The Simplest and Most Useful Advice I've Ever Gotten in Business

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.

I’m sure you know where this story is going. We got the business, and 13 years later, this firm remains a top client, and the founder is a dear friend. It turns out he was impressed that we wanted his business and more impressed that we were gritty enough to ask for a second chance. Founders connect with that behavior.

THE RULES I LIVE BY WHEN I MAKE AN ASK

Of course, there’s an art to asking, and as I practiced more and more, I began to identify common themes that got me from a yes to a no. Based on my experience, going by these principles have always served me well:

? What’s the downside?: If you’re trying to muster the courage, always ask yourself, “What’s the downside?” In most cases, you will find the answer is perhaps a little bit of embarrassment or a blow to one’s ego–not too much of a loss after all.

? Ask with humanity and authenticity: My ask to Andrew would not have gotten anywhere if we had not established a human connection and mutual respect for one another. I explained to him, authentically and humbly, that I was genuinely disappointed in myself and how much it would mean to me to have a second chance.

? Watch your timing: Timing your ask is incredibly crucial. Don’t ask for something when someone is under pressure or overwhelmed, running out the door or having a bad day.

? Don’t qualify your ask: Deliver your ask directly and confidently. Don’t apologize for your ask.

? What’s in it for them?: Your ask should deliver something for the other party, even if it’s just a sense of contribution. To this day, Andrew feels great that he was able to provide an opportunity to a young entrepreneur who was building her business at a critical time. To this day, I always remind him of the impact he made on my professional life and career.

There is something to the expression “the squeaky wheel gets the grease.” In business, if you don’t ask, you often don’t get. Remember, the downside is rarely as bad as you think, but the upside might be even better than what you’ve ever imagined.