The Importance of Asking Questions

This summer, a close friend and mentor of mine lost his battle with melanoma. Alex Livingston was a man with an innate ability to ask all the right questions. A Upenn and Harvard graduate, he was the kind of person you could tell, before he even uttered a word, was incredibly intelligent, with an aire and presence about him unheard of for someone under 30. We met at a conference over ten years ago and instantly connected — personally and professionally.

Though we sadly lost Alex, I will take away many lessons from him beyond just his friendship. His willingness to sit down with me, take my phone calls, and help in any way he could taught me the importance of being a genuine, good person. He taught me to always handle myself with the utmost professionalism, to always be willing to sit down and talk with even the smallest of businesses, to always think before responding and ask the right questions to make sure you’re setting yourself up for success and giving the best advice. He taught me to be a person who follows through, a person who is honest, a person who doesn’t just say what you want to hear but instead say what you need to hear.

Alex and I shared a mutual love of summer camp. Having spent 16 summers at Camp Lenox in Massachusetts, to Alex, camp was a place that represented joy and childhood and innocence and self-growth. He learned how to listen to others and himself, to reflect on and attack challenges. He used these lessons in school, in work, and with family and friends.

When I had an idea, he’d rattle off 30 questions that hit all the right angles, asking what he would have considered himself. He was teaching me how to deconstruct an idea and reconstruct it into something more powerful, more applicable.

Now, a year and a half into starting Craze Management, with Alex’s help, I am learning how to ask the right questions. He taught me how to collect the needed information to confidently and unbiasedly determine if a business idea or a potential client’s pitch is doable and a good fit for my team.

To build a trusting, open client relationship, you must see the complete picture to make mindful decisions. Learning to do this is not easy. In business, it’s easy to get over excited and make emotional decisions rather than those that are well-informed. Often, I have to remind myself to pause before I make decisions and internally answer what Alex would have asked. For example: Can we, Craze Management, really help this company? This is just important as questions we must ask ourselves daily to better our own well-being: Is waking up at 5 o’clock daily to workout the best decision for my day, my health, my social life? Is working 17-hour days a good thing or something that needs to change?

But this is not just something I know I must practice in running CM. This is something every business owner must do. Stepping back and self-analyzing your idea before you take a product to market, before you make a decision that may potentially have big implications and impact on your business, employees, and customers is paramount.

As I look to grow Craze Management and take on more clients, meeting with startup founders, I continue to push myself to ask these questions and feel compelled to push others to do the same.


Alex’s family set up a scholarship fund to send children to his camp. Craze Management will certainly be getting involved, and I hope others will support this effort. Visit https://www.youcaring.com/camp-lenox-590900 to learn more.

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