I often reflect on how lucky I am to have been taught, early on, the two most valuable words in business: just ask. As an entrepreneur who felt in over my head and unqualified to take on the roles I did (and do), asking became my magic.
And it’s damn addictive. Once I started to realize that asking leads to yes far more than it leads to no, it became a habit for me, fueled confidence, and led to self-fulfilling outcomes.
One of my favorite “just ask” stories came early on when I was building my marketing and communications firm, Prosek Partners. We were in a high-profile competition for a new piece of business. We did so well in the first round that we were told, “You’re going to get it. You just have to pass muster with the founder.”
The partner who delivered that news was named Andrew. He reinforced how impressed he was and how good the chemistry was between our teams. But unfortunately, at the meeting with the founder, we froze. He was among the most intimidating humans we had ever encountered, and we fell like dominoes in his presence. We knew, leaving that meeting, that we had blown it.
How I turned a “no” into a “yes”
When Andrew called, I knew it was bad news. He felt terrible but informed me that they would move in another direction. He promised he’d make other introductions for me and my business and that he hoped our paths would cross again.
Five minutes after we hung up, I decided to pick up the phone and call him back. When he answered, I told him that I was going to ask for something outrageous, that he shouldn’t feel obligated, but we are so interested in the business that I thought I’d ask.
I asked for another meeting with the founder. Another chance. With a fresh team. Silence fell between us for a few moments, and then he said, “Jen, I doubt it, but I will try.” We had our second chance a day later.