Why Not Ask?

Many people, myself included, often answer a question before they ask it. This prevents many from getting the right job, a salary increase, or the date. Read my take on the big ask below.

Recently, I was reading a story about a quote Steve Jobs made:

“Most people never pick up the phone and call. Most people never ask, and that separates the people who do things from those who just dream about them.”

The article talked about how, as a twelve-year-old, Jobs developed the courage to call Bill Hewlett of Hewlett and Packard fame to ask for spare parts so he could build a frequency counter. Not only did Packard give him some spare parts, but he also gave Jobs a summer internship. As Jobs’ says in the interview, he was in “heaven.”

The experience had an impact on his future success. Asking for things is something that many of us, including me, have a hard time doing. I know that my old-school, hard-working, pull-your-self-up-by-the-bootstraps father indoctrinated me to think that doing anything on your own is the ultimate virtue of human value. Asking for help or even asking someone for something I want continues to be difficult today.

As a former economic development organization leader and now a consultant and entrepreneur, having to “ask” is a daily challenge. Whether it is asking for a sale or advice, my irrational, deep-seated stories or limitations of the havoc and awful things that could happen sometimes prevent me from asking.

My best friend is a very successful executive in sales. He worked at the New York Times for over 25 years, achieving great success with major Fortune 500 companies, selling them advertising space in one of the world’s leading and most influential publications. He is still selling but now works in the electronic space of Podcast advertising.

We were talking the other day about selling and building relationships. I don’t think there is one person he has met or exchanged business cards with that he couldn’t call today and make some connection. He is good at ensuring that anyone he meets in a business sense might be helpful in the future to achieve his sales goal for that week or month or connect him to a new job.

He is the grand master of asking for help, for connections, for what he wants.

On the other hand, I can tell you stories of famous people I have met, people I have encountered, and potential future connections I have squandered due to my failure to maintain those connections. A few professional and personal opportunities have slipped past me due to this lack of attention.

Chip Conley, Founder of Joie de Vivre Hotels (now part of Hyatt), founder of the Modern Elder Academy, and storied social alchemist, tells a story about how he tapped into the wisdom of Herb Kelleher, former CEO of Southwest Airlines, by simply asking. While they never met, he and Kelleher enjoyed a ten-year relationship via mail. Kelleher would answer, via mail, Conley’s questions that he submitted on an annual basis.

Why? There could be various reasons Kelleher felt compelled to answer Conley, but the critical point is that Conley asked. He asked for help and advice, which Kelleher likely felt compelled to respond.

With asking comes rejection or a sense of awkwardness. Asking can be uncomfortable and even painful if you have already conjured up how you will feel when the rejection you most assuredly know is coming descends upon your psyche. Noah Kagan, founder of AppSumo, a software company, says the best way to “practice” rejection and become immune to it is to ask for discounts. He says to ask for a 10% discount everywhere you go. You will most likely get rejected, but it will toughen your mental capacity to accept rejection.

Asking for help. Advice, money, whatever, goes hand in hand with rejection.

What if Jobs never asked Dave Packard for parts and instead cowered in his room predicting what Packard would say as he rejected the request? Or what if he believed he would never get Packard on the phone? Perhaps we wouldn’t have the Apple products we enjoy and overpay for today (but I gotta have the new phone)!

What if Chip Conley never revived his hotel and hospitality company and created a positive culture in his company based on Kelleher’s coaching? Would Joie de Vivre, the Modern Elder Academy, or AirBnb, where he spent several years as an advisor, be what they are today?

As the Bible says, “Ask, and it shall be given you; seek, and ye shall find; knock, and it shall be opened unto you:” Matthew 7:7