an inordinate amount of questions. I have always been this way- it's how I navigate the world, gather information, and unlock creative solutions. 

And because of this, I FIRMLY believe that asking questions is not a weakness – it's an incredible strength.

Back in my early corporate days, I was a SUPER hesitant to ask questions. I worried that it would make me look inexperienced or clueless. But I quickly realized that asking questions isn't a sign of weakness – it's a sign of intelligence and demonstrates the desire to understand and do things right

It's how we learn, grow, and ultimately, excel in our roles.

I found that the more questions I asked (and the quicker I asked them) I became better at my job. It helped me gain clarity, challenge assumptions, and uncover insights that I wouldn't have discovered otherwise. 


Instead of being afraid of looking foolish, I embraced my curiosity and leaned into my ability to ask questions. It's been a game-changer ever since.

So, here's the deal – as business leaders, we need to be asking questions at every opportunity. 

It's hard to find answers without asking questions. Whether you're brainstorming new ideas, troubleshooting challenges, or making strategic decisions, questions are your secret weapon.

But not all questions are created equal. So, how do you ask good questions? Here are a few tips:

  • Be Curious: Approach every situation with a curious mindset. Ask yourself, "What do I want to know? What am I trying to achieve?" Curiosity is the fuel that drives meaningful inquiry.

  • Start with "Why": The question "why" is a powerful tool for understanding motivations, reasons, and underlying causes. When faced with a situation or problem, asking "why" can help uncover deeper insights and root causes. For example, instead of asking, "What went wrong?" try asking, "Why did this issue occur in the first place?" This can lead to a more comprehensive understanding and better solutions.

  • Be Specific: Instead of asking broad or vague questions, be specific and targeted. This helps focus the conversation and elicit more insightful responses.

  • Listen Actively: Asking questions is only half the battle – listening to the answers is just as important. Practice active listening and be fully present in the conversation.

  • Be Open-Minded: Don't be afraid to challenge your own assumptions or preconceived notions. Keep an open mind and be willing to consider alternative perspectives.

  • Use Open-Ended Questions: Instead of asking yes/no questions, try using open-ended questions that encourage conversation and exploration. Open-ended questions begin with words like "how," "what," and "tell me about." These types of questions invite more detailed responses and allow for a deeper exploration of the topic. For instance, instead of asking, "Did you like the presentation?" try asking, "What are your thoughts on the key points discussed in the presentation?"

  • Follow Up: Don't stop at just one question – keep the conversation going by asking follow-up questions. This shows that you're engaged and genuinely interested in the topic at hand.

  • Ask Empowering Questions: Empowering questions are those that encourage critical thinking, creativity, and problem-solving. These questions challenge assumptions, spark innovation, and inspire action. Examples of empowering questions include, "What would success look like in this scenario?" or "How can we approach this problem from a different angle?" By asking empowering questions, you empower yourself and others to find meaningful solutions and drive positive change.

Here’s the bottom line -  be unapologetic in your curiosity and make your questions work for you. Because when we ask the right questions, we unlock endless possibilities and pave the way for innovation and growth.

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