My First Job and The Power of Asking the Right Questions


Share on LinkedIn

My First Job and The Power of Asking the Right Questions

My First Job: Selling Computers on the South Side of Chicago

My first job in business was as a salesperson for IBM. I covered 13 zip codes on the south side of Chicago, selling AS400 mid-range systems. What a great, scary job packed with opportunity to learn how to sell.

Most every day, I would drive my old car down to the south side and park in one of my assigned zip codes. Then I would walk door-to-door from one manufacturing company to the next, asking to see the President. In those days, IBM had three rules of lead generation:

  1. Call on the President
  2. Call on the President
  3. Call on the President

It seems that they were trying to tell us something. That’s what they told us to do and that’s what I did…I called on the President! And I spent most of my time living in fear of getting thrown out of every decent company on the south side (and I pretty much was).

The Day It All Changed

One day, my boss wanted to do a ride-along. This, of course, took my already frayed nerves and shredded them. But I was prepared. I was ready. I had my best blue suit pressed, my white oxford done with heavy starch and my red tie. I thought through how each meeting would go in advance.

I set up appointments with the Presidents of various manufacturers and away we went. After the final meeting of the morning, my boss and I got in my car and he turned to me and asked; “What did you think? How did those go?”

Reflecting on several very cordial and productive meetings, I responded; “I thought they went really well. They seemed interested in what we have, and I think we can help them.”

He seemed to agree, but then asked a follow-up question; “What did you learn?”

This seemed like a trick question. He was looking for something, but I had no idea what. So I said; “Well, I learned that we have a couple of opportunities, and I think that’s great.

His response was unexpected, and I’ve never forgotten it. 25 years later, I think about it often as I walk into high-stakes meetings with clients and prospects.

“Craig, every question you asked this morning you should have known the answer to…”

It took me a second to process what he was saying. Here I was, thinking that I had done great, and he was suggesting that was not so.

He continued; “You asked questions about how many products these companies have, how many employees and where they do business. You could have looked those up and you would have had those answers. Then, you could have spent your time getting better, more-actionable information and building a stronger relationship.”

Ouch. This seemed so damn obvious, and of course he was right. I had prepared to ask those questions, thinking that I was on top of my game. Turns out, I had not moved the ball at all, only run around in circles.

The Power of Asking the Right Questions

I’ve never forgotten that lesson. That day, my boss gave me a great gift. The gift of asking impact questions that yield true insight.

One of the best tools that professionals have is our ability to ask impact questions. This means that we have spent time understanding and absorbing the foundational questions in advance, and that valuable face-to-face time can be spent building a stronger relationship by exploring the questions that really count.

I never looked at questions the same way again.

Republished with author's permission from original post.

Craig Wortmann
Craig Wortmann is the CEO and Founder of Sales Engine, a firm that helps companies build and tune their sales engine(s). He is also a renowned professor of entrepreneurship at the University of Chicago's Booth School of Business. His course, Entrepreneurial Selling, was ranked by Inc Magazine as one of the Best Courses of 2011. Craig published his book What's Your Story?: Using Stories to Ignite Performance and Be More Successful in the same year and continues to speak on the topic of using stories in the sales process.


Please use comments to add value to the discussion. Maximum one link to an educational blog post or article. We will NOT PUBLISH brief comments like "good post," comments that mainly promote links, or comments with links to companies, products, or services.

Please enter your comment!
Please enter your name here